CN109942648A - Sweet potato sitosterol glucosides saturated fatty acid, extract and the preparation method and application thereof - Google Patents
Sweet potato sitosterol glucosides saturated fatty acid, extract and the preparation method and application thereof Download PDFInfo
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
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- 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
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- 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
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- 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
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- 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
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Abstract
The present invention relates to medicinal chemistry arts, more particularly to sweet potato sitosterol glucosides polyunsaturated fatty acid ester, extract and the preparation method and application thereof, wherein sweet potato sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract has certain inhibiting effect to MCF-7, and inhibiting effect is very weak under low concentration；Sweet potato sitosterol glucosides polyunsaturated fatty acid ester has good inhibiting effect to MCF-7, wherein most strong to the inhibiting effect of MCF-7 breast cancer cell with sweet potato sitosterol glucosides palmitate, carbochain increases and reduces, the antitumor equal decrease to some degree of activity；Sweet potato sitosterol glucosides palmitate is apparently higher than sweet potato sitosterol glucosides linoleate and sweet potato sitosterol glucosides to the inhibiting effect of tumour, has good tumor prevention and/or treatment prospect.
Description
Technical field
The present invention relates to medicinal chemistry arts, and in particular to sweet potato sitosterol glucosides polyunsaturated fatty acid ester, extract and its
Preparation method and application
Background technique
Tumour is the malignant disease for seriously threatening human health, and in China, tumour is had become first of the disease cause of the death, and is fallen ill
Rate and the death rate are also riseing, and China in 2015 in respect of 429.2 ten thousand new hair tumor cases, is equivalent to averagely daily newly hair in advance
12000 cancers and 281.4 ten thousand deaths are equivalent to averagely daily 7500 people and die of cancer.It is true to find development efficacy
Cut, the anti-tumor drug that toxic side effect is small be always New drug discovery research and development hot and difficult issue.Traditional Chinese medicine is unique excellent because of its
Gesture, extracted from Chinese medicine safe and effective position for prevent and/or treating cancer be always chemotherapy of tumors study hot spot.
Sweet potato is also known as sweet potato, sweet tea administration, sweet potato, sweet potato, pachyrhizus etc., is one of the cereal crops in China, cultivated area and
Yield occupies first place in the world.It is recorded according to Compendium of Material Medica, sweet potato is " sweet in flavor, flat, nontoxic.Cure mainly weary qi-restoratives, benefiting energy, strengthening the spleen and stomach,
Strong kidney yin.The same Chinese yam of function ".Modern study is the result shows that (Wang Hongyun etc., Chinese food and nutrition, 2013,19 (12): 59-62)
Sweet potato has anticancer, improves immune, reducing blood lipid, hypoglycemic, inhibition thrombosis, prevention and treatment artery sclerosis and cardiovascular disease etc.
Multiple efficacies；Nearest research demonstrates again that sweet potato by good antitumous effect (Meimei Wang etc.Bioassay-
guided isolation of glycoprotein SPG-56from sweet potato Zhongshu-1and its
anti-colon cancer activity in vitro and in vivo。Journal of Functional
Foods.35, (2017), 315-324).But at present, on the one hand, the development and utilization of sweet potato are main or preliminary working --- generation is sweet
Sweet potato starch, in sweet potato starch production process, the plurality kinds of health care such as sweet potato, polysaccharide, vitamin ingredient (including it is antitumor at
Point) but as sweet potato starch mother liquor (being commonly called as yellow slurry or starch wastewater) is lost together, it not only polluted environment, but also waste significantly
Resource；On the other hand, the activated monomer separation identification in sweet potato is difficult, is not possible to which ingredient determination is actually with anti-swollen
Tumor effect.Therefore, the activated monomer of separation identification sweet potato studies the Rhizoma Dioscoreae esculentae extract prevention and/or treatment tumour of different process
Have great importance, to find antitumous effect is more preferable and safety, simple process, yield are high reverse anti-tumor drug or
Health food.
Summary of the invention
It is thin with significant tumour the first purpose of the invention is to provide sweet potato sitosterol glucosides polyunsaturated fatty acid ester
Intracellular growth inhibitory activity.
A second object of the present invention is to provide sweet potato sitosterol glucosides polyunsaturated fatty acid ester extracts.
