WO2019119675A1 - Ester d'acide gras saturé de sitostérol-glycoside de patate douce, extrait, procédé de préparation correspondant et application associée - Google Patents

Ester d'acide gras saturé de sitostérol-glycoside de patate douce, extrait, procédé de préparation correspondant et application associée Download PDF

Info

Publication number
WO2019119675A1
WO2019119675A1 PCT/CN2018/081664 CN2018081664W WO2019119675A1 WO 2019119675 A1 WO2019119675 A1 WO 2019119675A1 CN 2018081664 W CN2018081664 W CN 2018081664W WO 2019119675 A1 WO2019119675 A1 WO 2019119675A1
Authority
WO
WIPO (PCT)
Prior art keywords
sweet potato
fatty acid
acid ester
saturated fatty
extract
Prior art date
Application number
PCT/CN2018/081664
Other languages
English (en)
Chinese (zh)
Inventor
叶小利
李学刚
李滟临
李亚松
Original Assignee
西南大学
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 西南大学 filed Critical 西南大学
Publication of WO2019119675A1 publication Critical patent/WO2019119675A1/fr

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/39—Convolvulaceae (Morning-glory family), e.g. bindweed
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • C07H15/256—Polyterpene radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Definitions

  • the invention relates to the field of medicinal chemistry, in particular to sweet potato gluten glucoside saturated fatty acid ester, extract and preparation method and application thereof
  • Tumors are malignant diseases that pose a serious threat to human health.
  • tumors have become the leading cause of death, and morbidity and mortality are still rising.
  • China is expected to have 4.292 million new cases of tumors, equivalent to an average daily new birth. 12,000 cases of cancer, and 2.814 million deaths, equivalent to an average of 7,500 deaths per day from cancer.
  • Finding anti-tumor drugs with definite curative effects and small toxic side effects has always been a hot and difficult point in drug innovation research and development.
  • Traditional Chinese medicine has been a hot spot for cancer chemotherapy research because of its unique advantages, and the extraction of safe and effective parts from traditional Chinese medicine for the prevention and/or treatment of cancer.
  • Sweet potato also known as sweet potato, sweet potato, sweet potato, sweet potato, sweet potato, etc.
  • Sweet potato is one of China's food crops, and its planting area and output rank first in the world.
  • sweet potato “sweet, flat, non-toxic. Indications tonic deficiency, benefit strength, spleen and stomach, strong kidney yin. Gong with yam.”
  • Modern research results show that (Wang Hongyun et al., Chinese Food and Nutrition, 2013, 19 (12): 59-62) sweet potato has anti-cancer, improve immunity, lower blood fat, lower blood sugar, inhibit thrombosis, prevent arteriosclerosis and cardiovascular disease, etc.
  • sweet potato has a good anti-tumor effect (Meimei Wang etc. Bioassay-guided isolation of glycoprotein SPG-56 from sweet potato Zhongshu-1 and its anti-colon cancer activity in vitro and in vivo. Journal of Functional Foods. 35, (2017), 315-324).
  • sweet potato starch in the process of sweet potato starch production, sweet potato protein, polysaccharides, vitamins and other health care ingredients (including anti-tumor ingredients) but with sweet potato starch mother liquor (commonly known as yellow pulp or starch wastewater) is lost, not only pollutes the environment, but also greatly wastes resources; on the other hand, the separation and identification of active monomers in sweet potato is difficult, and it is still impossible to determine which components have anti-tumor effects.
  • a first object of the present invention is to provide a sweet potato sitosterol glycoside saturated fatty acid ester which has remarkable tumor cell growth inhibitory activity.
  • a second object of the present invention is to provide a sweet potato sitosterol glycoside saturated fatty acid ester extract.
  • a third object of the present invention is to provide a method for preparing a sweet potato sitosterol glycoside saturated fatty acid ester extract and a sweet potato sitosterol glycoside saturated fatty acid ester.
  • a fourth object of the present invention is to provide an application of a sweet potato sitosterol glycoside saturated fatty acid ester and/or a sweet potato sitosterol glycoside saturated fatty acid ester extract for the preparation of a medicament for preventing and/or treating a tumor, a health food.
  • the sweet potato valley sterol glycoside saturated fatty acid ester has a chemical formula as shown in Formula I:
