葱莲化学成分及其药理活性的研究
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摘要
葱莲[Zephyranthes candida (Lindl.) Herb]是石蒜科(Amaryllideceae)葱莲属(Zephyranthes Herb)多年生常绿草本植物。葱莲属是石蒜科中的一个较大的属,本属中全世界共有60种植物,主要分布在西半球温暖地区,在南美洲国家有集中分布,这些植物的球茎大部分被用于民间药用。
在中国仅有两种葱莲属植物,即葱莲Zephyranthes Candida和韭莲Zephyranthes carinata,原都是从南美洲国家引种的植物,多作为园艺观赏植物。葱莲现在我国江南地区广泛栽培,多用作城市地被观赏植物、或用于花坛边、林下绿化等。国外对于葱莲属植物的化学成分研究主要集中在生物碱和少部分黄酮类化合物方面；在我国,尚没有关于葱莲化学成分和药理活性研究的报道。
为了深入地研究该植物的药用价值,对产于南京的葱莲进行了系统的化学成分和部分药理活性研究。运用各种色谱方法(硅胶柱色谱、氧化铝色谱、凝胶柱色谱、常压ODS柱色谱等)提取、分离纯化和鉴定,得到45个单体化合物,通过理化方法和波谱分析(MS、1H-NMR、13C-NMR及2DNMR),鉴定了其中的40个化学成分的结构,包括8个新神经酰胺类化合物,2个新天然产物,5个黄烷,10个石蒜科生物碱和15个其它化学成分(甾醇、酚类、维生素、甘油脂、有机酸、芦丁等)。这些化学成分分别为：
Zec-1:石蒜碱
Zec-2:β-胡萝卜苷
Zec-3:β-谷甾醇
Zec-4:benzo[1,3]dioxol-5-yl-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-methanol
Zec-7:pseudolycorine
Zec-8:(2S,3S,4R,8E,2'R)-2-[N-(2'-hydroxyoctadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol
Zec-9:1,3,5,6-tetrahydroxy-2-(2'-hydroxytetracosanoylamino)-8-(E)-octadecadiene
Zec-10:9'-顺-十八烯酸甘油酯
Zec-lla:(2S)-3',7-二羟基-4'-甲氧基黄烷
Zec-11b:(2S)-4'-羟基-7-甲氧基黄烷
Zec-11c-(2S')-4',7-二羟基-8-甲氧基黄烷
Zec-11d:(2S-3',7-二羟基-4'-甲氧基-8-甲基黄烷
Zec-11e:(2S)-4',7-二羟基黄烷
Zec-12:haemanthidine
Zec-14:O-methyllycorenine
Zec-15:(1S,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-l-ol
Zec-16:(+)-5-methoxy-9-O-demethylhomolycorine
Zec-17:(2S,3S,4R)-1,3,4-trihydroxy-2-octacosanoylamino-hexadecene
Zec-18:1,3,4,5,6-pentahydroxy-2-(2'-hydroxytetracosanoylamino)-7-(E)-tetracosene
Zec-19:△5,22-豆甾烯醇
Zec-20:9-demethylhomolycorine
Zec-21:豆甾醇
Zec-23:硬脂酸
Zec-24:邻苯二甲酸丁酯异丁酯
Zec-25:黄葵内酯
Zec-26:正二十七烷
Zec-28:亚油酸
Zec-29:3p-乙酰氧基-熊果-11(12)-烯-28,13-内酯
Zec-31:(2S,6E,1"E,13R,16R,2'R)-39-methyl-3,4,5-hydroxymethyl-2-[N-(2'-hydroxyhexadecanoyl)-N-(3",4"-dihydroxyethyl)-amino]-6,13,16,1" tetraconta-1,8,10,21-triol
Zec-32:(2S,3S,4R,13E)-1,3,4-trihydroxy-2-[(2'R)-2'-hydroxytetracosanoylamino]-13-octadecene
Zec-33:(2S,3S,4R,21E,2'R)-2-[N-(2'-hydroxynonadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-21-hexacosene-1,3,4-triol
Zec-36:香草酸
Zec-37:1,3,4,5,6-pentahydroxy-2-(2'-hydroxyhexacosanoylamino)-18-(E)-tetracosene
Zec-38:力克拉敏
Zec-39:加兰他敏
Zec-40:维生素
Zec-41:2-hydroxy-4-methoxyphenyl)ethanol
Zec-50:芦
Zec-51:pancratistatin
Zec-53:3,11-O-(3',3"-dihydroxybutanoyl)hamayne
在已鉴定的化合物中,Zec-8、9、17、18、31、32、33、37为新化合物,这8个神经酰胺类成分在石蒜科、葱莲属都是首次发现。Zec-4、5为新天然产物；Zec-1、7、12、14、16、20、38、39、51、53为石蒜科生物碱;Zec-11a、11b、11c、11d、11e为黄烷；Zec-2、3、19、21为甾醇；Zec-40为维生素；Zec-41为酚类；Zec-50为芦丁；其它为甘油酯或有机酸类。除Zec-1外,其余39个化合物都是首次从该植物中分离得到。