Third object of the present invention is to provide sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract and sweet potato sitosterol
The preparation method of glucosides polyunsaturated fatty acid ester.
Fourth object of the present invention is to provide sweet potato sitosterol glucosides polyunsaturated fatty acid ester and/or sweet potato sitosterol glucosides
Polyunsaturated fatty acid ester extract preparation for prevent and/or tumor, health food in application.
For achieving the above object, technical solution provided by the invention is as follows:
In a first aspect, sweet potato sitosterol glucosides polyunsaturated fatty acid ester, chemical formula are shown in formula I:
Wherein, R=-CnH2n+1, 12≤n≤18.
Further, R=-CnH2n+1, n=15.
Further, R is straight-chain alkyl, and for chemical formula as shown in Formula II, Formula II is sweet potato sitosterol glucosides palmitinic acid
Ester.
Second aspect, sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract provided by the invention include chemical combination shown in Formulas I
Object, by weight, compound shown in Formulas I account for 1% of extract or more.
Sweet potato sitosterol glucosides saturated fatty acid extract provided by the invention includes compound shown in Formula II, by weight
Meter, the Formula II compound account for 1% of extract or more.
Further, the sweet potato sitosterol glucosides saturated fatty acid extract includes compound shown in Formula II, by weight
Meter, the Formula II compound account for 10% of extract or more.
Further, said extracted object be by sweet potato starch mother liquor by precipitating, filtering/centrifugation, organic solvent extraction and
What purifying obtained.
Further, said extracted object point is mixed in thin layer chromatography board in chloroform/methanol/water that volume ratio is 90:10:1
It closes and is unfolded in the solvent of solution, be sulfuric acid/methanol chromogenic reagent of 1:9 with volume ratio, it is described after 105 DEG C of heating 5min
Extract displaing amaranth.
The third aspect, the preparation method of sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract provided by the invention, including
Following steps:
At 1:50-100 DEG C of step, into sweet potato starch mother liquor be added weight ratio be 0.01%~5% precipitating reagent, centrifugation or
Filtering, takes solid to obtain sweet potato crude extract；
Step 2: the organic solvent that weight ratio is 1:1~10 is added into sweet potato crude extract, is filtered after stirring, concentration filter
Sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract is made in liquid.
Further, the preparation method of sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract, further includes step 3, will be sweet
Potato sitosterol glucosides polyunsaturated fatty acid ester extract carries out column chromatography, and collecting with volume ratio is chloroform/methanol/water of 90:10:1
Mixed solution is solvent, using volume ratio for 1:9 sulfuric acid/methanol solution as color developing agent, at 105 DEG C heat 5min displaing amaranth
Spot, the eluent that thin-layer chromatography Rf is 0.68-0.77, concentrate eluant are made sweet potato sitosterol glucosides saturation acid esters and extract
Object.
The preparation method of present invention offer sweet potato sitosterol glucosides polyunsaturated fatty acid ester, wherein precipitating described in step 1
Agent is selected from metal salt, organic acid, glucolactone, sodium alginate, xanthan gum and the carragheen of divalent or trivalent；Preferably,
Precipitating reagent described in step 1 be selected from calcium salt, magnesium salts, aluminium salt, acetic acid, malic acid, citric acid, tartaric acid, glucolactone,
Sodium alginate, xanthan gum and carragheen；Preferably, precipitating reagent described in step 1 is selected from calcium sulfate, magnesium sulfate, tartaric acid, apple
Tartaric acid, citric acid and glucolactone.Preferably, the additional amount of precipitating reagent described in step 1 is sweet potato starch mother liquor weight
The 0.05%-1% of amount.
It wherein, also include to be cooled to 0-80 DEG C of step before centrifugation described in step 1 or filtering；Preferably, institute in step 1
Also comprising being cooled to 20-50 DEG C of step before the centrifugation or filtering stated.
Wherein, organic solvent described in step 2 is selected from one of water-soluble alcohol or ketone or a variety of；Preferably, step 2
Described in organic solvent be selected from one of methanol, ethyl alcohol, propyl alcohol, acetone or a variety of.
Wherein, the dosage of organic solvent described in step 2 is 2-5 times of sweet potato crude extract weight.
