沙蜇Stomopholus meleagris有机小分子化合物的提取、分离纯化和结构鉴定
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摘要
沙蜇(Stomopholus meleagris)是一种大型可食性水母,广泛分布于我国的黄、渤海至东海。在我国,沙蜇已有一千多年的利用历史,传统医学典籍和现代科学研究都已证明沙蜇具有良好的营养价值和药用价值。但是,沙蜇在温度较高的夏秋季节收获,产量大,含水量高,极易自溶腐败。目前沙蜇的利用方式比较单一,主要是传统的“三矾两盐”腌渍加工,产品出成率很低,大量有益的活性成分在腌渍的过程中流失,资源利用率较低。如何有效地综合利用沙蜇资源,已越来越引起人们的关注。而沙蜇的有效加工与利用必须建立在对其功能成分的充分认识基础之上。目前,已有学者研究了包括沙蜇在内大型食用水母的化学成分及生物活性,主要涉及水母毒素、胶原蛋白、活性肽、多糖和糖蛋白等大分子物质,而对其中结构和活性多样的有机小分子类活性物质却鲜有涉及。
本研究首次聚焦沙蜇中的有机小分子化学物质,对其进行系统深入的提取、分离、纯化和结构鉴定。应用有机溶剂浸提、分级萃取、正相硅胶柱层析、RP18反相硅胶柱层析、凝胶过滤柱层析、制备薄层层析等分离技术,结合TLC、1H NMR、~(13)C NMR、DEPT、HMQC、HMBC、~1H-~1H COSY、NOESY、ESI MS、GC-MS、化学衍生和文献对照等分析手段,分离得到32个单体化合物,鉴定出其中的22个化合物;利用GC-MS在分离纯化过程中分析出43个化合物,共鉴定得到65个化合物。在65个化合物中,有1个新化合物,3个新天然产物,64个化合物为首次从沙蜇中鉴定得到。NMR解析鉴定的化合物:
胆甾-8-甲氧基-22-双键-3,6-二醇(1),胆甾-5-甲氧基-3,6-二醇(2),胆甾醇(3),麦角甾醇(4),邻苯二甲酸二丁酯(5),胆甾-5-双键-3-羟基-7酮(6),二十碳烷醇甘油醚(7),1-O-二十七碳酸甘油酯(8),十六碳烷醇甘油醚(9),二十五碳烷醇甘油醚(10),胆甾-5-双键-3β,7β-二醇(11),胆甾-5-双键-3β,7α-二醇(12),胆甾-6-甲氧基-3,5-二醇(13),1α-丁氧基,2-脱氧核糖(14),胸腺嘧啶(15),2’-甲氧基尿嘧啶核苷(16),尿嘧啶(17),2’-脱氧胸腺嘧啶核苷(18),2’-脱氧尿嘧啶核苷(19),尿嘧啶核苷(20),甘油(21),苯丙氨酸(22)。GC-MS鉴定的化合物:
胆甾-4-双键-3-酮(23),24-缺-22,23-亚甲基-胆甾-5-双键-3-醇(24),胆甾烷醇(25),豆甾醇(26),谷甾醇(27),豆甾-5,24(28)-二双键-3-醇(28),麦角甾-5,24-二双键-3-醇(29),麦角甾-5-双键-3-醇(30),麦角甾-5,22-二双键-3-醇(31),26,27-去甲基-麦角甾-5,22-二双键-3-醇(32),27-去甲基-麦角甾-5,22-二双键-3-醇(33),麦角甾烷醇(34),20-甲基-孕甾-20-双键-3-醇(35),胆甾-7-双键-3-酮(36),胆甾-3,5-二双键-7-酮(37),胆甾-3,5-二双键(38),孕甾-5-双键-20-酮-3-醇(39),胆甾-3,6-二酮(40),胆甾-5,6-环氧-3-醇(41),26-去甲基-胆甾-5-双键-3-醇(42),胆甾-8(14)-双键-3-酮(43),胆甾-5,24-二双键-3-醇(44),2-O-十四碳酸甘油酯(45),,2-O-十八碳酸甘油酯(46),1-O-十六碳酸甘油酯(47),2-O-9-十八碳烯酸甘油酯(48),1-O-9-十八碳烯酸甘油酯(49),阿拉伯糖(50),11-十六碳烯醛(51),角鲨烯(52),十四碳醛(53),10-十五碳-1-烯醇(54),9-十六碳-1-烯醇(55),9-十八碳-1-烯醇(56),13-十八碳醛(57),顺式-11-十六碳烯醛(58),14-二十三碳烯醇甲酸酯(59),9-十八碳烯醇(60),十八碳酰胺(61),十六碳酰胺(62),十二碳酰胺(63),13-二十二碳烯酰胺(64),9-十八碳烯酰胺(65)。
研究结果表明沙蜇中的有机小分子化学物质主要是甾醇类、核苷类、甘油醚类、甘油酯类、长链醇类、长链酰胺类等化合物,大多数化合物都是首次在沙蜇中发现的。通过SciFinder结构检索发现胆甾-8-甲氧基-22-双键-3,6-二醇为新化合物,胆甾-5-甲氧基-3,6-二醇、胆甾-6-甲氧基-3,5-二醇和1α-丁氧基,2-脱氧核糖。在已报道的海洋动物甾醇中,含有甲氧基的甾醇极为少见,本研究首次从沙蜇中发现了这类甾醇,并鉴定出了其中3个化合物。
本研究有效地补充了沙蜇有机小分子活性物质的化合物结构信息,为深入研究沙蜇有机小分子的功能活性,进而为沙蜇的开发利用提供了数据和理论支持。
Jellyfish (Stomopholus meleagris), one of edible giant jellyfish species, is widely distributed from the Yellow sea, Bohai Sea, to the Eastern Sea of China. Jellyfish has been consumed in China for more than one thousand years and proved to be of good nutrient and medicinal values by classics of Chinese traditional medicine and modern scientific research. Large quantities of jellyfish is harvested between summer and autumn when the ambient temperature is