CN105777845A - Extraction method and use of antibiosis components from Idesia polycarpa - Google Patents
Extraction method and use of antibiosis components from Idesia polycarpa Download PDFInfo
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- 238000000605 extraction Methods 0.000 title claims abstract description 20
- 241001299699 Idesia Species 0.000 title claims abstract description 15
- 230000003115 biocidal effect Effects 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 84
- 239000011347 resin Substances 0.000 claims description 39
- 229920005989 resin Polymers 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 30
- -1 1-hydroxyl-6-oxo-2-cyclohexenyl Chemical group 0.000 claims description 25
- 230000000844 anti-bacterial effect Effects 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- FSLPMRQHCOLESF-UHFFFAOYSA-N alpha-amyrenol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C)C(C)C5C4=CCC3C21C FSLPMRQHCOLESF-UHFFFAOYSA-N 0.000 claims description 20
- JFSHUTJDVKUMTJ-QHPUVITPSA-N beta-amyrin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C JFSHUTJDVKUMTJ-QHPUVITPSA-N 0.000 claims description 20
- QQFMRPIKDLHLKB-UHFFFAOYSA-N beta-amyrin Natural products CC1C2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CCC1(C)C QQFMRPIKDLHLKB-UHFFFAOYSA-N 0.000 claims description 20
- PDNLMONKODEGSE-UHFFFAOYSA-N beta-amyrin acetate Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C4(C)CCC5(C)CCC(C)(C)CC5C4=CCC23C)C1(C)C PDNLMONKODEGSE-UHFFFAOYSA-N 0.000 claims description 20
- 239000012046 mixed solvent Substances 0.000 claims description 20
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 20
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 19
- NEZJDVYDSZTRFS-RMPHRYRLSA-N Phenyl beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1 NEZJDVYDSZTRFS-RMPHRYRLSA-N 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims description 5
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 5
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
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- 230000004071 biological effect Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 2
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- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
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- CMWOPTLOKFKJEC-UHFFFAOYSA-N idesolide Natural products O1C(CCC=C2)(O)C2(C(=O)OC)OC21CCC=CC2(O)C(=O)OC CMWOPTLOKFKJEC-UHFFFAOYSA-N 0.000 description 2
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to an extraction method and a use of antibiosis components from Idesia polycarpa. The extraction method of the antibiosis components from Idesia polycarpa has a very high extraction rate and an excellent separation effect, and allows various active compounds to be obtained, and the extracted active compounds have high antibiosis activity on Staphylococcus aureus, Escherichia coli and Candida albicans, and have good application prospect in the antibiosis field.
Description
Technical field
The present invention relates to the extracting method of antimicrobial component in a kind of Idesia polycarpa and purposes, belong to field of plant extraction.
Background technology
Idesia polycarpa, is also called Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp., is the mutation of Radix seu Cortex Malloti nepalensis.Its fruit mainly contains fatty acid, phenols, glucoside, alkaloid, vitamin E etc., and there is certain biological activity, be widely used in the fields such as antibacterial, sterilization, antioxidation, heart tonifying, blood pressure lowering.
Great demand based on the application of Idesia polycarpa extract product broad spectrum activity, most of province on the south China Huanghe valley is such as: the ground such as Zhejiang, Jiangsu, Anhui, Hubei, Henan, Shandong, Guangdong, Jiangxi, Guizhou, Sichuan, Yunnan, Chongqing, Shaanxi all occur that large area is manually planted, and research and development of products mechanism and manufacturer also arise at the historic moment.
At present, extracting antibacterial Quality Research from natural plants has a lot, and the kind of these extracts is mainly by volatile oil, organic acid, alkaloid, tannin, some lactone etc..
Such as, CN1740137A discloses a kind of method of chlorogenic acid extracting and purifying from sunflower meal, and chlorogenic acid has anti-inflammation, function of gallbladder promoting, stops blooding and increases the effect of white blood cell count.
CN1789395A discloses the Tibetan medical dracocephalum heterophyllum benth volatile oil with antibacterial and/or bactericidal action and the application having in antibacterial and/or the product of bactericidal action in preparation thereof.
