CN113940952A - 人参发酵提取物及其制备方法 - Google Patents
人参发酵提取物及其制备方法 Download PDFInfo
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- CN113940952A CN113940952A CN202111411201.7A CN202111411201A CN113940952A CN 113940952 A CN113940952 A CN 113940952A CN 202111411201 A CN202111411201 A CN 202111411201A CN 113940952 A CN113940952 A CN 113940952A
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- CN
- China
- Prior art keywords
- beta
- ginseng
- ginsenoside
- dammar
- fermented
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 235000008434 ginseng Nutrition 0.000 title claims abstract description 80
- 241000208340 Araliaceae Species 0.000 title claims abstract description 72
- 235000003140 Panax quinquefolius Nutrition 0.000 title claims abstract description 71
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 title claims abstract description 70
- 239000000284 extract Substances 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000000605 extraction Methods 0.000 title claims description 7
- 238000000855 fermentation Methods 0.000 claims abstract description 36
- 230000004151 fermentation Effects 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 241000479753 Aspergillus niger ATCC 1015 Species 0.000 claims abstract description 15
- 241000228245 Aspergillus niger Species 0.000 claims abstract description 12
- 235000002789 Panax ginseng Nutrition 0.000 claims abstract description 11
- 240000004371 Panax ginseng Species 0.000 claims abstract description 10
- RAQNTCRNSXYLAH-RFCGZQMISA-N (20S)-ginsenoside Rh1 Chemical compound O([C@@H]1[C@H]2C(C)(C)[C@@H](O)CC[C@]2(C)[C@H]2C[C@@H](O)[C@H]3[C@@]([C@@]2(C1)C)(C)CC[C@@H]3[C@@](C)(O)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RAQNTCRNSXYLAH-RFCGZQMISA-N 0.000 claims abstract description 9
- RAQNTCRNSXYLAH-UHFFFAOYSA-N Ginsenoside Rh1 Natural products CC(C)=CCCC(C)(O)C1CCC(C2(C3)C)(C)C1C(O)CC2C1(C)CCC(O)C(C)(C)C1C3OC1OC(CO)C(O)C(O)C1O RAQNTCRNSXYLAH-UHFFFAOYSA-N 0.000 claims abstract description 9
- YNBYFOIDLBTOMW-QHNUHGIDSA-N ginsenoside C-Y Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O YNBYFOIDLBTOMW-QHNUHGIDSA-N 0.000 claims abstract description 9
- 241000511582 Actinomyces meyeri Species 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 235000020710 ginseng extract Nutrition 0.000 claims description 11
