KR102143342B1 - Composition comprising extract of Gynostemma longipes VK1 or compounds isolated thereof for preventing or treating AMPK-related diseases - Google Patents

Abstract

The present invention relates to a composition for preventing or treating AMPK-related diseases comprising, as an active ingredient, a Gynostemma longipes VK1 extract or a compound isolated therefrom, the Ginostema longipes VK1 extract or The composition of the present invention by confirming that the isolated compounds activate AMPK, which is involved in various physiological actions such as glucose transfer, fatty acid synthesis, and muscle regeneration, and promote the absorption of sugar into adipocytes as well as proliferation of myoblasts. It is expected to be able to develop a therapeutic agent for AMPK-related diseases such as muscle disease, obesity, diabetes, metabolic syndrome, etc., with excellent effects, as well as animal drugs, health functional foods for improvement, or compositions for animal feed.

Description

Composition comprising extract of Gynostemma longipes VK1 or compounds isolated thereof for preventing or treating AMPK-related diseases, comprising Ginostema longipes VK1 extract or a compound isolated therefrom as an active ingredient.

The present invention is Ginostema longipes VK1 ( Gynostemma longipes VK1) relates to a composition for preventing or treating AMPK-related diseases comprising an extract or a compound isolated therefrom as an active ingredient.

AMPK (5′-AMP-activated protein kinase) is activated by a decrease in cellular energy status (AMP/ATP and ADP/ATP ratio) such as nutritional status or exercise of cells. The activation of AMPK affects various physiological processes such as glucose transport, fatty acid synthesis, and cholesterol synthesis by regulating the phosphorylation of various enzymes involved in the energy metabolism of cells. It is known (Hardie, DG, 2007). The effect on the activation of AMPK is related to target organs such as liver, muscle, fat and pancreas, which are closely related to regulation of energy metabolism. When AMPK is activated in the liver, it inhibits the synthesis of fatty acids and cholesterol and promotes the oxidation of fatty acids. When AMPK is activated in skeletal muscle, it promotes oxidation of fatty acids and absorption of sugar, and inhibits fat breakdown and fat production in fat cells. In addition, activation of AMPK in pancreatic β cells is known to promote insulin secretion, so many studies have been conducted as a major drug target for metabolic diseases in relation to the role of AMPK (Ha, Joo-heon, et al. 2010).

Looking closely at the mechanism related to AMPK activation in each tissue, it was found that AMPK is involved in glucose uptake in muscle cells promoted by exercise, and AMPK is generally a sensor that monitors energy levels within cells. ) It turns out to play a role. During exercise or hunger, muscle cells, hepatocytes, and fat cells inhibit the synthesis of fat and glycogen to supply necessary energy, and play a role in generating energy needed by the body through fat decomposition from storage materials (fat). Perform. In addition, AMPK is also known as an intracellular signaling material for leptin and adiponectin secreted from adipocytes. In particular, adiponectin is estimated to have a high relationship with insulin resistance due to obesity, as adiponectin is measured at a lower concentration in the blood of obese people compared to those of normal weight. Accordingly, AMPK-activating substances are excellent drugs for obesity. This is possible as a target point (Hardie DG, 2007(1)).

Since it was found that metformin's drug target point, which had been used for oral diabetes treatment until now, but the mechanism was unknown, is related to AMPK activity, many companies have developed drugs as target points. The Garban Institute of Medicine in Korea reported that four components extracted from bitter melon (Gotchi) exhibit antidiabetic activity through the activation of AMPK, a protein enzyme known to be involved in regulating metabolism in the body (Tan, MJ, et al., 2008). Through this, the possibility of the AMPK activating substance as a therapeutic agent for metabolic syndrome including diabetes can be expected.

Muscle (muscle) is the most composed of the tissue in the human body, in order to maintain the functional ability of the human body and prevent metabolic diseases, it is essential to secure an appropriate muscle mass. Muscles are largely divided into smooth muscle, cardiac muscle, and skeletal muscle, and skeletal muscle occupies a significant part of the entire body and promotes skeletal movement, is a major tissue that maintains breathing, and obesity. It is the primary peripheral tissue that uses glucose and fatty acids, which are important in preventing and preventing type 2 diabetes (Fu, X., et al., 2015). In cells, AMPK consists of catalytic α-subunits (α1 and α2), regulatory β-subunits (β1 and β2), and γ-subunits (γ1, γ2 and γ3). Skeletal muscle, which occupies a significant part of our body, induces energy imbalance through the use of ATP during exercise, thereby increasing intracellular AMP and ADP concentrations. The binding of ADP and AMP in the γ-subunit causes a structural change that activates the AMPK enzyme up to 10 times through an allosteric mechanism. This structural change also triggers phosphorylation of threonine at position 172 (α-Thr172) of the catalytic α-subunit by the upper gene LKB1 (liver kinase B1), and protects the dephosphorylation by protein phosphatase, resulting in 100 activity. Times increase. Therefore, it is known that when the allosteric effect and α-Thr172 phosphorylation are used together, AMPK is activated by up to 1000 times or more. AMPK is also activated by the rise of the concentration of Ca ^{2 +} cells with α-Thr172 phosphorylation catalyzed by CaMKKβ (calcium / calmodulin-dependent protein kinase kinase β). AMPK activation in muscles through exercise is important for the treatment of various diseases mediated by AMPK activation (Kjobsted, R., et al., 2018).

Skeletal muscles, which occupy a large part of the human body, do not divide, are made of multinucleated muscle fibers, and are made during the formation of embryos. After the embryonic process is over, muscle is formed by postnatal growth or myogenesis. In particular, it has been reported that muscle differentiation for muscle regeneration occurs when the muscle is damaged by a muscle frostbite, sprain, or bruise. In muscle differentiation, satellite cells are activated first, and the activated satellite cells are differentiated into myoblasts (Morgan, J.E., et al., 2003). Differentiated myoblasts are proliferated and fusion occurs between myoblasts to develop into myotubes. These root canal cells gather to form muscle fibers, and the muscle fibers form bundles to finally form muscle.

According to a recent study, AMPKα1 is a dominant isoform in satellite cells, and Warburg-like glycolysis through an informal shh (sonic hedgehog) signal transduction of muscle cells during muscle regeneration. It has been shown to promote muscle regeneration by improving it. These results were also confirmed through the fact that AMPKα1 knock-out satellite cells have reduced AMPK activation and inhibited proliferation and differentiation of muscle progenitor cells (Fu, X., et al., 2015). ). Therefore, AMPK activation provides an effective drug target even in the process of promoting muscle regeneration. On the other hand, if a problem occurs during muscle differentiation such as aging, differentiation from satellite cells to myoblasts, division of myoblasts, etc., muscle atrophy, myopathy, muscle injury, muscle dystrophy dystrophy), sarcopenia, myoneural conductive disease and nerve injury (Bonaldo, P., et al., 2013; Wagatsuma) , A., et al., 2014).

In addition, the sarcopenia may appear due to cachexia. Cachexia is a type of chronic wasting complex syndrome and refers to a high degree of systemic weakness that can be seen at the end of cancer, tuberculosis, and hemophilia. In particular, it is accompanied by chronic diseases such as malignant tumors, chronic obstructive pulmonary disease, and chronic heart failure, and weight loss accompanied by anorexia, muscle mass and body fat reduction, and inflammatory reactions appear. Muscle loss due to cachexia is a complex syndrome due to continuous decrease in skeletal muscle mass and functional impairment. Unlike aging with progressive and gradual loss of muscle mass, and muscle loss caused by muscle differentiation disorder, acute muscle loss symptoms Appears. These differences in physiological characteristics also show differences in prevention and treatment. Therefore, even if a symptom of muscle loss occurs, treatment tailored to the characteristics of cachexia, aging, and muscle differentiation disorders, depending on the cause of the occurrence, is required (Seungwan Ryu, 2017).

As a method for overcoming muscle disorders and diseases, a method of regenerating muscle cells has been recently reported, and the regeneration of these muscle cells stimulates satellite cells existing outside the muscle cells, causing the satellite cells to divide, resulting in muscle tissue. It is known to form. The regeneration of muscle cells not only repairs damaged muscles, but also regulates metabolic syndrome, including natural muscle loss due to aging (Conboy, IM, et al., 2003) and obesity and diabetes (Mounier, R., et al., 2015). ) And wasting syndrome cachexia (Bossola, M., et al., 2016; Ramamoorthy, S., et al., 2009).

Gynostemma longipes is a perennial vine plant belonging to the Cucurbitaceae family.It grows naturally in Vietnam and southern China, and is a perennial plant growing in Ulleungdo and southern regions of Korea, Vietnam, Japan, and China. Gynostemma pentaphyllum ) and similar in external shape.

Dole ( Gynostemma pentaphyllum ) is a vine plant whose stem grows tangled around other objects with tendrils and grows, dried leaves, and is used as a "stone tea". Doloree is called a rhizome or outpost, and has been traditionally used for respiratory and circulatory diseases such as geodam, bronchitis, phlegm, seed poisoning, poisoning, and seawater. Leaves other than stones grow alternately, and there are multicellular white hairs on both sides, but soon disappears and lobules are usually 5, but there are 3-7 individual.

Ginostema longipes is characterized by relatively many leaves with 7 to 9 leaves compared to other stones. It is relatively difficult to distinguish between stones and leaves in Vietnam. However, Ginostema longipes is characterized by having more leaves than other stones, pubescent stems, and bitter taste than stones. Research on Ginostema longipes has not been conducted much, and studies on the chemical composition are recently being attempted, and a research team in Vietnam has been working with Gynostemma longipes CYWu (gylongiposide II-III). II-III) and gypentoside A were isolated (Anh PT, et al., 2015).

Ginostema longipes VK1 is a novel variety discovered by the present inventors, showing morphological differences from other plants of the genus Gynostemma spp., and has a single-base polymorphism different from the previously known Ginostem longipes. This is a confirmed new cultivar, and it was confirmed that the chemical composition differs in chemical composition not only from the genus Ginostem but also from the genus Ginostem longipes (Korean Patent No. 1811048).

Thus, the present inventors isolated compounds from the extract in the process of studying the Ginostem longipes VK1 extract, and these Ginostem longipes VK1 extracts and the compounds isolated therefrom are various such as glucose transfer, fatty acid synthesis, cholesterol biosynthesis, etc. By activating AMPK involved in physiological action and further, by activating AMPK in adipocytes and muscle cells, it was confirmed that muscle diseases, obesity, diabetes or metabolic syndrome can be treated, thereby completing the present invention.

As a prior art, Korean Patent Registration No. 1811048 describes Ginostema longipes VK1 extract and a compound isolated therefrom, but the AMPK activation and muscle regeneration effect of the present invention or metabolic syndrome related to the effect of preventing or treating cognitive dysfunction. No prophylactic or therapeutic effect on the disease is described or implied. In addition, Korean Patent Application Publication No. 2014-0108621 discloses a Gynostemma pentaphyllum extract containing a zipenoside compound, and Korean Patent No. 0945382 discloses a Gynostemma pentaphyllum extract, but the genos of the present invention Theme Longipes VK1 ( Gynostemma longipes VK1) extract and the effect related to AMPK activation of a compound isolated therefrom are not described, and thus there is a difference from the composition of the present invention. Chinese Patent No. 103238741 describes Gynostemma longipes , but the compounds of the present invention and their AMPK activating effects are not described at all, which is different from the composition of the present invention.

Korean Patent Registration No. 1811048, Ginostema longifes VK1 extract or a composition for preventing or treating cognitive dysfunction comprising as an active ingredient a longifenoside A compound isolated therefrom, 2017. 12. 14. Registration. Korean Patent Publication No. 2014-0108621, A composition for the treatment or prevention of type 2 diabetes, obesity, or hyperlipidemia, including a zipenoside extract other than Dole, 2014. 09. 12. Published. Registered Korean Patent No. 0945382, a pharmaceutical composition for the treatment and prevention of neurodegenerative diseases containing extract of vine tea as an active ingredient, 2010. 02. 24. Registered Chinese Patent No. 103238741, Nutritious animal food for improving pork quality, 2014. 05. 14.

Ryu Seung-Wan, Clinical characteristics of sarcopenia and cachexia, J. Clin. Nutr., 9(1), 2-6, 2017. Ha, Joo-heon, et al., The role of AMPK in the regulation of energy metabolism in living bodies, Journal of the Korean Endocrinology Society, 25(1), 9-17, 2010. Anh P.T., et al., Damarane-type saponins from Gynostemma longipes and their cytotoxicity activity, Nat. Prod. Commun., 10(8), 1351-1352, 2015. Bonaldo, P., et al., Cellular and molecular mechanism of muscle atrophy, Dis. Model & Mech., 6, 25-39, 2013. Bossola, M., et al., Skeletal muscle regeneration in cancer cacchexia, Clin. Exp. Pharmacol. Physiol., 43(5), 522-527, 2016. Conboy, I.M., et al., Notch-mediated restoration of regenerative potential to aged muscle. Science, 302(5650), 1575-1577, 2003. Fu, X., et al., AMP-activated protein kinase stimulates Warburg-like glycolysis and activation of satellite cells during muscle regeneration, Journal of Biological Chemistry, 290(44), 26445-26456, 2015. Hardie, D.G., AMP-activated protein kinase as a drug target, Annu. Rev. Pharmacol. Toxicol., 47, 185-210, 2007. Hardie, D.G., AMP-activated/SNF1 protein kinases: conserved guardians of celllular energy, Nat. Rev. Mol. Cell Biol., 8(10), 774-785, 2007(1). Kjobsted, R., et al., AMPK in skeletal muscle function and metabolism, FASEB J., 32(4), 1741-1777, 2018. Mounier, R., et al., Expanding roles for AMPK in skeletal muscle plasticity, Trends Endocrinol Metab. 26(6), 275-286, 2015. Morgan, J.E., et al., Muscle satellite cells. Int. J. Biochem. Cell Biol., 35(8), 1151-1156, 2003. Ramamoorthy, S., et al., Decreased Jun-D and myogenin expression in muscle wasting of human cachexia, Am. J. Physiol. Enodcrinol. Metab. 297(2), E239-E401, 2009. Rasmus, K., et al., AMPK in skeletal muscle function and metabolism, FASEB J. 32(4), 1741-1777, 2018. Tan, M.J., et al., Antidiabetic activities of triterpenoids isolated form bitter melon associated with activation of the AMPK pathway, Chem. Biol., 15(3), 263-273, 2008. Wagatsuma, A., et al., Vitamin D signlaing in Myogenesis: Potential for Treatment of Sarcopenia, BioMed Research International, 2014, 121254, 2014. Yamamoto, N., et al., Rapid Preparation of a Plasma Membrane Fraction: Western Blot Detection of Translocated Glucose Transporter 4 from Plasma Membrane of Muscle and Adipose Cells and Tissue, John Wiley&Sons, Inc.: Hoboken, NJ, USA, 6, 29.18.1-29.18.12, 2001.

An object of the present invention is to provide a composition for the prevention or treatment of AMPK-related diseases comprising, as an active ingredient, a Gynostemma longipes VK1 ( Gynostemma longipes VK1) extract or a compound isolated therefrom.

In addition, it is to provide a novel compound isolated from the extract of Ginostema longipes VK1 and a method of separation thereof.

The present invention is 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α of Formula 1 below. -L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L- rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside) (compound 1), 3β,20(S)-dihydroxydamar-24-ene- 12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20- O-β-D-glucopyranoside (3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L -rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyranoside) (compound 2), 3β,20(S)-dihydroxydamar-24-ene-12, 23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D- Glucopyranoside (3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α -L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside) (Compound 3), Gypentonoside A (Compound 4), 3β,20(S)-dihydroxydamar-24 -En-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3β,20(S)-dihydroxydammar-24-en-12 ,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside) (Compound 5), 3β,20(S)-dihydroxydamar-24-ene-12 ,23-dione (3β,20(S)-dihydroxydammar-24-en-12,23 -dione) (Compound 6), 20(S)-hydroxydammar-24-en-3,12,23-trione (20(S)-hydroxydammar-24-en-3,12,23-trione) (Compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamno Pyranosyl-(1→3)]-β-D-glucopyranoside (3β,20(S),25-trihydroxydammaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2) )-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside) (Compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O- α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (3β-hydroxydammar-20,24-dien-12 ,23-dione-3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside) (Compound 9), 4,20( S)-dihydroxy-3,4-seco-damar-24-ene-12,23-dione-3-oic acid (4,20(S)-dihydroxy-3,4-seco-dammar-24- en-12,23-dion-3-oic acid) (Compound 10), 4,20(S),25-trihydroxy-3,4-seco-damaran-12,23-dione-3-oic acid (4,20(S),25-trihydroxy-3,4-seco-dammaran-12,23-dion-3-oic acid) (Compound 11), 4-hydroxy-3,4-seco-22,23 ,24,25,26,27-hexanordammaran-12,20-dione-3-oic acid (4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordammaran-12 ,20-dion-3-oic acid) (compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L -Rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (3β-hydr oxy-22,23,24,25,26,27-hexanordammaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl(1→3)] -β-D-glucopyranoside) (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyra Nosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (3β -hydroxy-22,23,24,25,26,27-hexanordammaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3 )]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside)(Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3 -O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β -D-glucopyranoside (3β,20(S),25-trihydroxydammaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1) →3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside) (Compound 15), 3β-hydroxydamar-20,24-diene-12,23-dione-3 -O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β -D-glucopyranoside (3β-hydroxydammar-20,24-dien-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→ 3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside) (Compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene -12-one-3-O-α-L-rhamnopyranosyl-(1 →2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (3β,20(S),25-trihydroxydammar-23(E)-en-12-one -3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside) (compound 17), 3β,20(S),25 -Trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3) ]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (3β,20(S),25-trihydroxydammar-23(E)-en-12-one-3 -O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside)( Compound 18) and 3β,20(S)-dihydroxydamar-24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyrano Seed (3β,20(S)-dihydroxydammar-24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside) (Compound 19) Pharmaceutical compositions for the prevention or treatment of AMPK (5′-AMP-activated protein kinase)-related diseases containing Gynostemma longipes VK1 ( Gynostemma longipes VK1) extract containing one or more compounds as active ingredients, animal drugs, It relates to an improved health functional food composition and a composition for animal feed.