  • R -C n H 2n+1 and 12 ⁇ n ⁇ 18.
  • R is a linear hydrocarbon group having a chemical formula of the formula II, and the formula II is a sweet potato sterol glycoside palmitate.
  • the sweet potato sitosterol glycoside saturated fatty acid ester extract provided by the present invention comprises a compound of formula I, wherein the compound of formula I accounts for more than 1% by weight of the extract.
  • the sweet potato sitosterol glycoside saturated fatty acid extract provided by the present invention comprises a compound of the formula II, and the compound of the formula II accounts for more than 1% by weight of the extract.
  • the sweet potato sterol glycoside saturated fatty acid extract comprises a compound of the formula II, and the compound of the formula II accounts for more than 10% by weight of the extract.
  • the above extract is obtained by precipitating, filtering/centrifuging, organic solvent extraction and purification of sweet potato starch mother liquor.
  • the above extract is spotted on a thin layer chromatography plate and developed in a developing agent of a chloroform/methanol/water mixed solution having a volume ratio of 90:10:1, and a sulfuric acid/methanol having a volume ratio of 1:9 is used.
  • the color of the toner was developed, and after heating at 105 ° C for 5 min, the extract was purple-red.
  • the method for preparing a sweet potato glutenol glycoside saturated fatty acid ester extract comprises the following steps:
  • Step 1 50-100 ° C, adding a weight ratio of 0.01% to 5% precipitant to the mother liquor of sweet potato starch, centrifuging or filtering, taking a solid to obtain a crude extract of sweet potato;
  • Step 2 adding an organic solvent having a weight ratio of 1:1 to 10 to the crude sweet potato extract, stirring, filtering, and concentrating the filtrate to obtain a sweet potato gluten glucoside saturated fatty acid ester extract.
  • the method for preparing a sweet potato glutamate sucrose saturated fatty acid ester extract further comprises the step 3, wherein the sweet potato gluten glucoside saturated fatty acid ester extract is subjected to column chromatography to collect chloroform in a volume ratio of 90:10:1.
  • /Methanol/water mixed solution is a developing agent
  • a sulfuric acid/methanol solution with a volume ratio of 1:9 is used as a color developing agent
  • a purple-red spot is heated at 105 ° C for 5 minutes
  • an eluent having a thin layer chromatography Rf of 0.68-0.77 is used.
  • the concentrated eluate was prepared to obtain a sweet potato gluten glucoside saturated acid ester extract.
  • the present invention provides a method for preparing a sweet potato sterol glycoside saturated fatty acid ester, wherein the precipitating agent described in the step 1 is selected from the group consisting of a divalent or trivalent metal salt, an organic acid, a gluconolactone, a sodium alginate, and a xanthogen.
  • the precipitating agent described in step 1 is selected from the group consisting of calcium salts, magnesium salts, aluminum salts, acetic acid, malic acid, citric acid, tartaric acid, gluconolactone, sodium alginate, xanthan gum and Carrageenan; preferably, the precipitating agent described in step 1 is selected from the group consisting of calcium sulfate, magnesium sulfate, tartaric acid, malic acid, citric acid, and gluconolactone.
  • the precipitating agent described in the step 1 is added in an amount of 0.05% to 1% by weight of the sweet potato starch mother liquor.
  • the centrifugation or filtration described in the step 1 further comprises the step of cooling to 0-80 ° C; preferably, the centrifugation or filtration described in the step 1 further comprises the step of cooling to 20-50 ° C.
  • the organic solvent described in the step 2 is one or more selected from the group consisting of water-soluble alcohols or ketones; preferably, the organic solvent described in the step 2 is selected from the group consisting of methanol, ethanol, propanol and acetone. Or a variety.
  • the organic solvent used in the step 2 is used in an amount of 2-5 times the weight of the crude sweet potato extract.
  • step 2 may be repeated 1-5 times; preferably, step 2 may be repeated 2-4 times; further preferably, step 2 may be repeated 2-3 times.
  • the column chromatography described in the step 3 includes silica gel column chromatography, macroporous adsorption resin column chromatography, glucose gel column chromatography and high performance liquid chromatography column chromatography; specifically, the column described in the step 3 Chromatography is silica gel column chromatography or high performance liquid chromatography column chromatography.