- PYXFVCFISTUSOO-HKUCOEKDSA-N (20S)-protopanaxadiol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@H]([C@@](C)(O)CCC=C(C)C)[C@H]4[C@H](O)C[C@@H]3[C@]21C PYXFVCFISTUSOO-HKUCOEKDSA-N 0.000 claims description 10
- PYXFVCFISTUSOO-UHFFFAOYSA-N betulafolienetriol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC(C(C)(O)CCC=C(C)C)C4C(O)CC3C21C PYXFVCFISTUSOO-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 230000000259 anti-tumor effect Effects 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- AGBCLJAHARWNLA-DQUQINEDSA-N Ginsenoside RG2 Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@@H]2[C@H]3C(C)(C)[C@@H](O)CC[C@]3(C)[C@@H]3[C@@]([C@@]4(CC[C@@H]([C@H]4[C@H](O)C3)[C@@](C)(O)CCC=C(C)C)C)(C)C2)O[C@H](CO)[C@@H](O)[C@@H]1O AGBCLJAHARWNLA-DQUQINEDSA-N 0.000 claims description 6
- YURJSTAIMNSZAE-UHFFFAOYSA-N UNPD89172 Natural products C1CC(C2(CC(C3C(C)(C)C(O)CCC3(C)C2CC2O)OC3C(C(O)C(O)C(CO)O3)O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O YURJSTAIMNSZAE-UHFFFAOYSA-N 0.000 claims description 6
- TXEWRVNOAJOINC-UHFFFAOYSA-N ginsenoside Rb2 Natural products CC(=CCCC(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C3CCC4(C)C3C(O)CC5C6(C)CCC(OC7OC(CO)C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C(C)(C)C6CCC45C)C TXEWRVNOAJOINC-UHFFFAOYSA-N 0.000 claims description 6
- -1 (20S Chemical compound 0.000 claims description 5
- FVIZARNDLVOMSU-IRFFNABBSA-N ginsenoside C-K Chemical compound O([C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FVIZARNDLVOMSU-IRFFNABBSA-N 0.000 claims description 5
- SHCBCKBYTHZQGZ-CJPZEJHVSA-N protopanaxatriol Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2[C@@H](O)C[C@@]3(C)[C@]4(C)CC[C@H]([C@@](C)(O)CCC=C(C)C)[C@H]4[C@H](O)C[C@@H]3[C@]21C SHCBCKBYTHZQGZ-CJPZEJHVSA-N 0.000 claims description 5
- BBEUDPAEKGPXDG-UHFFFAOYSA-N protopanaxatriol Natural products CC(CCC=C(C)C)C1CCC2(C)C1C(O)CC3C4(C)CCC(O)C(C)(C)C4C(O)CC23C BBEUDPAEKGPXDG-UHFFFAOYSA-N 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- YURJSTAIMNSZAE-HHNZYBFYSA-N ginsenoside Rg1 Chemical compound O([C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(C[C@@H]([C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3C[C@H]2O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YURJSTAIMNSZAE-HHNZYBFYSA-N 0.000 claims description 4