[Formula 1]

The Ginostem longifes VK1 extract is a group consisting of Ginostem longifes VK1 in water, lower alcohols of C1-4, acetic esters of C1-4, acetone, and methylethylketone It may be an extract extracted with one or more solvents selected from.

In addition, the present invention is 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)- of Formula 1 [α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23- Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β- D-glucopyranoside (compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2 )-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β, 20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5 ), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trio Yes (Compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L -Rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy -3,4-Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara -12,23-dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione- 3-Oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-( 1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27 -Hexanordamaran-12, 20-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→ 6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15) , 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→ 3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23( E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyrano Seed (Compound 17), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S )-Dihydroxydamar-24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) It relates to a pharmaceutical composition for the prevention or treatment of AMPK-related diseases containing at least one selected compound as an active ingredient, an animal drug, a health functional food composition for improvement, and a composition for animal feed.

The compound is preferably 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α- L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3 -O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside ( Compound 3), zipentonoside A (compound 4), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1 →2)-β-D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydr Roxidamar-24-ene-3,12,23-trione (compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L- Rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 4,20(S)-dihydroxy- 3,4-Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara- 12,23-dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3 -Oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1 →2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27- Hexanordamaran-12,20-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L- Rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one- 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17) and 3β,20 (S)-dihydroxydamar-24 -En-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (Compound 19) is one or more compounds selected from the group consisting of.

The composition can activate AMPK.

The AMPK-related disease may be muscle disease, obesity, diabetes or metabolic syndrome.

The muscle diseases include muscle atrophy, myopathy, muscle injury, muscle dystrophy, myasthenia, sarcopenia, myoneural conductive disease, In the group consisting of dermatomyositis, diabetic amyotrophy, nerve injury, amyotrophic lateral sclerosis (ALS), cachexia, and degenerative muscle diseases. Can be chosen.

The cachexia is cancer, AIDS (acquired immune deficiency syndrome), celiac disease, chronic obstructive pulmonary disease (COPD), multiple sclerosis, rheumatoid arthritis, Chronic heart failure, congestive heart failure, uremia, tuberculous, Crohn's disease, untreated or severe type 1 diabetes, anorexia nervosa and hormone deficiency. It may be wasting syndrome.

In addition, the present invention is Ginostema extracted by using one or more selected from the group consisting of water, lower alcohols of C1-4, acetic acid esters of C1-4, acetone and methyl ethyl ketone as a solvent. 1 step of obtaining a Longifes VK1 extract; A second step of securing a fraction by adsorbing the Ginostema longifes VK1 extract of the first step on an ion exchange resin and eluting with an organic solvent; And the fraction of the second step is directly crystallized or subjected to column chromatography to obtain 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L- of Formula 1 Rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxyda Mar-24-en-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D- Glucopyranosyl-20-O-β-D-glucopyranoside (compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α- L-Rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (Compound 3), Zipen Tonoside A (Compound 4), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β -D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24 -Ene-3,12,23-trione (Compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-( 1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23 -Dione-3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4-seco-damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydre Roxy-3,4-Seco-Damaran-12,23-dione-3-oic acid (Compound 11), 4-hydroxy-3,4-Seco-22,23,24,25,26,27-hexa Nordamaran-12,20-dione-3-oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydr Roxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxy Damaran-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyra Nosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamno Pyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside ( Compound 16), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α -L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (Compound 17), 3β,20(S),25-trihydroxydamar-23(E)-ene-12 -One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6) )]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar-24-en-12-one-3-O-α-L-rhamnopyranosyl-( 3 step of separating at least one compound selected from the group consisting of 1→2)-β-D-glucopyranoside (Compound 19); It relates to a method for separating compounds 1 to 19 of Formula 1, characterized in that consisting of.

The present invention also provides a novel compound 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyranoside (compound 2), 3β,20 (S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L -Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3- O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-ene-12,23- Dione (Compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione (Compound 7), 3β,20(S), 25-trihydroxydamaran-12, 23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8) , 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→ 2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4-seco-damar-24-ene-12,23-dione-3-o Iksan (Compound 10), 4,20(S), 25-trihydroxy-3,4-seco-damaran-12,23-dione-3-oic acid (Compound 11), 4-hydroxy-3, 4-Seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26 ,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β- D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl -(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 14 ), 3β,20(S ),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]- [α-L-Rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar-20,24-diene-12,23-dione-3- O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β- D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-( 1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β,20(S),25-trihydroxydamar-23 (E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamno Pyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar-24-en-12-one-3-O-α- It relates to L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19).

[Formula 2]

Hereinafter, the present invention will be described in detail.

The present invention is 3β,20(S)-dihydroxydamar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α of Formula 1 -L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione- 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D- Glucopyranoside (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β,20( S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione (Compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione ( Compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamno Pyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3 ,4-Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12 ,23-dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3- Oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→ 2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexa Nordamaran-12,20-D One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6) ]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1 →2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β -Hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3) ]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E) -En-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside ( Compound 17), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α -L-Rhamnopyranosyl-(1→3)]-[α-L-Rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)- Dihydroxydamar-24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) selected from the group consisting of It relates to a composition for the prevention or treatment of AMPK-related diseases containing Ginostema rongipes VK1 extract containing at least one compound as an active ingredient.

The Ginostem rongifes VK1 extract is an extract obtained by extracting Ginostem rongifes VK1 with at least one solvent selected from the group consisting of water, C1-4 lower alcohols, C1-4 acetic acid esters, acetone and methyl ethyl ketone. Can be As the lower alcohols of C1 to 4, methanol, ethanol, alcohol, propanol, isopropanol, butanol, etc. can be used, and the acetic acid esters of C1 to 4 are low toxicity according to the Ministry of Food and Drug Safety "Standard Guidelines for Drug Residual Solvents" Classified as a solvent, methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, etc. You can use It is preferably water and a C1-4 lower alcohol, more preferably ethanol, and most preferably 70% [v/v] ethanol.

The solvent may be added in a weight of 2 to 500 times the weight of Ginostema longifes VK1.

In addition, the Ginostem rongifes VK1 extract is made of at least one solvent selected from the group consisting of water, C1-4 lower alcohols, C1-4 acetic acid esters, acetone and methyl ethyl ketone. It may be a fraction obtained by diluting the concentrated solution obtained by diluting the extracted extract and then adding the diluted solution to an ion exchange resin and eluting with an organic solvent.

The diluent may be made by adding distilled water to the concentrate of the extract of Ginostema longipes VK1, and the distilled water may be added in a weight of 5 to 200 times the weight of the concentrate.

The ion exchange resin may be selected from Diaion HP-20, SP825, AXT204, XAD1600T, MN200, SP70, SP710, and the like. It is preferably Diaion HP-20, SP70 or SP710, most preferably as a synthetic adsorbent, a standard that can be used by the US FDA for food and pharmaceutical products among aromatic unsubstituted resins (CFR173.62, Code of Federal Regulations Title 21). ) Is an adsorption resin that satisfies SP70 or SP710.

The organic solvent may be a lower alcohol of C1 to 4, an acetic acid ester of C1 to 4, and acetone. The lower alcohol of C1 to 4 may be methanol, alcohol, ethanol, propanol, isopropanol, butanol, and the like, and the acetic acid ester of C1 to 4 may be methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate Etc. Ethanol and acetone are preferred, and 95% [v/v] ethanol is most preferred.

In addition, the present invention is 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)- of Formula 1 [α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23- Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β- D-glucopyranoside (compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2 )-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β, 20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5 ), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trio Yes (Compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L -Rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy -3,4-Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara -12,23-dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione- 3-Oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-( 1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27 -Hexanordamaran-12, 20-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→ 6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15) , 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→ 3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23( E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyrano Seed (Compound 17), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S )-Dihydroxydamar-24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) It relates to a composition for preventing or treating AMPK-related diseases containing one or more selected compounds as an active ingredient.

The compound of Formula 1 may be isolated from the Ginostema longifes VK1 extract.

The compound of Formula 1 isolated from the Ginostem longipes VK1 extract can be obtained by fractionating the Ginostem longipes VK1 extract by chromatography, and the chromatography is performed by Diaion HP-20 column chromatography (Diaion HP-20 column chromatography), silica gel column chromatography, reverse phase silica gel column chromatography, RP-18 column chromatography, LH-20 column chromatography ( LH-20 column chromatography), preparative reversed-phase high performance chromatography, medium pressure liquid chromatography, high-performance liquid chromatography (HPLC), etc. You can choose and use it.

Meanwhile, the compound of the present invention may be synthesized according to a conventional method in the art, and may be prepared as a pharmaceutically acceptable salt.

The AMPK-related disease may be muscle disease, obesity, diabetes, or metabolic syndrome, but is not limited thereto.

The muscle disease is a disease that may occur due to a lack of muscle cells, an abnormal decrease or dysfunction of the muscle cells, and includes muscular atrophy, myopathy, muscle injury, muscular dystrophy, Myasthenia, sarcopenia, myoneural conductive disease, dermatomyositis, diabetic amyotrophy, nerve injury, amyotrophic lateral sclerosis , ALS), cachexia, degenerative muscle diseases, and the like, but are not limited thereto.

The cachexia is also referred to as wasting syndrome, and is characterized by weight loss accompanied by anorexia, loss of muscle mass and body fat, and inflammatory reactions. These cachexia include cancer, acquired immune deficiency syndrome (AIDS), celiac disease, chronic obstructive pulmonary disease (COPD), multiple sclerosis, rheumatoid arthritis, and Chronic heart failure, congestive heart failure, uremia, tuberculous, Crohn's disease, untreated or severe type 1 diabetes, anorexia nervosa, hormone deficiency, etc. It may appear by, but is not limited thereto.

The degenerative muscle disease is the continuous destruction of muscles, including Duchenne muscular dystrophy, Becker's muscular dystrophy, limb-girdle muscular dystrophy, congential muscular dystrophy, Facioscapulohumeral muscular dystrophy, myotonic dystrophy, oculopharyngeal muscular atrophy, distal muscular dystrophy, and emery muscular-dreifus trophy have.

The diabetes may be type 1 diabetes or type 2 diabetes. It is preferably type 2 diabetes.

The metabolic syndrome refers to a set of abnormal conditions such as an increase in body fat, an increase in blood pressure, an increase in blood sugar, and an abnormality in blood lipids that increase the risk of cerebrovascular disease and diabetes, and can be improved by reducing body fat and treating diabetes. have.

The composition for preventing or treating AMPK-related diseases including the Ginostem longipes VK1 extract or a compound isolated therefrom may activate AMPK.

The'AMPK (5'-AMP-activated protein kinase)' of the present invention is activated by a decrease in the energy state of the cell, such as the nutritional state or exercise of the cell, and the activation of AMPK is various By controlling the phosphorylation of enzymes, it affects various physiological functions such as glucose transfer, fatty acid synthesis, and cholesterol biosynthesis.

The activation of AMPK inhibits the synthesis of fatty acids and cholesterol, promotes fatty acid oxidation and sugar absorption, and promotes muscle regeneration.

The activation of AMPK may increase fatty acid oxidation by phosphorylating and inactivating acetyl-CoA carboxylase (ACC), an enzyme required for fatty acid synthesis.

The composition for preventing or treating AMPK-related diseases including the Ginostema longipes VK1 extract or a compound isolated therefrom may be a pharmaceutical composition.

The pharmaceutical composition may include the Ginostema longifes VK1 extract or a compound isolated therefrom, and a pharmaceutically acceptable carrier.

Each of the pharmaceutical compositions can be formulated and used in the form of oral dosage forms such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, and aerosols, external preparations, suppositories, and sterile injectable solutions according to conventional methods. Carriers, excipients and diluents that may be included in the pharmaceutical composition include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum acacia, alginate, gelatin, calcium phosphate, calcium silicate, cellulose , Methyl cellulose, microcrystalline cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, and mineral oils. In the case of formulation, it is prepared using diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrating agents and surfactants. Solid preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, and these solid preparations contain at least one excipient, for example, in the Ginostema longifes VK1 extract of the present invention or a compound isolated therefrom. , Starch, calcium carbonate, sucrose or lactose, gelatin, etc. are mixed and prepared. In addition to simple excipients, lubricants such as magnesium stearate and talc are also used. Liquid preparations for oral use include suspensions, liquid solutions, emulsions, syrups, etc. In addition to water and liquid paraffin, which are commonly used simple diluents, various excipients such as wetting agents, sweetening agents, fragrances, and preservatives may be included. . Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, and suppositories. Non-aqueous solvents and suspensions may include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate. As a base for suppositories, witepsol, macrogol, tween 61, cacao butter, laurin paper, glycerogelatin, and the like may be used.

The dosage of the pharmaceutical composition will vary depending on the age, sex, and weight of the subject to be treated, the specific disease or pathology to be treated, the severity of the disease or pathology, the route of administration, and the judgment of the prescriber. Dosage determination based on these factors is within the level of one of skill in the art, and dosages are generally in the range of 0.1-1000 mg/kg/day. A more preferred dosage is 0.5 to 500 mg/kg/day. Administration may be administered once a day, or may be divided several times. The above dosage does not limit the scope of the present invention in any way.

The pharmaceutical composition may be administered to mammals such as mice, livestock, companion animals, and humans by various routes. All modes of administration can be expected and can be administered, for example, by oral, rectal or intravenous, intramuscular, subcutaneous, intrauterine mucosal or cerebrovascular injection.

The pharmaceutical composition can be used to prevent or treat obesity, diabetes or metabolic syndrome by promoting fatty acid burning by activating AMPK in muscle cells and storing glucose into muscle and fat.

The pharmaceutical composition may also be used to prevent or treat muscle diseases by promoting the proliferation of myoblasts and activating AMPK, a signaling material important for muscle regeneration, thereby inducing muscle regeneration.

In addition, the composition for preventing or treating AMPK-related diseases including the Ginostema longipes VK1 extract or a compound isolated therefrom may be a health functional food composition.

The health functional food composition may include the Ginostema longifes VK1 extract or a compound isolated therefrom, and a food additive acceptable for food.

The Ginostema longipes VK1 extract or a compound isolated therefrom may be included in the health functional food composition of the present invention in an amount of 0.001 to 100% by weight.

The health functional food composition of the present invention includes the form of tablets, capsules, pills, liquids, etc., and as a food to which the Ginostema longipes VK1 extract of the present invention or a compound isolated therefrom can be added, for example For example, there are various foods, beverages, gum, tea, vitamin complexes, and health functional foods.

In another aspect of the present invention, a composition for preventing or treating AMPK-related diseases comprising the Ginostema longifes VK1 extract of the present invention or a compound isolated therefrom as an active ingredient is muscle disease, obesity, diabetes or metabolic syndrome It provides a composition for improving animal feed.

The composition for animal feed may include a feed additive. The feed additive of the present invention corresponds to the auxiliary feed in the feed management method.

The kind of animal feed is not particularly limited, and feed commonly used in the art may be used. Non-limiting examples of the feed include vegetable feeds such as grains, root fruits, food processing by-products, algae, fiber, pharmaceutical by-products, oils and fats, starches, meals or grain by-products; Animal feeds such as proteins, inorganic logistics, oils and fats, minerals, single-cell proteins, zooplanktons, or food. These may be used alone or in combination of two or more.