CN101084989A discloses the preparation method simultaneously preparing kuh-seng total flavone extract and total alkaloids extract, kuh-seng total flavone extract and Radix Sophorae Flavescentis total alkaloids extract and has antibacterial parasite killing, antiviral, antiinflammatory, can be used for the fields such as antibacterial and sterilization.
(the Zhou Yan etc. such as Zhou Yan, non-oil fat chemical composition [J] of Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. sarcocarp. research and development of natural products, 2003,15 (1): 13-17) find that the growth of wax bacillus cereus (gram positive bacteria) is had obvious inhibitory action by the extractum after the ethanol extraction petroleum ether degreasing of Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. peel, and find that the effect of Isolated Toad Heart be experiments show that this extract has certain cardiotonic by it, but each monomeric compound is not done further activity research.(the Ge Hongguang such as Ge Hongguang, Wu Wan moth, Chen Kaixun. Natural antioxidant research [J] in Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. seed. Chinese oil, 1998,23 (6): 49-51) when testing Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. seed extract antioxidant activity by Oven Method, it has been found that it has very strong suppression Adeps Sus domestica Oxidation.They by Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. seed ethanol extraction with aqueous suspension, respectively with ethyl acetate, n-butanol extraction, it has been found that n-butyl alcohol extract consumption is 4 × l0-4During %, its non-oxidizability has been better than the consumption 2 × l0 of 2,6-di-tert-butyl methyl phenol (BHT)-4%.
Based on the biological medicine activity that it is good, research worker has also carried out the chemical constitution study to this plant.(the Zhou Yan etc. such as Zhou Yan, non-oil fat chemical composition [J] of Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. sarcocarp. research and development of natural products, 2003,15 (1): 13-17) the cis-cyclohexanediol of common compounds 1,2-and catechol are also isolated from the n-butyl alcohol extract of Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. sarcocarp ethanol extract.(the KimSeungHyun etc. such as KimSeungHyun, Idesolide:ANewSpiroCompoundfromIdesiapolycarpa [J] .Org.Lett., 2005,7 (15): 3,275 3277) it is separated to baroque alcohols material from Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. fruit methanolic extract, and to obtaining the spiro-compound of a monomer in the chloroform portion of this methanolic extract, application NMR, MS and single crystal X-ray diffraction are identified and by its called after idesolide.nullIn 2007，(the KimSeungHyun etc. such as KimSeungHyun，InhibitoryactivityofphenolicglycosidesfromthefruitsofIdesiapolycaroaonlipopolysaccharide-inducednitricoxideproductioninBV2microglia[J].PlantaMedica,2007,73 (2): 167-169) it is partially separated from the ethyl acetate of Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. fruit methanolic extract again and obtains 1-hydroxy-6-oxocyclohex-2-enecarboxylicacidmethylester，The latter is probably the former catabolite.
Although it has been found that Radix seu Cortex Malloti nepalensis platymiscium contains important phenolic glycosides, diterpene isoreactivity composition, Idesia polycarpa fruit early has been used for the rural activity such as parasite killing, weeding, but chemical composition is less with biological activity report.
Thus, for prior art defect, it is contemplated that develop the extracting method of antimicrobial component in a kind of Idesia polycarpa, adopt simply, efficiently extracting method extract four compounds, and its structure analyzed and confirmed, respectively β-Amyrin, cupreol, 20 carbonic acid, 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside.Simultaneously, staphylococcus aureus, escherichia coli and Candida albicans are shown higher antibacterial activity by compound β-Amyrin, cupreol, 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside, will have application prospect in fields such as antibacterial, antibacterial, disinfectant, cleaning agent, abluent, preservative.
Summary of the invention
In order to solve drawbacks described above, present inventor has performed and concentrate on studies, after paying a large amount of creative work, thus completing the present invention.
The present invention relates to the extracting method of antimicrobial component in a kind of Idesia polycarpa and purposes, described extracting method is not only simple, convenient, and extraction ratio is higher, staphylococcus aureus, escherichia coli and Candida albicans is shown higher antibacterial activity simultaneously.More specifically, the present invention relates to the extracting method of antimicrobial component and β-Amyrin, cupreol and 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside in a kind of Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. and they application in antibacterial, antibacterial, disinfectant, cleaning agent, abluent, preservative field.