- AGBCLJAHARWNLA-UHFFFAOYSA-N (20R)-ginsenoside Rg2 Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C3C(C)(C)C(O)CCC3(C)C3C(C4(CCC(C4C(O)C3)C(C)(O)CCC=C(C)C)C)(C)C2)OC(CO)C(O)C1O AGBCLJAHARWNLA-UHFFFAOYSA-N 0.000 claims description 3
- PSOUXXNNRFNUAY-UHFFFAOYSA-N (24S)-Pseudoginsenoside RT4 Natural products O1C(C(C)(O)C)CCC1(C)C1C(C(O)CC2C3(CC(C4C(C)(C)C(O)CCC42C)OC2C(C(O)C(O)C(CO)O2)O)C)C3(C)CC1 PSOUXXNNRFNUAY-UHFFFAOYSA-N 0.000 claims description 3
- WMGBQZAELMGYNO-YMWSGFAJSA-N (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-[[(3s,5r,8r,9r,10r,12r,13r,14r,17s)-12-hydroxy-4,4,8,10,14-pentamethyl-17-(6-methylhepta-1,5-dien-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol Chemical compound O([C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4C(=C)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WMGBQZAELMGYNO-YMWSGFAJSA-N 0.000 claims description 3
- PSOUXXNNRFNUAY-BLSITOCHSA-N (3r,4s,5s,6r)-2-[[(3s,5r,6s,8r,9r,10r,12r,13r,14r,17s)-3,12-dihydroxy-17-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-6-yl]oxy]-6-(hydroxymethyl)oxane- Chemical compound O1[C@@H](C(C)(O)C)CC[C@@]1(C)[C@@H]1[C@@H]([C@H](O)C[C@H]2[C@]3(C[C@@H]([C@H]4C(C)(C)[C@@H](O)CC[C@@]42C)OC2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C)[C@@]3(C)CC1 PSOUXXNNRFNUAY-BLSITOCHSA-N 0.000 claims description 3
- GHWSMQHJFMAATF-DSHMRAQASA-N 20(S)-protopanaxadiol Natural products CC(=CCC[C@@](O)(CO)[C@H]1CC[C@]2(C)[C@@H]1CC[C@H]3[C@@]2(C)CC[C@H]4C(C)(C)[C@@H](O)CC[C@]34CO)C GHWSMQHJFMAATF-DSHMRAQASA-N 0.000 claims description 3
- BGHNZAWRRWLKPO-UHFFFAOYSA-N Ginsenoside F1 Natural products CC(=C)CCCC(C)(OC1OC(CO)C(O)C(O)C1O)C2CCC3(C)C2C(O)CC4C5(C)CCC(O)C(C)(C)C5C(O)CC34C BGHNZAWRRWLKPO-UHFFFAOYSA-N 0.000 claims description 3
- VOUCMBDNXOKLCQ-YATHHJDDSA-N Ginsenoside La Chemical compound O([C@]1(C[C@@H](O[C@H]2C3[C@]([C@H]4[C@@H]([C@]5(CC[C@@H](C(C)(C)C5CC4)O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C)C2)(C)CC[C@@H]31)C=C(C)C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VOUCMBDNXOKLCQ-YATHHJDDSA-N 0.000 claims description 3