The present invention also relates to a method for separating compounds 1 to 19 of Formula 1, wherein Ginostema rongifes VK1 is converted to water, C1 to 4 lower alcohol, C1 to 4 acetic acid ester, acetone and methyl ethyl ketone. 1 step of obtaining a Ginostem longipes VK1 extract extracted using at least one selected from the group consisting of a solvent; A second step of securing a fraction by adsorbing the Ginostema longifes VK1 extract of the first step on an ion exchange resin and eluting with an organic solvent; And the fraction of the second step is directly crystallized or subjected to column chromatography to obtain 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L- of Formula 1 Rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxyda Mar-24-en-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D- Glucopyranosyl-20-O-β-D-glucopyranoside (compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α- L-Rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (Compound 3), Zipen Tonoside A (Compound 4), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β -D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24 -Ene-3,12,23-trione (Compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-( 1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23 -Dione-3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4-seco-damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydre Roxy-3,4-Seco-Damaran-12,23-dione-3-oic acid (Compound 11), 4-hydroxy-3,4-Seco-22,23,24,25,26,27-hexa Nordamaran-12,20-dione-3-oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydr Roxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxy Damaran-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyra Nosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamno Pyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside ( Compound 16), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α -L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (Compound 17), 3β,20(S),25-trihydroxydamar-23(E)-ene-12 -One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6) )]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar-24-en-12-one-3-O-α-L-rhamnopyranosyl-( 1→2)-β-D-glucopyranoside (compound 19) in three steps of separating at least one compound selected from the group consisting of;

The Ginostema longifes VK1 extract of the first step may be concentrated to obtain a concentrate, and the obtained concentrate may be diluted and added to the ion exchange resin of the second step.

The ion exchange resin of the second step may be selected from Diaion HP-20, SP825, AXT204, XAD1600T, MN200, SP70, SP710, and the like. It is preferably Diaion HP-20, SP70 or SP710, most preferably as a synthetic adsorbent, a standard that can be used by the US FDA for food and pharmaceutical products among aromatic unsubstituted resins (CFR173.62, Code of Federal Regulations Title 21). ) Is an adsorption resin that satisfies SP70 or SP710.

The organic solvent of the second step may be a lower alcohol of C1 to 4, an acetic acid ester of C1 to 4, and acetone. The lower alcohol of C1 to 4 may be methanol, alcohol, ethanol, propanol, isopropanol, butanol, and the like, and the acetic acid ester of C1 to 4 may be methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate Etc. Ethanol and acetone are preferred, and 95% [v/v] ethanol is most preferred.

The column chromatography in the third step is Diaion HP-20 column chromatography, silica gel column chromatography, reverse phase silica gel column chromatography, RP-18 column chromatography, LH-20 column chromatography, preparative reversed-phase high performance chromatography, medium pressure liquid chromatography (medium pressure liquid chromatography), high-performance liquid chromatography (HPLC), etc. can be selected and used.

The present invention relates to a composition for the prevention or treatment of AMPK-related diseases comprising, as an active ingredient, a Gynostemma longipes VK1 extract or a compound isolated therefrom, the Ginostema longipes VK1 extract or It was confirmed that the isolated compounds activate AMPK, which is involved in various physiological actions such as glucose transfer, fatty acid synthesis, and muscle regeneration, and promote the absorption of sugar into adipocytes as well as promote the proliferation of myoblasts.

Through this, it is expected that the composition of the present invention can be used to develop excellent therapeutic agents for AMPK-related diseases such as muscle diseases, obesity, diabetes, and metabolic syndrome, as well as health functional foods for improvement, and compositions for animal feed.

1 is a result of confirming the cytotoxicity of compounds isolated from the extract of Ginostema rongifes VK1 of the present invention, (A) and (C) are the toxicity in adipocytes 3T3-L1 cells, (B) and ( D) shows toxicity in myoblasts, C2C12 cells. (A) and (B) show cytotoxicity when compounds 10 to 14 were treated at a concentration of 40 μM, and (C) and (D) show cytotoxicity according to the treatment concentration of compound 19 (10, 20, 30 μM). Are giving.
2 is a result of confirming the AMPK activation (phosphorylation) and ACC inactivation (phosphorylation) promoting effects of the Ginostem longipes VK1 extract of the present invention or the compounds isolated therefrom, (A) is a result of the Ginostem longipes VK1 extract , (B) shows the results of confirming the AMPK activation and ACC inactivation of compounds 1 to 19 isolated from the Ginostema longifes VK1 extract.
3 is a result of confirming the effect of promoting myoblast proliferation of the Ginostem longipes VK1 extract of the present invention or the compounds isolated therefrom, (A) and (B) are the roots according to the Ginostem longipes VK 1 extract treatment The results of confirming the blast proliferation promoting effect through MTT (A) and WST (B) assays, (C) shows the myoblast proliferation promoting effect of Compounds 1 to 9 isolated from Ginostema rongifes VK1 extract, MTT and WST. The results confirmed through the assay are shown.
Figure 4 shows the results of confirming whether or not the Ginostema longifes VK1 extract of the present invention or Compound 1 isolated therefrom promotes cell proliferation of cancer cells.
5 is a result of confirming the DNA synthesis promoting effect in the proliferation of myoblasts of Ginostema longifes VK1 extract of the present invention or Compound 1 isolated therefrom, (A) is an immunochemical staining method, (B) is The results of confirming the effect of promoting DNA synthesis using flow cytometry are shown.
6 is a result of confirming the effect of promoting glucose uptake in adipocytes of the Ginostema longifes VK1 extract of the present invention or compounds 10 to 19 isolated therefrom, (A) is a fat of 2-NBDG, a fluorescent derivative of glucose The result of confirming the fluorescence image due to intracellular absorption, (B) shows the result of measuring the intracellular fluorescence intensity.
7 is a result of confirming the potential of the glucose transporter (GLUT4) in adipocytes of Ginostema longifes VK1 extract of the present invention or compounds 10, 11, 13 and 17 isolated therefrom, (A) is an adipocyte The result of confirming the amount of GLUT4 in the plasma membrane of the band as a band, (B) shows the result of quantifying the band (B).

Hereinafter, a preferred embodiment of the present invention will be described in detail. However, the present invention is not limited to the embodiments described herein and may be embodied in other forms. Rather, the contents introduced herein are thorough and complete, and are provided to sufficiently convey the spirit of the present invention to those skilled in the art.

<Example 1. Preparation of Ginostema Longifes VK1 Extract>

Example 1-1. Manufacture of Ginostema Longifes VK1 extract

Gynostemma longipes VK1 of the present invention was collected in March and September 2016 in Ha Giang (GPS 23°08'34.9"N 105°25'42.6"E) of Vietnam. As a result, Professor Tran Van On of Hanoi University in Vietnam confirmed that it is Ginostema longifes VK1 based on external morphological features.

After adding 300 ml each of the extraction solvents corresponding to Table 1 to 10 g of Ginostema longipes VK1 of the powdered aerial parts (leaf and stem of a plant), each of the extraction solvents in Table 1 was mixed, and the ultrasonic extraction was repeated 3 times. An extract (3 x 300 mL) was obtained. The obtained extract was filtered and the solvent was evaporated in a vacuum to prepare each extract.

High-performance liquid chromatography (HPLC) was performed to confirm the content of Compound 1 of the present invention in the extract according to each of the extraction solvents prepared above. Each 1 g of the extract was dissolved in 1 ml of each extraction solvent and filtered through a 0.2 μm filter to prepare a sample for HPLC analysis. Using each sample, HPLC (Agilent 1200 HPLC system) (INNO C18 column, 4.6×250) according to the elution conditions of acetonitrile:water (1:9→1:0[v/v]) at 30°C. Mm, 5 µm particle size, flow rate 0.5 ml/min) was performed to analyze changes in the components and contents of Compound 1 of the present invention, and the results are shown in Table 1 below. At this time, the isolated and purified compound 1 of the present invention was used as a standard sample.

Extraction solvent Comprising Compound 1 of the present invention
Extraction amount (%) Compound 1 content of the present invention
(%) Distilled water 16.5 1.27 30% ethanol 18.5 6.6 50% ethanol 17.5 12.2 70% ethanol 14.0 16.5 95% ethanol 11.5 10.3 100% methanol 11.5 9.7 n-hexane 8 0 Acetone 4 1.3 Ethyl acetate 8.5 5.9 n-butanol 11.0 3.1

Example 1-2. Ginosthema Longifes VK1 Fraction Produce

500 ml of 70% [v/v] ethanol was added to 30 g of dried Ginostema longipes VK1, and ultrasonic extraction was repeated three times to obtain an extract. Thereafter, the extract was concentrated with a vacuum concentrator to obtain 5.1 g of the concentrate, and 500 ml of 20% [v/v] ethanol was added to the obtained concentrate to prepare a 20% [v/v] ethanol suspension. A 20% [v/v] ethanol suspension was passed through an SP70 resin to be adsorbed, and 500 ml of distilled water, 20% [v/v] ethanol, 40% [v/v] ethanol, corresponding to 100 times the weight of the extracted concentrate, 60%[v/v] ethanol, 80%[v/v] ethanol, and 95%[v/v] ethanol were sequentially treated to elute the adsorbed material to obtain a fraction, and finally, acetone was used as a solvent for adsorption. The material was eluted.

The content of the compound 1 of the present invention in the ethanol extract and fractions of Ginostema longifes VK1 70%[v/v] obtained through the above process was analyzed. At this time, the analysis method used the same method as the method for quantifying Compound 1 of the present invention of Example 1-1, and the results are shown in Table 2 below.

Extract or fraction Content of compound 1 of the present invention
(%) Configuration Concentration (mg/ml) Injection volume (µl) 70% ethanol extract One 10 14.0 Distilled water fraction One 10 0 20% ethanol fraction One 10 0 40% ethanol fraction One 10 1.2 60% ethanol fraction One 10 17.2 80% ethanol fraction One 10 47.7 95% ethanol fraction One 10 8.6

< Example 2. Compound separation>

For the separation of the compounds, in order to confirm the diversity of the compounds according to the collection period, the Ginostema longifes K1 of Example 1-1 was cultivated and collected in the Ha Giang area of Vietnam in March and September 2016. .

Based on the result of confirming the content of Compound 1 of the present invention in the Ginostema longifes VK1 fraction prepared in Example 1-2, 95% [v /v] An ethanol fraction was obtained. More specifically, the extract was obtained using 70% [v/v] ethanol from Ginostema longifes VK1 grown and collected in March, and the obtained extract was concentrated. Thereafter, the concentrate was suspended in 20% [v/v] ethanol and added to the SP70 resin, and the resin was washed with 30% [v/v] ethanol in which the compound 1 of the present invention does not leak out, and then 95% It was eluted with [v/v] ethanol to obtain a 95% [v/v] ethanol fraction. After concentrating the obtained 95% [v/v] ethanol fraction, a portion of the concentrated fraction (75 g) was added to ethyl acetate: methanol: distilled water (10:1:0.1→4:1:0.1[v/v/v]) After performing silica gel column chromatography (column size: 10 × 35 cm, particle size: 63-200 μm) under the concentration gradient elution conditions of, a thin-layer chromatography profile was obtained. Based on 9 fractions were obtained (C1 ~ C9).

The C7 fraction was crystallized in acetone solvent to obtain compound 1 (50.5 g).

After the C8 fraction was added to C18-reverse phase silica gel (RP-C18) column chromatography, it was eluted under a concentration gradient condition of methanol: distilled water (1:1→1:0[v/v]). After that, HPLC (column: Optima Pak C ₁₈ ) was successively carried out with an isocratic solvent of acetonitrile: distilled water (2:3 [v/v]) at a flow rate of 2 ml/min to obtain compound 2 (12.5 mg) and compound. 3 (21.3 mg) was isolated.

The C9 fraction was subjected to RP-C18 column chromatography under a concentration gradient condition of methanol: distilled water (1:1→1:0[v/v]) to obtain 8 small fractions (C9-1 to C9-8. ).

The C9-3 small fraction was subjected to HPLC (column: Optima Pak C ₁₈ ) with an isocratic solvent of acetonitrile: distilled water (3:6 [v/v]) at a flow rate of 2 ml/min to obtain compound 4 (20.4 mg). And compound 5 (10.5 mg) was isolated.

The C9-4 small fraction was subjected to HPLC (column: Optima Pak C ₁₈ ) with an isocratic solvent of acetonitrile: distilled water (2:3 [v/v]) at a flow rate of 2 ml/min to obtain compound 6 (22.2 mg). And compound 7 (17.1 mg) was isolated.

A part of the 95% [v/v] ethanol fraction was subjected to Sephadex LH-20 column chromatography and acetonitrile: distilled water (7:3[v] under the condition of 100% [v/v] methanol isocratic solvent. /v]), HPLC (column: Optima Pak C ₁₈ ) was successively performed under a flow rate of 2 ml/min with an isocratic solvent to separate compound 8 (18.5 mg) and compound 9 (16.0 mg).

In addition, 95% [v/v] ethanol fraction of 95% [v/v] ethanol fraction of Ginostem longipes VK1 cultivated and collected in March using the Ginostem longipes VK1 cultivated and collected in September 95 %[v/v] ethanol fraction was obtained. The obtained 95% [v/v] ethanol fraction was concentrated to obtain 35.6 g of a concentrate. The concentrate was dissolved in 95% [v/v] ethanol and left to separate into a precipitate (28.8 g) and a lysate (hereinafter referred to as GLS, 6.8 g).

The GLS was methanol: reverse phase silica gel (RP-18) under a concentration gradient condition of distilled water (1:1→1:0[v/v]) Six fractions were obtained using column chromatography (GLS-M1 to GLS-M6).

After the GLS-M4 fraction was added to RP-C18 column chromatography, acetonitrile: isocratic solvent of distilled water (1:1 [v/v]), HPLC (column: Optima Pak C ₁₈ ) under flow rate conditions of 2 ml/min. Was performed to isolate compound 10 (6.5 mg).

The GLS-M6 fraction was subjected to Sephadex LH-20 column chromatography and acetonitrile: isocratic solvent of distilled water (6:4 [v/v]) under 100% [v/v] methanol isocratic conditions, flow rate 2 ml/min. As conditions, HPLC (Optima Pak C ₁₈ ) was successively performed to separate compound 11 (22.5 mg) and compound 19 (15.5 mg).

After removing the compound 1 by recrystallization of the precipitate, silica gel column chromatography (column size: 10 x 35 cm, under the conditions of a concentration gradient of n-hexane: ethyl acetate (4:1 → 0:1 [v/v])) Particle size: 63-200㎛), followed by elution under a concentration gradient condition of ethyl acetate:methanol (20:1→0:1[v/v]), and then 11 samples based on the thin layer chromatography profile. Fractions were obtained (GLP-N1 ~ GLP-N11).

After applying the GLP-N6 fraction to Sephadex LH-20 column chromatography using 100% [v/v] methanol as a solvent, acetonitrile: distilled water (7:20 [v/v]) isocratic conditions HPLC was performed to isolate compound 12 (6.1 mg), compound 13 (17.0 mg) and compound 14 (12.0 mg).

The GLP-N11 fraction was subjected to RP-C18 column chromatography under acetonitrile:distilled water (1:1→0:1 [v/v]) concentration gradient to obtain three small fractions (GLP-N11-1 ~ GLP -N11-3).

The small fraction of GLP-N11-2 was subjected to HPLC (column: Optima Pak C ₁₈ ) under conditions of acetonitrile: distilled water (3:10 [v/v]) and a flow rate of 2 ml/min to obtain compound 15 (5.5 Mg), compound 17 (6.0 mg) and compound 18 (11.2 mg) were isolated.

remind A small fraction of GLP-N11-3 was subjected to HPLC with an isocratic solvent of acetonitrile:distilled water (2:5[v/v]) at a flow rate of 2 ml/min to isolate compound 16 (7.2 mg).

In addition, through the cultivation process of Ginostem longipes VK1 for standardization in the same place, the composition changes of the compounds of the two samples of Ginostem longipes VK1 were cultivated and collected in March and September, respectively. As a result, Ginostema longipes VK1 cultivated and collected in September increased the number of substituted sugars than Ginostem longipes VK1 cultivated and collected in March, resulting in an increase in the contents of compounds 3 and 4, but It was confirmed that there was no change in the overall composition.

Accordingly, it was confirmed that the diversity of the constituent compounds of the present invention's Ginostem longipes VK1 was confirmed for each collection period, but the compounds obtained in the present invention were present in both Ginostem longipes K1 collected at both collection periods. .

<Example 3. Confirmation of the physicochemical structure of the compound>

Example 3-1. 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl- (1→3)]-β-D-glucopyranoside (compound 1).

3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β -D-glucopyranoside;

White crystals;

-32.0 (c 0.1, 메탄올);[α]

-32.0 (c 0.1, methanol);

UV (methanol) λ _max (log ε) 244 nm (3.8);

IR (KBr) ν _max 3404, 2973, 2938, 1697, 1616, 1073, 1055, 1010 cm ^-1 ;

HRESIMS m/z 925.5157 [MH] ^- (calcd 925.5166);

^{For 1} H NMR and ¹³ C NMR data, see Tables 3 and 4 below.