Wherein, step 2 can repeat 1-5 times；Preferably, step 2 can repeat 2-4 times；It is further preferred that step 2
It can repeat 2-3 times.
Wherein, the chromatography of column described in step 3 includes silica gel column chromatography, macroporous adsorbent resin column chromatography, glucose gel
Column chromatography and performance liquid chromatographic column chromatography；Specifically, the chromatography of column described in step 3 is silica gel column chromatography or high-efficient liquid phase color
Compose column chromatography.
Wherein, when the chromatography of column described in step 3 is silica gel column chromatography, chromatography condition is successively with 1-5 times of column volume
The methanol elution of petroleum ether, the ethyl acetate of 1-5 times of column volume, the ethyl alcohol of 1-5 times of column volume, 1-5 times of column volume.
The present invention provides the preparation method of above-mentioned sweet potato sitosterol glucosides palmitate, by above-mentioned resulting sweet potato sitosterol
Glucosides polyunsaturated fatty acid ester extract is dissolved in ethyl alcohol, is to wash with alcohol solution by alkyl silane bonded silica gel column chromatography for separation
De- agent collects the eluent of corresponding retention time, obtains each sweet potato sitosterol glucosides saturated fatty acid ester monomer.
Fourth aspect, the present invention provide above-mentioned sweet potato sitosterol glucosides polyunsaturated fatty acid ester and its extract and prevent in preparation
And/or the application in tumor or health food.
Sweet potato sitosterol glucosides polyunsaturated fatty acid ester/or sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of the invention
The ways such as oral, spraying, sublingual administration, intravenous injection, venoclysis, intramuscular injection, intraperitoneal administration, intradermal administration can be passed through
Diameter administration.
Sweet potato sitosterol glucosides polyunsaturated fatty acid ester/or sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of the invention
It can be individually used for preventing and/or treating tumour, can also be used in combination with other anti-tumor drugs.
Sweet potato anti-tumor activity monomer and/or sweet potato antineoplastic extract of the invention is derived from food materials, pacifies very much to human body
Entirely, food, beverage, functional food, function can be prepared as individually or with other nutriments and/or food additives processing
Property beverage etc., play food therapy function, be used for health food, food processing and other fields.
Sweet potato sitosterol glucosides palmitate of the invention is significant to the growth inhibition effect of tumour cell, gives in 10mg/L
Under concentration, sweet potato sitosterol glucosides palmitate monomer of the invention is 96% to the inhibiting rate of MCF-7 cell, control drug
Sweet potato sitosterol glucosides linoleate monomer is 65% to the inhibiting rate of MCF-7 cell, control drug sweet potato sitosterol glucosides list
Body is 55% to the inhibiting rate of MCF-7 cell；Under 1mg/L administration concentration, sweet potato sitosterol glucosides palmitate list of the invention
Body is 65% to the inhibiting rate of MCF-7 cell, suppression of the control drug sweet potato sitosterol glucosides linoleate monomer to MCF-7 cell
Rate processed is 15%, and control drug sweet potato sitosterol glucosides monomer is 10% to the inhibiting rate of MCF-7 cell.It is significantly higher than comparison medicine
Object.
Detailed description of the invention
Fig. 1 is the hydrogen spectrum of sweet potato sitosterol glucosides palmitate (Formula II) monomer；
Fig. 2 is the carbon spectrum of sweet potato sitosterol glucosides palmitate (Formula II) monomer；
Fig. 3 is the gas chromatography mass spectrometry spectrogram of sweet potato sitosterol glucosides palmitate (Formula II) monomer, wherein a) is sweet potato paddy steroid
Alcohol glucosides palmitate total ion chromatogram, b) first mass spectrometric figure of the retention time for the ion stream of 23.735min, c) palm
The second order ms figure of sour methyl esters fragment.
Specific embodiment
The present invention is further elaborated below with reference to embodiment, however, the present invention is not limited to these examples.
Reagent and raw material used herein can be prepared by commercially available or conventional method in that art.
Sweet potato starch mother liquor of the present invention refers to the mother liquor for eliminating sweet potato starch, is commonly called as yellow slurry or starch wastewater.
It can be the waste liquid generated in sweet potato starch production, can also be by the way that sweet potato be crushed together with water, be sieved to obtain sweet potato slurry, then
Except desizing, the method preparation of slurries is collected, such as crushes sweet potato and 0-2 times of water together, crossed 80 meshes and obtain sweet potato slurry, then mistake
Desizing is filtered out, the method preparation of slurries is collected.