- HXXZFHABSSZFHB-UHFFFAOYSA-N Ginsenoside La Natural products C12CCC(C3(CCC4C(C)(C)C(OC5C(C(O)C(O)C(CO)O5)O)CCC4(C)C3C3)C)(C)C2C3OC(C=C(C)C)CC1(C)OC1OC(CO)C(O)C(O)C1O HXXZFHABSSZFHB-UHFFFAOYSA-N 0.000 claims description 3
- UFNDONGOJKNAES-UHFFFAOYSA-N Ginsenoside Rb1 Natural products CC(=CCCC(C)(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C3CCC4(C)C3C(O)CC5C6(C)CCC(OC7OC(CO)C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C(C)(C)C6CC(O)C45C)C UFNDONGOJKNAES-UHFFFAOYSA-N 0.000 claims description 3
- PHLXREOMFNVWOH-YAGNRYSRSA-N Ginsenoside Rh3 Chemical compound O([C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4C(\C)=C/CC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PHLXREOMFNVWOH-YAGNRYSRSA-N 0.000 claims description 3
- PHLXREOMFNVWOH-DNQFHFKUSA-N Ginsenoside Rh3 Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@H]1C(C)(C)[C@H]2[C@@](C)([C@@H]3[C@](C)([C@@]4(C)[C@H]([C@H](O)C3)[C@@H](/C(=C/C/C=C(\C)/C)/C)CC4)CC2)CC1 PHLXREOMFNVWOH-DNQFHFKUSA-N 0.000 claims description 3
- OZTXYFOXQFKYRP-TXRYYSRHSA-N Ginsenoside Rh4 Chemical compound O([C@@H]1[C@H]2C(C)(C)[C@@H](O)CC[C@]2(C)[C@H]2C[C@@H](O)[C@H]3[C@@]([C@@]2(C1)C)(C)CC[C@@H]3C(/C)=C/CC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OZTXYFOXQFKYRP-TXRYYSRHSA-N 0.000 claims description 3
- OZTXYFOXQFKYRP-RISAHGKBSA-N Ginsenoside Rh4 Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@H]1[C@H]2C(C)(C)[C@@H](O)CC[C@]2(C)[C@@H]2[C@](C)([C@@]3(C)[C@H]([C@H](O)C2)[C@@H](/C(=C\C/C=C(\C)/C)/C)CC3)C1 OZTXYFOXQFKYRP-RISAHGKBSA-N 0.000 claims description 3
- UZRSSXUIXNCYLP-UHFFFAOYSA-N Ginsenoside Rk2 Natural products CC(=CCCC(=C)C1CCC2(C)C1C(O)CC3C4(C)CCC(OC5CC(O)C(O)C(CO)O5)C(C)(C)C4CCC23C)C UZRSSXUIXNCYLP-UHFFFAOYSA-N 0.000 claims description 3
- MYBAONSAUGZRAX-UBQYYSLZSA-N Notoginsenoside Fe Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O MYBAONSAUGZRAX-UBQYYSLZSA-N 0.000 claims description 3
- XNGXWSFSJIQMNC-FIYORUNESA-N ginsenoside F1 Chemical compound O([C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(C[C@H](O)[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XNGXWSFSJIQMNC-FIYORUNESA-N 0.000 claims description 3
- GZYPWOGIYAIIPV-JBDTYSNRSA-N ginsenoside Rb1 Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GZYPWOGIYAIIPV-JBDTYSNRSA-N 0.000 claims description 3