Example 3-2. 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl- (1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyranoside (compound 2).

3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β -D-glucopyranosyl-20-O-β-D-glucopyranoside;

White amorphous powder;

-37.5 (c 0.1, 메탄올);[α]

-37.5 (c 0.1, methanol);

UV (methanol) λ _max (log ε) 244 nm (3.8);

IR (KBr) ν _max 3400, 2970, 2938, 1698, 1617, 1069, 1053, 1008 cm ^-1 ;

HRESIMS m/z 1087.5682 [MH] ^- (calcd 1087.5694);

^{For 1} H NMR and ¹³ C NMR data, see Tables 3 and 4 below.

Example 3-3. 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)- α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3).

3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl- (1→3)]-β-D-glucopyranoside;

White amorphous powder;

-35.2 (c 0.1, 메탄올);[α]

-35.2 (c 0.1, methanol);

UV (methanol) λ _max (log ε) 244 nm (3.8);

IR (KBr) ν _max 3402, 2971, 2938, 1702, 1616, 1060, 1054, 1010 cm ^-1 ;

HRESIMS m/z 967.5276 [MH] ^- (calcd 967.5272);

^{For 1} H NMR and ¹³ C NMR data, see Tables 3 and 4 below.

Example 3-4. Zipentonoside A (compound 4).

Gypentonoside A;

White amorphous powder;

-37.5 (c 0.1, 메탄올);[α]

-37.5 (c 0.1, methanol);

UV (methanol) λ _max (log ε) 244 nm (3.8), 190 nm (3.5);

IR (KBr) ν _max 3400, 2970, 2938, 1698, 1617, 1069, 1053, 1008 cm ^-1 ;

HRESIMS m/z 1087.5682 [MH] ^- (calcd 1087.5694).

Example 3-5. 3β,20(S)-dihydroxydamar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside ( Compound 5).

3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside;

White amorphous powder;

-33.0 (c 0.1, 메탄올);[α]

-33.0 (c 0.1, methanol);

UV (methanol) λ _max (log ε) 244 nm (3.7);

IR (KBr) ν _max 3403, 2972, 2940, 1702, 1616, 1060, 1054, 1010 cm ^-1 ;

HRESIMS m/z 780.4712 [MH] ^- , C ₄₂ H ₆₈ O ₁₃ (calcd 780.4710);

^{For 1} H NMR and ¹³ C NMR data, see Tables 3 and 4 below.

Example 3-6. 3β,20(S) - Dihydroxydamar -24-yen-12,23- Dione (Compound 6).

3β,20(S)-dihydroxydammar-24-en-12,23-dione;

White amorphous powder;

-33.0 (c 0.1, 메탄올);[α]

-33.0 (c 0.1, methanol);

UV (methanol) λ _max (log ε) 244 nm (3.9);

IR (KBr) ν _max 3403, 2972, 2940, 1702, 1616, 1060, 1010 cm ^-1 ;

HRESIMS m/z 472.5276 [MH] ^- , C ₃₀ H ₄₈ O ₄ (calcd 472.5270);

¹ H NMR and ¹³ C NMR data see Tables 5 and 6 below.

Example 3-7. 20(S)- Hydroxydamar -24-N-3,12,23-trione (Compound 7).

20(S)-hydroxydammar-24-en-3,12,23-trione;

White amorphous powder;

-38.0 (c 0.1, 메탄올);[α]

-38.0 (c 0.1, methanol);

UV (methanol) λ _max (log ε) 244 nm (3.8);

IR (KBr) ν _max 3403, 2972, 2940, 1702, 1616, 1060, 1054, 1010 cm ^-1 ;

HRESIMS m/z 470.5272 [MH] ^- , C ₃₀ H ₄₆ O ₄ (calcd 472.5270);

¹ H NMR and ¹³ C NMR data see Tables 5 and 6 below.

Example 3-8. 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1 →3)]-β-D-glucopyranoside (compound 8).

3β,20(S),25-trihydroxydammaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D -glucopyranoside;

White amorphous powder;

-32.5 (c 0.1, 메탄올);[α]

-32.5 (c 0.1, methanol);

IR (KBr) ν _max 3403, 2972, 2940, 1702, 1616, 1060, 1054, 1010 cm ^-1 ;

HRESIMS m/z 949.5129 [M+Na] ⁺ (calcd 949.5131), m/z 943.5374 [M+H] ⁺ ion peak (calcd 943.5380);

¹ H NMR and ¹³ C NMR data see Tables 5 and 6 below.

Example 3-9. 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2) )]-β-D-glucopyranoside (compound 9).

3β-hydroxydammar-20,24-dien-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D- glucopyranoside;

White amorphous powder;

-33.0 (c 0.1, 메탄올);[α]

-33.0 (c 0.1, methanol);

UV (methanol) λ _max (log ε) 275 nm (3.6);

IR (KBr) ν_max 3403, 2972, 2940, 1702, 1616, 1060, 1054, 1010㎝^-One;

HRESIMS m/z 907.5066 [MH] ^- , C ₄₈ H ₇₆ O ₁₆ (calcd 907.5061);

¹ H NMR and ¹³ C NMR data see Tables 5 and 6 below.

Example 3-10. 4,20(S)-dihydroxy-3,4- Seco - Damar -24-yen-12,23- Dion -3- Oiksan (Compound 10).

4,20(S)-dihydroxy-3,4-seco-dammar-24-en-12,23-dion-3-oic acid;

White amorphous powder;

+13.5 (c 0.2, 메탄올);[α]

+13.5 (c 0.2, methanol);

UV (methanol) λ _max (log ε) 254 nm (3.8);

IR (KBr) ν _max 3402, 2972, 2923, 1711, 1053, 1008 cm ^-1 ;

HRESIMS m/z 503.3382 [MH] ^- , C ₃₀ H ₄₇ O ₆ (calcd 503.3378);

^{For 1} H NMR and ¹³ C NMR data, see Tables 7 and 8 below.

Example 3-11. 4,20(S),25- Trihydroxy -3,4- Seco - Damaran -12,23- Dion -3- Oiksan (Compound 11).

4,20(S),25-trihydroxy-3,4-seco-dammaran-12,23-dion-3-oic acid;

White amorphous powder;

+4.9 (c 0.2, 메탄올);[α]

+4.9 ( c 0.2, methanol);

IR (KBr) ν _max 3398, 2972, 2361, 1701, 1051, 1013 cm ^-1 ;

HRESIMS m/z 521.3496 [MH] ^- , C ₃₀ H ₄₉ O ₇ (calcd 521.3484);

^{For 1} H NMR and ¹³ C NMR data, see Tables 7 and 8 below.

Example 3-12. 4-Hydroxy-3,4-Seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid (Compound 12).

4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordammaran-12,20-dion-3-oic acid;

White amorphous powder;

+5.5 (c 0.2, 메탄올);[α]

+5.5 ( c 0.2, methanol);

IR (KBr) ν _max 3400, 2970, 2938, 1698, 1617, 1069, 1053, 1008 cm ^-1 ;

HRESIMS m/z 405.2647 [MH] ^- , C ₂₄ H ₃₇ O ₅ (calcd 405.2646);

^{For 1} H NMR and ¹³ C NMR data, see Tables 7 and 8 below.

Example 3-13. 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L -Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13).

3β-hydroxy-22,23,24,25,26,27-hexanordammaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl(1→3 )]-β-D-glucopyranoside;

White amorphous powder;

+2.7 (c 0.2, 메탄올);[α]

+2.7 ( c 0.2, methanol);

IR (KBr) ν _max 3709, 2971, 2870, 1698, 1617, 1069, 1053, 1013 cm ^-1 ;

HRESIMS m/z 873.4525 [M-HCOO] ^- , C ₄₃ H ₆₉ O ₁₈ (calcd for 827.4489);

^{For 1} H NMR and ¹³ C NMR data, see Tables 7 and 8 below.

Example 3-14. 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L -Rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 14).

3β-hydroxy-22,23,24,25,26,27-hexanordammaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→ 3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside;

White amorphous powder;

+5.9 (c 0.2, 메탄올);[α]

+5.9 ( c 0.2, methanol);

IR (KBr) ν _max 3403, 2935, 1704, 1388, 1134, 1048, 1005 cm ^-1 ;

HRESIMS m/z 1019.5104 [M+HCOO] ^- , C ₄₉ H ₇₉ O ₂₂ (calcd 1019.5068);

¹ H NMR and ¹³ C NMR data see Tables 7 and 8 below.

Example 3-15. 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1 →3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15).

3β,20(S),25-trihydroxydammaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α- L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside;

White amorphous powder;

-1.5 (c 0.2, 메탄올);[α]

-1.5 ( c 0.2, methanol);

IR (KBr) ν _max 3401, 2971, 2923, 2371, 2320, 1053, 1008 cm ^-1 ;

HRESIMS m/z 1135.5946 [M+HCOO] ^- , C ₅₅ H ₉₁ O ₂₄ (calcd 1135.5906);

¹ H NMR and ¹³ C NMR data see Table 9 and Table 10 below.

Example 3-16. 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3 )]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16).

3β-hydroxydammar-20,24-dien-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L -rhamnopyranosyl-(1→6)]-β-D-glucopyranoside;

White amorphous powder;

-1.6 (c 0.2, 메탄올);[α]

-1.6 ( c 0.2, methanol);

UV (methanol) λ _max (log ε) 280 nm (3.7), 250 nm (3.8);

IR (KBr) ν _max 3400, 2972, 2942, 2371, 2320, 1053, 1013 cm ^-1 ;

HRESIMS m/z 1099.5730 [M+HCOO] ^- , C ₅₅ H ₈₇ O ₂₂ (calcd 1099.5694);

¹ H NMR and ¹³ C NMR data see Table 9 and Table 10 below.

Example 3-17. 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamno Pyranosyl-(1→3)]-β-D-glucopyranoside (compound 17).

3β,20(S),25-trihydroxydammar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3) ]-β-D-glucopyranoside;

White amorphous powder;

-2.5 (c 0.2, 메탄올);[α]

-2.5 ( c 0.2, methanol);

IR (KBr) ν _max 3400, 2971, 2921, 2346, 2313, 1053, 1008 cm ^-1 ;

HRESIMS m/z 973.5414 [M+HCOO] ^- , C ₄₉ H ₈₁ O ₁₉ (calcd 973.5378);

¹ H NMR and ¹³ C NMR data see Table 9 and Table 10 below.

Example 3-18. 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamno Pyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18).

3β,20(S),25-trihydroxydammar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3) ]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside;

White amorphous powder;

-0.5 (c 0.2, 메탄올);[α]

-0.5 ( c 0.2, methanol);

IR (KBr) ν _max 3400, 2982, 2372, 2320, 1052, 1037 cm ^-1 ;

HRESIMS m/z 1119.6008 [M+HCOO] ^- , C ₅₅ H ₉₁ O ₂₃ (calcd 1119.5957);

¹ H NMR and ¹³ C NMR data see Table 9 and Table 10 below.

Example 3-19. 3β,20(S)-dihydroxydamar-24-en-12-one-3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranoside (compound 19) .

3β,20(S)-dihydroxydammar-24-en-12-one-3-O-α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside;

White amorphous powder;

-0.8 (c 0.2, 메탄올);[α]

-0.8 ( c 0.2, methanol);

UV (methanol) λ _max (log ε) 225 nm (2.8);

IR (KBr) ν _max 3390, 2971, 1057, 1013 cm ^-1 ;

HRESIMS m/z 811.4872 [M+HCOO] ^- , C ₄₃ H ₇₁ O ₁₄ (calcd 811.4849);

¹ H NMR and ¹³ C NMR data see Table 9 and Table 10 below.

¹ H NMR spectrocopic data (in Pyridine- d ₅ ) No Compound 1
δ _H ( J in Hz) 500Mhz Compound 2 ^a
δ _H ( J in Hz) 600Mhz Compound 3 ^b
δ _H ( J in Hz) 600Mhz Compound 5
δ _H ( J in Hz) 500Mhz One 1.20, overlap
0.69, overlap 1.18, overlap
0.69, overlap 1.20, overlap
0.69, overlap 1.22, overlap
0.73, overlap 2 2.11, overlap
1.70, overlap 2.12, overlap
1.71, overlap 2.11, overlap
1.70, overlap 2.23, overlap
1.80, overlap 3 3.25, overlap 3.26, dd (11.2, 4.4) 3.32, dd (11.2, 4.4) 3.32, dd (11.6, 4.0) 5 0.66, overlap 0.65, overlap 0.66, m 0.67, d (9.6) 6 1.50, overlap
1.39, overlap 1.49, overlap
1.40, overlap 1.50, m
1.39, m 1.49, m, overlap
1.41, m, overlap 7 1.39, overlap
1.25, overlap 1.38, overlap
1.25, overlap 1.39, m
1.25, m 1.42, m, overlap
1.26, m, overlap 9 1.62, overlap 1.79, overlap 1.62, m 1.65 (dd, 13.0, 4.0) 11 2.24, overlap
2.22, dd (10.5, 3.1) 2.24, overlap
2.22, overlap 2.24, overlap
2.22, dd (10.5, 3.1) 2.23, overlap (2H) 13 3.26, d (9.6) 3.66, d (9.4) 3.28, d (9.6) 3.27, d (10.0) 15 1.15, overlap
2.07, overlap 1.12, overlap
1.97, overlap 1.15, overlap
2.07, overlap 1.16, m, overlap
1.84, m, overlap 16 2.07, overlap
1.91, overlap 2.30, overlap
2.00, overlap 2.07, overlap
1.91, overlap 2.10, m, overlap
1.93, m, overlap 17 2.77, td (10.0, 5.1) 3.12, td (10.0, 5.1) 2.80, td (10.0, 5.0) 2.80, td (10.0, 5.1) 18 1.12, s 1.28, s 1.11, s 1.13, s 19 0.76, s 0.76, s 0.82, s 0.79, s 21 1.50, s 1.80, s 1.53, s 1.53, s 22 2.90, d (14.2)
2.72, d (14.2) 3.38, d (14.2)
3.21, d (14.2) 2.90, d (14.2)
2.72, d (14.2) 2.93, d (14.2)
2.74, d (14.2) 24 6.28, s 6.22, s 6.30, s 6.31, brs 26 2.15, s 2.14, s 2.17, s 2.17, s 27 1.70, s 1.67, s 1.71, s 1.71, s 28 1.17, s 1.17, s 1.19, s 1.24, s 29 1.11, s 1.11, s 1.11, s 1.19, s 30 0.84, s 0.83, s 0.86, s 0.86, s One' 4.80, d (7.7) 4.82, d (7.5) 4.84, d (7.7) 4.96, d (7.7) 2' 4.01, overlap 4.01, overlap 4.06, overlap 4.30, overlap 3' 4.11, overlap 4.11, overlap 4.11, overlap 4.29, overlap 4' 4.01, overlap 4.01, overlap 4.01, overlap 4.16, t (9.1) 5' 3.85, overlap 3.87, overlap 3.89, overlap 3.98, overlap 6' 4.48, overlap
4.33, overlap 4.53, overlap
4.43, overlap 4.61, overlap
4.47, overlap 4.61, dd (12.0, 2.4)
4.41, dd (12.0, 6.6) One'' 5.92, br s 5.95, br s 5.99, br s 6.59, brs 2'' 4.66, overlap 4.66, overlap 4.72, overlap 4.88, m 3'' 4.45, overlap 4.45, overlap 4.48, overlap 4.70, dd (9.4, 3.4) 4'' 4.26, overlap 4.28, overlap 5.79, t (10.0) 4.35, overlap 5'' 4.61, overlap 4.62, overlap 4.74, overlap 4.81, dq (9.5, 6.0) 6'' 1.64, d (6.0) 1.65, d (6.0) 1.41, d (6.0) 1.73, d (6.0) One''' 5.70, br s 5.72, br s 5.72, br s 2''' 4.87, br s 4.87, br s 4.84, br s 3''' 4.53, overlap 4.52, overlap 4.53, overlap 4''' 4.28, overlap 4.30, overlap 4.30, overlap 5''' 4.70, overlap 4.69, overlap 4.72, overlap 6''' 1.60, d (6.0) 1.62, d (6.0) 1.63, d (6.0) a: Chemical shift of 20-0-glu: H-1''''[5.16, d(7.76)], H-2''''[4.53, overlap],
C-3''''[4.62, overlap], C-4''''[4.35, overlap], C-5''''[3.93, overlap],
C-6``''[4.52, overlap]
b: Chemical shift of 3''-Acetyl: CH ₃ (2.10, s)

