KR101794995B1 - ANTI-IMPOTENCE DRUG CONTAINING β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside EXTRACTED FROM LESPEDEZA CUNEATA, AND FUNCTIONAL FOODS FOR SAME - Google Patents
ANTI-IMPOTENCE DRUG CONTAINING β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside EXTRACTED FROM LESPEDEZA CUNEATA, AND FUNCTIONAL FOODS FOR SAME Download PDFInfo
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Abstract
The present invention relates to β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside which exhibits blood flow improving effect, ≪ / RTI > More specifically, the present invention relates to the effect of Nitric Oxide (Nitric Oxide) generation on the extracts of the yam Kanto ginseng extract and its derived physiologically active substance derivatives. Improvement of sexual function in male of beta-sitosterol-6-linolenoyl-3-O-beta-D-glucopyranoside of the present invention And a neurotransmitter mediating vasodilator mediating vasodilation by the production of nitric oxide (NO) in vascular endothelial cells and improving erectile dysfunction. ≪ / RTI > The present invention also provides a process for extracting the compound β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside and a composition containing the compound β-sitosterol-improving effect and sexual function improvement .
Description
The present invention relates to β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside which exhibits blood flow improving effect, ≪ / RTI > More specifically, the present invention relates to a composition for improving male sexual function, improving blood flow, and lowering blood pressure, and is a neurotransmitter that mediates vasodilatory activity by producing nitric oxide from vascular endothelium, Beta-sitosterol-6 ' -linolenoyl-3-O-beta-D-glucopyranoside -D-glucopyranoside. ≪ / RTI >
Still another object of the present invention is to provide a compound having beta-sitosterol-6-linolenoyl-3-O-beta-D-glucopyranoside having an effect of improving blood flow and improving sexual function -3-O-? -D-glucopyranoside) and an extract containing the same.
Still another object of the present invention is to provide a compound having beta-sitosterol-6-linolenoyl-3-O-beta-D-glucopyranoside having an effect of improving blood flow and improving sexual function -3-O-? -D-glucopyranoside) or a composition containing the same as an active ingredient.
The scientific name of the school is Lespedeza cuneata . It is a perennial plant with legumes. In our language, it is called as ishi, and kanji is called 葉)))))))))), 관 문)))))))))))))))))))))))))))))))). There are several names such as 공 공 공 공 공 공.............................
The physiologically active substances found in the doorway include pinitol, flavonoid, phenol, tannin and betasitosterol, and among the flavonoids, quercetin, , Kaempferol, vitexin, and orientin have been reported to be separated from the yard gate.
The physiologically active ingredients of the above-described doorway sterilize or inhibit Staphylococcus aureus, pneumococcal bacteria, streptococcal bacteria, and Qatar bacteria. It is also effective in treating various male diseases, such as lack of ovaries, premature ejaculation, oil wells, and venereal diseases. Therefore, the yuan gate is recognized as a herbal medicine with the efficacy of natural Viagra without side effects.
There is an effective way to cough cough with bronchitis or bronchial asthma and to exert a lot of sputum. It also strengthens the liver, brightens the eyes and cures the dark eyes and eliminates the eosinophils. It also has acute gastritis, gastric ulcer, diarrhea, It also has effects on bowel movements, bruises, and boils.
According to the conventional art, the extract of the yuan guano is mixed with other foods to produce the yuan guanyum extract (Korean patent No. 10-1205446), the chocolate composition containing the yuan guanyum extract (Korean patent registration No. 10-1213740) A pharmaceutical composition for the treatment and prevention of erectile dysfunction and male sexual function including the method of manufacturing (Korean Patent No. 10-1080940), sesame noodle (Korean Patent No. 10-0821613) No. 07-0117299) have been known.
On the other hand, in the art, the action mechanism has been studied in relation to the improvement of sexual function of nitrogen oxides (NO). For example, the main agonist of erection is nitric oxide (NO).
