CN115894217B - Preparation and application of heptadecanoic acid with hypoglycemic effect - Google Patents
Preparation and application of heptadecanoic acid with hypoglycemic effect Download PDFInfo
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- CN115894217B CN115894217B CN202211279106.0A CN202211279106A CN115894217B CN 115894217 B CN115894217 B CN 115894217B CN 202211279106 A CN202211279106 A CN 202211279106A CN 115894217 B CN115894217 B CN 115894217B
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- heptadecanoic acid
- grifola frondosa
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- reducing effect
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- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 230000002218 hypoglycaemic effect Effects 0.000 title abstract description 4
- 240000001080 Grifola frondosa Species 0.000 claims abstract description 26
- 235000007710 Grifola frondosa Nutrition 0.000 claims abstract description 26
- 239000008280 blood Substances 0.000 claims abstract description 22
- 210000004369 blood Anatomy 0.000 claims abstract description 22
- 230000001603 reducing effect Effects 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000000284 extract Substances 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 3
- 238000002137 ultrasound extraction Methods 0.000 claims description 3
- 102100024295 Maltase-glucoamylase Human genes 0.000 abstract description 11
- 108010028144 alpha-Glucosidases Proteins 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 8
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 abstract description 5
- 229960002632 acarbose Drugs 0.000 abstract description 5
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000000638 solvent extraction Methods 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 238000009777 vacuum freeze-drying Methods 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 241000233866 Fungi Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 1
- 241000222684 Grifola Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000222341 Polyporaceae Species 0.000 description 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- NSEXTLCTTCFJCT-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCC(O)=O NSEXTLCTTCFJCT-UHFFFAOYSA-N 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses a preparation method and application of heptadecanoic acid with a blood sugar reducing effect, and belongs to the field of biology and medicine. The invention takes grifola frondosa as a raw material, and the heptadecanoic acid is prepared by two-phase solvent extraction and silica gel column chromatography separation. The invention has the advantages of simple method, high product purity and high yield, and the heptadecanoic acid prepared by the invention has the purity of more than 95 percent and the yield of 3.25 percent, and the inhibition capability (IC 50 value is 106.91 mug/mL) of alpha-glucosidase is stronger than acarbose (IC 50 value is 216.42 mug/mL), thus being capable of being used as a potential hypoglycemic active ingredient and being beneficial to industrial application.
Description
Technical Field
The invention belongs to the field of biology and medicine, and particularly relates to a preparation method and application of heptadecanoic acid with a blood sugar reducing effect.
Background
According to the published data of the international diabetes alliance, 2021 global diabetics reach 5.37 million people, wherein the type 2 diabetes accounts for more than 90 percent. Type 2 diabetes is a chronic metabolic disorder characterized by high blood glucose levels, where persistent hyperglycemia can cause multiple complications that are dangerous to health. Controlling and lowering blood glucose levels is the only method of treating diabetes. Although the conventional medicines for treating diabetes can effectively control blood sugar level, the side effects on the intestinal tract of a patient are not quite a lot, and the conventional medicines are expensive, so that a great burden is brought to the patient. The absorption of saccharide in human body is dependent on alpha-glucosidase, and can inhibit the activity of alpha-glucosidase, slow down the generation and absorption of glucose, reduce postprandial blood glucose peak value, and regulate blood glucose level. Thus, it is highly desirable to find a safe and effective α -glucosidase inhibitor.
Grifola frondosa (Grifola frondosa) belongs to fungi of genus Grifola of family Polyporaceae, and is a rare fungus for both medicine and food. The meat is crisp, tender and tasty, and has rich nutrients and rich proteins, amino acids and vitamins. Besides rich nutritive value, the grifola frondosa also has higher medicinal value, such as reducing blood sugar and blood fat, improving lipid metabolism, regulating immune function, resisting tumor, resisting oxidation, etc. At present, little research is carried out on chemical components of the grifola frondosa, but the preparation of heptadecanoic acid in the grifola frondosa and the hypoglycemic activity of the heptadecanoic acid are not reported yet.