¹³ C NMR spectroscopic data (in Pyridine- d ₅ ) No Compound 1
δ _C , type 125Mhz Compound 2 ^a
δ _C , type 150Mhz Compound 3 ^b
δ _C , type 150Mhz Compound 5
δ _C , type 125Mhz One 39.3, CH ₂ 39.4, CH ₂ 39.4, CH ₂ 39.4, CH ₂ 2 26.9, CH ₂ 26.9, CH ₂ 27.0, CH ₂ 27.1, CH ₂ 3 88.5, CH 88.6, CH 88.6, CH 88.8, CH 4 39.9, C 39.9, C 39.9, C 40.0, C 5 56.6, CH 56.6, CH 56.7, CH 56.7, CH 6 18.8, CH ₂ 18.8, CH ₂ 18.8, CH ₂ 18.9, CH ₂ 7 34.8, CH ₂ 35.0, CH ₂ 34.8, CH ₂ 34.9, CH ₂ 8 40.9, C 41.1, C 41.0, C 41.0, C 9 54.6, CH 54.9, CH 54.8, CH 54.7, CH 10 37.7, C 37.7, C 37.7, C 37.7, C 11 40.1, CH ₂ 40.3, CH 40.1, CH ₂ 40.2, CH 12 211.7, C 211.4, C 211.8, C 211.8, C 13 56.2, CH 56.5, CH 56.3, CH 56.3, CH 14 56.5, C 56.5, C 56.5, C 56.7, C 15 32.2, CH ₂ 32.6, CH ₂ 32.2, CH ₂ 32.3, CH ₂ 16 25.2, CH ₂ 25.3, CH ₂ 25.2, CH ₂ 25.2, CH ₂ 17 45.2, CH 43.5, CH 45.2, CH 45.3, CH 18 16.0, CH ₃ 16.2, CH ₃ 16.0, CH ₃ 16.1, CH ₃ 19 16.5, CH ₃ 16.6, CH ₃ 16.5, CH ₃ 16.5, CH ₃ 20 74.0, C 80.7, C 74.1, C 74.1, C 21 27.2, CH ₃ 23.7, CH ₃ 27.2, CH ₃ 27.3, CH ₃ 22 54.8, CH ₂ 55.1, CH ₂ 55.0, CH ₂ 55.0, CH ₂ 23 201.7, C 199.8, C 201.7, C 201.7, C 24 126.4, CH 126.6, CH 126.5, CH 126.6, CH 25 154.9, C 154.5, C 154.9, C 154.9, C 26 20.9, CH ₃ 20.8, CH ₃ 21.0, CH ₃ 21.0, CH ₃ 27 27.7, CH ₃ 27.6, CH ₃ 27.7, CH ₃ 27.7, CH ₃ 28 28.1, CH ₃ 28.1, CH ₃ 28.2, CH ₃ 28.3, CH ₃ 29 16.9, CH ₃ 16.9, CH ₃ 16.8, CH ₃ 17.2, CH ₃ 30 17.4, CH ₃ 17.3, CH ₃ 17.5, CH ₃ 17.5, CH ₃ One' 105.3, CH 105.3, CH 105.1, CH 105.8, CH 2' 78.3, CH 78.5, CH 78.6, CH 78.1, CH 3' 87.5, CH 87.6, CH 87.8, CH 80.3, CH 4' 70.6, CH 70.4, CH 70.6, CH 72.5, CH 5' 78.3, CH 78.3, CH 78.6, CH 78.7, CH 6' 62.8, CH ₂ 62.8, CH 62.8, CH ₂ 63.3, CH ₂ One'' 102.5, CH 102.4, CH 101.9, CH 102.1, CH 2'' 72.2, CH 71.0, CH 70.3, CH 72.8, CH 3'' 72.7, CH 72.7, CH 72.3, CH 72.9, CH 4'' 73.9, CH 73.9, CH 76.0, CH 74.5, CH 5'' 70.5, CH 70.6, CH 67.6, CH 69.9, CH 6'' 18.9, CH ₃ 18.9, CH ₃ 18.2, CH ₃ 19.1, CH ₃ One''' 103.9, CH 104.0, CH 104.1, CH 2''' 72.7, CH 72.6, CH 72.7, CH 3''' 72.9, CH 73.0, CH 72.9, CH 4''' 73.8, CH 73.8, CH 73.8, CH 5''' 71.0, CH 71.0, CH 71.1, CH 6''' 18.7, CH ₃ 18.7, CH ₃ 18.7, CH ₃ a: Chemical shift of 20-0-glu: C-1''''(98.8, CH), C-2''''(73.0, CH), C-3''''(72.9, CH),
C-4''''(74.0, CH), C-5''''(78.2, CH), C-6''''(63.3, CH ₂ )
b: Chemical shift of 3"-Acetyl: 171.9 (C=0); 21.4 (CH ₃ )

¹ H NMR spectrocopic data (in Pyridine- d ₅ ) No Compound 6
δ _H ( J in Hz) 600Mhz Compound 7
δ _H ( J in Hz) 500Mhz Compound 8
δ _H ( J in Hz) 500Mhz Compound 9
δ _H ( J in Hz) 600Mhz One 1.20, overlap
0.69, overlap 1.58, m
1.23, m 1.24, m
0.75, m 1.22, overlap
0.73, overlap 2 2.10, overlap
1.70, overlap 2.48, m
2.42, m 2.15, m
1.75, m 2.04, m
1.56, overlap 3 3.40, dd (10.8, 5.4) 3.28, dd (11.7, 4.1) 3.30, dd (11.7, 4.2) 5 0.80, overlap 1.35, m 0.69, m 0.69, overlap 6 1.50, overlap
1.39, overlap 1.50, m
1.41, m 1.54, m
1.41, m 1.52, m
1.42, m 7 1.39, overlap
1.25, overlap 1.43, m
1.28, m 1.41, m
1.27, m 1.45, m
1.27, m 9 1.62, overlap 1.78, m 1.66, overlap 1.62, m 11 2.34, overlap
2.32, overlap 2.37, overlap
2.28, dd (10.5, 3.8) 2.24, overlap
2.22, overlap 2.27, overlap
2.21, overlap 13 3.31, d (9.6) 3.31, d (9.6) 3.20, d (9.7) 3.04, d (10.5) 15 1.17, overlap
1.88, overlap 1.17, m
1.87, m 1.80, m
1.14, m 1.45, m
1.27, m 16 2.10, overlap
1.92, overlap 2.12, m
1.93, m 2.02, m
1,88, m 2.07, m
1.91, m 17 2.80, td (10.0, 5.1) 2.8, td (5.2, 9.6) 2.78, td (10.1, 5.3) 3.20, ddd (17.0, 10.6, 6.7) 18 1.19, s 1.19, s 1.12, s 1.15, s 19 0.85, s 0.83, s 0.78, s 0.81, s 21 1.54, s 1.54, s 1.53, s 2.34, s 22 2.94, d (14.2)
2.74, d (14.2) 2.94, d (14.2)
2.75, d (14.2) 3.11, d (15.6)
2.83, d (15.6) 6.47, s 24 6.32, s 6.31, s 2.96, d (14.8)
2.95, d (14.8) 6.18, s 26 2.17, s 2.17, s 1.46, s 2.23, s 27 1.72, s 1.72, s 1.46, s 1.70, s 28 1.23, s 1.14, s 1.19, s 1.22, s 29 1.04, s 1.05, s 1.12, s 1.16, s 30 0.88, s 0.89, s 0.83, s 0.89, s One' 4.82, d (7.4) 4.86, d (7.7) 2' 4.03, overlap 4.07, overlap 3' 4.12, t (8.0) 4.11, t (8.0) 4' 4.02, overlap 4.07, overlap 5' 3.85, m 3.89, m 6' 4.46, dd (11.8, 3.4)
4.32, dd (11.8, 5.4) 4.60, overlap
4.52, overlap One'' 5.94, br s 6.00, br s 2'' 4.66, overlap 4.72, overlap 3'' 4.45, overlap 4.50, overlap 4'' 4.25, t (9.4) 4.31, overlap 5'' 4.66, overlap 4.68, overlap 6'' 1.66, d (6.0) 1.70, d (6.0) One''' 5.70, br s 5.77, br s 2''' 4.87, br s 4.93, br s 3''' 4.53, dd (9.5, 3.1) 4.59, overlap 4''' 4.26, t (9.4) 4.32, overlap 5''' 4.66, overlap 4.75, overlap 6''' 1.61, d (6.0) 1.66, d (6.0)

¹³ C NMR spectroscopic data (in Pyridine- d ₅ ) No Compound 6
δ _C , type 150Mhz Compound 7
δ _C , type 125Mhz Compound 8
δ _C , type 125Mhz Compound 9
δ _C , type 150Mhz One 39.3, CH ₂ 39.5, CH ₂ 39.4, CH ₂ 39.4, CH ₂ 2 29.0, CH ₂ 34.4, CH ₂ 26.9, CH ₂ 28.7, CH ₂ 3 78.1, CH 216.2, C 88.7, CH 88.7, CH 4 39.9, C 47.7, C 40.0, C 39.8, C 5 56.7, CH 55.3, CH 56.7, CH 56.6, CH 6 19.2, CH ₂ 20.3, CH ₂ 18.9, CH ₂ 19.0, CH ₂ 7 34.9, CH ₂ 34.1, CH ₂ 34.9, CH ₂ 34.8, CH ₂ 8 41.0, C 40.9, C 41.1, C 41.0, C 9 54.9, CH 54.0, CH 54.7, CH 54.1, CH 10 38.2, C 37.7, C 37.8, C 37.7, C 11 40.3, CH ₂ 40.3, CH ₂ 40.2, CH 39.8, CH ₂ 12 211.9, C 211.2, C 211.9, C 209.9, C 13 56.3, CH 56.8, CH 56.9, CH 59.0, CH 14 56.7, C 56.3, C 56.3, C 55.3, C 15 32.3, CH ₂ 32.3, CH ₂ 32.2, CH ₂ 32.2, CH ₂ 16 25.2, CH ₂ 25.2, CH ₂ 25.2, CH ₂ 28.7, CH ₂ 17 45.3, CH 45.2, CH 45.4, CH 45.7, CH 18 16.1, CH ₃ 15.7, CH ₃ 16.0, CH ₃ 16.1, CH ₃ 19 16.5, CH ₃ 16.0, CH ₃ 16.5, CH ₃ 16.4, CH ₃ 20 74.1, C 74.1, C 73.9, C 159.7, C 21 27.2, CH ₃ 27.3, CH ₃ 27.0, CH ₃ 17.7, CH ₃ 22 55.0, CH ₂ 55.0, CH ₂ 55.1, CH ₂ 126.3, CH 23 201.8, C 201.7, C 212.9, CH ₂ 191.7, C 24 126.6, CH 126.5, CH 54.8, CH 127.5, CH 25 154.9, C 155.0, C 70.0, C 154.1, C 26 21.0, CH ₃ 21.0, CH ₃ 30.8, CH ₃ 20.8, CH ₃ 27 27.7, CH ₃ 27.7, CH ₃ 30.4, CH ₃ 27.7, CH ₃ 28 28.4, CH ₃ 27.0, CH ₃ 28.2, CH ₃ 28.2, CH ₃ 29 16.6, CH ₃ 21.5, CH ₃ 17.0, CH ₃ 17.1, CH ₃ 30 17.5, CH ₃ 17.3, CH ₃ 17.5.CH ₃ 17.7, CH ₃ One' 105.3, CH 105.4, CH 2' 78.4, CH 78.5, CH 3' 87.8, CH 87.7, CH 4' 70.8, CH 70.8, CH 5' 78.4, CH 78.4, CH 6' 63.0, CH ₂ 63.0, CH ₂ One'' 102.5, CH 102.6, CH 2'' 72.4, CH 72.5, CH 3'' 72.8, CH 72.9, CH 4'' 74.1, CH 74.1, CH 5'' 70.5, CH 70.6, CH 6'' 18.9, CH ₃ 18.9, CH ₃ One''' 104.0, CH 104.1, CH 2''' 72.9, CH 72.7, CH 3''' 73.0, CH 73.0, CH 4''' 73.9, CH 74.0, CH 5''' 71.1, CH 71.2, CH 6''' 18.7, CH ₃ 18.8, CH ₃

¹ H NMR spectrocopic data (in Pyridine- d ₅ ) No Compound 10
δ _H ( J in Hz)
500Mhz Compound 11
δ _H ( J in Hz)
500Mhz Compound 12
δ _H ( J in Hz)
500Mhz Compound 13
δ _H ( J in Hz)
600Mhz Compound 14
δ _H ( J in Hz)
600Mhz One 3.21, ddd (4.7, 11.5, 15.5)
1.95, ddd (4.6, 11.8, 15.5) 3.21, ddd (4.7, 11.5, 15.5)
1.94, ddd (4.6, 11.8, 15.5) 3.17, ddd (4.7, 11.5, 15.5)
1.92, ddd (4.6, 11.8, 15.5) 1.45, overlap
1.11, overlap 1.46, overlap
1.09, overlap 2 2.56, overlap
3.00, overlap 2.54, overlap
2.98, overlap 2.51, ddd (4.7, 11.8, 15.6)
2.98, ddd (4.6, 11.5, 15.6) 1.23, overlap
2.77, overlap 2.25, overlap
1.79, overlap 3 3.24, overlap 3.29, overlap 5 1.69, overlap 1.67, overlap 1.67, overlap 0.69, m 0.72, m 6 1.67, overlap
1.65, overlap 1.69, overlap
1.65, overlap 1.65, overlap
1.63, overlap 1.50, m
1.40, m 1.50, overlap
1.40, overlap 7 1.29, m
1.28, m 1.29, m
1.26, m 1.29, m
1.28, m 1.40, m
1.20, m 1.40, overlap
1.20, overlap 9 2.20 dd (13.4, 3.3) 2.19, dd (13.4, 3.3) 2.16, dd (14.2, 3.3) 1.70, m 1.71, overlap 11 2.60, dd (13.4, 3.3)
2.39, t (13.4) 2.59, dd (13.4, 3.3)
2.35, t (13.4) 2.58, dd (14.2, 3.3)
2.30, t (14.2) 2.23, overlap
2.15, overlap 2.27, overlap
2.14, t (13.0) 13 3.33, d (9.7) 3.27, d (9.7) 3.31, d (9.7) 3.21, d (9.7) 3.19, d (9.7) 15 1.85, m
1.17, overlap 1.83, m
1.16, overlap 1.74, m
1.53, overlap 1.69, overlap
1.10, overlap 1.70, overlap
1.09, overlap 16 2.10, overlap
1.92, overlap 2.06, overlap
1.89, overlap 2.00, m
1.76, overlap 2.00, overlap
1.70, overlap 1.96, overlap
1.72, overlap 17 2.79, td (10.2, 5.2) 2.80, td (10.2, 5.2) 3.38, m 3.35, m 3.30, m 18 1.26, s 1.24, s 1.15, s 1.00, s 1.01, s 19 1.19, s 1.18, s 1.16, s 0.77, s 0.75, s 21 1.52, s 1.52, s 2.22, s 2.23, s 2.21, s 22 2.92, d (14.2)
2.70, d (14.2) 3.12, d (14.2)
2.83, d (14.2) 24 6.31, br s 3.00, br s 26 1.72, s 1.50, s 27 2.18, s 1.50, s 28 1.46, s 1.46, s 1.45, s 1.07, s 1.09, s 29 1.50, s 1.50, s 1.49, s 1.15, s 1.19, s 30 0.86, s 0.85, s 0.81, s 0.71, s 0.78, s One' 4.76, d (7.7) 4.73, d (8.0) 2' 3.97, overlap 3.94, t (8.0) 3' 4.07, overlap 4.06, t (8.0) 4' 3.84, overlap 3.80, overlap 5' 3.84, overlap 3.90, overlap 6' 4.59, overlap
4.47, overlap 4.48, overlap
4.08, overlap One'' 5.88, br s 5.89, br s 2'' 4.68, overlap 4.68, overlap 3'' 4.50, overlap 4.50, overlap 4'' 4.25, overlap 4.29, overlap 5'' 4.64, overlap 4.62, overlap 6'' 1.63, d (4.6) 1.63, d (6.3) One''' 5.67, br s 5.69, br s 2''' 4.84, overlap 4.87, overlap 3''' 4.51, overlap 4.53, overlap 4''' 4.31, overlap 4.28, overlap 5''' 4.68, overlap 4.70, overlap 6''' 1.60, d (4.6) 1.62, overlap One'''' 5.39, br s 2'''' 4.53, overlap 3'''' 4.62, overlap 4'''' 4.35, overlap 5'''' 4.34, overlap 6'''' 1.64, overlap