  • the column chromatography described in the step 3 is silica gel column chromatography, and the chromatographic conditions are sequentially using 1-5 column volumes of petroleum ether, 1-5 column volumes of ethyl acetate, and 1-5 columns. A volume of ethanol, eluting with 1-5 column volumes of methanol.
  • the present invention provides a method for preparing the above sweet potato gluten glucoside palmitate, which is obtained by dissolving the sweet potato gluten glucoside saturated fatty acid ester extract obtained above in ethanol, separating by alkyl silane-bonded silica gel column chromatography, and washing with an aqueous alcohol solution. The agent was desorbed, and the eluate corresponding to the retention time was collected to obtain each sweet potato gluten glycoside saturated fatty acid ester monomer.
  • the present invention provides the use of the above-described sweet potato glutenol glucoside saturated fatty acid ester and an extract thereof for the preparation of a medicament for preventing and/or treating a tumor or a health food.
  • sweet potato gluten glucoside saturated fatty acid ester/or sweet potato gluten glucoside saturated fatty acid ester extract of the present invention can be administered orally, sprayed, sublingually, intravenously, intravenously, intramuscularly, intraperitoneally, Administration by intradermal administration or the like.
  • the sweet potato gluten glucoside saturated fatty acid ester/or sweet potato gluten glucoside saturated fatty acid ester extract of the present invention can be used alone for the prevention and/or treatment of tumors, and can also be used in combination with other antitumor drugs.
  • the sweet potato anti-tumor active monomer and/or sweet potato anti-tumor extract of the invention are taken from the foodstuff and are very safe to the human body, and can be processed into food, beverage, functional food and function by using alone or with other nutrients and/or food additives. Sexual beverages, etc., play a therapeutic function for health food, food processing and other fields.
  • the sweet potato sitosterol glycoside palmitate of the present invention has a remarkable inhibitory effect on the growth of tumor cells, and the inhibition rate of the sweet potato sitosterol glycoside palmitate monomer of the present invention on MCF-7 cells is 96 at a concentration of 10 mg/L.
  • the control drug sweet potato gluten glucoside linoleate monomer inhibition rate of MCF-7 cells was 65%, and the control drug sweet potato gluten glucoside monomer inhibited MCF-7 cells by 55%; 1mg/L gave
  • the inhibition rate of the sweet potato glutenyl glucoside palmitate monomer of the present invention to MCF-7 cells was 65%, and the inhibition rate of the control drug sweet potato gluten glucoside linoleate monomer to MCF-7 cells was 15 %, the control drug sweet potato gluten glucoside monomer inhibited MCF-7 cells by 10%.
  • Figure 1 is a hydrogen spectrum of a sweet potato gluten palmitoyl palmitate (formula II) monomer
  • Figure 2 is a carbon spectrum of a sweet potato gluten palmitoyl palmitate (formula II) monomer
  • Figure 3 is a GC/MS spectrum of sweet potato sterol glycoside palmitate (formula II) monomer, wherein a) is the total ion chromatogram of sweet potato gluten palmitoyl palmitate, b) ion with a retention time of 23.735 min Primary mass spectrum of the flow, c) Secondary mass spectrum of methyl palmitate fragments.
  • the sweet potato starch mother liquor of the present invention refers to a mother liquor from which sweet potato starch is removed, commonly known as yellow pulp or starch wastewater. It may be a waste liquid produced in the production of sweet potato starch, or may be prepared by pulverizing sweet potato with water, sifting sweet potato pulp, then removing the starch, and collecting the slurry, such as crushing sweet potato with 0-2 times water. The sweet potato slurry was sieved through 80 mesh, and then the starch was removed by filtration to collect the slurry.
  • Step 1 100 ° C, adding 0.01% by weight of mother liquor to calcium chloride mother liquor, stirring uniformly, cooling to 80 ° C, centrifuging, vacuum drying at 60 ° C, to obtain crude extract of sweet potato;
  • Step 2 Add 1% by weight of 10% ethanol (w/w) to the crude sweet potato extract obtained in step 1, stir for 1 min, filter, and filter the residue with 10 times the weight of 10% ethanol, filter, repeat 2 Then, the filtrate was collected and combined, concentrated, and dried to obtain a sweet potato gluten glucoside saturated fatty acid ester extract, wherein the content of sweet potato sterol glycoside palmitate was 1.1%.