The preparation of 1 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
At 1:100 DEG C of step, the calcium sulfate that weight is mother liquor weight 0.01% is added into 100L sweet potato mother liquor, stirring is equal
It is even, 80 DEG C are cooled to, is centrifuged, is dried in vacuo at 60 DEG C, obtains sweet potato crude extract；
Step 2: 10% ethyl alcohol (w/w) of 1 times of its weight amount being added into step 1 gained sweet potato crude extract, stirs
1min to be mixed, is filtered, 10% ethyl alcohol that filter residue is measured with 1 times of its weight dissolves, and filtering is repeated 2 times, collection and merging filtrate, concentration,
It is dried to obtain sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract, wherein the content of sweet potato sitosterol glucosides palmitate is
1.1%.
The preparation of 2 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
At 1:50 DEG C of step, the aluminum sulfate that weight is mother liquor weight 1% is added into 100L sweet potato starch mother liquor, stirring is equal
It is even, 20 DEG C are cooled to, is centrifuged, is dried in vacuo at 60 DEG C, obtains sweet potato crude extract；
Step 2: 50% propyl alcohol (w/w) stirring of 5 times of its weight amounts being added into step 1 gained sweet potato crude extract
20min, filtering, 50% propyl alcohol that filter residue is measured with 5 times of its weight dissolve, and filtering is repeated 4 times, collection and merging filtrate, concentration,
It is dried to obtain sweet potato polyunsaturated fatty acid ester extract, wherein the content of sitosterol glucosides palmitate is 1.2%.
The preparation of 3 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
At 1:70 DEG C of step, the acetic acid that weight is mother liquor weight 0.1% is added into 100L sweet potato starch mother liquor, stirring is equal
It is even, 20 DEG C are cooled to, is centrifuged, is dried in vacuo at 60 DEG C, obtains sweet potato crude extract；
Step 2: 80% acetone (w/w) stirring of 3 times of its weight amounts being added into step 1 gained sweet potato crude extract
10min, filtering, 80% propyl alcohol that filter residue is measured with 3 times of its weight dissolve, and filtering is repeated 3 times, collection and merging filtrate, concentration,
It is dried to obtain sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract, wherein the content of sweet potato sitosterol glucosides palmitate is
1.3%.
The preparation of 4 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
At 1:90 DEG C of step, the citric acid that weight is mother liquor weight 0.05% is added into 100L sweet potato starch mother liquor, stirs
It mixes uniformly, is cooled to 30 DEG C, be centrifuged, be dried in vacuo at 60 DEG C, obtain sweet potato crude extract；
Step 2: 95% ethyl alcohol (w/w) stirring of 7 times of its weight amounts being added into step 1 gained sweet potato crude extract
10min, filtering, 95% ethyl alcohol that filter residue is measured with 7 times of its weight dissolve, and filtering is repeated 2 times, collection and merging filtrate, concentration,
It is dried to obtain sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract, wherein the content of sweet potato sitosterol glucosides palmitate is
1.2%.
The preparation of 5 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
At 1:80 DEG C of step, the malic acid that weight is mother liquor weight 0.5%, stirring are added into 100L sweet potato starch mother liquor
Uniformly, 40 DEG C are cooled to, is centrifuged, is dried in vacuo at 60 DEG C, obtains sweet potato crude extract；
Step 2: 80% ethyl alcohol (w/w) stirring of 2 times of its weight amounts being added into step 1 gained sweet potato crude extract
30min, filtering, 80% ethyl alcohol that filter residue is measured with 2 times of its weight dissolve, and filtering is repeated 2 times, collection and merging filtrate, concentration,
It is dried to obtain sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract, wherein the content of sweet potato sitosterol glucosides palmitate is
1.4%.