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- PWAOOJDMFUQOKB-WCZZMFLVSA-N ginsenoside Re Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@@H]2[C@H]3C(C)(C)[C@@H](O)CC[C@]3(C)[C@@H]3[C@@]([C@@]4(CC[C@@H]([C@H]4[C@H](O)C3)[C@](C)(CCC=C(C)C)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C)(C)C2)O[C@H](CO)[C@@H](O)[C@@H]1O PWAOOJDMFUQOKB-WCZZMFLVSA-N 0.000 claims description 3
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- Medicines Containing Plant Substances (AREA)
Abstract
本发明公开了人参发酵提取物及其制备方法。本发明所提供的人参发酵提取物源自用包含黑曲霉菌株(Aspergillus niger ATCC 1015)的发酵液发酵的人参(Panax ginseng C.A.Meyer);所述人参发酵提取物包含下述化合物中的一种或多种:人参皂苷Rh1、人参皂苷Y、20(S)‑达玛‑3β,6α,12β,20,25‑五醇、20(S)‑达玛‑3β,12β,20,25‑四醇、20(S)‑达玛‑3β,6α,12β,20,24‑五醇。本发明将人参通过黑曲霉菌株(Aspergillusniger ATCC 1015)发酵后,产生了稀有人参皂苷以及一些在人参中首次报道的人参皂苷和三萜皂苷元成分。
Description
技术领域
本发明涉及提取物及其制备方法,特别地涉及人参发酵提取物及其制备方法。
背景技术
五加科(Araliaceae)人参属植物在全世界共有8个种和3个变种。其中,名贵中药材人参(Panax ginseng C.A.Meyer)主要产于中国东北及朝鲜半岛,素有“百草之王”的美誉。在中国、韩国和日本被用作传统名贵中药材已经超过2000多年。人参在东北三省已经广泛栽培。据《神农本草经》记载,人参具有“主补五脏,安精神,定魂魄,止惊悸,除邪气,明目益智,久服轻身延年;其干燥的根和根茎是法定的药用部位,人参味甘、微苦,微温,具有大补元气、复脉固脱、补脾益肺、生津养血、安神益智的功效。现代中医药学研究表明,人参具有抗肿瘤、调节神经中枢神经系统、调节免疫、抗心律失常、抗溶血等多重药理活性作用;人参具有降低血糖、控制肝指数和肝功能、调节荷尔蒙和调节血压等功能,其主要的药用效果是补充能量、增强身体抵抗力、增强免疫反应等功效。目前公认人参皂苷为人参主要有效成分。
迄今为止,从人参根和根茎、茎叶、果实、种子和果及人参的加工产品红参和黑参中分离鉴定了230多个三萜类人参皂苷及其衍生物。人参皂苷是由人参皂苷苷元与糖基通过糖苷键连接而成的糖苷类化合物,尤其以三萜类皂苷为主要成分。按人参皂苷的苷元结构不同,可分为四环三萜类的达玛烷型(dammarane-type,I型)、奥科梯隆(ocotillol-type,II型)和五环三萜的齐墩果酸型(oleanene acid-type,III型)三种类型(如图1)。
达玛烷型根据母核上的C-6位是否有羟基,可分为原人参二醇(protopanaxadioltype,PPD)和原人参三醇型(protopanaxatriol type,PPT),根据PPD和PPT的手性碳C-20又进一步分为20(S)和20(R)型(如图2)。
研究表明,人参皂苷具有诸多的生物活性:Rb1具有保护神经、抗氧化、雌激素样作用,Rb2具有抑制肿瘤转移作用,Rc具有增强免疫力、抗炎作用,Rd具有增强免疫力、抗氧化、保护心血管作用,Rg3具有抗肿瘤、保护神经、保护血管、抗血小板凝聚作用,Rh2、Rs3、C-Mx、DM1、PM1、SM1、25-OH-PPD具有抗肿瘤作用;IH-902、IH-903具有抗遗传毒性作用;人参皂苷CK具有抗肿瘤、抗遗传毒性作用,PPD具有增强免疫力作用;Re具有抑制增殖、保护神经作用,Rg1具有保护神经、诱导细胞凋亡、雌激素样作用,Rh1具有增强免疫力、抑制增殖、雌激素样作用;P-F11具有保护神经作用;Rg5具有改善记忆障碍、抗焦虑、抗血小板凝聚,Rh3具有诱导分化作用。从以上人参皂苷单体成分各自的药理和药学活性可知,人参皂苷作为人参的主要有效成分之一。
从其生物活性可知,人参皂苷的类型、取代基、糖的数量及构型等因素影响其抗肿瘤活性。人参皂苷不同母核类型活性大小为:齐墩果酸型皂苷>原人参二醇型皂苷>原人参三醇型皂苷。随着皂苷中糖基数量增加,人参皂苷抗癌活性降低,原人参二醇型皂苷的活性强度依次为:25-OHPPD>PPD>单糖皂苷>双糖皂苷>三糖皂苷>四糖皂苷。抗肿瘤活性受C-20构型的影响,20(R)构型强于20(S)构型人参皂苷。马成俊通过比较20(S)-Rh2和人参皂苷CK的抗肿瘤活性,发现C-3位和C-6位成糖苷并不影响抗肿瘤活性,侧链环化以后,活性明显降低。