  • Step 1 50 ° C, adding 100% by weight of mother liquor to the mother liquor of 100 L sweet potato starch, stirring uniformly, cooling to 20 ° C, centrifugation, vacuum drying at 60 ° C, to obtain crude extract of sweet potato;
  • Step 2 Add 5 times the amount of 50% propanol (weight/weight) to the crude sweet potato extract obtained in step 1 and stir for 20 min, filter, and filter the residue by 50 times the amount of 50% propanol, filter, repeat 4 times, the filtrate was collected and combined, concentrated, and dried to obtain a sweet potato saturated fatty acid ester extract in which the content of sitosterol glycoside palmitate was 1.2%.
  • Step 1 70 ° C, into the mother liquor of 100 L sweet potato starch, adding 0.1% by weight of the mother liquor of acetic acid, stirring uniformly, cooling to 20 ° C, centrifugation, vacuum drying at 60 ° C, to obtain crude extract of sweet potato;
  • Step 2 Adding 3 times the weight of 80% acetone (w/w) to the crude sweet potato extract obtained in step 1 and stirring for 10 min, filtering, filtering the residue with 80 times the weight of 80% propanol, filtering, repeating 3 Then, the filtrate was collected and combined, concentrated, and dried to obtain a sweet potato gluten glucoside saturated fatty acid ester extract, wherein the content of sweet potato sterol glycoside palmitate was 1.3%.
  • Step 1 Add 90% citric acid by weight to the mother liquor of 100 L sweet potato starch at 90 ° C, stir evenly, cool to 30 ° C, centrifuge, and vacuum dry at 60 ° C to obtain crude extract of sweet potato;
  • Step 2 Add 7 times the amount of 95% ethanol (w/w) to the crude sweet potato extract obtained in step 1 and stir for 10 min, filter, and filter the residue with 7 times the amount of 95% ethanol, filter, repeat 2 times.
  • the filtrate was collected and combined, concentrated, and dried to obtain a sweet potato gluten glucoside saturated fatty acid ester extract, wherein the content of the sweet potato sterol glycoside palmitate was 1.2%.
  • Step 1 Add 80% of the weight of the mother liquor to the 100 L sweet potato starch mother liquor at 80 ° C, stir evenly, cool to 40 ° C, centrifuge, and vacuum dry at 60 ° C to obtain a crude extract of sweet potato;
  • Step 2 adding the crude sweet potato extract obtained in step 1 to a weight of 2 times 80% ethanol (w/w), stirring for 30 min, filtering, filtering the residue with 80 times the weight of 80% ethanol, filtering, repeating 2 times
  • the filtrate was collected and combined, concentrated, and dried to obtain a sweet potato gluten glucoside saturated fatty acid ester extract, wherein the content of sweet potato sterol glycoside palmitate was 1.4%.
  • Step 1 60% C was added to the mother liquor of 100 L sweet potato starch by adding 2% by weight of gluconolactone, stirred uniformly, cooled to 25 ° C, centrifuged, and dried under vacuum at 60 ° C to obtain a crude extract of sweet potato;
  • Step 2 Adding 3 times the amount of 60% ethanol (w/w) to the crude sweet potato extract obtained in step 1 and stirring for 30 min, filtering, filtering the residue with 60 times the weight of 60% ethanol, filtering, repeating 2 times The filtrate was collected and combined, concentrated, and dried to obtain a sweet potato gluten glucoside saturated fatty acid ester extract, wherein the content of sweet potato gluten glucoside palmitate was 1.3%.
  • Step 1 Add 100% sodium alginate to the mother liquor of 100L fresh sweet potato starch at 60 ° C, stir evenly, cool to 25 ° C, centrifuge, and vacuum dry at 60 ° C to obtain crude extract of sweet potato;
  • Step 2 Adding 3 times the amount of 30% ethanol (w/w) to the crude sweet potato extract obtained in step 1 and stirring for 30 min, filtering, filtering the residue with 30 times the weight of 30% ethanol, filtering, repeating 2 times
  • the filtrate was collected and combined, concentrated, and dried to obtain a sweet potato gluten glucoside saturated fatty acid ester extract, wherein the content of sweet potato sterol glycoside palmitate was 1.4%.
  • the sweet potato sitosterol glycoside saturated fatty acid ester extract obtained in Example 1 and silica gel were subjected to silica gel column chromatography at a weight ratio of 1:10, followed by 5 column volumes of petroleum ether, 5 column volumes of ethyl acetate, 5 column volumes of ethanol, 5 column volumes of methanol were eluted, and a sulfuric acid/methanol solution with a volume ratio of 1:9 was collected as a color developer, heated at 105 ° C for 5 min, and thin layer chromatography Rf was 0.68-0.77.