Specifically, first aspect, the invention provides the extracting method of antimicrobial component in a kind of Idesia polycarpa, comprise the following steps:
(1) peel and seed are isolated from dry Idesia polycarpa fruit, after seed is pulverized dry powder, with ethyl acetate for solvent microwave digestion 3-5 time, microwave power is 500-1000W, each 10-20 minute, extraction fluid, concentrated extracting solution obtains ethyl acetate and extracts extractum, and separating obtained filtering residue is again with the ethanol extraction that mass percent concentration is 70% 4 times, each 10 hours, united extraction liquid, is concentrated into without alcohol taste, obtains ethanol extraction extractum；Taking ethanol extraction extractum, through 100-200 order silicagel column, dry method loading, silicagel column successively carries out eluting with dichloromethane, ethyl acetate and methanol, thus being classified as 3 parts, and respectively dichloromethane fractions, ethyl acetate portion and methanol fractions.
(2) step (1) gained ethyl acetate is extracted extractum through solid phase column chromatography, carry out gradient elution with cyclohexane-acetone mixed solvent, respectively obtain compound β-Amyrin and compound cupreol；
(3) ethyl acetate portion that will obtain after ethanol extraction extractum chromatographic column eluting in above-mentioned steps (1), crosses macroporous adsorptive resins, carries out gradient elution with petroleum ether-ethyl acetate mixed solvent, respectively obtain compound 20 carbonic acid CH3(CH2)18COOH and 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside.
Wherein, β-Amyrin, cupreol, 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside structural formula as follows:
In the Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. of the present invention in the extracting method of antimicrobial component, the microwave power in described step (1) is 500-1000W, for instance for 500W, 600W, 700W, 800W, 900W or 1000W, more preferably 600-800W, it is most preferred that for 700W.
In the Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. of the present invention in the extracting method of antimicrobial component, the concrete operations of described step (2) are as follows: step (1) gained ethyl acetate is extracted extractum through solid phase column chromatography, carry out gradient elution with cyclohexane-acetone mixed solvent, gradient elution mixed solvent cyclohexane, acetone volume ratio be followed successively by 30:1,25:1,20:1,15:1,10:1 and 5:1；Collecting both volume ratios is the eluted fraction of 30:1,25:1,20:1, and rotation is evaporated off solvent, dry, obtains compound β-Amyrin；Collecting the eluted fraction that both volume ratios are 15:1,10:1 and 5:1, rotation is evaporated off solvent, dry, obtains compound cupreol.
In the Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. of the present invention in the extracting method of antimicrobial component, the concrete operations of described step (3) are as follows: the ethyl acetate portion that will obtain after ethanol extraction extractum chromatographic column eluting in above-mentioned steps (1), cross macroporous adsorptive resins, gradient elution is carried out with petroleum ether-ethyl acetate mixed solvent, petroleum ether in gradient elution mixed solvent, ethyl acetate volume ratio be followed successively by 25:1,20:1,15:1,10:1 and 5:1, collect the eluted fraction of 25:1 and 20:1, rotation is evaporated off solvent, dries and obtains compound 20 carbonic acid CH3(CH2)18COOH；Collecting the eluted fraction of 15:1,10:1 and 5:1, rotation is evaporated off solvent, dries and obtains 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside.
In the Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. of the present invention in the extracting method of antimicrobial component, the solid phase column in described step (2) is neutral alumina column.
Wherein, the granularity of described neutral alumina is 100-500 order, it is most preferred that for 100-200 order.
In the Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. of the present invention in the extracting method of antimicrobial component, the macroporous adsorbent resin in described step (3) is DM301 resin, AB-8 resin, DA201 resin, D101 resin, X-5 resin or DM130 resin.
Wherein, described macroporous adsorbent resin is preferably AB-8 resin, DM301 resin, DA201 resin or D101 resin, it is most preferred that for D101 resin.
Second aspect, the present invention relates to and make to extract the β-Amyrin, cupreol or 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside that obtain in aforementioned manners.
The third aspect, the present invention relates to the purposes of the reactive compound that said extracted arrives.