high. Jellyfish has high water content and is apt to suffer from autolysis afer harvest. So far, jellyfish is mainly processed according to traditional procedures of low yield as a lot of biologically ative constituents were lost during processing which leads to low utilization ratio of the resource and environmental pollution. Thus more and more conerns have been attracted to the efficient comprehensive exploitation of jellyfish. Researchers have reported some macromolecules, such as venom, collagen, peptide, polysaccharide and glycoprotein, and their biological activities from jellyfish while low molecular weight organic components, among which compounds of new structures and unique activities are possibly to be be found, were rarely investigated.
For the first time, systemic extaction, separation, purification and structure elucidation were carried out on the low molecular weight natural products of jellyfish (Stomopholus meleagris). Methanol extracts of fresh jellyfish was partitioned successively with petroleum ether, ethyl acetate, and n-butanol. Then silica gel chromatography,flash RP18 silica gel chromatography, Sephadex LH-20 gel filtration and PTLC were performed for the isolation and purification of the compounds, and TLC,~1H NMR,~(13)C NMR, DEPT, HMQC, HMBC, 1H1H COSY, NOESY, GC-MS, ESI MS, and chemical derivatization analyses as well as data comparison with reported literatures were applied for the structure elucidation. Thirty-five compounds, of which 22were identified, were isolated and purified from jellyfish (Stomopholus meleagris), and other 43compounds were identified according to the results of GC-MS analysis of all the purified and partially purified compounds. Generally, 65 compounds were identified from jellyfish, among which there were 1 new compound, 3 new natural products while 64 in all were identified fom this species for the first time.The 64compounds are as follows:
Compounds identified by NMR:
cholesta-8α-methoxyl-22-en-3β, 6β-diol(1), cholesta-5-methoxyl-3, 6-diol(2), cholesterol(3), ergosterol(4), dibatyl phthalate(5), cholesta-5-en-3-hydroxy-7-one(6), eicosanol, 2, 3-dihydroxypropyl ether(7), carboceric acid, 2, 3-dihydroxypropyl ester(8), hexadecanol, 2, 3-dihydroxypropyl ether(9), pentacosanol, 2, 3-dihydroxypropyl ether(10), cholesta-5-en-3,7β-diol (11), choleta-5-en-3β,7α-diol (12), cholesta-6-methoxyl-3, 5-diol(13), 1α-butoxy, 2-desoxyribose(14), thymine(15), 2’-O-methyluridine(16), uracil(17), 2’-deoxythymidine(18), 2’-deoxyuridine(19), uridine(20), glycerol(21), phenyl- alanine(22) ,