Nitric oxide (NO) is synthesized by Nitric Oxide Synthase (NOS) in the conversion of L-arginine into L-citruline, and nonadrenergic noncholinergic neurons (NANC , nonadrenergic noncholinergic). Nitric oxide (NO) is also produced in vascular endothelial cells or cavernosal smooth muscle itself. Nitric oxide (NO) activates guanylate cyclase to increase intracellular cGMP (cyclic guanosine monophosphate) concentration.
Guanosine monophosphate (cGMP) activates the protein kinase involved in the ion channel, thereby opening the potassium channel and causing hyperpolarization in the smooth muscle cell membrane, thereby transferring intracellular calcium to the endoplasmic reticulum, To block the entry of extracellular calcium into the cells. In other words, when the intracellular calcium concentration is lowered to relax the cavernosal smooth muscle, an erection occurs.
Clinically, nitric oxide (NO) has been shown to play a role in one of the erectile dysfunctions of the penis, and intravenous injection of nitric oxide (NO) release can cause erectile dysfunction in men as well as men with normal sexual function The fact is known.
According to the contents described in yagwanmun using response surface methodology (Lespedeza cuneata) Optimization of ethanol extraction conditions of the functional component (Journal of the Korea Food and Cookery, KOREAN J. FOOD COOKERY SCI. Vol . 28, No. 3 June, 2012), response surface methodology A method for optimizing the extraction conditions for the functional components of the ethanol extract of the yamamatsu tea was disclosed.
In order to optimize the extraction conditions of functional materials in the field, the range of optimal conditions determined by extracting yield, total polyphenol content, electron donating ability and nitrite scavenging ability according to extraction conditions is as follows: extraction temperature is 78 ° C. to 85 ° C., extraction time For 6 to 7 hours, and the ethanol concentration was 38% to 60%.
However, the physiologically active functions of various compounds of the substance extracted from the yam instructor are not known, and the purpose of the present invention is to improve beta-sitosterol-6-linolenol-3-O-beta-D -Sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside is not known.
Therefore, the inventors of the present invention found that β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside 3-O-beta-D-glucopyranoside (beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside) glucopyranoside. As a result, it was found that the mixture extracted from the yam cabinet door was effectively purified to obtain beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside -3-O-? -D-glucopyranoside) as a single compound, thereby completing the present invention.
The β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside is a compound of the nitric oxide (NO) The present invention has been accomplished by ascertaining the effect of male sexual enhancement through the generation of the male sex.
A basic object of the present invention is to provide a method for treating erectile dysfunction in a male patient through the production of nitric oxide (NO) in vascular endothelial cells, sitosterol-6 ' -linolenoyl-3-O- [beta] -D-glucopyranoside.
A further object of the present invention is to provide a method for inhibiting beta-sitosterol-6'-linolenoyl-3-O-beta -D-glucopyranoside- glucopyranoside in the presence of the extract.
A further object of the present invention is to provide a method for the production of beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside O-beta-D-glucopyranoside).
Another object of the present invention is to provide β-sitosterol-6'-linolenoyl-3-O-β-D (β-D-glucopyranoside) -glucopyranoside) as a food additive.
The basic object of the present invention is to provide a method for producing beta-sitosterol-6'-linolenoyl-3-O-beta -D- glucopyranoside, glucopyranoside was isolated and purified to obtain blood vessels of beta-sitosterol-6'-linolenoyl-3-O- beta -D-glucopyranoside By ensuring the ability to produce nitric oxide in endothelial cells.
It is a further object of the present invention to provide a method for producing granules, which comprises: 1) pulverizing a dry door in a dry state with a grinder; 2) an alcohol extraction step of immersing the milled door in the alcohol in the step 1) and repeating the extraction; 3) further extracting the extract obtained in the alcohol extraction step using an organic solvent; And 4) heating the extract of 3) above the boiling point of ethanol to sterilize the ethanol while volatilizing it.
At this time, according to an aspect of the present invention, it is preferable that the yam door extract is extracted with water, an alcohol, an organic solvent, or a fraction purified by using column chromatography.
It is still another object of the present invention to provide a compound beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside having an effect of improving blood flow and improving sexual function -3-O-? -D-glucopyranoside) as an active ingredient.