The inventors discovered that, extracted compound β-Amyrin of obtaining by the inventive method, staphylococcus aureus, escherichia coli and Candida albicans are shown higher antibacterial activity by cupreol, 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside, thus may be used on the fields such as antibacterial, antibacterial, disinfectant, cleaning agent, abluent, preservative.
Detailed description of the invention
Below by specific embodiment, the present invention is described in detail, but these exemplary embodiments are only used for enumerating, and not the real protection scope of the present invention is constituted any type of any restriction.
Embodiment 1
(1) peel and seed are isolated from dry Idesia polycarpa fruit.Dry powder is obtained after being pulverized by seed, with ethyl acetate microwave digestion 5 times, microwave power is: 700W, each 15 minutes, concentrated extracting solution obtained ethyl acetate and extracts extractum, and separating obtained filtering residue is again with the ethanol extraction that mass percent concentration is 70% 4 times, each 10 hours, united extraction liquid, is concentrated into without alcohol taste, obtains ethanol extraction extractum.Taking ethanol extraction extractum, through the silicagel column that specification is 100-200 order particle size range, dry method loading, silicagel column is successively with dichloromethane, ethyl acetate and methanol elution gradient.Result according to TLC detection, is classified as 3 parts, respectively dichloromethane fractions, ethyl acetate portion and methanol fractions.
(2) step (1) gained ethyl acetate is extracted extractum and carry out column chromatography through 100-200 order neutral alumina, carry out gradient elution with cyclohexane-acetone mixed solvent, gradient elution mixed solvent cyclohexane, acetone volume ratio be followed successively by 30:1,25:1,20:1,15:1,10:1 and 5:1；Collecting both volume ratios is the eluted fraction of 30:1,25:1,20:1, and rotation is evaporated off solvent, dry, obtains compound β-Amyrin；Collecting the eluted fraction that both volume ratios are 15:1,10:1 and 5:1, rotation is evaporated off solvent, dry, obtains compound cupreol.
(3) ethyl acetate portion that will obtain after ethanol extraction extractum chromatographic column eluting in above-mentioned steps (1), cross D101 macroporous adsorptive resins, gradient elution is carried out with petroleum ether-ethyl acetate mixed solvent, petroleum ether in gradient elution mixed solvent, ethyl acetate volume ratio be followed successively by 25:1,20:1,15:1,10:1 and 5:1, collect the eluted fraction of 25:1 and 20:1, rotation is evaporated off solvent, dries and obtains compound 20 carbonic acid CH3(CH2)18COOH；Collecting the eluted fraction of 15:1,10:1 and 5:1, rotation is evaporated off solvent, dries and obtains 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside.
Embodiment 2-6
Except embodiment 1 step (1) middle extraction microwave power is replaced with 500W, 600W, 800W, 900W, 1000W respectively, implement embodiment 2-6 with the same way with embodiment 1 respectively.
Embodiment 7-9
Except except D101 macroporous adsorbent resin replaces with AB-8 resin, DM301 resin, DA201 resin respectively in embodiment 1 step (3), embodiment 7-9 being implemented with the same way with embodiment 1.
The sign data of four compounds that above-described embodiment 1-9 obtains are as follows respectively:
β-Amyrin
M.p.:183-185 DEG C.
IR(KBr)cm-1: 2919,2872,1463,1034.
EI-MSm/z:426 [M]+。
1H-NMR(CDCl3, 500MHz) δ: 0.78 (3H, s), 0.82 (3H, s), 0.86 (6H, s), 0.93 (3H, s), 0.95 (3H, s), 1.04 (3H, s), 1.11 (3H, s), 5.18 (1H, t, J=3.4Hz, H-12), 3.22 (1H, dd, J=4.4,11.2Hz, H-3 α), wherein 0.78 (3H, s), 0.81 (3H, s), 0.86 (6H, s), 0.92 (3H, s), 0.95 (3H, s), 1.01 (3H, s), 1.10 (3H, s) it is that 8 angular methyls are unimodal, for pentacyclic triterpenoid；
13C-NMR(CDCl3) δ: 38.6,27.5,79.1,39.6,55.1,18.2,32.5,38.6,47.3,37.1,23.3,21.6,145.1,39.8,26.1,27.0,32.3,47.3,46.6,31.1,34.6,37.1,28.1,15.4,15.4,16.6,26.1,38.2,33.1,23.5.