Disclosure of Invention
In order to overcome the defects and the shortcomings of the prior art, the invention aims to provide the preparation method of the heptadecanoic acid which is simple in procedure, high in purity and yield and has the function of reducing blood sugar, and has important significance for developing new medicines and improving the commercial value of grifola frondosa.
In order to achieve the above purpose, the invention adopts the following technical scheme:
A method for preparing heptadecanoic acid with blood sugar reducing effect, which comprises the following steps:
(1) Extracting coarse powder of grifola frondosa with 70vol% ethanol solution, concentrating the extractive solution, extracting with ethyl acetate, concentrating the extractive solution, and drying to obtain grifola frondosa extract;
(2) Dissolving Maitake Mushroom extract in small amount of dichloromethane by silica gel column chromatography, eluting with dichloromethane and methanol, identifying by thin layer chromatography, mixing the eluting fractions with R f value of 0.79, concentrating, and drying to obtain heptadecanoic acid.
Further, the mass-volume ratio of the grifola frondosa coarse powder to the ethanol solution is 1:10-1:30 g/mL.
Further, the extraction adopts an ultrasonic extraction method, the ultrasonic frequency is 20-40KHZ, the temperature is 40-60 ℃, the time is 1-3h, and the times are 2-4 times.
Further, the silica gel column chromatography adopts 200-400 meshes, the mass ratio of the silica gel to the grifola frondosa extract is 80:1-120:1, and the volume ratio of dichloromethane to methanol in the eluent is 10:1.
Further, the developing agent for the thin layer chromatography is prepared by mixing methylene dichloride and methanol according to a volume ratio of 7:1.
Further, in operation, the concentration is performed by vacuum concentration at a temperature of 40-60 ℃, and the drying is performed by vacuum freeze drying.
Further, the purity of the obtained heptadecanoic acid is more than 95%.
The prepared heptadecanoic acid has good blood sugar reducing function, and can be used for preparing medicines or health care products with blood sugar reducing effect.
The invention has the beneficial effects that:
(1) The invention adopts a separation and purification technology combining solvent extraction and column chromatography, and is a preparation method with low cost, simple and convenient procedure, high sample yield and suitability for industrial production.
(2) The heptadecanoic acid prepared by the invention has high purity and good blood sugar reducing effect, has stronger inhibiting capability (IC 50 value is 106.91 mug/mL) to alpha-glucosidase than acarbose (IC 50 value is 216.42 mug/mL), can be used as a potential blood sugar reducing medicine, and simultaneously provides theoretical support for improving the commercial value of grifola frondosa.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of heptadecanoic acid prepared in example, wherein A is 1 H-NMR spectrum and B is ten 13 C-NMR spectrum;
FIG. 2 is a graph showing analysis of purity of heptadecanoic acid prepared in example;
FIG. 3 is a graph showing the inhibition of alpha-glucosidase by heptadecanoic acid prepared in the example.
Detailed Description
A method for preparing heptadecanoic acid with blood sugar reducing effect, which comprises the following steps:
(1) Taking grifola frondosa coarse powder, adding 70vol% ethanol solution into the grifola frondosa coarse powder according to the mass volume ratio of 1:10-1:30 g/mL for ultrasonic extraction, wherein the ultrasonic frequency is 20-40KHZ, the temperature is 40-60 ℃, the time is 1-3h, the times are 2-4 times, then concentrating the extract, extracting for multiple times by using ethyl acetate, then merging the extracts, concentrating under reduced pressure at 40-60 ℃, and performing vacuum freeze drying to obtain the grifola frondosa extract;
(2) Silica gel chromatographic column (column volume is 250-350 mL) is prepared by adopting silica gel with 200-400 meshes and mass ratio of 1:80-1:120 with the grifola frondosa extract, then the grifola frondosa extract is dissolved in a small amount of dichloromethane for loading, dichloromethane/methanol=1:10 (v/v) is used as eluent for eluting, thin layer chromatography identification is carried out (dichloromethane and methanol are mixed according to volume ratio of 7:1 as developing agent) and the eluting fraction with R f value of 0.79 is combined, and then the eluting fraction is concentrated under reduced pressure at 40-60 ℃ and is subjected to vacuum freeze drying, thus obtaining the heptadecanoic acid.