Compounds identified by GC-MS: cholesta-4-en-3-one(23), 24-nor-22, 23-methylenecholest-5-en-3β-ol TMS ether(24), cholestanol(25), stigmasterol(26), sitosterol(27), stigmasta-5, 24(28)-dien-3β-ol(28) cholesta-4-en-3-one(29), ergosta-5, 24-dien-3β-ol(30), ergosta-5-en-3β-ol(31), ergosta-5, 22-dien-3β-ol(32) , 26, 27-dinorergosta-5, 22-dien-3β-ol(33), 27-norergosta-5, 22-dien-3β-ol(34), ergostanol(35), 20-methyl-pregn-20-en-3β-ol(36), cholesta-7-en-3-one(37), cholesta-3, 5-diene-7-one(38), cholesta-3, 5-diene, 3-hydroxy- pregn-5en-20-one(39), cholesta-3, 6-dione(40), 5α, 6α-epoxy-cholestan-3β-ol(41), 26-nor- cholesten-5- en-3β-ol-25-one(42), cholest- 8(14)-en-3-one(43) ,cholesta-5,24-dien-3-ol(44),
tetradecanoic acid,2-hydroxy-1- [hydroxymethyl]ethyl ester(45), Octadecanoic acid,2-hydroxy-1- [hydroxymethyl]ethyl ester(46), hexadecanoic acid, 2, 3-bis {[trimethylsilyl]oxy}propyl ester(47), [Z]-9-octadecanoic acid, 2-hydroxy- 1-[hydroxymethyl]ethyl ester(48), [Z]-9-octadecanoic acid, 2, 3-dihydroxypropyl ester(49), 1, 2, 3 , 5-tetrakis-o- [trimethylsilyl] -arabinofuranose(50), [E]-11-hexadecenal(51), squalene(52), tetradecanal(53), [Z]-10-pentadecen-1-ol(54), [Z]-9-hexadecen-1-ol(55), [E]-9-octadecen-1-ol(56), [Z]-13-octadecenal(57), cis-11-hexadecenal(58), [Z]-14-Tricosenyl formate (59), oleyl alchohol(60), otadecenamide(61), hexadecanamide(62), dodecanamide(63), [Z]-13-docosenamide(64), [Z]-9-dtadecenamide(65).
The results showed jellyfish Stomopholus meleagris contains sterols, nucleosides, glycerylethers, glycerylesters, long-chain aliphatic alcohols, and long-chain amides. After structure searching on SciFinder cholesta-8-methoxyl-22-en-3, 6-diol was found to be a new compound, cholesta-5-methoxyl-3, 6-diol, 1α-butoxy, 2-desoxyribose and 1β-butoxy, 2-desoxyribose were found to be new natural products. For the first time sterols with methoxyl, seldom reported from marine animals, were found in our research and 3 of them were identified.
Our research supplied useful fundamental chemical data of micromolecular compositon of jellyfish Stomopholus meleagris, which may contribute to further study of biologically active functional factors and exploitation of jellyfish (Stomopholus meleagris) .
本研究首次聚焦沙蜇中的有机小分子化学物质,对其进行系统深入的提取、分离、纯化和结构鉴定。应用有机溶剂浸提、分级萃取、正相硅胶柱层析、RP18反相硅胶柱层析、凝胶过滤柱层析、制备薄层层析等分离技术,结合TLC、1H NMR、~(13)C NMR、DEPT、HMQC、HMBC、~1H-~1H COSY、NOESY、ESI MS、GC-MS、化学衍生和文献对照等分析手段,分离得到32个单体化合物,鉴定出其中的22个化合物;利用GC-MS在分离纯化过程中分析出43个化合物,共鉴定得到65个化合物。在65个化合物中,有1个新化合物,3个新天然产物,64个化合物为首次从沙蜇中鉴定得到。NMR解析鉴定的化合物:
