CN117247415A - Preparation method of 4,6, 8-decynyl-beta-D-glucoside - Google Patents
Preparation method of 4,6, 8-decynyl-beta-D-glucoside Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 claims abstract description 20
- 244000035851 Chrysanthemum leucanthemum Species 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 238000010828 elution Methods 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000011068 loading method Methods 0.000 claims description 13
- 239000012046 mixed solvent Substances 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 12
- 238000010898 silica gel chromatography Methods 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004440 column chromatography Methods 0.000 claims description 9
- 238000001514 detection method Methods 0.000 claims description 9
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 9
- 239000002024 ethyl acetate extract Substances 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000287 crude extract Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 claims description 3
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 3
- 238000002386 leaching Methods 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002953 preparative HPLC Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 235000007516 Chrysanthemum Nutrition 0.000 abstract description 3
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 241000723353 Chrysanthemum Species 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 5
- 241000628997 Flos Species 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 240000005250 Chrysanthemum indicum Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- -1 8-decynyl beta-D-glucopyranoside Chemical class 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 235000018959 Chrysanthemum indicum Nutrition 0.000 description 1
- 241000229184 Mediasia macrophylla Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
Classifications
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- 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
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
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Abstract
The invention discloses a preparation method of 4,6, 8-decynyl-beta-D-glucoside. The invention takes the Chinese medicinal wild chrysanthemum flower as the raw material to prepare the compound 4,6, 8-decynyl-beta-D-glucoside for the first time. The prior art does not report that the wild chrysanthemum contains the compound 4,6, 8-decynyl-beta-D-glucoside, nor that other plants in the chrysanthemum genus where the wild chrysanthemum is located contain the compound 4,6, 8-decynyl-beta-D-glucoside. The method of the invention develops a new way for obtaining the compound 4,6, 8-decynyl-beta-D-glucoside by taking the relatively cheap wild chrysanthemum as a source, and is beneficial to the application and development of the compound.
Description
Technical Field
The invention belongs to the field of natural pharmaceutical chemistry, relates to a preparation method of a known compound, and in particular relates to a preparation method of 4,6, 8-decynyl-beta-D-glucoside.
Background
The compound 4,6, 8-decynyl- β -D-glucoside is a natural product having the chemical structure:
the research shows that the 4,6, 8-decynyl-beta-D-glucoside has excellent anti-inflammatory activity.
Unfortunately, although 4,6, 8-decynyl- β -D-glucoside has excellent activity, the natural sources available for extraction and isolation of this compound are very few, which limits its application development.
The flos Chrysanthemi Indici is a dry head-like inflorescence of Chrysanthemum indicum L. Of Compositae, and is recorded in the part of the year 2020 of Chinese pharmacopoeia, and has slightly cold, bitter and pungent taste, and has effects of clearing heat, detoxicating, purging pathogenic fire and suppressing hyperactive liver. Is widely distributed in regions such as Henan, zhejiang, anhui and the like in China.
The invention provides a special preparation method for expanding the source of 4,6, 8-decynyl-beta-D-glucoside.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of 4,6, 8-decynyl-beta-D-glucoside.
The above object of the present invention is achieved by the following technical scheme:
the preparation method of 4,6, 8-decynyl-beta-D-glucoside comprises the following steps of taking Chinese medicinal wild chrysanthemum flower as a separation raw material:
further, the preparation method comprises the following steps:
step S1, leaching Chinese medicinal wild chrysanthemum with ethanol solution at normal temperature, concentrating an extract to obtain wild chrysanthemum crude extract, suspending the obtained crude extract with a proper amount of water, extracting with ethyl acetate, collecting ethyl acetate extract, and concentrating to obtain ethyl acetate extract;