发明内容
有鉴于此,本发明提供了人参发酵提取物及其制备方法。
本发明的一个方面提供了一种人参发酵提取物。
本发明所提供的人参发酵提取物,源自用包含黑曲霉菌株(Aspergillus nigerATCC 1015)的发酵液发酵的人参(Panax ginseng C.A.Meyer);所述人参发酵提取物包含下述化合物中的一种或多种:人参皂苷Rh1、人参皂苷Y、20(S)-达玛-3β,6α,12β,20,25-五醇、20(S)-达玛-3β,12β,20,25-四醇、20(S)-达玛-3β,6α,12β,20,24-五醇。
进一步,所述人参发酵提取物是醇提取物并且经过大孔吸附树脂纯化。
本发明的另一个方面提供了人参发酵提取物的制备方法。
本发明所提供的人参发酵提取物的制备方法,包括如下步骤:
(1)发酵:将包含黑曲霉菌株(Aspergillus niger ATCC 1015)的发酵液接种到人参上,进行发酵培养,得到人参发酵物;
(2)提取:将步骤(1)得到的人参发酵物用醇提取,即得到所述人参发酵提取物。
进一步,在所述发酵前,还包括使用发酵培养基对所述黑曲霉菌株(Aspergillusniger ATCC 1015)进行发酵培养的步骤。
进一步,在所述发酵前,还包括对人参进行灭菌和/或粉碎的步骤。
进一步,在所述提取后,还包括使用大孔吸附树脂对所述人参发酵提取物进行纯化的步骤。
优选地,将步骤(2)得到的人参发酵提取物经过浓缩后,使用非极性大孔吸附树脂层析柱和体积百分比浓度为80%的乙醇作为洗脱剂进行纯化,将乙醇洗脱液浓缩干燥后,即得纯化的人参发酵提取物。
所述方法制备得到的人参发酵提取物也属于本发明的保护范围。
本发明还提供了一种纯化的人参发酵提取物。
本发明所提供的纯化的人参发酵提取物,包含下述32种化合物:20(S)-原人参三醇、20(S)-原人参二醇、20(R)-达玛-24-烯-6α,12β,20,25-四羟基-3-酮、人参皂苷CK、20(S)-异人参皂苷-Rh3、人参皂苷Rh1、人参皂苷F1、人参皂苷Rg1、人参皂苷Y、人参皂苷Rd、人参皂苷la、人参皂苷Rg2、三七皂苷Fe、人参皂苷Re、人参皂苷Rb2、人参皂苷Rb1、20(R)-达玛-6α,12β,20,25-四羟基-3-酮、20(S)-达玛-3β,6α,12β,20,25-五醇、20(S)-达玛-3β,12β,20,25-四醇、20(R)-达玛-3β,6α,12β,20,25-五醇、20(S)-达玛-3β,12β,20,25-四醇-6-O-β-D-吡喃葡萄糖苷、20(S)-达玛-3β,12β,20,25-四醇-6-O-α-L-吡喃鼠李糖基-(1→2)-O-β-D-吡喃葡萄糖苷、20(S)-达玛-3β,12β,20,25-三醇-3-O-β-D-吡喃葡萄糖基-(1→2)-O-β-D-吡喃葡萄糖苷、20(S)-达玛-25(26)-烯-3β,6α,12β,20,24-五醇、20(S)-达玛-3β,6α,12β,20,24-五醇、20(R)-达玛-24(25)-环氧-3β,6α,12β,20-四醇、人参皂苷Rh4、人参皂苷Rk2、(20S,23E)-达玛-23-烯-3β,6α,12β,20,25-五醇、人参皂苷Rh3、拟人参皂苷RT5、27-去甲基-(E,E)-20(22),23-二烯-3β,6α,12β-三羟基-达玛-25-酮。
所述人参发酵提取物、所述人参发酵提取物或所述纯化的人参发酵提取物在制备抗肿瘤活性的产品中的应用也属于本发明的保护范围。
本发明将人参通过黑曲霉菌株(Aspergillus niger ATCC 1015)发酵后,产生了稀有人参皂苷以及一些在人参中首次报道的人参皂苷和三萜皂苷元成分,具体为:人参皂苷Rh1、人参皂苷Y、20(S)-达玛-3β,6α,12β,20,25-五醇、20(S)-达玛-3β,12β,20,25-四醇、20(S)-达玛-3β,6α,12β,20,24-五醇。
附图说明
为了说明而非限制的目的,现在将根据本发明的优选实施例、特别是参考附图来描述本发明,其中:
图1为达玛烷型、奥科梯隆型和齐墩果酸型人参皂苷元的结构。
图2为达玛烷型人参皂苷元的结构。
图3为化合物9(人参皂苷Rh1)和化合物12(人参皂苷Y)的结构。
图4为化合物21(20(S)-达玛-3β,6α,12β,20,25-五醇)和22(20(S)-达玛-3β,12β,20,25-四醇)的结构。
图5为化合物28(20(S)-达玛-3β,6α,12β,20,24-五醇)的结构。
具体实施方式
实施例1、制备人参发酵提取物
1、人参的发酵:
(1)配制PD液体发酵培养基:每升PD液体发酵培养基中马铃薯为200克,葡萄糖20克。
(2)将配制好的PD液体发酵培养基灭菌后冷却至室温,移至超净工作台中进行操作,取培养好的黑曲霉菌株(Aspergillus niger ATCC 1015)(购自中国科学院微生物研究所),用无菌接种环轻刮长满菌丝体的培养基表面,将黑曲霉均匀分散地接种到液体发酵培养基中静置放在30℃的恒温培养箱中培养24h,得到黑曲霉培养液。
(3)粉碎人参:将购买自万良人参交易市场的人参(Panax ginseng C.A.Meyer)粉碎成60目,在115℃灭菌30分钟。