胆甾-8-甲氧基-22-双键-3,6-二醇(1),胆甾-5-甲氧基-3,6-二醇(2),胆甾醇(3),麦角甾醇(4),邻苯二甲酸二丁酯(5),胆甾-5-双键-3-羟基-7酮(6),二十碳烷醇甘油醚(7),1-O-二十七碳酸甘油酯(8),十六碳烷醇甘油醚(9),二十五碳烷醇甘油醚(10),胆甾-5-双键-3β,7β-二醇(11),胆甾-5-双键-3β,7α-二醇(12),胆甾-6-甲氧基-3,5-二醇(13),1α-丁氧基,2-脱氧核糖(14),胸腺嘧啶(15),2’-甲氧基尿嘧啶核苷(16),尿嘧啶(17),2’-脱氧胸腺嘧啶核苷(18),2’-脱氧尿嘧啶核苷(19),尿嘧啶核苷(20),甘油(21),苯丙氨酸(22)。GC-MS鉴定的化合物:
胆甾-4-双键-3-酮(23),24-缺-22,23-亚甲基-胆甾-5-双键-3-醇(24),胆甾烷醇(25),豆甾醇(26),谷甾醇(27),豆甾-5,24(28)-二双键-3-醇(28),麦角甾-5,24-二双键-3-醇(29),麦角甾-5-双键-3-醇(30),麦角甾-5,22-二双键-3-醇(31),26,27-去甲基-麦角甾-5,22-二双键-3-醇(32),27-去甲基-麦角甾-5,22-二双键-3-醇(33),麦角甾烷醇(34),20-甲基-孕甾-20-双键-3-醇(35),胆甾-7-双键-3-酮(36),胆甾-3,5-二双键-7-酮(37),胆甾-3,5-二双键(38),孕甾-5-双键-20-酮-3-醇(39),胆甾-3,6-二酮(40),胆甾-5,6-环氧-3-醇(41),26-去甲基-胆甾-5-双键-3-醇(42),胆甾-8(14)-双键-3-酮(43),胆甾-5,24-二双键-3-醇(44),2-O-十四碳酸甘油酯(45),,2-O-十八碳酸甘油酯(46),1-O-十六碳酸甘油酯(47),2-O-9-十八碳烯酸甘油酯(48),1-O-9-十八碳烯酸甘油酯(49),阿拉伯糖(50),11-十六碳烯醛(51),角鲨烯(52),十四碳醛(53),10-十五碳-1-烯醇(54),9-十六碳-1-烯醇(55),9-十八碳-1-烯醇(56),13-十八碳醛(57),顺式-11-十六碳烯醛(58),14-二十三碳烯醇甲酸酯(59),9-十八碳烯醇(60),十八碳酰胺(61),十六碳酰胺(62),十二碳酰胺(63),13-二十二碳烯酰胺(64),9-十八碳烯酰胺(65)。
研究结果表明沙蜇中的有机小分子化学物质主要是甾醇类、核苷类、甘油醚类、甘油酯类、长链醇类、长链酰胺类等化合物,大多数化合物都是首次在沙蜇中发现的。通过SciFinder结构检索发现胆甾-8-甲氧基-22-双键-3,6-二醇为新化合物,胆甾-5-甲氧基-3,6-二醇、胆甾-6-甲氧基-3,5-二醇和1α-丁氧基,2-脱氧核糖。在已报道的海洋动物甾醇中,含有甲氧基的甾醇极为少见,本研究首次从沙蜇中发现了这类甾醇,并鉴定出了其中3个化合物。
本研究有效地补充了沙蜇有机小分子活性物质的化合物结构信息,为深入研究沙蜇有机小分子的功能活性,进而为沙蜇的开发利用提供了数据和理论支持。
Jellyfish (Stomopholus meleagris), one of edible giant jellyfish species, is widely distributed from the Yellow sea, Bohai Sea, to the Eastern Sea of China. Jellyfish has been consumed in China for more than one thousand years and proved to be of good nutrient and medicinal values by classics of Chinese traditional medicine and modern scientific research. Large quantities of jellyfish is harvested between summer and autumn when the ambient temperature is high. Jellyfish has high water content and is apt to suffer from autolysis afer harvest. So far, jellyfish is mainly processed according to traditional procedures of low yield as a lot of biologically ative constituents were lost during processing which leads to low utilization ratio of the resource and environmental pollution. Thus more and more conerns have been attracted to the efficient comprehensive exploitation of jellyfish. Researchers have reported some macromolecules, such as venom, collagen, peptide, polysaccharide and glycoprotein, and their biological activities from jellyfish while low molecular weight organic components, among which compounds of new structures and unique activities are possibly to be be found, were rarely investigated.