¹³ C NMR spectroscopic data (in Pyridine- d ₅ ) No Compound 10
δ _C , type 125Mhz Compound 11
δ _C , type 125Mhz Compound 12
δ _C , type 125Mhz Compound 13
δ _C , type 150Mhz Compound 14
δ _C , type 150Mhz One 35.8, CH ₂ 35.9, CH ₂ 35.7, CH ₂ 39.2, CH ₂ 39.1, CH ₂ 2 30.0, CH ₂ 30.0, CH ₂ 30.0, CH ₂ 28.1, CH ₂ 28.0, CH ₂ 3 177.4, C 177.3, C 177.3, C 88.6, CH 88.8, CH 4 75.1, C 75.1, C 75.1, C 39.3, C 39.2, C 5 52.6, CH 52.6, CH 52.5, CH 56.5, CH 56.5, CH 6 23.2, CH ₂ 23.3, CH ₂ 23.1, CH ₂ 18.7, CH ₂ 18.8, CH ₂ 7 34.1, CH ₂ 34.1, CH ₂ 34.0, CH ₂ 34.6, CH ₂ 34.6, CH ₂ 8 40.8, C 40.8, C 40.5, C 40.7, C 40.6, C 9 47.1, CH 47.1, CH 46.1, CH 53.8, CH 53.6, CH 10 42.2, C 42.2, C 42.1, C 37.5, C 37.6, C 11 40.0, CH ₂ 40.0, CH ₂ 39.2, CH ₂ 39.8, CH ₂ 39.8, CH 12 211.8, C 211.8, C 209.8, C 210.3, C 209.9, C 13 56.8, CH 57.0, CH 58.5, CH 58.5, CH 58.4, CH 14 56.6, C 56.6, C 55.1, C 54.8, C 54.6, C 15 32.3, CH ₂ 32.3, CH ₂ 31.9, CH ₂ 31.8, CH ₂ 31.7, CH ₂ 16 25.3, CH ₂ 25.3, CH ₂ 26.3, CH ₂ 26.1, CH ₂ 26.0, CH ₂ 17 45.3, CH 45.4, CH 48.0, CH 47.9, CH 47.9, CH 18 15.8, CH ₃ 15.8, CH ₃ 15.7, CH ₃ 15.9, CH ₃ 15.9, CH ₃ 19 21.2, CH ₃ 21.2, CH ₃ 20.9, CH ₃ 16,2, CH ₃ 16,2, CH ₃ 20 74.1, C 73.9, C 210.2, C 210.0, C 210.2, C 21 27.1, CH ₃ 26.8, CH ₃ 30.2, CH ₃ 30.2, CH ₃ 30.2, CH ₃ 22 54.8, CH ₂ 55.1, CH ₂ 23 201.9, C 213.1, C 24 126.6, CH 57.8, CH ₂ 25 154.9, C 70.0, C 26 27.7, CH ₃ 30.8, CH ₃ 27 21.0, CH ₃ 30.5, CH ₃ 28 28.6, CH ₃ 28.6, CH ₃ 28.6, CH ₃ 28.1, CH ₃ 28.0, CH ₃ 29 34.5, CH ₃ 34.5, CH ₃ 34.5, CH ₃ 16.9, CH ₃ 16.8, CH ₃ 30 17.3, CH ₃ 17.3, CH ₃ 17.2, CH ₃ 17.4, CH ₃ 17.4, CH ₃ One' 105.3, CH 105.2, CH 2' 78.3, CH 78.4, CH 3' 87.5, CH 87.0, CH 4' 70.6, CH 70.5, CH 5' 78.3, CH 76.2, CH 6' 62.8, CH ₂ 68.1, CH ₂ One'' 102.5, CH 102.4, CH 2'' 72.3, CH 72.1, CH 3'' 72.7, CH 72.1, CH 4'' 74.0, CH 73.7, CH 5'' 70.1, CH 70.0, CH 6'' 18.9, CH ₃ 18.9, CH ₃ One''' 104.0, CH 103.8, CH 2''' 72.7, CH 72.4, CH 3''' 72.9, CH 72.6, CH 4''' 73.8, CH 73.8, CH 5''' 71.0, CH 70.9, CH 6''' 18.7, CH ₃ 18.8, CH ₃ One'''' 102.6, CH 2'''' 72.9, CH 3'''' 72.6, CH 4'''' 74.0, CH 5'''' 70.6, CH 6'''' 18.6, CH ₃

¹ H NMR spectrocopic data (in Pyridine- d ₅ ) No Compound 15
δ _H ( J in Hz)
600Mhz Compound 16
δ _H ( J in Hz)
600Mhz Compound 17
δ _H ( J in Hz)
500Mhz Compound 18
δ _H ( J in Hz)
500Mhz Compound 19
δ _H ( J in Hz)
600Mhz One 1.24, m
0.75, m 1.22, overlap
0.73, overlap 1.21, overlap
0.72, overlap 1.21, overlap
0.78, overlap 1.20, overlap
0.78, overlap 2 2.15, m
1.75, m 2.22, overlap
1.75, overlap 2.22, overlap
1.75, overlap 2.21, overlap
1.78, overlap 2.21, overlap
1.77, overlap 3 3.26, dd (11.7, 4.1) 3.32, overlap 3.27, dd (11.9, 4.3) 3.27, dd (11.9, 4.3) 3.29, overlap 5 0.72, m 0.68, overlap 0.67, overlap 0.70, overlap 0.67, overlap 6 1.54, m
1.41, m 1.52, m
1.42, m 1.53, overlap
1.42, overlap 1.51, overlap
1.42, overlap 1.49, overlap
1.40, overlap 7 1.41, m
1.27, m 1.45, m
1.27, m 1.45, overlap
1.26, overlap 1.40, overlap
1.27, overlap 1.40, overlap
1.26, overlap 9 1.66, overlap 1.67, m 1.67, overlap 1.66, overlap 1.66, overlap 11 2.24, overlap
2.22, overlap 2.27, overlap
2.22, overlap 2.27, t (13.0)
2.22, dd (13.0, 4.0) 2.23, overlap (2H) 2.22, overlap (2H) 13 3.17, d (9.7) 3.02, d (10.5) 3.36, d (9.6) 3.33, d (9.6) 3.30, overlap 15 1.80, m
1.14, m 1.85, m
1.23, m 1.87, m
1.17, m 1.86, m
1.14, m 1.86, overlap
1.17, overlap 16 2.02, m
1.88, m 2.07, m
1.91, m 2.14, m
1.90, m 2.10, m
1.89, m 2.08, m
1.90, m 17 2.74, td (10.1, 10.0, 5.3) 3.17, ddd (17.0, 10.6, 6.7) 2.76, m 2.72, m 2.73, td (10.0, 5.3) 18 1.09, s 1.14, s 1.13, s 1.11, s 1.11, s 19 0.75, s 0.82, s 0.78, s 0.77, s 0.78, s 21 1.46, s 2.33, s 1.45, s 1.42, s 1.42, s 22 3.10, d (15.6)
2.81, d (15.6) 6.44, s 2.59, dd (13.8, 6.5)
2.53, dd (13.8, 8.6) 2.57, dd (13.8, 6.5)
2.51, dd (13.8, 8.3) 1.76, overlap (2H) 23 6.25, ddd (15.1, 8.3, 6.5) 6.21, ddd (15.1, 8.3, 6.5) 2.41, m2.28, m 24 2.94, br s 6.16, s 5.99, d (15.1) 5.97, d (15.1) 5.27, m 26 1.44, s 1.70, s 1.52, s 1.51, s 1.66, s 27 1.45, s 2.22, s 1.52, s 1.51, s 1.62, s 28 1.18, s 1.24, s 1.19, s 1.21, s 1.23, s 29 1.12, s 1.10, s 1.14, s 1.11, s 1.17, s 30 0.78, s 0.88, s 0.86, s 0.83, s 0.89, s One' 4.72, d (7.5) 4.80, d (7.5) 4.83, d (7.5) 4.79, d (7.5) 4.92, d (7.2) 2' 4.01, overlap 4.02, overlap 4.09, overlap 4.00, overlap 4.28, overlap 3' 4.11, overlap 4.13, overlap 4.18, overlap 4.12, overlap 4.26, overlap 4' 3.86, overlap 3.87, overlap 3.89, overlap 3.84, overlap 4.13, t (9.3) 5' 3.94, overlap 3.95, overlap 4.07, overlap 3.95, overlap 3.95, ddd (9.3, 5.4, 2.6) 6' 4.53, overlap
4.13, overlap 4.53, overlap
4.13, overlap 4.53, overlap
4.38, overlap 4.49, overlap
4.14, overlap 4.57, dd (11.8, 2.6)
4.37, dd (11.8, 5.4) One'' 5.86, br s 5.96, br s 5.99, br s 6.00, br s 6.56, br s 2'' 4.66, overlap 4.68, overlap 4.71, overlap 4.68, overlap 4.84, dd (3.0, 1.3) 3'' 4.45, overlap 4.50, overlap 4.50, overlap 4.49, overlap 4.66, dd (9.4, 3.0) 4'' 4.27, overlap 4.33, overlap 4.30, overlap 4.33, overlap 4.33, t (9.4) 5'' 4.60, overlap 4.62, overlap 4.66, overlap 4.62, overlap 4.79, dq (9.4, 6.2) 6'' 1.61, d (6.3) 1.68, d (6.3) 1.68, d (6.3) 1.67, d (6.3) 1.70, d (6.2) One''' 5.65, br s 5.75, br s 5.76, br s 5.74, br s 2''' 4.86, overlap 4.92, overlap 4.93, overlap 4.92, overlap 3''' 4.50, d (9.3) 4.52, d (9.3) 4.58, overlap 4.52, d (9.3) 4''' 4.25, overlap 4.28, overlap 4.32, overlap 4.28, overlap 5''' 4.67, overlap 4.70, overlap 4.74, overlap 4.70, overlap 6''' 1.57, d (6.3) 1.64, d (6.3) 1.64, d (6.3) 1.62, d (6.3) One'''' 5.37, br s 5.44, br s 5.43, br s 2'''' 4.50, overlap 4.53, overlap 4.52, overlap 3'''' 4.59, overlap 4.62, overlap 4.63, overlap 4'''' 4.32, overlap 4.35, overlap 4.35, overlap 5'''' 4.31, overlap 4.34, overlap 4.34, overlap 6'''' 1.59, d (6.3) 1.65, d (6.3) 1.64, d (6.3)

¹³ C NMR spectroscopic data (in Pyridine- d ₅ ) No Compound 15
δ _C , type 150Mhz Compound 16
δ _C , type 125Mhz Compound 17
δ _C , type 125Mhz Compound 18
δ _C , type 150Mhz Compound 19
δ _C , type 150Mhz One 39.3, CH ₂ 39.3, CH ₂ 39.4, CH ₂ 39.3, CH ₂ 39.3, CH ₂ 2 26.8, CH ₂ 27.0, CH ₂ 27.0, CH ₂ 27.0, CH ₂ 27.1, CH ₂ 3 89.2, CH 89.0, CH 88.6, CH 89.1, CH 88.7, CH 4 39.9, C 39.8, C 41.0, C 39.9, C 40.0, C 5 56.7, CH 56.6, CH 56.6, CH 56.7, CH 56.7, CH 6 18.7, CH ₂ 19.0, CH ₂ 18.9, CH ₂ 18.4, CH ₂ 18.8, CH ₂ 7 34.8, CH ₂ 34.7, CH ₂ 34.9, CH ₂ 34.8, CH ₂ 34.9, CH ₂ 8 41.0, C 41.0, C 41.4, C 41.0, C 41.0, C 9 54.7, CH 54.0, CH 54.7, CH 54.7, CH 54.8, CH 10 37.8, C 37.8, C 37.7, C 37.8, C 37.7, C 11 40.2, CH 40.0, CH ₂ 40.2, CH ₂ 40.2, CH ₂ 40.2, CH ₂ 12 212.5, C 210.0, C 212.2, C 212.3, C 212.1, C 13 56.8, CH 59.0, CH 56.9, CH 56.8, CH 56.9, CH 14 56.7, C 55.2, C 56.2, C 56.2, C 56.7, C 15 32.3, CH ₂ 32.1, CH ₂ 32.3, CH ₂ 32.2, CH ₂ 32.3, CH ₂ 16 25.2, CH ₂ 28.8, CH ₂ 24.8, CH ₂ 24.7, CH ₂ 24.8, CH ₂ 17 45.1, CH 45.7, CH 44.4, CH 44.3, CH 44.4, CH 18 16.1, CH ₃ 16.1, CH ₃ 16.1, CH ₃ 16.1, CH ₃ 16.1, CH ₃ 19 16.6, CH ₃ 16.4, CH ₃ 16.5, CH ₃ 16.6, CH ₃ 17.2, CH ₃ 20 73.9, C 159.8, C 74.0, C 73.8, C 73.6, C 21 26.8, CH ₃ 17.7, CH ₃ 27.5, CH ₃ 27.5, CH ₃ 26.9, CH ₃ 22 55.2, CH ₂ 126.2, CH 45.8, CH ₂ 45.8, CH ₂ 42.3, CH ₂ 23 212.9, C 191.7, C 123.2, CH 123.1, CH 23.9, CH ₂ 24 57.7, CH ₂ 127.4, CH 143.1, CH 143.0, CH 126.2, CH 25 70.1, C 154.0, C 70.1, C 70.1, C 131.2, C 26 30.7, CH ₃ 27.7, CH ₃ 31.1, CH ₃ 31.0, CH ₃ 26.1, CH ₃ 27 30.3, CH ₃ 20.8, CH ₃ 31.0, CH ₃ 31.0, CH ₃ 18.0, CH ₃ 28 28.1, CH ₃ 28.2, CH ₃ 28.1, CH ₃ 28.1, CH ₃ 28.1, CH ₃ 29 16.8, CH ₃ 16.9, CH ₃ 17.0, CH ₃ 16.6, CH ₃ 16.5, CH ₃ 30 17.5, CH ₃ 17.7, CH ₃ 17.6, CH ₃ 17.6, CH ₃ 17.6, CH ₃ One' 105.3, CH 105.3, CH 105.4, CH 105.3, CH 105.8, CH 2' 78.5, CH 78.5, CH 78.3, CH 78.4, CH 77.6, CH 3' 87.1, CH 87.3, CH 87.6, CH 87.2, CH 80.2, CH 4' 71.0, CH 70.7, CH 70.7, CH 70.8, CH 72.5, CH 5' 76.4, CH 76.4, CH 78.5, CH 76.4, CH 78.6, CH 6' 68.4, CH ₂ 68.4, CH ₂ 62.9, CH ₂ 68.3, CH ₂ 63.2, CH ₂ One'' 102.5, CH 102.6, CH 102.6, CH 102.6, CH 102.1, CH 2'' 72.2, CH 72.1, CH 72.4, CH 72.1, CH 72.5 CH 3'' 72.5, CH 72.3, CH 72.8, CH 72.3, CH 72.9, CH 4'' 73.7, CH 73.9, CH 74.1, CH 73.9, CH 74.5, CH 5'' 70.2, CH 70.2, CH 70.2, CH 70.2, CH 69.9, CH 6'' 19.0, CH ₃ 19.0, CH ₃ 18.9, CH ₃ 18.9, CH ₃ 19.0, CH ₃ One''' 103.9, CH 104.0, CH 104.1, CH 104.0, CH 2''' 72.7, CH 72.8, CH 72.8, CH 72.8, CH 3''' 72.8, CH 73.1, CH 73.0, CH 73.0, CH 4''' 73.9, CH 74.1, CH 74.0, CH 74.0, CH 5''' 70.8, CH 70.7, CH 71.1, CH 70.6, CH 6''' 18.9, CH ₃ 19.0, CH ₃ 18.8, CH ₃ 19.0, CH ₃ One'''' 102.8, CH 102.8, CH 102.8, CH 2'''' 73.0, CH 72.9, CH 73.0, CH 3'''' 72.8, CH 72.8, CH 72.9, CH 4'''' 74.1, CH 74.2, CH 74.2, CH 5'''' 70.8, CH 70.8, CH 70.8, CH 6'''' 18.7, CH ₃ 18.7, CH ₃ 18.7, CH ₃

<Example 4. Animal cell culture>

In order to confirm the activation of AMPK in muscle or adipose tissue of the Ginostema longipes VK1 extract of the present invention or a compound isolated therefrom, C2C12 (mouse skeletal muscle cells) cells, which are myoblasts, or 3T3, which are adipocytes, -L1 cells were used.

The C2C12 cells and 3T3-L1 cells are DMEM (Dulbecco's modified Eagle's medium, Gibco) containing 10% fetal bovine serum (FBS), 100 U/ml penicillin and 100 μg/ml streptomycin. ) It was cultured in a 37°C, 5% CO ₂ incubator using a medium.

<Example 5. Cytotoxicity confirmation>

MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay was performed in order to confirm whether the compound isolated from the present invention Ginostema longifes VK1 is cytotoxic.

The C2C12 cells or 3T3-L1 cells cultured in Example 4 were dispensed into a 96-well plate and cultured for 24 hours, and Compounds 1 to 19 isolated in Example 2 were treated to be 40 μM, and further cultured for 24 hours. . After the cultivation was completed, 20 µl of 2 mg/ml MTT solution was added to each well and allowed to react for 4 hours. After removing the culture solution, the formed formazan precipitate was dissolved in 100 µl of dimethyl sulfoxide (DMSO) at 550 nm. The absorbance was measured, and the results are shown in Figs. 1(A) and 1(B).