(4)发酵人参:按照1:100的比例(人参质量:发酵液体积)取黑曲霉培养液,转接到粉碎的灭菌的人参上,摇匀后在30℃的恒温培养箱中培养28天,然后烘干,得到烘干的发酵物。
2、提取:
取烘干的发酵物20公斤,用50升75%乙醇(V/V)室温浸泡一个星期,过滤提取三次,真空浓缩后至无乙醇味道的溶液,倒入15升的大孔吸附树脂D101层析柱中,水洗后再用50升80%乙醇(V/V)慢慢洗脱,乙醇洗脱液真空浓缩干燥后得约400g总皂苷。
3、分离纯化
发酵的人参总皂苷400g拌样后经硅胶柱层析,用二氯甲烷:甲醇进行梯度洗脱分为七个部分(Fr1~Fr7)。各个部分再经过反复硅胶柱层析和RP-C18柱层析分离纯化得到34个化合物。
Fr1经过硅胶柱层析以二氯甲烷:甲醇系统(55:1~20:1)洗脱得到二部分。这二部分再经过硅胶柱层析以二氯甲烷:甲醇系统(200:1)洗脱,以及再经过反相制备液相C-18柱以50%~80%甲醇水溶液(V/V)梯度洗脱得到纯化得到化合物1(3.5g)、2(0.3g)和3(0.075g)。
Fr2经硅胶柱层析以二氯甲烷26:甲醇系统(100:1~20:1)梯度洗脱得到三部分。各部分再经过反相制备液相C-18柱以30%~75%甲醇水溶液梯度洗脱,以及硅胶柱层析以二氯甲烷:甲醇系统(70:1~40:3)梯度洗脱得到化合物32(0.04g)、29(0.008g)、24(0.04g)、25(0.215g)、17(0.015g)、33(0.105g)、26(0.090g)、34(0.065g)和4(0.105g)。
Fr3经硅胶柱层析以二氯甲烷:甲醇系统(100:1~10:1)梯度洗脱得到二部分。各部分再经硅胶柱层析以二氯甲烷:甲醇系统(50:1~10:1)梯度洗脱得到以及经反相制备液相C-18柱分别以30%~85%甲醇水溶液梯度洗脱分别纯化得到化合物21(0.108g)、22(0.096g)、27(0.108g)、28(0.017g)、20(0.22g)、31(0.037g)、5(0.05g)、9(0.57g)、30(0.126g)、7(0.072g)和18(0.028g)。
Fr4经反相制备液相C-18柱以35%~75%甲醇水溶液梯度洗脱得到二部分。这二部分再经硅胶柱层析以二氯甲烷:甲醇系统(15:1~8:1),以及经反相制备液相C-18柱以35%~70%甲醇水溶液等梯度反复洗脱,纯化得到8(0.112g)、12(0.03g)和10(0.52g)。
Fr5经反相制备液相C-18柱分别以25%~55%甲醇水溶液等梯度洗脱分别得到三部分。各部分再经过硅胶柱层析以二氯甲烷:甲醇系统(25:1~10:1)等梯度洗脱纯化得到化合物19(0.22g)、11(0.09g)和23(0.341g)。
Fr6经反相制备液相C-18柱以20%~70%甲醇水溶液梯度洗脱得到三部分。各部分经硅胶柱层析以二氯甲烷:甲醇系统(10:1~10:1.5)等梯度洗脱纯化得到化合物6(0.4g)和13(0.148g)。
Fr7经过硅胶柱层析以二氯甲烷:甲醇系统(10:1~6:1)梯度洗脱得到二部分。各部分再经反相制备液相C-18柱以30%甲醇水溶液等梯度洗脱和硅胶柱层析以二氯甲烷:甲醇系统(7:1~6:1)梯度反复洗脱,纯化得到化合物14(3.6g)、15(0.55g)和16(0.126g)。
通过采用反复不同的柱层析方法从发酵的人参中分离得到34个化合物,采用1D和2D NMR和MS波谱方法鉴定了其中的32个化合物,分别鉴定为20(S)-原人参三醇(1)、20(S)-原人参二醇(2)、20(R)-达玛-24-烯-6α,12β,20,25-四羟基-3-酮(3)、人参皂苷CK(4)、20(S)-异人参皂苷-Rh3(5)、人参皂苷Rg2(6)、人参皂苷F1(7)、人参皂苷Rg1(8)、人参皂苷Rh1(9)、人参皂苷Rd(10)、人参皂苷la(11)、人参皂苷Y(12)、三七皂苷Fe(13)、人参皂苷Re(14)、人参皂苷Rb2(15)、人参皂苷Rb1(16)、20(R)-达玛-6α,12β,20,25-四羟基-3-酮(17)、20(S)-达玛-3β,12β,20,25-四醇-6-O-β-D-吡喃葡萄糖苷(18)、20(S)-达玛-3β,12β,20,25-四醇-6-O-α-L-吡喃鼠李糖基-(1→2)-O-β-D-吡喃葡萄糖苷(19)、20(R)-达玛-3β,6α,12β,20,25-五醇(20)、20(S)-达玛-3β,6α,12β,20,25-五醇(21)、20(S)-达玛-3β,12β,20,25-四醇(22)、20(S)-达玛-3β,12β,20,25-三醇-3-O-β-D-吡喃葡萄糖基-(1→2)-O-β-D-吡喃葡萄糖苷(23)、20(S)-达玛-25(26)-烯-3β,6α,12β,20,24-五醇(24)、人参皂苷Rk2(25)、20(R)-达玛-24(25)-环氧-3β,6α,12β,20-四醇(26)、人参皂苷Rh4(27)、20(S)-达玛-3β,6α,12β,20,24-五醇(28)、(20S,23E)-达玛-23-烯-3β,6α,12β,20,25-五醇(29)、人参皂苷Rh3(30)、拟人参皂苷RT5(31)、27-去甲基-(E,E)-20(22),23-二烯-3β,6α,12β-三羟基-达玛-25-酮(32)。化合物9、12、21、22和28首次从人参中分离得到。