The preparation of 6 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
At 1:60 DEG C of step, the glucolactone that weight is mother liquor weight 2% is added into 100L sweet potato starch mother liquor,
It stirs evenly, is cooled to 25 DEG C, be centrifuged, be dried in vacuo at 60 DEG C, obtain sweet potato crude extract；
Step 2: 60% ethyl alcohol (w/w) stirring of 3 times of its weight amounts being added into step 1 gained sweet potato crude extract
30min, filtering, 60% ethyl alcohol that filter residue is measured with 3 times of its weight dissolve, and filtering is repeated 2 times, collection and merging filtrate, concentration,
It is dried to obtain sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract, wherein the content of sweet potato sitosterol glucosides palmitate is
1.3%.
The preparation of 7 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
The alginic acid that weight is mother liquor weight 2% is added at 1:60 DEG C of step, in the sweet potato starch mother liquor fresh to 100L
Sodium stirs evenly, and is cooled to 25 DEG C, is centrifuged, and is dried in vacuo at 60 DEG C, obtains sweet potato crude extract；
Step 2: 30% ethyl alcohol (w/w) stirring of 3 times of its weight amounts being added into step 1 gained sweet potato crude extract
30min, filtering, 30% ethyl alcohol that filter residue is measured with 3 times of its weight dissolve, and filtering is repeated 2 times, collection and merging filtrate, concentration,
It is dried to obtain sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract, wherein the content of sweet potato sitosterol glucosides palmitate is
1.4%.
The preparation of 8 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
By 1 gained sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment and silica gel according to the ratio of weight ratio 1:10
Example carries out silica gel column chromatography, successively with the petroleum ether of 5 times of column volumes, the ethyl acetate of 5 times of column volumes, 5 times of column volumes ethyl alcohol,
The methanol elution of 5 times of column volumes, collect using volume ratio for 1:9 sulfuric acid/methanol solution as color developing agent, heat 5min at 105 DEG C,
Thin-layer chromatography Rf is the eluent position of 0.68-0.77, the eluent part of displaing amaranth, concentration, obtained sweet potato sitosterol sugar
Glycosides polyunsaturated fatty acid ester extract, wherein sweet potato sitosterol glucosides palmitate content is 11%.
The preparation of 9 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
By 2 gained sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment and silica gel according to weight ratio 1:100's
Ratio carries out silica gel column chromatography, successively with the second of the petroleum ether of 2 times of column volumes, the ethyl acetate of 2 times of column volumes, 2 times of column volumes
The methanol elution of alcohol, 2 times of column volumes, collect using volume ratio for 1:9 sulfuric acid/methanol solution as color developing agent, heated at 105 DEG C
5min, thin-layer chromatography Rf are the eluent position of 0.68-0.77, the eluent part of displaing amaranth, concentration, obtained sweet potato paddy steroid
Alcohol glucosides polyunsaturated fatty acid ester extract, wherein sweet potato sitosterol glucosides palmitate content is 12%.
The preparation of 10 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
By 3 gained sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment and silica gel according to the ratio of weight ratio 1:50
Example carries out silica gel column chromatography, successively with the petroleum ether of 3 times of column volumes, the ethyl acetate of 3 times of column volumes, 3 times of column volumes ethyl alcohol,
The methanol elution of 3 times of column volumes, collect using volume ratio for 1:9 sulfuric acid/methanol solution as color developing agent, heat 5min at 105 DEG C,
Thin-layer chromatography Rf is the eluent position of 0.68-0.77, the eluent part of displaing amaranth, concentration, obtained sweet potato sitosterol sugar
Glycosides polyunsaturated fatty acid ester extract, wherein sweet potato sitosterol glucosides palmitate content is 14%.
The preparation of 11 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
By 4 gained sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment and silica gel according to weight ratio 1:500's
Ratio carries out silica gel column chromatography, successively with the second of the petroleum ether of 2 times of column volumes, the ethyl acetate of 2 times of column volumes, 2 times of column volumes
The methanol elution of alcohol, 2 times of column volumes, collect using volume ratio for 1:9 sulfuric acid/methanol solution as color developing agent, heated at 105 DEG C
5min, thin-layer chromatography Rf are the eluent position of 0.68-0.77, the eluent part of displaing amaranth, concentration, obtained sweet potato paddy steroid
Alcohol glucosides polyunsaturated fatty acid ester extract, wherein sweet potato sitosterol glucosides palmitate content is 13%.