The β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside compound of the present invention derived from β-sitosterol-6-linolenoyl- And the naked eye extract and the physiologically active substances and derivatives contained therein increase the ability to produce nitric oxide (NO) related to the dilatation of blood vessels related to erectile dysfunction, which is one of male sexual dysfunction diseases, and thus exhibit erectile dysfunction treatment effect.
In addition, the yamancheon is widely used as a plant for growing wastes and paper waste, and is widely distributed in many countries. Therefore, it can be supplied as a low-priced functional food to consumers because it is used natural materials.
In addition, beta-sitosterol-6'-linolenoyl-3-O-beta-D-glucopyranoside, which can improve male sexual function, glucopyranoside compound and a physiologically active substance and a derivative thereof, it is possible to develop and supply medicines, functional foods and derivatives thereof.
BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a graph showing the effect of β-sitosterol-6'-linolenoyl-3-O-β-D (β-D-glucopyranoside) -glucopyranoside (NO) in human umbilical vein endothelial cells (HUVECs).
FIG. 2 is a graph showing the results of measurement of nitric oxide (NO) production by human-umbilical vein endothelial cells (HUVECs) by D-Pinitol.
Figure 3 is a graph showing the results of measurement of nitric oxide (NO) produced by Kaempferol in human umbilical vein endothelial cells (HUVECs).
FIG. 4 is a graph showing the results of measurement of nitric oxide (NO) produced by nicotiflorin in human umbilical vein endothelial cells (HUVECs).
Figure 5 is a graph showing the results of measurement of nitric oxide (NO) produced by quercetin in human umbilical vein endothelial cells (HUVECs).
Figure 6 is a graph showing the results of measurement of nitric oxide (NO) produced by Rutin in human umbilical vein endothelial cells (HUVECs).
FIG. 7 is a graph showing the changes in the concentration of nitric oxide (NO) by β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside NO) is produced in human umbilical vein endothelial cells (HUVECs).
8 is a graph showing the results of measurement of nitric oxide (NO) production by human ovarian vein endothelial cells (HUVECs) by Loroxanthin.
FIGS. 9 to 13 are graphs showing the results of cytotoxicity analysis of the MTT assay of FIGS. 1 to 8. FIG.
FIG. 14 is a graph summarizing the EC 50 based on the results of FIGS. 1 to 8. FIG.
FIG. 15 is a view showing a process of extracting a naked eye gate extract and a physiologically active substance according to the present invention. FIG.
FIG. 16 is a view showing a process of purifying the naked eye gate extract and the physiologically active substance of the present invention. FIG.
The present invention relates to a compound of the present invention having a blood flow improving effect and a compound of beta-sitosterol-6-linolenoyl-3-O-beta-D-glucopyranoside D-glucopyranoside, and a yam cabbage extract containing the same, a specific example of a health functional food having a male sexual function improving effect is described as follows.
However, the following embodiments are only illustrative of the gist of the present invention and are not intended to limit the scope of the present invention. It will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the present invention as defined by the following claims, .
In order to accomplish the object of the present invention, the present inventors extracted methanol from an extract of a yam Kwan-Moon extract obtained by alcohol extraction from a yam door, and extracted it with methanol using an organic solvent such as n-hexane, ethyl acetate and butanol Beta -sitosterol-6-linolenol-3-O-beta-D (O-beta -D-glucopyranosyl) -3-O-beta-D-glucopyranoside obtained by separating the obtained organic solvent- Β-D-glucopyranoside (β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside) exhibited improved blood flow and improved sexual function.
The β-sitosterol-6'-linolenoyl-3-O-β-D-glucopyranoside compound isolated and purified from the yam Kanto extract The formula and 1 H-NMR data are as follows.
[Chemical Formula 1]
[Table 1] H-NMR data
The present invention also relates to a compound of the present invention having the effect of improving the blood flow and improving sexual function, such as beta-sitosterol-6-linolenol-3-O-beta-D-glucopyranoside linolenoyl-3-O- [beta] -D-glucopyranoside) and extracts containing the same.