1(A) and 1(B), of the compounds isolated in Example 2, compounds 10 to 18 have toxicity to 3T3-L1 cells (A) or C2C12 cells (B) at a concentration of 40 μM. It was confirmed that there was no. In addition, although the results were not shown directly in the present specification, even in the case of compounds 1 to 9, no cytotoxicity was observed. On the other hand, in the case of compound 19, toxicity was observed in both types of cells at a concentration of 40 μM.

Accordingly, in order to confirm the concentration of compound 19 at which cytotoxicity does not appear, compound 19 was treated so that the concentration was 10, 20, and 30 μM to confirm cytotoxicity, and the results are shown in FIGS. 1(C) and 1(C). Indicated.

As shown in Figs. 1(C) and 1(D), in the case of compound 19, it was confirmed that no toxicity appeared in either 3T3-L1 cells (C) or C2C12 cells (D) at a concentration of 10 μM.

Accordingly, compounds 1 to 18 were treated with 20 μM and compound 19 with 10 μM to confirm the activity of each compound.

<Example 6. AMPK activation confirmation>

It has been reported that AMPK activation promotes muscle regeneration in the process of muscle regeneration. In addition, when AMPK is phosphorylated and activated in skeletal muscle, it promotes oxidation of fatty acids and absorption of sugar, and activated AMPK phosphorylates and inactivates acetyl-CoA carboxylase (ACC), an enzyme necessary for fatty acid synthesis. Increases fatty acid oxidation.

Accordingly, it was confirmed that the effects of the Ginostema longifes VK1 extract or compounds isolated therefrom of the present invention on activation of AMPK and inactivation of ACC in muscle-related cells.

The C2C12 cells cultured in Example 4 were dispensed into a 6-well plate and cultured until the cells were about 70-80% full. The culture medium was removed, and DMEM medium (differentiation medium) containing 2% horse serum (Gibco) was added and cultured to induce differentiation into root canal cells. At this time, it was replaced with a new differentiation medium at intervals of 2 days until root canal cells were generated.

In the process of separating the compound of Example 2 from the differentiated myotube cells, 70% [v/v] ethanol Ginostema longifes VK1 extract was added to the SP70 resin, and then 30% [v/v] ethanol was used. After washing the resin, the 95% [v/v] ethanol fraction obtained by eluting with 95% [v/v] ethanol was 10, 20, and 40 µg/ml, and the compounds 1 to 18 of Example 2 were 20 μM. Then, compound 19 was treated with 10 μM and incubated for 30 to 60 minutes. At this time, cells were obtained by treatment with 0.2mM of Aicar (5-aminoimidazole-4-carboxamide ribonucleotide) known as an AMPK activating material as a positive control. Western blot was performed using the obtained cells.

The cells treated with each of the samples were collected and washed with PBS (phosphat buffered saline), and a cell lysis buffer (50 mM Tris-HCl (pH 7.6), 120 mM NaCl, 1 mM EDTA, 0.5%) NP-40, 50 mM NaF) was added to lyse the cells, followed by centrifugation to obtain a supernatant protein. The protein in the obtained supernatant was separated through sodium dodecyl polyacrylamide gel electrophoresis (SDS-PAGE) and transferred to a polyvinylidenefluoride (PVDF) membrane. After blocking the membrane with a blocking solution, the first antibody is treated to determine the amount of AMPKα, phosphorylated AMPKα (p-AMPKα), ACC, and phosphorylated ACC (p-ACC). The secondary antibody to the antibody was treated, and protein expression was confirmed using ECL (enhanced chemiluminescence) (Amersham), and the results are shown in FIG. 2.

As shown in FIG. 2, when the 95% [v/v] ethanol fraction of Example 2 of (A) was treated by concentration, it was confirmed that phosphorylation of AMPK increased according to the concentration of the fraction treatment. In addition, when the compounds 1 to 19 of Example 2 of (B) were treated, the protein expression band (the upper figure of (B)) and the protein expression band were numerically expressed (lower graph of (B)) As shown in, it was confirmed that phosphorylation of AMPK and ACC was mostly increased in cells treated with each compound compared to cells not treated with anything.

Through this, the Ginostema longifes extract of the present invention and the compounds isolated therefrom induce and activate AMPK phosphorylation in muscle-related cells in which differentiation from myoblasts to myotubes is induced, and inactivate ACC to regenerate muscle. I could see that it promotes.

<Example 7. Proliferation confirmation of myoblasts>

Example 7-1. Confirmation of myoblast proliferation promoting effect

The effect of promoting myoblast proliferation using the MTT assay and the water-soluble tetrazolium salt-1 (WST-1) assay in order to confirm the muscle regeneration effect of the Ginostema longipes VK1 extract of the present invention or the compounds isolated therefrom Was confirmed.

4,000 cells per well were dispensed into a 96-well plate, cultured for 8 hours, replaced with a medium containing 5% FBS, and the 95% [v/v] ethanol fraction of Example 2 was 10 μg/ml. Treatment and incubation for 24 hours or 48 hours, the compounds 1 to 18 of Example 2 was treated to 20 μM, compound 19 to 10 μM, and cultured for 48 hours, followed by MTT assay or WST-1 assay. .

After the cultivation was completed, 20 µl of 2 mg/ml MTT solution was added to each well and allowed to react for 4 hours. After removing the culture, the formed formazan precipitate was dissolved in 100 µl of DMSO, and the absorbance was measured at 550 nm to perform an MTT assay. Performed. In addition, after the cultivation was completed, 10 µl of WST-1 solution was added to each well, reacted for 2 hours, and absorbance was measured at 440 nm, and the results are shown in FIG. 3.

As shown in FIG. 3, when the 95% [v/v] ethanol fraction of Example 2 was treated, the fraction was not treated in both the MTT assay (A) and WST-1 assay (B) results, and In comparison, the cell viability was increased, and the cell viability according to time when the 95% [v/v] ethanol fraction of Example 2 was treated as compared to the case where the fraction was not treated even in the case of the cell viability according to the treatment time It was confirmed that this is 20-30% higher.

In addition, even when compounds 1 to 19 of Example 2 were treated, C2C12 cell viability in all of compounds 10 to 19 as well as compounds 1 to 9 shown in the result of (C) increased compared to cells that were not treated with anything. It was confirmed through the MTT assay and the WST-1 assay.

Through this, it was found that the Ginostema longipes VK1 extract of the present invention or the compounds isolated therefrom promotes the proliferation of myoblasts, and it is predicted that muscle regeneration can be induced by promoting the proliferation of these myoblasts Could

Example 7-2. Confirmation of myoblast-specific proliferation promoting effect

In order to confirm whether the effect of promoting myoblast proliferation of the Ginostem longipes VK1 extract of the present invention or a compound isolated therefrom occurs specifically in myoblasts, the above was carried out using cancer cell lines MCF-7 and MDA-MB cells. It was carried out in the same manner as in the MTT assay method of Example 7-1. At this time, the 95% [v/v] ethanol fraction of Example 2 was treated to 10 µg/ml, and Compound 1 of Example 2 to 10 µM, and then cultured for 48 hours was used. It is shown in Figure 4.

As shown in FIG. 4, even if the 95% [v/v] ethanol fraction of Example 2 and Compound 1 of Example 2 were treated, it was confirmed that the cell viability did not increase in both MCF-7 and MDA-MB cells.

Through this, it was found that the cell proliferation promoting effect of the Ginostema longifes VK1 extract of the present invention or a compound isolated therefrom is specific to myoblasts rather than acting on all cells including cancer cells.

<Example 8. Confirmation of the effect of promoting DNA synthesis in the process of proliferation of myoblasts>

Immunechemical staining using BrdU (5-bromo-2′-deoxyuridine) to confirm that the Ginostema longifes VK1 extract of the present invention or a compound isolated therefrom promotes DNA synthesis during myoblast proliferation. ) Method and flow cytometry were used. BrdU can stain cells in the S-phase, which is a DNA synthesizer during the cell cycle.

In the immunochemical staining method, the C2C12 cells cultured in Example 4 were dispensed into a cell culture dish containing a cover slide, and the 95% [v/v] ethanol fraction of Example 2 was 20 μg/ml or the Example Compound 1 of 2 was treated with 20 μM and incubated for 8 hours. At this time, the cells treated with DMSO were used as a control. After incubation, 50 μM of BrdU labeling solution (Sigma-Aldrich, USA) was treated at 37° C. for 2 hours, and the cells were washed with PBS after 2 hours. The washed cells were treated with 4% formaldehyde for 15 minutes at room temperature to fix the cells, washed with PBS, added Triton X-100 buffer, and treated at room temperature for 20 minutes to increase cell permeability, and then 2N HCl The solution was treated on ice for 20 minutes. The 2N HCl solution was removed, and phosphate/citric acid buffer (pH 7.4) was treated at room temperature for 10 minutes, and the cells were washed with Triton X-100 buffer, and then anti-BrdU antibody was treated overnight. The next day, the anti-BrdU antibody was removed, and the secondary antibody conjugated with FITC (fluorescein isothiocyanate) capable of recognizing the anti-BrdU antibody was treated for 1 hour, and then DAPI (4',6-diamidino-2-phenylindole) Was treated to stain the nuclei of the cells. After fixing the cover slide to which the cells are attached with a mounting solution, the cell image was observed with a fluorescence microscope (Olympus ix70 Fluorescence Microscope, Olympus Corporation, JPN), and the results are shown in FIG. 5(A).

As shown in FIG. 5(A), it was confirmed that the number of cells stained with BrdU (red color) increased when the 95% [v/v] ethanol fraction of Example 2 or Compound 1 of Example 2 was treated. .

In the case of flow cytometry, the C2C12 cells cultured in Example 4 were dispensed into a 36 mm cell culture dish, and Compound 1 of Example 2 was treated to be 5, 10, and 20 μM, and cultured for 8 hours. At this time, cells treated with nothing were used as a normal group, and cells treated with DMSO were used as a control. After incubation, 50 μM of BrdU labeling solution was treated at 37° C. for 2 hours, and after 2 hours, the cells were washed with PBS, and the cells were collected using trypsin. 70% ethanol was added to the collected cells and treated at 4°C for 1 hour to increase the cell permeability, and then centrifuged for 2 minutes at 1000 rpm to separate the cells, and a 2N HCl solution containing 0.5% Triton X-100 was added. It was treated for 30 minutes at room temperature. After washing the cells with PBS containing 1% BSA (bovine serum albumin), and suspending the cells with PBS containing 0.5% Triton X-100 and 1% BSA, add anti-BrdU antibody and add it at room temperature for 4 hours. After reacting for 30 minutes, PBS containing 20 µg/ml PI (propidium iodide) was added and reacted in the dark for 30 minutes to obtain cells. The obtained cells were analyzed for cells double stained with BrdU and PI using a flow cytometer (FACSCalibur, BD, USA), and the results are shown in FIG. 5(B).

As shown in FIG. 5(B), it was confirmed that the number of cells in the S phase increased according to the treatment concentration of Compound 1 of Example 2.

Therefore, through the results of FIGS. 5(A) and 5(B), it was found that the Ginostema longifes VK1 extract of the present invention or a compound isolated therefrom promotes DNA synthesis of cells during the proliferation of myoblasts. Could know.

<Example 9. Obesity, diabetes or metabolic syndrome treatment effect confirmation>

Example 9-1. Check the effect of promoting sugar absorption

Based on the fact that AMPK activation becomes an important target in the development of a therapeutic agent for obesity, diabetes or metabolic syndrome, the Ginostema longipes VK1 extract having AMPK activation effect of the present invention or a compound isolated therefrom is glucose uptake of adipocytes. ) It was confirmed whether it was accelerated.

3T3-L1 cells, which are adipocytes cultured in Example 4, were dispensed into a 96-well plate, and cultured for 24 hours in a DMEM medium containing 10% FBS and no glucose. 2-NBDG(2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose)(Invtrogen, USA), a fluorescent analogue of glucose ) 50 μM was treated in all wells, and 100 nM insulin (positive control) or 20 μM of compounds 1 to 18 of Example 2 and 10 μM of compound 19 were treated in each well and incubated for 1 hour. At this time, the DMSO-treated one was used as a control. After 1 hour, the cells were washed with cold PBS, and the excitation/emission wavelength was 450/535 nm using a fluorescence microplate reader (Spectra Max GEMINI XPS, Molecular Devices, USA). The fluorescence intensity was measured under conditions. In addition, fluorescence images were taken using a fluorescence microscope (Olympus ix70 Fluorescence Microscope, Olympus Corporation, Japan), and the results are shown in FIG. 6.

As shown in Figure 6, in the result of confirming the fluorescence image due to the absorption of 2-NBDG in 3T3-L1 cells (A) and the result of measuring the intracellular fluorescence intensity (B), when the compounds 10 to 19 were treated, the cells It was confirmed that the inner fluorescence was increased compared to the control group treated with only DMSO.

In addition, although not shown directly in the present specification, it was confirmed that the fluorescence by 2-NBDG in 3T3-L1 cells, which is adipocytes, was increased even when compounds 1 to 9 were treated.

Through this, it was found that the Ginostema longifes VK1 extract of the present invention or a compound isolated therefrom promotes the absorption of sugar by adipocytes, thereby showing an effect of treating obesity, diabetes, or metabolic syndrome.

Example 9-2. Check sugar transporter translocation

Metabolic syndrome refers to insulin resistance in which glucose absorption into peripheral tissues is resistant. It is known that weight loss in obesity and metabolic syndrome decreases insulin resistance and promotes glucose absorption into storage tissues. In addition, promotion of glucose absorption into peripheral tissues is an essential mechanism of action to remove glucose from blood, a prerequisite for managing type 2 diabetes. Glucose transporter 4 (GLUT4) is a major glucose transporter that is activated in response to insulin, and the translocation of adipocytes to the plasma membrane is essential. Thus, in order to confirm whether the Ginostema longifes VK1 extract of the present invention or a compound isolated therefrom affects the translocation of GLUT4 in adipocytes, the protoplasmic membrane protein of adipocytes was isolated and Western blot was performed.

The adipocytes 3T3-L1 cells cultured in Example 4 were dispensed into a 6-well plate, and cultured in DMEM medium containing 10% FBS. Thereafter, of the compounds of Example 2, compounds 10, 11, 13, and 17 were mixed so as to be 20 μM in a DMEM medium containing no FBS, treated with cells, and cultured for 24 hours. At this time, 100nM of insulin was added as a positive control and cultured for 2 hours was used. After collecting each cell, a plasma membrane fraction of 3T3-L1 cells was obtained using the cellular plasma membrane fractionation method of Yamamoto, N., et al., (2001). The protein concentration of the obtained plasma membrane fraction was quantified using a BCA protein analysis kit (Bio-Rad Laboratories, Inc., USA). Using the protein quantification result, the amount of protein in the plasma membrane fraction was made the same, and then separated by size through 12% SDS-PAGE, and then transferred to a PVDF membrane. The membrane was blocked with a blocking solution containing 5% skim milk, and then an antibody against GLUT4 was treated for 2 hours. At this time, the antibody was treated to confirm Na+/K+ ATPase α1 as a loading control. After 2 hours, the secondary antibody for each antibody was treated, and protein expression was confirmed using ECL (Amersham), and the results are shown in FIG. 7.

As shown in Fig. 7, in the band result (A) and the result of quantifying the protein band (B) confirming the amount of GLUT4 protein translocated in the plasma membrane of 3T3-L1 cells, compared to cells that were not treated with anything, insulin, the Example When the compounds 10, 11, 13 and 14 of 2 were treated, it was confirmed that the amount of GLUT4 present in the plasma membrane of 3T3-L1 cells increased.

Through this, the Ginostema longifes VK1 extract of the present invention or a compound isolated therefrom promotes the absorption of glucose through the potential of GLUT4, thereby reducing insulin resistance in obesity, diabetes or metabolic syndrome, thereby reducing the content of sugar in the blood. It was found that obesity, diabetes, or metabolic syndrome could be treated.

<Formulation Example 1. Pharmaceutical formulation>

Formulation Example 1-1. Manufacture of tablets

20g of Ginostema longipes VK1 extract or 200 mg of compound 1 of the present invention were mixed with 175.9g of lactose, 180g of potato starch and 32g of colloidal silicic acid, respectively. After adding a 10% gelatin solution to this mixture, it was pulverized and passed through a 14 mesh sieve. The mixture obtained by drying it was added to 160 g of potato starch, 50 g of talc and 5 g of magnesium stearate to form a tablet.

Formulation Example 1-2. Preparation of injection solution

100 mg of the compound 1 of the present invention, 0.6 g of sodium chloride, and 0.1 g of ascorbic acid were dissolved in distilled water to make 100 ml. The solution was put in a bottle and sterilized by heating at 20°C for 30 minutes.