The preparation of 12 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
By 5 gained sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment and silica gel according to weight ratio 1:200's
Ratio carries out silica gel column chromatography, successively with the second of the petroleum ether of 3 times of column volumes, the ethyl acetate of 3 times of column volumes, 3 times of column volumes
The methanol elution of alcohol, 3 times of column volumes, collect using volume ratio for 1:9 sulfuric acid/methanol solution as color developing agent, heated at 105 DEG C
5min, thin-layer chromatography Rf are the eluent position of 0.68-0.77, the eluent part of displaing amaranth, concentration, obtained sweet potato paddy steroid
Alcohol glucosides polyunsaturated fatty acid ester extract, wherein sweet potato sitosterol glucosides palmitate content is 14%.
The preparation of 13 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
By 6 gained sweet potato sitosterol glycoside fatty acid ester extract of embodiment and silica gel according to the ratio of weight ratio 1:600
Silica gel column chromatography is carried out, successively with the petroleum ether of 2 times of column volumes, the ethyl acetate of 2 times of column volumes, the ethyl alcohol of 2 times of column volumes, 2
The methanol elution of times column volume, collect using volume ratio for 1:9 sulfuric acid/methanol solution as color developing agent, heat 5min at 105 DEG C,
Thin-layer chromatography Rf is the eluent position of 0.68-0.77, the eluent part of displaing amaranth, concentration, obtained sweet potato sitosterol sugar
Glycosides polyunsaturated fatty acid ester extract, wherein sweet potato sitosterol glucosides palmitate content is 15%.
The preparation of 14 sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment
By 7 gained sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment and silica gel according to weight ratio 1:600's
Ratio carries out silica gel column chromatography, successively with the second of the petroleum ether of 2 times of column volumes, the ethyl acetate of 2 times of column volumes, 2 times of column volumes
The methanol elution of alcohol, 2 times of column volumes, collect using volume ratio for 1:9 sulfuric acid/methanol solution as color developing agent, heated at 105 DEG C
5min, thin-layer chromatography Rf are the eluent position of 0.68-0.77, the eluent part of displaing amaranth, concentration, obtained sweet potato paddy steroid
Alcohol glucosides polyunsaturated fatty acid ester extract, wherein sweet potato sitosterol glucosides palmitate content is 13%.
The preparation of 15 sweet potato sitosterol glucosides saturated fatty acid ester monomer of embodiment
14 gained sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract of embodiment is dissolved in methanol, C18 is crossed and prepares column (silicon
The granularity of glue is 25 μm), the eluting peak near 50min is collected using ethanol elution with 200nm wavelength detecting, is sweet potato paddy steroid
Alcohol glucosides dodecylate, yield 1.3%；The eluting peak near 85min is collected, is sweet potato sitosterol glucosides myristate,
Yield 2.4%；The eluting peak near 115min is collected, is sweet potato sitosterol glucosides hexadecane acid esters, yield 12.5%；It collects
Eluting peak near 150min is sweet potato sitosterol glucosides octadecane acid esters, yield 1.6%.
The hydrogen spectrum and carbon spectrum of sitosterol glucosides hexadecane acid esters (sitosterol glucosides palmitate) are as shown in Figure 1, 2, spectrogram
Data are as follows:
H-NMR(600MHz,CDCl3) 5.30 ((H, m, H-6), 4.40 (1H, d, J=6Hz, H-6 '), 4.30 (1H, d, J
=6Hz, H-1 '), 4.22 (1H, d, J=12Hz, H-1 '), 3.36-3.56 (' -5 ' m, H-3,2), 2.28 (2H, t, J=6Hz, -
CH2CO-)1.30[m,-(CH2)n-],0.94(3H,s,CH3- 19), 0.85 (3H, d, J=6Hz, CH3-21),0.81(3H,t,J
=6Hz, CH3-18”),0.79(9H,m,CH3-26,CH3-27CH3-29,),0.61(3H,S,CH3-18,)。
13C NMR(600MHz,CDCl3)37.28(C-1),29.65(C-2),79.56(C-3),38.92(C-4),
140.32(C-5),122.15(C-6),31.95(C-7),31.91(C-8),50.83(C-9),36.75(C-10),21.08(C-
11),39.79(C-12),42.35(C-13),56.79(C-14),24.29(C-15),28.22(C-16),56.13(C-17),
11.85(C-18),19.33(C-19),36.14(C-20),18.78(C-21),33.99(C-22),26.19(C-23),45.89
(C-24),29.18(C-25),19.04(C-26),19.78(C-27),23.11(C-28),11.97(C-29),101.21(C-
1'),73.65(C-2'),76.05(C-3'),70.15(C-4'),73.98(C-5),63.18(C-6'),174.59(C-1”),
34.23(C-2”),24.95(C-3”),29.22(C-4”),29.34(C-5”),29.51(C-6”),29.70(C-7”-12”),
29.30(C-13”),31.89(C-14”),22.67(C-15”),14.07(C-16”)。
The inhibiting tumour cells activity test of the sweet potato sitosterol glucosides palmitate monomer of the present invention of experimental example 16
Experimental material: MCF-7 breast cancer cell and HCT8 colon cancer cell are purchased from Third Military Medical University, cow's serum etc.