Human umbilical vein endothelial cells (HUVECs), which are a kind of endothelial cells, were used to examine the ability of the physiologically active substances and their derivatives contained in the extracts and extracts of the present invention to produce nitric oxide (NO). Physiologically active substances and derivatives may be selected from the group consisting of kaempferol, nicotiflorin, quercetin, rutin, beta-sitosterol
Cell culture was performed on EGM-2 medium prepared by adding 10% FBS, 1% penicillin / streptomycin, and supplement to EBM-2. The culture conditions were incubated in a 5% CO 2 incubator at 37 °
And 50 mg / ml were treated with 500, 250 and 100 ug / ml, respectively. Experimental group was treated with 400 ng / ml of LPS and supplemented with camphorol, nicotiflorin, quercetin, rutin, beta-sitosterol
Nitric oxide (NO) measurements are based on a total of 8 wells starting from 10 μg / ml Na 2 SO 4 to 0 μg / ml. After 3 hours of sample treatment, the supernatant was transferred to a 96-well plate (50 μl) containing 50 μl of 1% sulfanilamide in 5% phosphoric acid and 50 μl of 0.1% N-1-napthylethylenediamine dihydrochloride in water) were mixed at a ratio of 1: 1, and then 50 μl was added to a well containing the supernatant. After incubating for 10 min at 37 ° C in 5% CO 2 , the wavelength range of the ELISA reader was measured at 590 nm.
Nitric oxide (NO) production was greater in the 500 ㎍ / ml extract than in the control group and significantly higher than in the control group.
(D-Pinitol) 0.01 μM,
The supernatant was taken from a 96-well plate, and 50 μl of the remaining 50 μl of the MTT reagent was added to the MTT reagent (1: 4). The reaction was then continued for 2 hours at 37 ° C in a 5% CO 2 incubator. After 2 hours, Suction was performed and 100 μl of DMSO was added to measure the wavelength range of the ELISA reader at 570 nm.
Compared with the control group, cytotoxicity was observed in the naked eye extract and the physiologically active nicotiflorin.
In addition, the present invention provides a method for producing an extract for extracting a compound derived from a yamba gate. Hereinafter, the extraction method of the present invention will be described in detail.
Firstly, the yam cabbage extract having the effect of improving the blood flow and improving the sexual function is separated from the gazebo.
The present invention relates to a method of extracting a nightstand gate, comprising the steps of: 1) crushing a dry nightstand with a crusher;
2) an alcohol extraction step of immersing the milled door in the alcohol in the step 1) and repeating the extraction;
3) further extracting the extract obtained in the alcohol extraction step using an organic solvent; And
4) heating the extract of 3) above the boiling point of ethanol to sterilize the ethanol while volatilizing it.
For this purpose, the present inventors obtained an alcohol fraction of the yamba mushroom extract which exhibited nitric oxide (NO) activity by submerging and inserting a night gate in alcohol. At this time, it is preferable to use the raw, hay, ground, and roots of the nightclub door including natural or artificial nightclubs. It is preferable to use methanol as the alcohol. As described above, the basement door is extracted with methanol, and then extracted with an organic solvent such as N-hexane, ethyl acetate or butanol to separate the yam Kwan-Moon extract.
Specifically, the present inventors concentrated on extracting methanol from the hay of a night gate and fractionating it using an organic solvent such as N-hexane, ethyl acetate or butanol, thereby obtaining various solvent-extracted fractions .
At this time, extraction with an organic solvent is carried out in the order of a nonpolar solvent, a polar solvent, and an organic solvent including a lower alcohol, such as N-hexane, ethyl acetate or butanol. As a preferred embodiment, the present invention was used to prepare each solvent-extracted fraction and water fraction by successively using N-hexane, ethyl acetate, butanol, and the like. When extracting the solvent using the above-described solvent, the temperature for extracting the door opener is preferably in the range of 4 ° C to 100 ° C, more preferably room temperature or 4 ° C to 30 ° C.