  • the fraction of the eluate was partially magenta eluate and concentrated to obtain a sweet potato glutamate sucrose saturated fatty acid ester extract, wherein the sweet potato sterol glycoside palmitate content was 11%.
  • the sweet potato sitosterol glycoside saturated fatty acid ester extract obtained in Example 2 and silica gel were subjected to silica gel column chromatography at a weight ratio of 1:100, followed by 2 column volumes of petroleum ether, 2 column volumes of ethyl acetate, 2 column volumes of ethanol, 2 column volumes of methanol were eluted, and a sulfuric acid/methanol solution with a volume ratio of 1:9 was collected as a color developer, heated at 105 ° C for 5 min, and thin layer chromatography Rf was 0.68-0.77.
  • the fraction of the eluate was partially magenta eluate and concentrated to obtain a sweet potato glutamate sucrose saturated fatty acid ester extract, wherein the sweet potato gluten glucoside palmitate content was 12%.
  • the sweet potato glutenol glycoside saturated fatty acid ester extract obtained in Example 3 and silica gel were subjected to silica gel column chromatography at a weight ratio of 1:50, followed by 3 column volumes of petroleum ether, 3 column volumes of ethyl acetate, 3 column volumes of ethanol, 3 column volumes of methanol were eluted, and a sulfuric acid/methanol solution with a volume ratio of 1:9 was collected as a color developer, heated at 105 ° C for 5 min, and thin layer chromatography Rf was 0.68-0.77.
  • the fraction of the eluate was partially magenta eluate and concentrated to obtain a sweet potato glutamate sucrose saturated fatty acid ester extract, wherein the sweet potato sterol glycoside palmitate content was 14%.
  • the sweet potato sitosterol glycoside saturated fatty acid ester extract obtained in Example 4 and silica gel were subjected to silica gel column chromatography at a weight ratio of 1:500, followed by 2 column volumes of petroleum ether, 2 column volumes of ethyl acetate, 2 column volumes of ethanol, 2 column volumes of methanol were eluted, and a sulfuric acid/methanol solution with a volume ratio of 1:9 was collected as a color developer, heated at 105 ° C for 5 min, and thin layer chromatography Rf was 0.68-0.77.
  • the fraction of the eluate was partially magenta eluate and concentrated to obtain a sweet potato glutamate sucrose saturated fatty acid ester extract, wherein the sweet potato sterol glycoside palmitate content was 13%.
  • the sweet potato sitosterol glycoside saturated fatty acid ester extract obtained in Example 5 and silica gel were subjected to silica gel column chromatography at a weight ratio of 1:200, followed by 3 column volumes of petroleum ether, 3 column volumes of ethyl acetate, 3 column volumes of ethanol, 3 column volumes of methanol were eluted, and a sulfuric acid/methanol solution with a volume ratio of 1:9 was collected as a color developer, heated at 105 ° C for 5 min, and thin layer chromatography Rf was 0.68-0.77.
  • the fraction of the eluate was partially magenta eluate and concentrated to obtain a sweet potato glutamate sucrose saturated fatty acid ester extract, wherein the sweet potato sterol glycoside palmitate content was 14%.
  • the sweet potato glutenol glycoside fatty acid ester extract obtained in Example 6 and silica gel were subjected to silica gel column chromatography at a weight ratio of 1:600, followed by 2 column volumes of petroleum ether, 2 column volumes of ethyl acetate, 2 The column volume of ethanol and 2 column volumes of methanol were eluted, and the sulfuric acid/methanol solution with a volume ratio of 1:9 was collected as a color developer, heated at 105 ° C for 5 min, and the thin layer chromatography Rf was 0.68-0.77. The portion of the eluate which is in the liquid-depleted portion is concentrated and concentrated to obtain a sweet potato ester sterol glycoside saturated fatty acid ester extract, wherein the sweet potato gluten glucoside palmitate content is 15%.
  • the sweet potato sitosterol glycoside saturated fatty acid ester extract obtained in Example 7 and silica gel were subjected to silica gel column chromatography at a weight ratio of 1:600, followed by 2 column volumes of petroleum ether, 2 column volumes of ethyl acetate, 2 column volumes of ethanol, 2 column volumes of methanol were eluted, and a sulfuric acid/methanol solution with a volume ratio of 1:9 was collected as a color developer, heated at 105 ° C for 5 min, and thin layer chromatography Rf was 0.68-0.77.