step S2, loading the ethyl acetate extract on a normal phase silica gel column chromatography, performing gradient elution by using a dichloromethane-methanol mixed solvent, performing TLC detection, concentrating under reduced pressure, and combining the same parts to obtain 12 fractions Fr.1-12, wherein Fr.10 fractions are used for subsequent separation; wherein, the elution proportion, volume and sequence of the normal phase silica gel column chromatography gradient are: 100:0 eluting 6 column volumes, 100:1 eluting 2 column volumes, 50:1 eluting 2 column volumes, 30:1 eluting 5 column volumes, 20:1 eluting 5 column volumes, 15:1 eluting 4 column volumes, 10:1 eluting 2 column volumes, 5:1 eluting 1 column volume;
step S3, loading the fraction Fr.10 on a normal phase silica gel column chromatography, performing gradient elution by using a dichloromethane-methanol mixed solvent, performing TLC detection, and combining the same parts to obtain 4 fractions Fr.10.1-10.4, wherein Fr.10.3 fractions are used for subsequent separation; wherein, the elution proportion, volume and sequence of the normal phase silica gel column chromatography gradient are: 20:1 elution of 2 column volumes→15:1 elution of 4 column volumes→10:1 elution of 4 column volumes→5:1 elution of 2 column volumes;
s4, loading the fraction Fr.10.3 on an ODS column chromatograph, performing gradient elution by using a methanol-water mixed solvent, performing TLC detection, and combining the same parts to obtain 12 fractions Fr.10.3.1-10.3.12, wherein Fr.10.3.9 fractions are used for subsequent separation; wherein, the ODS column chromatography gradient elution proportion, volume and sequence are as follows: 10:90 eluting 1 column volume, 25:75 eluting 2 column volumes, 40:60 eluting 4 column volumes, 55:45 eluting 5 column volumes, 70:30 eluting 6 column volumes, 85:15 eluting 4 column volumes, 100:0 eluting 2 column volumes;
s5, loading the fraction Fr.10.3.9 on an ODS column chromatograph, performing gradient elution by using a mixed solvent of methanol and 0.1% acetic acid water, performing TLC detection, and combining the same parts to obtain 8 fractions Fr.10.3.9.1-10.3.9.8, wherein Fr.10.3.9.5 fractions are used for subsequent separation; wherein, the ODS column chromatography gradient elution proportion, volume and sequence are as follows: 35:75 eluting 13 column volumes→40:60 eluting 6 column volumes→45:55 eluting 2 column volumes→50:50 eluting 2 column volumes→100:0 eluting 1 column volume;
step S6, loading the fractions Fr.10.3.9.5 on a gel column chromatography, eluting with dichloromethane-methanol 1:1, detecting by TLC, and combining the same parts to obtain 6 fractions Fr.10.3.9.5.1-10.3.9.5.6, wherein the Fr.10.3.9.5.5 fractions are used for subsequent separation;
and S7, performing preparative HPLC (high Performance liquid chromatography) chromatography on the Fr.10.3.9.5.5 fraction, eluting with acetonitrile-water in a volume ratio of 22:78, collecting the fraction at the peak of the 4,6, 8-decynyl-beta-D-glucoside, and drying to obtain the 4,6, 8-decynyl-beta-D-glucoside.
Further, the ethanol solution in step S1 is 95% ethanol.
Further, step S1 is carried out for 3 times, and the extracting solutions are filtered and combined.
The beneficial effects are that:
the invention takes the Chinese medicinal wild chrysanthemum flower as the raw material to prepare the compound 4,6, 8-decynyl-beta-D-glucoside for the first time. The prior art does not report that the wild chrysanthemum contains the compound 4,6, 8-decynyl-beta-D-glucoside, nor that other plants in the chrysanthemum genus where the wild chrysanthemum is located contain the compound 4,6, 8-decynyl-beta-D-glucoside. The method of the invention develops a new way for obtaining the compound 4,6, 8-decynyl-beta-D-glucoside by taking the relatively cheap wild chrysanthemum as a source, and is beneficial to the application and development of the compound.
Drawings
FIG. 1 is a mass spectrum of the compound 4,6, 8-decynyl- β -D-glucoside;
FIG. 2 is a nuclear magnetic resonance spectrum of the compound 4,6, 8-decynyl-beta-D-glucoside;
FIG. 3 is a nuclear magnetic carbon spectrum of the compound 4,6, 8-decynyl- β -D-glucoside;
FIG. 4 is a nuclear magnetic DEPT135 spectrum of the compound 4,6, 8-decynyl-beta-D-glucoside.
Detailed Description
The following describes the essential aspects of the present invention in detail with reference to examples, but is not intended to limit the scope of the present invention.