Cupreol
M.p.:135-138 DEG C.
IR spectrum shows-OH (3433cm-1) ,-C=C-group (1630cm-1, weak).
EI-MSm/z:414 [M]+。
1H-NMR(CDCl3) δ: 5.35 (1H, d, J=5.2Hz), 3.50 (1H, m), 1.01 (3H, s), 0.92 (3H, d, J=6.8Hz), 0.91 (3H, d, J=6.7Hz), 0.84 (3H, t, J=7.3Hz), 0.82 (3H, d, J=7.2Hz), 0.66 (3H, s).
13C-NMR(CDCl3): 37.1,31.5,71.6,42.1,140.5,121.5,31.8,32.0,50.1,36.4,21.0,39.6,42.1,56.6,24.2,28.0,56.0,11.6,19.2,36.0,18.6,34.0,26.0,45.7,29.0,19.6,19.2,23.0,11.9.
20 carbonic acid
M.p.:47-48 DEG C.
IR:-C=O (1707cm-1), long-chain CH2(2920、2851、1466、730cm-1),
EI-MSm/z:312.2 [m]+、284.2、256.2、185.1、171.1、129.0、111.0、97.0、83.0。
1H-NMR(CDCl3) δ: 0.75ppm (3H, CH3), there are 17 CH in 1-2ppm2, in 2-3ppm, have 1 each and every one CH2。
6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside
M.p.:152-153 DEG C.
IR: glycosyl (3422cm-1The peak that place is wide and blunt) ,-C=C-(1636cm-1) ,-C=O (1740cm-1)、-C-O-C-(1077cm-1、1046cm-1)、CH2(2825cm-1、1474cm-1)。
EI-MSm/z:301.4,162.0,139.9,123.0,121.9.
1H-NMR(CD3OD) δ: 7.06 (1H, t, J=7.7Hz), 6.86 (1H, d, J=7.6Hz), 6.81 (1H, dd, J=7.7Hz), 6.11 (1H, m), 5.78 (1H, dd), 5.53 (1H, d, J=12.2Hz), 5.31 (1H, d, J=12.5Hz), 4.60 (1H, d, J=5.8Hz), 3.84 (1H, m), 3.76 (1H, m), 3.52 (3H, m), 3.42 (1H, m), 2.90 (1H, m), 2.63 (1H, m), 2.52 (2H, m).
13C-NMR(CD3OD): 144.5,131.4,120.9,126.9,118.1,151.3,65.1,107.4,75.2,77.9,80,78.4,62.4,79.3,129.6,132.8,27.2,36.9,207.6,171.8.
Comparative example 1
Except " microwave digestion 5 times; microwave power is: 700W; each 15 minutes " in embodiment 1 being replaced with " extracting 5 times at 40 DEG C with ethyl acetate for solvent; 2h every time " outward, implement this comparative example 1 with the same way with embodiment 1, obtain compound β-Amyrin, cupreol, 20 carbonic acid and 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside.
Comparative example 2-3
Except the mixed solvent cyclohexane-acetone in embodiment 1 step (2) is replaced with cyclohexane-ethyl acetate, hexamethylene-petroleum ether respectively, this comparative example 2-3 is implemented with the same way with embodiment 1, find through TLC detection, in step (2), β-Amyrin and cupreol are difficult to separately, cause that its productivity is very low.
This proves that the separating effect for product has significant impact when the acetone changed in mixed solvent.
Comparative example 4-5
Except the macroporous adsorbent resin in embodiment 1 step (3) is replaced with respectively " silica gel column chromatography that granularity is 300-400 order " and the neutral aluminum oxide column chromatography of 100-200 order " granularity be ", implement this comparative example 4-5 with the same way with embodiment 1, and obtain compound 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside.