  • the fraction of the eluate was partially magenta eluate and concentrated to obtain a sweet potato glutamate sucrose saturated fatty acid ester extract, wherein the sweet potato sterol glycoside palmitate content was 13%.
  • the sweet potato glutenol glycoside saturated fatty acid ester extract obtained in Example 14 was dissolved in methanol, and the column was prepared by C18 (silica gel particle size: 25 ⁇ m), detected at a wavelength of 200 nm, and eluted with ethanol to collect an elution peak near 50 min.
  • the yield of sweet potato glutamate dodecanoate was 1.3%; the elution peak near 85min was collected, and the yield of sweet potato glutamate tetradecanoate was 2.4%; the elution peak near 115min was collected as sweet potato valley.
  • the yield of sterol glycoside hexadecanoate was 12.5%; the elution peak near 150 min was collected, which was sweet potato gluten succinate octadecanoate, and the yield was 1.6%.
  • sitosterol glycoside palmitate sitosterol monophosphate palmitate
  • MCF-7 breast cancer cells and HCT8 colon cancer cells were purchased from the Third Military Medical University.
  • Other biochemical reagents such as bovine serum and cell culture materials were purchased from Beijing Dingguo Biotechnology Co., Ltd.
  • Cell resuscitation and culture The cell cryotube is taken out from liquid nitrogen, quickly placed in warm water at 37 ° C, and after it is completely melted, it is quickly transferred to a clean bench, and the solution is transferred to a 10 mL centrifuge after sterilization. In the tube, add 7mL of RIPM-1640 medium (containing 10% FBS, 1% streptomycin mixture), centrifuge in 3000rmp for 5min in centrifuge, then discard the supernatant and add 4mL RIPM-1640 medium (including 10% FBS, 1% streptomycin mixture), mixed by blowing and transferred to a culture flask for culture at 37 ° C, 5% CO 2 .
  • RIPM-1640 medium containing 10% FBS, 1% streptomycin mixture
  • sweet potato gluten glucoside saturated fatty acid ester extract 1%, Example 1
  • sweet potato gluten glucoside saturated fatty acid ester extract at concentrations of 100 mg/L, 10 mg/L and 1 mg/L. (10%, Example 8)
  • sweet potato sterol glycoside saturated fatty acid ester monomer sitosterol glycosidic dodecanoate, sitosterol glycosyl myristate, sitosterol hexadecanoate, sitosterol glycoside
  • Table 1 The inhibition rate of octadecanoate on MCF-7 cells is shown in Table 1.
  • the experiment used sweet potato gluten glucoside linoleate and sweet potato gluten glucoside as a control.
  • Table 1 show that: at high concentration, the sweet potato sweet potato ester sterol glycoside saturated fatty acid ester extract has a certain inhibitory effect on MCF-7, and the inhibition is weak at low concentration; sweet potato gluten glucoside saturated fatty acid ester to MCF -7 has a good inhibitory effect.
  • sweet potato gluten glucoside palmitate has the strongest inhibitory effect on MCF-7 breast cancer cells, and the carbon chain increases and decreases, and its anti-tumor activity is reduced to some extent; sweet potato
  • the inhibitory effect of sitosterol glycoside palmitate on tumor is significantly higher than that of sweet potato gluten linoleic acid oleate and sweet potato gluten glucoside, which has good prospects for tumor prevention and/or treatment.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Botany (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medical Informatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un ester d'acide gras saturé de sitostérol-glycoside de patate douce, un extrait et un procédé de préparation correspondant. L'extrait d'ester d'acide gras saturé de sitostérol-glycoside de patate douce présente un certain effet inhibiteur sur MCF-7, et l'effet inhibiteur est faible en faible concentration. L'ester d'acide gras saturé de sitostérol-glycoside de patate douce présente un bon effet inhibiteur sur les cellules du cancer du sein MCF-7, le palmitate de sitostérol-glycoside de patate douce ayant l'effet inhibiteur le plus fort, et l'augmentation et la diminution des chaînes de carbone de l'acide gras saturé diminuent l'activité antitumorale dans une certaine mesure.
PCT/CN2018/081664 2017-12-21 2018-04-03 Ester d'acide gras saturé de sitostérol-glycoside de patate douce, extrait, procédé de préparation correspondant et application associée WO2019119675A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201711390608.XA CN109942648A (zh) 2017-12-21 2017-12-21 甘薯谷甾醇糖苷饱和脂肪酸、提取物及其制备方法与应用
CN201711390608.X 2017-12-21