The method for preparing the compound 4,6, 8-decynyl-beta-D-glucoside from the traditional Chinese medicine wild chrysanthemum comprises the following steps:
extracting 5.0kg of Chinese medicinal flos Chrysanthemi Indici with 95% ethanol (5L) at room temperature for 3 times, sequentially for 7d, 4d and 3d, filtering and mixing the extractive solutions, and concentrating under reduced pressure to obtain crude extract of flos Chrysanthemi Indici about 1.0kg; suspending the crude extract of flos Chrysanthemi Indici with appropriate amount of water, extracting with ethyl acetate, collecting ethyl acetate extract, concentrating to obtain ethyl acetate extract; loading the wild chrysanthemum ethyl acetate extract (304.5 g) on a normal phase silica gel column chromatography, and carrying out gradient elution by using a dichloromethane-methanol mixed solvent (100:0×6-100:1×2-50:1×2-30:1×5-20:1×5-15:1×4-10:1×2-5:1×1), carrying out TLC detection, and merging the same parts by TLC analysis to obtain 12 fractions Fr.1-12, wherein Fr.10 is an enrichment substance containing a compound 4,6, 8-decynyl-beta-D-glucoside;
subjecting the fraction Fr.10 (21.0 g) to normal phase silica gel column chromatography, gradient eluting with dichloromethane-methanol mixed solvent (20:1X2→15:1X4→10:1X4→5:1X2), detecting by TLC, and combining the same parts by TLC analysis to obtain 4 fractions Fr.10.1-10.4, wherein Fr.10.3 fraction is an enriched product containing 4,6, 8-decynyl-beta-D-glucoside;
loading the fraction Fr.10.3 (11.3 g) on ODS column chromatography, gradient eluting with methanol-water mixed solvent (10:90×1→25:75×2→40:60×4→55:45×5→70:30×6→85:15×4→100:0×2), detecting by TLC, and combining the same parts by TLC analysis to obtain 12 fractions Fr.10.3.1-10.3.12, wherein Fr.10.3.9 fraction is enriched with 4,6, 8-decynyl-beta-D-glucoside;
subjecting the fraction Fr.10.3.9 (2.8 g) to ODS column chromatography, gradient eluting with methanol-0.1% acetic acid water mixed solvent (35:75X13→40:60deg.C→45:55X2→50:50X12→100:0X1), detecting by TLC, and combining the same parts by TLC analysis to obtain 8 fractions Fr.10.3.9.1-10.3.9.8, wherein Fr.10.3.9.5 fraction is enriched with 4,6, 8-decynyl-beta-D-glucoside;
loading the fraction Fr.10.3.9.5 (0.4 g) on a gel column chromatography, eluting with dichloromethane-methanol at 1:1 isocratic, detecting by TLC, and combining the same parts by TLC analysis to obtain 6 fractions Fr.10.3.9.5.1-10.3.9.5.6, wherein Fr.10.3.9.5.5 is separated into an enriched substance containing 4,6, 8-decynyl-beta-D-glucoside;
fr.10.3.9.5.5 (109.4 mg) fractions were separated by preparative HPLC chromatography (acetonitrile-water 22:78) and the fractions which peaked at 45.0min were concentrated under reduced pressure to give the compound 4,6, 8-decynyl- β -D-glucoside (4.2 mg).
Structural confirmation: yellow oily matter with a molecular formula of C 16 H 20 O 6 。ESI-MS m/z:331.11[M+Na] + 。 1 H NMR(500MHz,MeOD)δ:4.25(1H,d,J＝7.8Hz,H-1'),3.95(1H,dt,J＝10.0,6.0Hz,H-1a),3.86(1H,dd,J＝11.8,1.9Hz,H-6'a),3.67(1H,dd,J＝11.6,4.8Hz,H-6'b),3.62(1H,dd,J＝10.1,6.2Hz,H-1b),3.34(1H,d,J＝10.47Hz,H-3'),3.27(1H,d,J＝7.83Hz,H-4',5'),3.16(1H,dd,J＝9.0,7.8Hz,H-2'),2.46(2H,t,J＝7.2Hz,H-3),1.94(3H,s,H-10),1.83(2H,p,J＝6.6Hz,H-2)； 13 CNMR (125 MHz, meOD) delta 104.5 (C-1 '), 79.6 (C-4), 78.1 (C-3'), 77.9 (C-5 '), 76.1 (C-9), 75.1 (C-2'), 71.6 (C-4 '), 69.1 (C-1), 66.3 (C-5), 65.2 (C-8), 62.7 (C-6'), 61.2 (C-7), 60.2 (C-6), 29.6 (C-2), 16.6 (C-3), 3.7 (C-10). The above spectral data are consistent with literature report controls (Kurimoto S, et al, A.C. 14-polyacetylenic glucoside with an. Alpha. -pyrone moiety and four C, 10-polyacetylenic glucosides from Mediasia macrophylla, phytochemistry, 2010), and thus the identified compound is 4,6, 8-decynyl-beta-D-glucoside (4, 6, 8-decynyl beta-D-glucopyranoside), having the following structure:
FIG. 1 is a mass spectrum of the compound 4,6, 8-decynyl- β -D-glucoside; FIG. 2 is a nuclear magnetic resonance spectrum of the compound 4,6, 8-decynyl-beta-D-glucoside; FIG. 3 is a nuclear magnetic carbon spectrum of the compound 4,6, 8-decynyl- β -D-glucoside; FIG. 4 is a nuclear magnetic DEPT135 spectrum of the compound 4,6, 8-decynyl-beta-D-glucoside.