In order to make the contents of the present invention more easily understood, the technical scheme of the present invention will be further described with reference to the specific embodiments, but the present invention is not limited thereto.
Examples
A preparation method of heptadecanoic acid with blood sugar reducing effect comprises the following steps:
(1) Taking 100g of grifola frondosa coarse powder, adding 1.5L of 70 vol% ethanol solution, performing ultrasonic treatment for 2 times under the conditions of ultrasonic frequency of 25 KHZ and temperature of 55 ℃, concentrating the extract liquid each time, extracting 3 times by using ethyl acetate each time after concentrating the extract liquid, merging the extract liquid each time by 500mL, concentrating the extract liquid under reduced pressure at 45 ℃ and performing vacuum freeze drying to obtain 32.53g of grifola frondosa extract.
(2) Loading 100 g, 200-300 mesh silica gel into chromatographic column, adding 1g Maitake Mushroom extract dissolved in dichloromethane, eluting with 300 mL dichloromethane/methanol mixed solution (10:1, v/v) as eluent to ensure flow rate of 1mL/min, simultaneously identifying eluate by thin layer chromatography with dichloromethane and methanol (7:1, v/v) as developing agent, mixing eluate fractions with R f value of 0.79, concentrating under reduced pressure at 45deg.C, vacuum freeze drying to obtain product 0.10g, namely heptadecanoic acid @) The purity is more than 95%, and the yield is about 3.25%.
FIG. 1 is a nuclear magnetic resonance spectrum of the obtained product. As shown in figure ,1H-NMR DMSO-d6,400 MHz) δH: 2.15 (2H, t, J = 7.6 Hz),1.46 (2H, m),1.22 (26H, m),0.83 (3H, t, J = 7.2 Hz).13C-NMR (DMSO-d6,100 MHz) δC: 174.4（C-1）,33.7（C-2）,31.5（C-3）,29.3（C-4）,29.3（C-5）,29.3（C-6）,29.3（C-7）,29.3（C-8）,29.3（C-9）,29.3（C-10）,29.1（C-11）,28.9（C-12）,28.8（C-13）,28.7（C-14）,24.6（C-15）,22.3（C-16）,13.9（C-17）. the above data are substantially identical to those reported in the literature (Sun Dongdong, li Xiang, chen Jianwei, et al. J. Hua Xiyao J. Chem. 2007,22 (5): 487-488.) and thus identify heptadecanoic acid (heptadecanoic acid) with a molecular formula of C 17H34O2.
Application example
Heptadecanoic acid solutions (62.5, 125, 250, 500, 1000. Mu.g/mL) of different concentration gradients were prepared using phosphate buffer (0.1 mmol/L, pH 6.8), 30. Mu.L each was placed in a 96-well plate, 30. Mu.L of alpha-glucosidase (0.2U/mL) was added, allowed to stand at 37℃for 10min, then 30. Mu.L of substrate P-NPG (5 mmol/L) was added, incubated at 37℃for 15min, and finally the reaction was terminated by adding 90. Mu.L of Na 2CO3 solution (0.1 mol/L), absorbance was measured at 405: 405 nm, and the inhibition of alpha-glucosidase was calculated (inhibition calculation formula is as follows). Acarbose at the same concentration was used as a positive control, phosphate buffer was used as a control instead of the sample solution, and phosphate buffer was used as a background instead of alpha-glucosidase.