Publications (1)

Publication Number Publication Date
WO2019119675A1 true WO2019119675A1 (fr) 2019-06-27

Family

ID=63142328

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2018/081664 WO2019119675A1 (fr) 2017-12-21 2018-04-03 Ester d'acide gras saturé de sitostérol-glycoside de patate douce, extrait, procédé de préparation correspondant et application associée

Country Status (3)

Country Link
CN (1) CN109942648A (fr)
AU (1) AU2018100981A4 (fr)
WO (1) WO2019119675A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11132923B2 (en) 2018-04-10 2021-09-28 Raytheon Company Encryption using spatial voting

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258100A (ja) * 1994-03-24 1995-10-09 Osamu Michioka サツマイモに分布するガン細胞の増殖抑制および分化を促進することで抗がん作用を示す糖脂質およびその精製方法
WO2002079219A2 (fr) * 2001-03-30 2002-10-10 Yissum Research Development Company Of The Hebrew University Of Jerusalem Composes antiproliferatifs

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07258100A (ja) * 1994-03-24 1995-10-09 Osamu Michioka サツマイモに分布するガン細胞の増殖抑制および分化を促進することで抗がん作用を示す糖脂質およびその精製方法
WO2002079219A2 (fr) * 2001-03-30 2002-10-10 Yissum Research Development Company Of The Hebrew University Of Jerusalem Composes antiproliferatifs