神经酰胺类化合物是一类比较特殊的次生代谢产物,多种类型的神经酰胺已经从海洋生物、真菌和部分植物中被分离得到,大部分都显示了良好的药理活性,如细胞毒活性、抗细菌真菌、抗病毒、抗利什曼虫、免疫调节、抑制细胞生长等。这类化学成分因其较好的药理药效而引起了广大药物研究者的的浓厚兴趣。对天然药物化学研究人员来说,从植物中分离、鉴定脑苷和神经酰胺类化学成分是一类具有挑战性意义的工作。
结合近十年来的文献,重点综述了脑苷和神经酰胺化学成分的分离纯化、结构分析方法和药理药效。参考了有关植物神经酰胺类化合物合成途径的文献,推测了葱莲中植物神经酰胺类成分可能的生物合成途径。
运用MTT试验方法对部分新化合物进行了初步的细胞毒活性筛选,结果表明,这些化学成分具有弱的抑制肿瘤细胞的药理活性,为葱莲作为药用植物开发提供了科学依据。
Zephyranthes candida (Lindl.) Herb belongs to the genus Zephyranthes Herb and family Amaryllideceae, and it is a common perennial plant and used as a horticultural and traditional medicinal plant with its bulbs in many countries. The genus Zephyranthes Herb is a big genus containing about60species, mainly distributes in the warm temperate regions of west global, especially in the countries of South America.
Only two species of the genus Zephyranthes Herb, Zephyranthes candida and Zephyranthes carinata grow in China, and they were early introduced from South America only for horticultural purpose, and have not being occupied an important place in the Chinese traditional medicines from then on. At present, Zephyranthes candida is widely planted in many areas in Chinese cities, mainly the South area of Yangtse River for horticultural or ornamental utilization. Both the previous investigations and the present works on chemical constituents of the plants from the genus Zephyranthes Herb mainly focused on some alkaloids and a few flavans in foreign countries.In China, phytochemical works on Zephyranthes candida have not been attached importance to and there are no reports on chemical composition and pharmacological activity to date, and even the genus Zephyranthes Herb or family Amaryllidaceae.
In order to furtherly understand the pharmacological value of Zephyranthes candida, studies were carried systematically on the chemical constituents and pharmacological activities of this plant collected in the nursery of Nanjing Agricultural University.
On account of this, we undertook a thorough chemical investigation of the methanol extract of the plant, using macroreticular resin, sephadex LH-20,ODS, and silica gel chromatography. Forty compounds were isolated and identified and the structures of them were elucidated by chemical and spectural technology (infrared spectroscopy IR, mass spectroscopy MS,nuclear magnetic resonance NMR, ultraviolet spectroscopy UV).