Other biochemical reagents and cell culture material are purchased from Beijing Ding Guo biotechnology Co., Ltd.
The recovery and culture of cell: cell cryopreservation tube is removed from liquid nitrogen, and is put into rapidly in 37 DEG C of warm water, complete to its
It is complete to melt, it is quickly transferred in superclean bench, solution is transferred in the 10mL centrifuge tube after sterilizing, the RIPM- of 7mL is added
1640 culture mediums (contain 10%FBS, 1% mycillin mixed liquor), 3000rmp is centrifuged 5min in centrifuge, after discard supernatant,
Be added 4mL RIPM-1640 culture medium (contain 10%FBS, 1% mycillin mixed liquor), piping and druming gone to after mixing in culture bottle into
Row culture, condition of culture are 37 DEG C, 5% CO2。
The administration of cell: selection form is normal, and the MCF-7 cell and HCT8 cell to grow fine is covered with to cell
80% or so, with trypsin digestion and cell, addition has blood meida, and cell is blown and beaten, after be transferred to 90mm culture dish,
Carry out adhere-wall culture.Sweet potato sitosterol glucosides palmitate is added in culture afterwards for 24 hours, controls final concentration of 10mg/L and 1mg/L, trains
Support 18h；Sweet potato sitosterol glucosides linoleate and sweet potato sitosterol glucosides are reference substance, each test parameters control and drug one
It causes.
MTT experiment the result shows that: 100mg/L, 10mg/L and 1mg/L give under concentration, sweet potato sitosterol glucosides saturated fat
Fat acid esters extract (1%, embodiment 1), sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract (10%, embodiment 8) and sweet
Potato sitosterol glucosides saturated fatty acid ester monomer (sitosterol glucosides dodecylate, sitosterol glucosides myristate, sitosterol
Glucosides hexadecane acid esters, sitosterol glucosides octadecane acid esters) 1 is shown in Table to the inhibiting rate of MCF-7 cell.Experiment is with sweet potato sitosterol
Glucosides linoleate and sweet potato sitosterol glucosides I be control.
Table 1, in relation to monomer to the inhibiting rate (%) of MCF-7 tumour cell
In table 1 as the result is shown: under high concentration, sweet potato sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract is to MCF-7
There is certain inhibiting effect, inhibiting effect is very weak under low concentration；Sweet potato sitosterol glucosides polyunsaturated fatty acid ester has very well MCF-7
Inhibiting effect, wherein most strong to the inhibiting effect of MCF-7 breast cancer cell with sweet potato sitosterol glucosides palmitate, carbochain increases
Adduction reduces, the antitumor equal decrease to some degree of activity；Inhibition of the sweet potato sitosterol glucosides palmitate to tumour
Effect is apparently higher than sweet potato sitosterol glucosides linoleate and sweet potato sitosterol glucosides, has good tumor prevention and/or controls
Treatment prospect.
Claims (10)
1. sweet potato sitosterol glucosides polyunsaturated fatty acid ester, chemical formula are shown in formula I:
Wherein, R=-CnH2n+1, 12≤n≤18, n are integer.
2. sweet potato sitosterol glucosides polyunsaturated fatty acid ester as described in claim 1, which is characterized in that n=15.