<Formulation Example 2. Preparation of health functional food>

Formulation Example 2-1. Manufacturing of health functional food

Ginostema longipes VK1 extract of the present invention 20g, vitamin mixture appropriate amount, vitamin A acetate 70㎍, vitamin E 1.0mg, vitamin B1 0.13mg, vitamin B2 0.15mg, vitamin B6 0.5mg, vitamin B12 0.2㎍, vitamin C 10 Mg, biotin 10 µg, nicotinic acid amide 1.7 mg, folic acid 50 µg, calcium pantothenate 0.5 mg, an appropriate amount of mineral mixture, ferrous sulfate 1.75 mg, zinc oxide 0.82 mg, magnesium carbonate 25.3 mg, potassium monophosphate 15 mg, second 55 mg of calcium phosphate, 90 mg of potassium citrate, 100 mg of calcium carbonate, and 24.8 mg of magnesium chloride were mixed to form granules, but can be prepared by modifying various formulations according to the use. In addition, the composition ratio of the vitamin and mineral mixture may be arbitrarily modified, and may be prepared by mixing the above ingredients according to a conventional health functional food manufacturing method.

Formulation Example 2-2. Manufacturing of health functional beverages

A beverage was prepared by mixing 1 g of Ginostema longipes VK1 extract 1 of the present invention, 0.1 g of citric acid, 100 g of fructooligosaccharide, and 900 g of purified water, and stirring, heating, filtering, sterilizing, and refrigerating according to a conventional beverage preparation method.

Claims (31)

3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- of Formula 1 Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-( 1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside) (Compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23 -Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β -D-glucopyranoside (3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl- (1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyranoside) (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione -3-O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyrano Seed (3β,20(S)-dihydroxydammar-24-en-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L- rhamnopyranosyl-(1→3)]-β-D-glucopyranoside) (Compound 3), Gypentonoside A (Compound 4), 3β,20(S)-dihydroxydamar-24-ene- 12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3β,20(S)-dihydroxydammar-24-en-12,23- dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside) (Compound 5), 3β,20(S)-dihydroxydamar-24-ene-12,23- Dione (3β,20(S)-dihydroxydammar-24-en-12,23-dione ) (Compound 6), 20(S)-hydroxydammar-24-en-3,12,23-trione (20(S)-hydroxydammar-24-en-3,12,23-trione) (Compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl -(1→3)]-β-D-glucopyranoside (3β,20(S),25-trihydroxydammaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside) (Compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α- L-Rhamnopyranosyl-(1→3)-[α-L-Rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (3β-hydroxydammar-20,24-dien-12,23 -dione-3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside) (Compound 9), 4,20(S) -Dihydroxy-3,4-seco-damar-24-en-12,23-dione-3-oic acid (4,20(S)-dihydroxy-3,4-seco-dammar-24-en- 12,23-dion-3-oic acid) (Compound 10), 4,20(S),25-trihydroxy-3,4-seco-damaran-12,23-dione-3-oic acid (4 ,20(S),25-trihydroxy-3,4-seco-dammaran-12,23-dion-3-oic acid) (Compound 11), 4-hydroxy-3,4-seco-22,23,24 ,25,26,27-hexanordammaran-12,20-dione-3-oic acid (4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordammaran-12,20 -dion-3-oic acid) (compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamno Pyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (3β-hydroxy-22 ,23,24,25,26,27-hexanordammaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl(1→3)]-β- D-glucopyranoside) (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-( 1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (3β-hydroxy- 22,23,24,25,26,27-hexanordammaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]- [α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside) (Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O- α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D- Glucopyranoside (3β,20(S),25-trihydroxydammaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3) ]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside) (compound 15), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O- α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D- Glucopyranoside (3β-hydroxydammar-20,24-dien-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)] -[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside) (Compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene-12- One-3-O-α-L-rhamnopyranosyl-(1→2)-[α -L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (3β,20(S),25-trihydroxydammar-23(E)-en-12-one-3-O-α -L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside) (Compound 17), 3β,20(S),25-trihydroxydamar -23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L -Rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (3β,20(S),25-trihydroxydammar-23(E)-en-12-one-3-O-α-L -rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside) (compound 18) and 3β, 20(S)-dihydroxydamar-24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (3β,20( S)-dihydroxydammar-24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside) (Compound 19) at least one compound selected from the group consisting of In the pharmaceutical composition for preventing or treating diseases related to AMPK (5′-AMP-activated protein kinase), characterized in that it contains an extract of Gynostemma longipes VK1 containing as an active ingredient,
The AMPK-related disease is a pharmaceutical composition for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome.
[Formula 1]

The method of claim 1,
The Ginostem rongifes VK1 extract is an extract obtained by extracting Ginostem rongifes VK1 with at least one solvent selected from the group consisting of water, C1-4 lower alcohols, C1-4 acetic acid esters, acetone and methyl ethyl ketone. In the pharmaceutical composition for preventing or treating AMPK (5′-AMP-activated protein kinase) related diseases, characterized in that,
The AMPK-related disease is a pharmaceutical composition for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- of Formula 1 Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyrano Seed (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4 -O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β,20(S)- Dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20 (S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione (compound 7) , 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-( 1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4- Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23- Dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid ( Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran -12,20-Dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D -Glucopyranoside (Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[ α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar -20,24-Diene-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α- L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene-12- One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β ,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar -24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) at least one compound selected from the group consisting of In the pharmaceutical composition for preventing or treating diseases related to AMPK (5′-AMP-activated protein kinase), characterized in that it contains as an active ingredient,
The AMPK-related disease is a pharmaceutical composition for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome.
[Formula 1]

The method of claim 3,
The compound is 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamno Pyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O- α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3) , Zipentonoside A (Compound 4), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2) -β-D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-en-12,23-dione (compound 6), 20(S)-hydroxydamar -24-ene-3,12,23-trione (compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl -(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 4,20(S)-dihydroxy-3,4 -Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23 -Dion-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2) -[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordama Ran-12,20-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl -(1→6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17) and 3β,20(S) -Dihydroxydamar-24-en-12-o AMPK (5), characterized in that it is at least one compound selected from the group consisting of four-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) In the pharmaceutical composition for preventing or treating'-AMP-activated protein kinase) related diseases,
The AMPK-related disease is a pharmaceutical composition for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. The method according to any one of claims 1 to 4,
In the pharmaceutical composition for preventing or treating diseases related to AMPK (5′-AMP-activated protein kinase), wherein the pharmaceutical composition activates AMPK,
The AMPK-related disease is a pharmaceutical composition for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. delete The method according to any one of claims 1 to 4,
The muscle diseases include muscle atrophy, myopathy, muscle injury, muscle dystrophy, myasthenia, sarcopenia, myoneural conductive disease, AMPK (5′-AMP), characterized in that it is selected from the group consisting of dermatomyositis, diabetic amyotrophy, amyotrophic lateral sclerosis (ALS), and degenerative muscle diseases. In the pharmaceutical composition for preventing or treating -activated protein kinase) related diseases,
The AMPK-related disease is a pharmaceutical composition for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. delete 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- of Formula 1 Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyrano Seed (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4 -O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β,20(S)- Dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20 (S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione (compound 7) , 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-( 1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4- Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23- Dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid ( Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran -12,20-Dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D -Glucopyranoside (Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[ α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar -20,24-Diene-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α- L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene-12- One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β ,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar -24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) at least one compound selected from the group consisting of In the health functional food composition for improving AMPK-related diseases, characterized in that it contains the Ginostema longifes VK1 extract containing as an active ingredient,
The AMPK-related disease is a health functional food composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome.
[Formula 1]

The method of claim 9,
The Ginostem rongifes VK1 extract is an extract obtained by extracting Ginostem rongifes VK1 with at least one solvent selected from the group consisting of water, C1-4 lower alcohols, C1-4 acetic acid esters, acetone and methyl ethyl ketone. In the health functional food composition for improving AMPK-related diseases, characterized in that,
The AMPK-related disease is a health functional food composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- of Formula 1 Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyrano Seed (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4 -O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β,20(S)- Dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20 (S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione (compound 7) , 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-( 1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4- Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23- Dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid ( Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran -12,20-Dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D -Glucopyranoside (Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[ α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar -20,24-Diene-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α- L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene-12- One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β ,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar -24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) at least one compound selected from the group consisting of In the health functional food composition for improving AMPK-related diseases, characterized in that it contains as an active ingredient,
The AMPK-related disease is a health functional food composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome.
[Formula 1]

The method of claim 11,
The compound is 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamno Pyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O- α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3) , Zipentonoside A (Compound 4), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2) -β-D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-en-12,23-dione (compound 6), 20(S)-hydroxydamar -24-ene-3,12,23-trione (compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl -(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 4,20(S)-dihydroxy-3,4 -Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23 -Dion-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2) -[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordama Ran-12,20-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl -(1→6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17) and 3β,20(S) -Dihydroxydamar-24-en-12-o AMPK-related disease, characterized in that it is at least one compound selected from the group consisting of -3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) In the health functional food composition for improvement,
The AMPK-related disease is a health functional food composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. The method according to any one of claims 9 to 12,
In the health functional food composition for improving AMPK-related diseases, characterized in that the health functional food composition activates AMPK,
The AMPK-related disease is a health functional food composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. delete The method according to any one of claims 9 to 12,
The muscle diseases include muscle atrophy, myopathy, muscle injury, muscle dystrophy, myasthenia, sarcopenia, myoneural conductive disease, Health for improving AMPK-related diseases, characterized in that it is selected from the group consisting of dermatomyositis, diabetic amyotrophy, amyotrophic lateral sclerosis (ALS), and degenerative muscle diseases. In the nutraceutical composition,
The AMPK-related disease is a health functional food composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. delete 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- of Formula 1 Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyrano Seed (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4 -O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β,20(S)- Dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20 (S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione (compound 7) , 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-( 1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4- Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23- Dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid ( Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran -12,20-Dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D -Glucopyranoside (Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[ α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar -20,24-Diene-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α- L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene-12- One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β ,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar -24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) at least one compound selected from the group consisting of In the animal drug for preventing or treating AMPK-related diseases, characterized in that it contains the extract of Ginostema rongifes VK1, which contains as an active ingredient,
The AMPK-related disease is an animal drug for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome.
[Formula 1]

The method of claim 17,
The Ginostem rongifes VK1 extract is an extract obtained by extracting Ginostem rongifes VK1 with at least one solvent selected from the group consisting of water, C1-4 lower alcohols, C1-4 acetic acid esters, acetone and methyl ethyl ketone. In the animal drug for preventing or treating AMPK-related diseases, characterized in that,
The AMPK-related disease is an animal drug for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- of Formula 1 Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyrano Seed (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4 -O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β,20(S)- Dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20 (S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione (compound 7) , 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-( 1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4- Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23- Dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid ( Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran -12,20-Dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D -Glucopyranoside (Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[ α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar -20,24-Diene-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α- L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene-12- One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β ,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar -24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) at least one compound selected from the group consisting of In the animal drug for preventing or treating AMPK-related diseases, characterized in that it contains as an active ingredient,
The AMPK-related disease is an animal drug for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome.
[Formula 1]

The method of claim 19,
The compound is 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamno Pyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O- α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3) , Zipentonoside A (Compound 4), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2) -β-D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-en-12,23-dione (compound 6), 20(S)-hydroxydamar -24-ene-3,12,23-trione (compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl -(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 4,20(S)-dihydroxy-3,4 -Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23 -Dion-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2) -[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordama Ran-12,20-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl -(1→6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17) and 3β,20(S) -Dihydroxydamar-24-en-12-o AMPK-related disease, characterized in that it is at least one compound selected from the group consisting of -3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) In animal medicines for prophylaxis or treatment,
The AMPK-related disease is an animal drug for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. The method according to any one of claims 17 to 20,
In the animal drug for preventing or treating AMPK-related diseases, wherein the animal drug activates AMPK,
The AMPK-related disease is an animal drug for preventing or treating AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. delete 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- of Formula 1 Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyrano Seed (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4 -O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β,20(S)- Dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20 (S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione (compound 7) , 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-( 1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4- Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23- Dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid ( Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran -12,20-Dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D -Glucopyranoside (Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[ α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar -20,24-Diene-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α- L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene-12- One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β ,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar -24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) at least one compound selected from the group consisting of In the animal feed composition for improving AMPK-related diseases, characterized in that it contains the extract of Ginostema longifes VK1, which contains as an active ingredient,
The AMPK-related disease is an animal feed composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome.
[Formula 1]

The method of claim 23,
The Ginostema longifes VK1 extract is an extract obtained by extracting Ginostema longifes VK1 with at least one solvent selected from the group consisting of water, lower alcohols of C1-4, acetic acid esters of C1-4, acetone, and methyl ethyl ketone. In the composition for animal feed for improving AMPK-related diseases, characterized in that,
The AMPK-related disease is an animal feed composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L- of Formula 1 Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyrano Seed (Compound 2), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4 -O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3), zipentonoside A (compound 4), 3β,20(S)- Dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20 (S)-dihydroxydamar-24-ene-12,23-dione (compound 6), 20(S)-hydroxydamar-24-ene-3,12,23-trione (compound 7) , 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-( 1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl- (1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound 9), 4,20(S)-dihydroxy-3,4- Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23- Dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid ( Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)- [α-L-Rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran -12,20-Dione-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D -Glucopyranoside (Compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[ α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 15), 3β-hydroxydamar -20,24-Diene-12,23-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α- L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-ene-12- One-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β ,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyra Nosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18) and 3β,20(S)-dihydroxydamar -24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) at least one compound selected from the group consisting of In the animal feed composition for improving AMPK-related diseases, characterized in that it contains as an active ingredient,
The AMPK-related disease is an animal feed composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome.
[Formula 1]

The method of claim 25,
The compound is 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamno Pyranosyl-(1→3)]-β-D-glucopyranoside (compound 1), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O- α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 3) , Zipentonoside A (Compound 4), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2) -β-D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-en-12,23-dione (compound 6), 20(S)-hydroxydamar -24-ene-3,12,23-trione (compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3-O-α-L-rhamnopyranosyl -(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 4,20(S)-dihydroxy-3,4 -Seco-Damar-24-ene-12,23-dione-3-oic acid (Compound 10), 4,20(S),25-trihydroxy-3,4-Seco-Damara-12,23 -Dion-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-oic acid (Compound 12), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2) -[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25,26,27-hexanordama Ran-12,20-Dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl -(1→6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one-3-O -α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17) and 3β,20(S) -Dihydroxydamar-24-en-12-o AMPK-related disease, characterized in that it is at least one compound selected from the group consisting of -3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 19) In the composition for animal feed for improvement,
The AMPK-related disease is an animal feed composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. The method according to any one of claims 23 to 26,
In the composition for animal feed for improving AMPK-related diseases, characterized in that the composition for animal feed activates AMPK,
The AMPK-related disease is an animal feed composition for improving AMPK-related diseases, characterized in that at least one selected from the group consisting of muscle diseases, obesity, diabetes and metabolic syndrome. delete delete New compound 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2) having the chemical structure of the following formula (2) -[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl-20-O-β-D-glucopyranoside (compound 2), 3β,20(S)-di Hydroxydamar-24-ene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-α-L-rhamnopyranosyl- (1→3)]-β-D-glucopyranoside (compound 3), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione-3-O-α-L -Rhamnopyranosyl-(1→2)-β-D-glucopyranoside (compound 5), 3β,20(S)-dihydroxydamar-24-ene-12,23-dione (compound 6) , 20(S)-hydroxydamar-24-ene-3,12,23-trione (compound 7), 3β,20(S),25-trihydroxydamaran-12,23-dione-3 -O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 8), 3β-hydroxy Damar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β -D-glucopyranoside (compound 9), 3β-hydroxy-22,23,24,25,26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyra Nosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 13), 3β-hydroxy-22,23,24,25, 26,27-hexanordamaran-12,20-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[ α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 14), 3β,20(S),25-trihydroxydamaran-12,23-dione-3 -O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β -D-glucopyranoside (compound 15), 3β-hydroxydamar-20,24-diene-12,23-dione-3-O-α-L-rhamnopyranosyl-(1→2)-[ α-L-rhamnopyranosyl-(1→3)]-[α-L- Rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 16), 3β,20(S),25-trihydroxydamar-23(E)-en-12-one- 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (compound 17), 3β,20 (S),25-trihydroxydamar-23(E)-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl- (1→3)]-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (compound 18), and 3β,20(S)-dihydroxydamar- Any one compound selected from the group consisting of 24-en-12-one-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (Compound 19).
[Formula 2]

New compound 4,20(S)-dihydroxy-3,4-seco-damar-24-ene-12,23-dione-3-oic acid (Compound 10) having the chemical structure of the following formula (3), 4 ,20(S),25-trihydroxy-3,4-seco-damaran-12,23-dione-3-oic acid (compound 11), 4-hydroxy-3,4-seco-22,23 Any one compound selected from the group consisting of, 24,25,26,27-hexanordamaran-12,20-dione-3-oic acid (Compound 12).
[Chemical Formula 3]

Images