These novel ceramides and known compounds are listed as follows:
Zec-1:lycorine;Zec-2:β-daucosterin;Zec-3:β-sitosterol;
Zec-4:benzo[1,3]dioxol-5-y]-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-methanol;
Zec-7:pseudolycorine;
Zec-8:(2S,3S,4R,8E,2'R)-2-[N-(2'-hydroxyoctadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol;
Zec-9:1,3,5,6-tetrahydroxy-2-(2'-hydroxytetracosanoylamino)-8-(E)-octadecadiene;
Zec-10:(Z)-9'-octadecenoie acid;
Zee-11a:(2S)-3',7-dihydroxy-4'-methoxyflavan;
Zec-11b:(2S)-4'-hydroxy-7-methoxyflavan;
Zec-11c:(2S)-4',7-dihydroxy-8-methoxyflavan;
Zec-11d:(2S)-4',7-dihydroxy-8-methoxyflavan;
Zec-11e:(2S)-4',7-dihydroxyflavan;
Zec-12:haemanthidine;Zec-14:O-methyllycorenine;
Zec-15:(1S,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-l-ol;
Zec-16:(+)-5-Methoxy-9-O-demethylhomolycorine;
Zec-17:(2S,3S,4R)-1,3,4-trihydroxy-2-octacosanoylamino-hexadecene;
Zec-18:1,3,4,5,6-pentahydroxy-2-(2'-hydroxytetracosanoylamino)-7-(E)-tetracosene;
Zec-19:stigmasta-5,22-dien-3β-ol; Zec-20:9-demethylhomolycorine;
Zec-21:stigmasterol; Zec-23:stearic acid; Zec-24:butylisobutyl phthalat;
Zec-25:ambrettolide; Zec-26:heptacosane; Zec-28:linoleic Acid;
Zec-29:3β-acetoxyurs-11-en-28,13-olide;
Zec-31:(2S,6E,1"E,13R,16R,2'R)-39-methyl-3,4,5-hydroxymethyl-2-[N-(2'-hydroxyhexadecanoyl)-N-(3",4"-dihydroxyethyl)-amino]-6,13,16,1"-tetraconta-1,8,10,21-triol;
Zec-32:(2S,3S,4R,513E)-1,3,4-trihydroxy-2-[(2'R)-2'-hydroxytetracosanoylamino]-13-octadecene;
Zec-33:(2S,3S,4R,21E,2'R)-2-[N-(2'-hydroxynonadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-21-hexacosene-1,3,4-triol;
Zec-36:vanillic acid;
Zec-37:1,3,4,5,6-pentahydroxy-2-(2'-hydroxyhexacosanoylamino)-18-(E)-tetracosene;
Zec-38:lycoramine; Zec-39:galanthamine; Zec-40:α-Tocopherol;
Zec-41:2-hydroxy-4-methoxyphenyl)ethanol; Zec-50:rutin; Zec-51:pancratistatin;
Zec-53:3,11-O-(3',3"-dihydroxybutanoyl)hamayne o
Among them, compounds8、9、17、18、31、32、33、37are8novel ceramides,and they are isolated from the genus Zephyranthes and family Amaryllideceae for the first time. compounds4、15are2new natural compounds.compounds lla、11b、11c、111d、11e are5flavans. And there are10Amaryllideceae alkaloids numbered as1、12、14、16、2038、39、51、53. Apart from compound1, all these compounds were isolated from this herb for the first time.
Ceramides are a unique class of secondary metabolites, and various ceramides have been isolated from a number of marine organisms, fungi, and some plants, some of which exhibit cytotoxic, antifungal, antimicrobial, antileishmanial and immunomodulatory, and cytostatic activities. Due to their promising biological and pharmacological activities, they have aroused much increasing research interest. It is a challenging task for pharmaceutical researchers to isolate and identify the ceramides from the plants.
A significant review on the isolation, purification, structure analysis and pharmacological activities of the phyto-ceramides and cerebrosides were given on the basis of the references of recent ten years and our own study work. In addition, the presumed biosynthesis pathway of phyto-ceramides and cerebrosides in this plant was discussed according to the references reported previously.
Also, MTT method were used to screen effective activities of some novel ceramides, mainly for their cytotoxic activity. The pharmacological experiments showed weak activity in inhibiting Hela carcinoma cell line. This study will be the basis of a better medicinal research and development of the plant Zephyr anthes candida (Lindl.) Herb.