For the first time, systemic extaction, separation, purification and structure elucidation were carried out on the low molecular weight natural products of jellyfish (Stomopholus meleagris). Methanol extracts of fresh jellyfish was partitioned successively with petroleum ether, ethyl acetate, and n-butanol. Then silica gel chromatography,flash RP18 silica gel chromatography, Sephadex LH-20 gel filtration and PTLC were performed for the isolation and purification of the compounds, and TLC,~1H NMR,~(13)C NMR, DEPT, HMQC, HMBC, 1H1H COSY, NOESY, GC-MS, ESI MS, and chemical derivatization analyses as well as data comparison with reported literatures were applied for the structure elucidation. Thirty-five compounds, of which 22were identified, were isolated and purified from jellyfish (Stomopholus meleagris), and other 43compounds were identified according to the results of GC-MS analysis of all the purified and partially purified compounds. Generally, 65 compounds were identified from jellyfish, among which there were 1 new compound, 3 new natural products while 64 in all were identified fom this species for the first time.The 64compounds are as follows:
Compounds identified by NMR:
cholesta-8α-methoxyl-22-en-3β, 6β-diol(1), cholesta-5-methoxyl-3, 6-diol(2), cholesterol(3), ergosterol(4), dibatyl phthalate(5), cholesta-5-en-3-hydroxy-7-one(6), eicosanol, 2, 3-dihydroxypropyl ether(7), carboceric acid, 2, 3-dihydroxypropyl ester(8), hexadecanol, 2, 3-dihydroxypropyl ether(9), pentacosanol, 2, 3-dihydroxypropyl ether(10), cholesta-5-en-3,7β-diol (11), choleta-5-en-3β,7α-diol (12), cholesta-6-methoxyl-3, 5-diol(13), 1α-butoxy, 2-desoxyribose(14), thymine(15), 2’-O-methyluridine(16), uracil(17), 2’-deoxythymidine(18), 2’-deoxyuridine(19), uridine(20), glycerol(21), phenyl- alanine(22) ,
Compounds identified by GC-MS: cholesta-4-en-3-one(23), 24-nor-22, 23-methylenecholest-5-en-3β-ol TMS ether(24), cholestanol(25), stigmasterol(26), sitosterol(27), stigmasta-5, 24(28)-dien-3β-ol(28) cholesta-4-en-3-one(29), ergosta-5, 24-dien-3β-ol(30), ergosta-5-en-3β-ol(31), ergosta-5, 22-dien-3β-ol(32) , 26, 27-dinorergosta-5, 22-dien-3β-ol(33), 27-norergosta-5, 22-dien-3β-ol(34), ergostanol(35), 20-methyl-pregn-20-en-3β-ol(36), cholesta-7-en-3-one(37), cholesta-3, 5-diene-7-one(38), cholesta-3, 5-diene, 3-hydroxy- pregn-5en-20-one(39), cholesta-3, 6-dione(40), 5α, 6α-epoxy-cholestan-3β-ol(41), 26-nor- cholesten-5- en-3β-ol-25-one(42), cholest- 8(14)-en-3-one(43) ,cholesta-5,24-dien-3-ol(44),
tetradecanoic acid,2-hydroxy-1- [hydroxymethyl]ethyl ester(45), Octadecanoic acid,2-hydroxy-1- [hydroxymethyl]ethyl ester(46), hexadecanoic acid, 2, 3-bis {[trimethylsilyl]oxy}propyl ester(47), [Z]-9-octadecanoic acid, 2-hydroxy- 1-[hydroxymethyl]ethyl ester(48), [Z]-9-octadecanoic acid, 2, 3-dihydroxypropyl ester(49), 1, 2, 3 , 5-tetrakis-o- [trimethylsilyl] -arabinofuranose(50), [E]-11-hexadecenal(51), squalene(52), tetradecanal(53), [Z]-10-pentadecen-1-ol(54), [Z]-9-hexadecen-1-ol(55), [E]-9-octadecen-1-ol(56), [Z]-13-octadecenal(57), cis-11-hexadecenal(58), [Z]-14-Tricosenyl formate (59), oleyl alchohol(60), otadecenamide(61), hexadecanamide(62), dodecanamide(63), [Z]-13-docosenamide(64), [Z]-9-dtadecenamide(65).
The results showed jellyfish Stomopholus meleagris contains sterols, nucleosides, glycerylethers, glycerylesters, long-chain aliphatic alcohols, and long-chain amides. After structure searching on SciFinder cholesta-8-methoxyl-22-en-3, 6-diol was found to be a new compound, cholesta-5-methoxyl-3, 6-diol, 1α-butoxy, 2-desoxyribose and 1β-butoxy, 2-desoxyribose were found to be new natural products. For the first time sterols with methoxyl, seldom reported from marine animals, were found in our research and 3 of them were identified.
Our research supplied useful fundamental chemical data of micromolecular compositon of jellyfish Stomopholus meleagris, which may contribute to further study of biologically active functional factors and exploitation of jellyfish (Stomopholus meleagris) .
引文
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