化合物9:人参皂苷Rh1(图3),存在于竹节参中,本发明首次从人参的黑曲霉菌株(Aspergillus niger ATCC 1015)发酵提取物中鉴定到了化合物9。
化合物12:人参皂苷Y(图3),存在于西洋参的黑曲霉发酵物中,本发明首次从人参的黑曲霉菌株(Aspergillus niger ATCC 1015)发酵提取物中鉴定到了化合物12。
化合物21:20(S)-达玛-3β,6α,12β,20,25-五醇(图4),是酶水解人参茎叶发现的新化合物,本发明首次从人参的黑曲霉菌株(Aspergillus niger ATCC 1015)发酵提取物中鉴定到了化合物12。
化合物22:20(S)-达玛-3β,12β,20,25-四醇(图4),发现来自三七茎叶酸水解产物,本发明首次从人参的黑曲霉菌株(Aspergillus niger ATCC 1015)发酵提取物中鉴定到了化合物22。
化合物28:20(S)-达玛-3β,6α,12β,20,24-五醇(图5),存在于越南人参中,本发明首次从人参的黑曲霉菌株(Aspergillus niger ATCC 1015)发酵提取物中鉴定到了化合物28。
上述具体实施方式,并不构成对本发明保护范围的限制。本领域技术人员应该明白的是,取决于设计要求和其他因素,可以发生各种各样的修改、组合、子组合和替代。任何在本发明的精神和原则之内所作的修改、等同替换和改进等,均应包含在本发明保护范围之内。
Claims (10)
1.人参发酵提取物,其特征在于:所述人参发酵提取物源自用包含黑曲霉菌株(Aspergillus niger ATCC 1015)的发酵液发酵的人参(Panax ginseng C.A.Meyer);所述人参发酵提取物包含下述化合物中的一种或多种:人参皂苷Rh1、人参皂苷Y、20(S)-达玛-3β,6α,12β,20,25-五醇、20(S)-达玛-3β,12β,20,25-四醇、20(S)-达玛-3β,6α,12β,20,24-五醇。
2.根据权利要求1所述的人参发酵提取物,其特征在于:所述人参发酵提取物是醇提取物并且经过大孔吸附树脂纯化。
3.人参发酵提取物的制备方法,包括如下步骤:
(1)发酵:将包含黑曲霉菌株(Aspergillus niger ATCC 1015)的发酵液接种到人参上,进行发酵培养,得到人参发酵物;
(2)提取:将步骤(1)得到的人参发酵物用醇提取,即得到所述人参发酵提取物。
4.根据权利要求3所述的人参发酵提取物的制备方法,其特征在于:在所述发酵前,还包括使用发酵培养基对所述黑曲霉菌株(Aspergillus niger ATCC1015)进行发酵培养的步骤。
5.根据权利要求3或4所述的人参发酵提取物的制备方法,其特征在于:在所述发酵前,还包括对人参进行灭菌和/或粉碎的步骤。
6.根据权利要求3或4所述的人参发酵提取物的制备方法,其特征在于:在所述提取后,还包括使用大孔吸附树脂对所述人参发酵提取物进行纯化的步骤。
7.根据权利要求6所述的人参发酵提取物的制备方法,其特征在于:将步骤(2)得到的人参发酵提取物经过浓缩后,使用非极性大孔吸附树脂层析柱和体积百分比浓度80%的乙醇作为洗脱剂进行纯化,将乙醇洗脱液浓缩干燥后,即得纯化的人参发酵提取物。
8.由权利要求3~7中任一所述的方法制备得到的人参发酵提取物。
9.纯化的人参发酵提取物,包含下述32种化合物:20(S)-原人参三醇、20(S)-原人参二醇、20(R)-达玛-24-烯-6α,12β,20,25-四羟基-3-酮、人参皂苷CK、20(S)-异人参皂苷-Rh3、人参皂苷Rh1、人参皂苷F1、人参皂苷Rg1、人参皂苷Y、人参皂苷Rd、人参皂苷la、人参皂苷Rg2、三七皂苷Fe、人参皂苷Re、人参皂苷Rb2、人参皂苷Rb1、20(R)-达玛-6α,12β,20,25-四羟基-3-酮、20(S)-达玛-3β,6α,12β,20,25-五醇、20(S)-达玛-3β,12β,20,25-四醇、20(R)-达玛-3β,6α,12β,20,25-五醇、20(S)-达玛-3β,12β,20,25-四醇-6-O-β-D-吡喃葡萄糖苷、20(S)-达玛-3β,12β,20,25-四醇-6-O-α-L-吡喃鼠李糖基-(1→2)-O-β-D-吡喃葡萄糖苷、20(S)-达玛-3β,12β,20,25-三醇-3-O-β-D-吡喃葡萄糖基-(1→2)-O-β-D-吡喃葡萄糖苷、20(S)-达玛-25(26)-烯-3β,6α,12β,20,24-五醇、20(S)-达玛-3β,6α,12β,20,24-五醇、20(R)-达玛-24(25)-环氧-3β,6α,12β,20-四醇、人参皂苷Rh4、人参皂苷Rk2、(20S,23E)-达玛-23-烯-3β,6α,12β,20,25-五醇、人参皂苷Rh3、拟人参皂苷RT5、27-去甲基-(E,E)-20(22),23-二烯-3β,6α,12β-三羟基-达玛-25-酮。
10.权利要求1所述的人参发酵提取物、权利要求8所述的人参发酵提取物或权利要求9所述的纯化的人参发酵提取物在制备抗肿瘤活性的产品中的应用。
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