In conclusion, the compound 4,6, 8-decynyl-beta-D-glucoside is prepared by taking the traditional Chinese medicine wild chrysanthemum flower as a raw material for the first time. The prior art does not report that the wild chrysanthemum contains the compound 4,6, 8-decynyl-beta-D-glucoside, nor that other plants in the chrysanthemum genus where the wild chrysanthemum is located contain the compound 4,6, 8-decynyl-beta-D-glucoside. The method of the invention exploits a new way for obtaining the compound 4,6, 8-decynyl-beta-D-glucoside by taking cheaper wild chrysanthemum as a source.
The above-described embodiments serve to describe the substance of the present invention in detail, but those skilled in the art should understand that the scope of the present invention should not be limited to this specific embodiment.
Claims (4)
1. The preparation method of the 4,6, 8-decynyl-beta-D-glucoside is characterized in that the chemical structure of the 4,6, 8-decynyl-beta-D-glucoside is as follows: the method takes Chinese medicine wild chrysanthemum flower as a separation raw material:
2. the method of manufacturing according to claim 1, comprising the steps of:
step S1, leaching Chinese medicinal wild chrysanthemum with ethanol solution at normal temperature, concentrating an extracting solution to obtain wild chrysanthemum crude extract, suspending the obtained crude extract with a proper amount of water, extracting with ethyl acetate, collecting an ethyl acetate extract, and concentrating to obtain an ethyl acetate extract;
step S2, loading the ethyl acetate extract on a normal phase silica gel column chromatography, performing gradient elution by using a dichloromethane-methanol mixed solvent, performing TLC detection, concentrating under reduced pressure, and combining the same parts to obtain 12 fractions Fr.1-12, wherein Fr.10 fractions are used for subsequent separation; wherein, the elution proportion, volume and sequence of the normal phase silica gel column chromatography gradient are: 100:0 eluting 6 column volumes, 100:1 eluting 2 column volumes, 50:1 eluting 2 column volumes, 30:1 eluting 5 column volumes, 20:1 eluting 5 column volumes, 15:1 eluting 4 column volumes, 10:1 eluting 2 column volumes, 5:1 eluting 1 column volume;
step S3, loading the fraction Fr.10 on a normal phase silica gel column chromatography, performing gradient elution by using a dichloromethane-methanol mixed solvent, performing TLC detection, and combining the same parts to obtain 4 fractions Fr.10.1-10.4, wherein Fr.10.3 fractions are used for subsequent separation; wherein, the elution proportion, volume and sequence of the normal phase silica gel column chromatography gradient are: 20:1 elution of 2 column volumes→15:1 elution of 4 column volumes→10:1 elution of 4 column volumes→5:1 elution of 2 column volumes;
s4, loading the fraction Fr.10.3 on an ODS column chromatograph, performing gradient elution by using a methanol-water mixed solvent, performing TLC detection, and combining the same parts to obtain 12 fractions Fr.10.3.1-10.3.12, wherein Fr.10.3.9 fractions are used for subsequent separation; wherein, the ODS column chromatography gradient elution proportion, volume and sequence are as follows: 10:90 eluting 1 column volume, 25:75 eluting 2 column volumes, 40:60 eluting 4 column volumes, 55:45 eluting 5 column volumes, 70:30 eluting 6 column volumes, 85:15 eluting 4 column volumes, 100:0 eluting 2 column volumes;
s5, loading the fraction Fr.10.3.9 on an ODS column chromatograph, performing gradient elution by using a mixed solvent of methanol and 0.1% acetic acid water, performing TLC detection, and combining the same parts to obtain 8 fractions Fr.10.3.9.1-10.3.9.8, wherein Fr.10.3.9.5 fractions are used for subsequent separation; wherein, the ODS column chromatography gradient elution proportion, volume and sequence are as follows: 35:75 eluting 13 column volumes→40:60 eluting 6 column volumes→45:55 eluting 2 column volumes→50:50 eluting 2 column volumes→100:0 eluting 1 column volume;
step S6, loading the fractions Fr.10.3.9.5 on a gel column chromatography, eluting with dichloromethane-methanol 1:1, detecting by TLC, and combining the same parts to obtain 6 fractions Fr.10.3.9.5.1-10.3.9.5.6, wherein the Fr.10.3.9.5.5 fractions are used for subsequent separation;
and S7, performing preparative HPLC (high Performance liquid chromatography) chromatography on the Fr.10.3.9.5.5 fraction, eluting with acetonitrile-water in a volume ratio of 22:78, collecting the fraction at the peak of the 4,6, 8-decynyl-beta-D-glucoside, and drying to obtain the 4,6, 8-decynyl-beta-D-glucoside.
3. The preparation method according to claim 2, characterized in that: the ethanol solution in step S1 is 95% ethanol.
4. A method of preparation according to claim 3, characterized in that: step S1, leaching for 3 times, filtering and combining the extracting solutions.
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