The weight of each compound extracted in all embodiments and the comparative example gross weight divided by former Saurauia tristyla DC. var. oldhamii (Hemsl.) Finet & Gagncp. seed is drawn extraction ratio, and the extraction ratio of compound β-Amyrin, cupreol, 20 carbonic acid and 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside is as shown in table 1.
Table 1
As can be seen from the above table:
1., when carrying out microwave extracting, extraction ratio to be significantly higher than extraction ratio when not carrying out microwave extracting, and have best extraction effect when microwave power is 700W.
2., when using in step (3) specific macroporous adsorbent resin to be easily separated, extraction ratio will far above silica gel column chromatography and neutral aluminum oxide column chromatography, but the extraction effect of D101 resin is better than other resin.
3. when step (2) changes the component of eluting mixed solvent, it is possible to interfere significantly on the separation of β-Amyrin and cupreol, it is seen that the type selecting of the mixed solvent in this step is very crucial and important.
Performance test and stability test
The bactericidal property of compound β-Amyrin, cupreol and 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D-glucoside that the present invention that each embodiment obtains by following measuring extracts.
Take reference culture: staphylococcus aureus (ATCC25923), escherichia coli (441490) bacterial strain a little, are inoculated in nutrient broth medium respectively, cultivate 18h for 37 DEG C.Take the 18h each bacterial strain nutrient broth culture cultivated, make 10 with nutrient broth-3Dilution is used for testing.Extracting waste candidiasis bacterial strain is a little, is inoculated in improvement Martin's culture medium, cultivates 24h for 35 DEG C.Take the 24h Candida albicans culture cultivated, by improvement Martin's culture medium 10-3Dilution is used for testing.Sample is prepared with doubling dilution (test tube method), namely test-compound is made into initial concentration respectively is 10mg/ml, taking 0.1ml, to add 5.9ml nutrient broth dilute filtration standby, takes sterilizing test tubes 8 for each test-compound, and the 1st pipe adds by reagent diluent 1ml, 2-8 pipe respectively adds 1ml nutrient broth, take respectively and added in the 2nd pipe by reagent diluent 1ml, take 1ml to the 3rd pipe after mixing, dilute successively, 7th pipe sucking-off 1ml discards, and the 8th pipe is not added with medicinal liquid as comparison.Often pipe adds dilution bacterium solution 0.1ml, cultivates 24h for 37 DEG C.Take out and observe bacterial growth situation.As drug liquid tube is muddy, namely represent bacterial growth, for reagent thing without bacteriostasis；As drug liquid tube is limpid, represent that bacterial growth is suppressed, the medicinal liquid of the greatest dilution of its energy bacteria growing inhibiting, it is the minimal inhibitory concentration (MIC) of this medicine.Take ciprofloxacin hydrocloride tablets (Guangzhou white clouds pharmaceutical Co. Ltd, specification: 0.25g/ sheet, be made into 0.05g/m1 solution), Nysfungin (Zhejiang Zhenyuan Pharmaceutical Co., Ltd, specification: 500mg/ sheet, is made into 200mg/ml solution), as stated above, dilute successively, cultivating, make positive control, result is shown in table 2 below.
Table 2
As can be seen from the above table, the present invention extracts compound β-Amyrin, cupreol and 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D-glucoside have good bactericidal activity and can be used for the fields such as antibacterial, antibacterial, disinfectant, cleaning agent, abluent, preservative.
Should be appreciated that the application of these embodiments is merely to illustrate the present invention and is not intended to limit the scope of the invention.In addition; it is also contemplated that; after the technology contents having read the present invention, the present invention can be made various change, amendment and/or modification by those skilled in the art, and all these equivalent form of value falls within the application appended claims protection defined equally.