Wherein A 1 is the absorbance of the experimental group, A 2 is the absorbance of the background group, and A 3 is the absorbance of the control group.
FIG. 3 is a graph showing the inhibition of alpha-glucosidase activity by heptadecanoic acid. As shown in the figure, the heptadecanoic acid has good inhibition effect on alpha-glucosidase and dose-dependent increase, and the IC 50 value of the heptadecanoic acid is 106.91 mug/mL and the IC 50 value of the acarbose is 216.42 mug/mL, which shows that the inhibition effect of the heptadecanoic acid on the alpha-glucosidase is stronger than that of the acarbose, and the heptadecanoic acid has better hypoglycemic effect.
The foregoing description is only of the preferred embodiments of the invention, and all changes and modifications that come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Claims (4)
1. A preparation method of heptadecanoic acid with blood sugar reducing effect is characterized by comprising the following steps:
(1) Extracting coarse powder of grifola frondosa with 70vol% ethanol solution, concentrating the extractive solution, extracting with ethyl acetate, concentrating the extractive solution, and drying to obtain grifola frondosa extract;
(2) Dissolving Maitake Mushroom extract in small amount of dichloromethane by silica gel column chromatography, eluting with dichloromethane and methanol as eluent, identifying by thin layer chromatography, mixing the eluting fractions with R f value of 0.79, concentrating, and drying to obtain heptadecanoic acid;
The silica gel column chromatography adopts 200-400 meshes of silica gel, the mass ratio of the silica gel dosage to the grifola frondosa extract is 80:1-120:1, and the volume ratio of dichloromethane to methanol in the eluent is 10:1;
The purity of the obtained heptadecanoic acid is more than 95 percent.
2. The method for preparing heptadecanoic acid with blood sugar reducing effect according to claim 1, wherein the mass-volume ratio of the grifola frondosa coarse powder to the ethanol solution is 1:10-1:30 g/mL.
3. The method for preparing heptadecanoic acid with blood sugar reducing effect according to claim 1, wherein the ultrasonic extraction method is adopted, the ultrasonic frequency is 20-40KHZ, the temperature is 40-60 ℃, the time is 1-3h, and the times are 2-4 times.
4. The method for preparing heptadecanoic acid with blood sugar reducing effect according to claim 1, wherein the developing agent of the thin layer chromatography is prepared by mixing methylene dichloride and methanol according to a volume ratio of 7:1.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2377118A1 (en) * | 1996-03-22 | 1997-09-25 | Moady, Said | Antipsoriatic compositions, method of making, and method of using |
| JP2017200910A (en) * | 2016-04-28 | 2017-11-09 | ライオン株式会社 | An agent for inhibiting increase of blood glucose level |
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| CN104155371B (en) * | 2013-05-15 | 2015-09-30 | 广州白云山中一药业有限公司 | The method for building up of the compound Chinese medicinal preparation diabetes pill HPLC finger-print for the treatment of diabetes and HPLC finger-print thereof |
| ES2915377T3 (en) * | 2013-08-02 | 2022-06-22 | Enevolv Inc | Procedures and host cells for genomic, pathway and biomolecular engineering |
| CN103724445B (en) * | 2013-12-25 | 2016-08-17 | 广东省微生物研究所 | The preparation method of grifolan F2 and function of blood sugar reduction thereof |
| US9561206B2 (en) * | 2015-01-07 | 2017-02-07 | The United States Of America, As Represented By The Secretary Of The Navy | Use of heptadecanoic acid (C17:0) to detect risk of and treat hyperferritinemia and metabolic syndrome |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2377118A1 (en) * | 1996-03-22 | 1997-09-25 | Moady, Said | Antipsoriatic compositions, method of making, and method of using |
| JP2017200910A (en) * | 2016-04-28 | 2017-11-09 | ライオン株式会社 | An agent for inhibiting increase of blood glucose level |
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