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
DATABASE CAS 13 November 2014 (2014-11-13), "STN", Database accession no. RN 1616685-00-7 *
DATABASE CAS 13 November 2014 (2014-11-13), retrieved from STN Database accession no. RN 120000-27-3 *
DATABASE CAS 13 November 2014 (2014-11-13), retrieved from STN Database accession no. RN 1632494-75-7 *
DATABASE CAS 13 November 2014 (2014-11-13), retrieved from STN Database accession no. RN 177564-57-7 *
DATABASE CAS 13 November 2014 (2014-11-13), retrieved from STN Database accession no. RN 272118-14-6 *
DATABASE CAS 13 November 2014 (2014-11-13), retrieved from STN Database accession no. RN 883723-98-6 *
DATABASE CAS 13 November 2014 (2014-11-13), retrieved from STN Database accession no. RN 883724-00-3 *
DATABASE CAS 13 November 2014 (2014-11-13), retrieved from STN Database accession no. RN 956699-41-5 *
LIU, YUPENG: "Studies on Extraction, Isolation and Structure Identification of the Chemical Constituents of Ipomoea Batatas Stem Leaf", CHINA MASTER'S THESES FULL-TEXT DATABASE, no. 8, 15 August 2013 (2013-08-15) *
WIMMEROVA, MARTIN A: "Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of β-sitosterol", STEROIDS, vol. 117, 17 September 2016 (2016-09-17), pages 38 - 43, XP029858304, ISSN: 0039-128X *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11132923B2 (en) 2018-04-10 2021-09-28 Raytheon Company Encryption using spatial voting

Also Published As

Publication number Publication date
CN109942648A (zh) 2019-06-28
AU2018100981A4 (en) 2018-08-16

Similar Documents

Publication Publication Date Title
WO2017190422A1 (fr) Procédé de préparation d'un nouveau dérivé de mogrol à partir de mogroside total
Yu et al. Research and application of adlay in medicinal field
CN102670764B (zh) 酸枣的活性部位及其制备方法与应用
CN102178741A (zh) 具有降血糖作用的番石榴叶提取物及其制备方法与应用
CN110105458A (zh) 从罗汉果甜苷提取废液中提取多糖和d-甘露醇的方法
CN103405577B (zh) 一种增强免疫力、缓解疲劳的药用组合物
Zhang et al. A zinc-modified Anemarrhena asphodeloides polysaccharide complex enhances immune activity via the NF-κB and MAPK signaling pathways
WO2019119675A1 (fr) Ester d'acide gras saturé de sitostérol-glycoside de patate douce, extrait, procédé de préparation correspondant et application associée
CN108610433B (zh) 可有效抑制肝肿瘤细胞Hca-F的笼目海带提取物及制备方法
CN113999272A (zh) 香蜂草苷的制备方法及其应用
JP6170246B2 (ja) エルゴステロール系化合物、並びにその製造方法及び使用
KR101625474B1 (ko) 진세노사이드 알에이치4의 대량 제조방법
WO2005095436A1 (fr) Glucoside comportant un squelette de 4-méthylergost-7-en-3-ol et médicament destiné à améliorer l'hyperglycémie
US20050287230A1 (en) Method of producing ginsenoside 20 (R)-Rh2 and composition of matter thereof
WO2018001296A1 (fr) Composé de pyrazolophényl-pyridine.
WO2017190421A1 (fr) Nouveau monomère dérivé de mogrol
CN101642207A (zh) 一种降血脂营养米及其生产工艺
Liu et al. A systematic review on polysaccharides from Morinda officinalis How: Advances in the preparation, structural characterization and pharmacological activities
CN107266516B (zh) 具有抗肿瘤活性的三萜化合物及其制备方法与应用
CN105963307B (zh) 一种罗汉果醇衍生物单体及其组合物的用途
WO2019011010A1 (fr) Ester d'acide gras insaturé de sitostérol-glycoside de patate douce, extrait, procédé de préparation correspondant et application associée
CN113214214B (zh) 关苍术中一种萜类化合物的制备方法和应用
CN106188205B (zh) 一种罗汉果醇衍生物单体及其组合物的用途
KR20090130538A (ko) 노루오줌 추출물, 분획물, 이로부터 분리한 트리테르펜화합물 또는 이의 약학적으로 허용가능한 염을유효성분으로 함유하는 암 예방 및 치료용 약학적 조성물
CN109942661B (zh) 甘薯谷甾醇糖苷不饱和脂肪酸、提取物及其制备方法和应用

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18891493

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18891493

Country of ref document: EP

Kind code of ref document: A1