Claims (10)
1. an extracting method for antimicrobial component in Idesia polycarpa, comprises the following steps:
(1) peel and seed are isolated from dry Idesia polycarpa fruit, after seed is pulverized dry powder, with ethyl acetate for solvent microwave digestion 3-5 time, microwave power is 500-1000W, each 10-20 minute, extraction fluid, concentrated extracting solution obtains ethyl acetate and extracts extractum, and separating obtained filtering residue is again with the ethanol extraction that mass percent concentration is 70% 4 times, each 10 hours, united extraction liquid, is concentrated into without alcohol taste, obtains ethanol extraction extractum；Taking ethanol extraction extractum, through 100-200 order silicagel column, dry method loading, silicagel column successively carries out eluting with dichloromethane, ethyl acetate and methanol, thus being classified as 3 parts, and respectively dichloromethane fractions, ethyl acetate portion and methanol fractions；
(2) step (1) gained ethyl acetate is extracted extractum through solid phase column chromatography, carry out gradient elution with cyclohexane-acetone mixed solvent, respectively obtain compound β-Amyrin and compound cupreol；
(3) ethyl acetate portion that will obtain after ethanol extraction extractum chromatographic column eluting in above-mentioned steps (1), crosses macroporous adsorptive resins, carries out gradient elution with petroleum ether-ethyl acetate mixed solvent, respectively obtain compound 20 carbonic acid CH3(CH2)18COOH and 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside.
2. the method for claim 1, it is characterised in that: the microwave power in described step (1) is 500-1000W, it is most preferred that for 700W.
3. method as claimed in claim 1 or 2, it is characterized in that: the concrete operations of described step (2) are as follows: step (1) gained ethyl acetate is extracted extractum through solid phase column chromatography, carry out gradient elution with cyclohexane-acetone mixed solvent, gradient elution mixed solvent cyclohexane, acetone volume ratio be followed successively by 30:1,25:1,20:1,15:1,10:1 and 5:1；Collecting both volume ratios is the eluted fraction of 30:1,25:1,20:1, and rotation is evaporated off solvent, dry, obtains compound β-Amyrin；Collecting the eluted fraction that both volume ratios are 15:1,10:1 and 5:1, rotation is evaporated off solvent, dry, obtains compound cupreol.
4. the method as described in any one of claim 1-3, it is characterized in that: the concrete operations of described step (3) are as follows: the ethyl acetate portion that will obtain after ethanol extraction extractum chromatographic column eluting in above-mentioned steps (1), cross macroporous adsorptive resins, gradient elution is carried out with petroleum ether-ethyl acetate mixed solvent, petroleum ether in gradient elution mixed solvent, ethyl acetate volume ratio be followed successively by 25:1,20:1,15:1,10:1 and 5:1, collect the eluted fraction of 25:1 and 20:1, rotation is evaporated off solvent, dries and obtains compound 20 carbonic acid CH3(CH2)18COOH；Collecting the eluted fraction of 15:1,10:1 and 5:1, rotation is evaporated off solvent, dries and obtains 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside.
5. the method as described in any one of claim 1-4, it is characterised in that: the solid phase column in described step (2) is neutral alumina column.
6. method as claimed in claim 5, it is characterised in that: the granularity of described neutral alumina is 100-500 order, it is most preferred that for 100-200 order.
7. the method as described in any one of claim 1-6, it is characterised in that: the macroporous adsorbent resin in described step (3) is DM301 resin, AB-8 resin, DA201 resin, D101 resin, X-5 resin or DM130 resin.
8. method as claimed in claim 7, it is characterised in that: described macroporous adsorbent resin is preferably AB-8 resin, DM301 resin, DA201 resin or D101 resin, it is most preferred that for D101 resin.
9. the method as described in any one of claim 1-8 extracts the β-Amyrin, cupreol or 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside that obtain.
10. the method as described in any one of claim 1-8 extracts the β-Amyrin, cupreol or 6-hydroxyl-2-[[[(1-hydroxyl-6-oxo-2-cyclohexenyl group) carbonyl] oxygen] methyl] phenyl-β-D glucoside purposes in antibacterial, antibacterial, disinfectant, cleaning agent, abluent, preservative that obtain.
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| CN107556348B (en) * | 2017-09-30 | 2019-05-10 | 四川大学 | Acryloyl acid esters compound and preparation method thereof |
| CN111636243A (en) * | 2020-05-23 | 2020-09-08 | 湖北嘉韵化工科技有限公司 | Preparation method of surface sizing agent for papermaking |
| CN115836646A (en) * | 2022-11-28 | 2023-03-24 | 贵州省林业学校(贵州省林业干部学校) | Tissue culture method of idesia polycarpa |
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