3. sweet potato sitosterol glucosides polyunsaturated fatty acid ester as described in claim 1, which is characterized in that R is straight-chain alkyl, is changed
Formula is as shown in Formula II:
4. sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract includes compound shown in Formulas I, by weight, chemical combination shown in Formulas I
Object accounts for 1% of extract or more, it is preferred that the extract includes compound shown in Formula II, by weight, the Formula II chemical combination
Object accounts for 1% of extract or more.
5. sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract as claimed in claim 4, which is characterized in that include Formula II institute
Show compound, by weight, the Formula II compound accounts for 10% of extract or more.
6. such as the described in any item sweet potato sitosterol glucosides polyunsaturated fatty acid ester extracts of claim 4~5, which is characterized in that
The extract is to be extracted by sweet potato starch mother liquor by precipitating, filtering/centrifugation, organic solvent, it is preferred that described to mention
It takes object point in thin layer chromatography board, is unfolded in chloroform/methanol/water mixed solution solvent that volume ratio is 90:10:1, with
Volume ratio is sulfuric acid/methanol chromogenic reagent of 1:9, after 105 DEG C of heating 5min, extract in aubergine spot.
7. the preparation method of the described in any item sweet potato sitosterol glucosides polyunsaturated fatty acid ester extracts of claim 4-6, including
Following steps:
At 1:50-100 DEG C of step, it is 0.01%~5% precipitating reagent, centrifugation or mistake that weight ratio is added into sweet potato starch mother liquor
Filter, takes solid to obtain sweet potato crude extract；
Step 2: the organic solvent that weight ratio is 1:1~10 being added into sweet potato crude extract, is filtered after stirring, filtrate system is concentrated
Obtain sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract.
8. sweet potato sitosterol glucosides polyunsaturated fatty acid ester method for preparing extractive as claimed in claim 7, further includes step 3,
Sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract is subjected to column chromatography, collecting with volume ratio is chloroform/first of 90:10:1
Alcohol/water mixed solution is solvent, and sulfuric acid/methanol solution using volume ratio for 1:9 heats 5min as color developing agent, at 105 DEG C and shows
Aubergine spot, the eluent that thin-layer chromatography Rf is 0.68-0.77, concentrate eluant are made sweet potato sitosterol glucosides and are saturated acid esters
Extract.
9. the preparation method of any one of the claim 1-3 sweet potato sitosterol glucosides polyunsaturated fatty acid ester, which is characterized in that will
Above-mentioned resulting sweet potato sitosterol glucosides polyunsaturated fatty acid ester extract is dissolved in ethyl alcohol, is chromatographed by alkyl silane bonded silica gel column
Separation collects the eluent of corresponding retention time, obtains each sweet potato sitosterol glucosides saturated fat using alcohol solution as eluant, eluent
Acid ester monomer.
10. the described in any item sweet potato sitosterol glucosides polyunsaturated fatty acid esters of claim 1-3 and/or such as claim 4-8
Sweet potato sitosterol glucosides polyunsaturated fatty acid ester described in one is being used to prepare treatment and/or prevention tumour medicine, health food
In application.
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| PCT/CN2018/081664 WO2019119675A1 (en) | 2017-12-21 | 2018-04-03 | Sweet potato sitosterol glycoside saturated fatty acid ester, extract, preparation method therefor, and application thereof |
| AU2018100981A AU2018100981A4 (en) | 2017-12-21 | 2018-07-10 | Sweet potato sitosterol glucoside saturated fatty acid ester, extract, preparation methods and application thereof |
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| WO2002079219A2 (en) * | 2001-03-30 | 2002-10-10 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Anti-proliferative 6-o-acyl-beta-d-glucosyl-beta-sitosterol compounds |
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| JPH07258100A (en) * | 1994-03-24 | 1995-10-09 | Osamu Michioka | Glycolipid contained in sweet potato and exhibiting anticancer action by suppressing proliferation and promoting differentiation of cancer cell and purification process therefor |
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| WO2002079219A2 (en) * | 2001-03-30 | 2002-10-10 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Anti-proliferative 6-o-acyl-beta-d-glucosyl-beta-sitosterol compounds |
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| Title |
|---|
| /: "RN: 1632494-75-7的化合物等", 《REGISTRY数据库》 * |
| WIMMEROVA, MARTINA 等.: "Improved enzyme-mediated synthesis and supramolecular self-assembly of naturally occurring conjugates of β-sitosterol.", 《STEROIDS》 * |
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