In step 2) of the present invention, 8 kg of methanol (MeOH, methanol) was added to 3 kg of the dried yard door which was pulverized by a pulverizer and repeatedly extracted 5 times for 3 hours using a reflux condenser. The extracted methanol (MeOH) extracts were collected and the methanol extract (MeOH extract) (300 g) was obtained after removing the solvent using a vacuum concentrator. This methanol extract (MeOH extract) was suspended in 2 L of distilled water, and then the same amount of N-hexane was added thereto and fractionation with a fractionation funnel was repeated three times. The fractions were collected and the solvent was removed using a vacuum concentrator To obtain 65.7 g of an n-hexane extract. Ethanol (EtOAc, Ethyl Acetate) and butanol (BuOH, Buthanol) were fractionated in the order of polarity, and EtOAc extract and BuOH extract were added to the remaining water layer (H 2 O layer) , 67.5 g. (Fig. 15 )
Among the fractions obtained from the extracted methanol extract (MeOH extract), vacuum liquid chromatography was performed on n-hexane extract (65.7 g). A sample was coated on silica gel and eluted with n-hexane: ethyl acetate (EtOAc) (50: 1 20: 1 10: 1 5: 1) n-hexane): ethyl acetate (EtOAc): methanol (MeOH) (2.5: 1: 0.1 1: 1: 0.2), ethyl acetate (EtOAc): methanol (MeOH)
For the experiment, the fractions 5 (11.2 g) were further subjected to silica gel column chromatography, and the fraction was extracted with n-hexane: ethyl acetate Eluting with ethyl acetate (EtOAc) (4: 1 3: 1 2: 1), n-hexane: ethyl acetate (EtOAc): methanol (MeOH) (2: 1: 0.05 2: 1: 0.1) A total of 9 fractions are obtained (Fraction 5-1 to 5-9). The fraction (Fraction) 5-8 (1.1 g) was subjected to repeated silica gel column chromatography. Four fractions were obtained (Fraction 5-8-1 to 5-8-4) by elution with chloroform (CHCl 3, Chloroform) and acetone gradient (8: 1 1: 1). The compound of the present invention 3 (beta-sitosterol-6-linolenol-3-O-beta-D-glucopyranoside (beta-sitosterol-6 -linolenoyl-3-O- [beta] -D-glucopyranoside) (68.5 mg) was obtained (Fig. 16).
According to a preferred specific example of the present invention, there is provided a composition comprising the yam door extract. The extract composition derived from the naked eye of the present invention can be contained in foods or medicines. When it is manufactured by a pharmaceutical, it can be added to one or more pharmaceutically acceptable carriers to produce a pharmaceutical product.
The present invention also provides a functional food containing an essential ingredient of a dried cabbage extract which contains 20 to 80% by weight of a dry powder extracted from a general functional food, such as Lespedeza cuneata.
The functional food containing the naked eye extract component of the present invention improves erectile dysfunction and blood circulation in a male, provides a drug for improving erectile dysfunction, and a health functional food.
More preferably, the present invention provides a functional food containing an essential component of the extract of a yam Kwan Kwan, which contains 50 to 70% by weight of powder extracted from Lespedeza cuneata and has excellent physiological activity, efficacy and overall acceptability.
To add nutrients to the functional food containing the extract of the yamanco extract, one or more vitamins selected from vitamin A blend, vitamin B1 hydrochloride, vitamin B2, nicotinic acid amide, vitamin C, vitamin D3 mixture, vitamin E mixture and vitamin B6 hydrochloride And may further include additional. The content thereof can be adjusted to such an extent as not to deteriorate the function of the functional food containing the gate opening extract. Preferably, the total content of the additive to be added should not exceed 40% by weight.
More preferably, the vitamin A blend may further include at least one selected from retinyl acetate, vitamin E blend, maltodextrin, corn starch, and gum arabic.
More preferably, the vitamin D3 mixture may further include at least one selected from the group consisting of gum arabic, sugar, corn starch, heavy chain triglyceride, silicon dioxide, vitamin D3 and vitamin E.
More preferably, the vitamin E blend may further comprise at least one additive selected from DL-? -Tocopherol acetate, maltodextrin, modified starch and silicon dioxide.
While the present invention has been particularly shown and described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, do.
Claims (8)
[Chemical Formula 1]
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| Title |
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| J, Agric. Food Chem., 52, 228-233, 2004. |
| J. Korean Soc. Food Sci. Nur, 41(11), 1508-1514, 2012. |
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