在中国仅有两种葱莲属植物,即葱莲Zephyranthes Candida和韭莲Zephyranthes carinata,原都是从南美洲国家引种的植物,多作为园艺观赏植物。葱莲现在我国江南地区广泛栽培,多用作城市地被观赏植物、或用于花坛边、林下绿化等。国外对于葱莲属植物的化学成分研究主要集中在生物碱和少部分黄酮类化合物方面；在我国,尚没有关于葱莲化学成分和药理活性研究的报道。
为了深入地研究该植物的药用价值,对产于南京的葱莲进行了系统的化学成分和部分药理活性研究。运用各种色谱方法(硅胶柱色谱、氧化铝色谱、凝胶柱色谱、常压ODS柱色谱等)提取、分离纯化和鉴定,得到45个单体化合物,通过理化方法和波谱分析(MS、1H-NMR、13C-NMR及2DNMR),鉴定了其中的40个化学成分的结构,包括8个新神经酰胺类化合物,2个新天然产物,5个黄烷,10个石蒜科生物碱和15个其它化学成分(甾醇、酚类、维生素、甘油脂、有机酸、芦丁等)。这些化学成分分别为：
Zec-1:石蒜碱
Zec-2:β-胡萝卜苷
Zec-3:β-谷甾醇
Zec-4:benzo[1,3]dioxol-5-yl-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-methanol
Zec-7:pseudolycorine
Zec-8:(2S,3S,4R,8E,2'R)-2-[N-(2'-hydroxyoctadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol
Zec-9:1,3,5,6-tetrahydroxy-2-(2'-hydroxytetracosanoylamino)-8-(E)-octadecadiene
Zec-10:9'-顺-十八烯酸甘油酯
Zec-lla:(2S)-3',7-二羟基-4'-甲氧基黄烷
Zec-11b:(2S)-4'-羟基-7-甲氧基黄烷
Zec-11c-(2S')-4',7-二羟基-8-甲氧基黄烷
Zec-11d:(2S-3',7-二羟基-4'-甲氧基-8-甲基黄烷
Zec-11e:(2S)-4',7-二羟基黄烷
Zec-12:haemanthidine
Zec-14:O-methyllycorenine
Zec-15:(1S,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-l-ol
Zec-16:(+)-5-methoxy-9-O-demethylhomolycorine
Zec-17:(2S,3S,4R)-1,3,4-trihydroxy-2-octacosanoylamino-hexadecene
Zec-18:1,3,4,5,6-pentahydroxy-2-(2'-hydroxytetracosanoylamino)-7-(E)-tetracosene
Zec-19:△5,22-豆甾烯醇
Zec-20:9-demethylhomolycorine
Zec-21:豆甾醇
Zec-23:硬脂酸
Zec-24:邻苯二甲酸丁酯异丁酯
Zec-25:黄葵内酯
Zec-26:正二十七烷
Zec-28:亚油酸
Zec-29:3p-乙酰氧基-熊果-11(12)-烯-28,13-内酯
Zec-31:(2S,6E,1"E,13R,16R,2'R)-39-methyl-3,4,5-hydroxymethyl-2-[N-(2'-hydroxyhexadecanoyl)-N-(3",4"-dihydroxyethyl)-amino]-6,13,16,1" tetraconta-1,8,10,21-triol
Zec-32:(2S,3S,4R,13E)-1,3,4-trihydroxy-2-[(2'R)-2'-hydroxytetracosanoylamino]-13-octadecene
Zec-33:(2S,3S,4R,21E,2'R)-2-[N-(2'-hydroxynonadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-21-hexacosene-1,3,4-triol
Zec-36:香草酸
Zec-37:1,3,4,5,6-pentahydroxy-2-(2'-hydroxyhexacosanoylamino)-18-(E)-tetracosene
Zec-38:力克拉敏
Zec-39:加兰他敏
Zec-40:维生素
Zec-41:2-hydroxy-4-methoxyphenyl)ethanol
Zec-50:芦
Zec-51:pancratistatin
Zec-53:3,11-O-(3',3"-dihydroxybutanoyl)hamayne
在已鉴定的化合物中,Zec-8、9、17、18、31、32、33、37为新化合物,这8个神经酰胺类成分在石蒜科、葱莲属都是首次发现。Zec-4、5为新天然产物；Zec-1、7、12、14、16、20、38、39、51、53为石蒜科生物碱;Zec-11a、11b、11c、11d、11e为黄烷；Zec-2、3、19、21为甾醇；Zec-40为维生素；Zec-41为酚类；Zec-50为芦丁；其它为甘油酯或有机酸类。除Zec-1外,其余39个化合物都是首次从该植物中分离得到。
神经酰胺类化合物是一类比较特殊的次生代谢产物,多种类型的神经酰胺已经从海洋生物、真菌和部分植物中被分离得到,大部分都显示了良好的药理活性,如细胞毒活性、抗细菌真菌、抗病毒、抗利什曼虫、免疫调节、抑制细胞生长等。这类化学成分因其较好的药理药效而引起了广大药物研究者的的浓厚兴趣。对天然药物化学研究人员来说,从植物中分离、鉴定脑苷和神经酰胺类化学成分是一类具有挑战性意义的工作。
结合近十年来的文献,重点综述了脑苷和神经酰胺化学成分的分离纯化、结构分析方法和药理药效。参考了有关植物神经酰胺类化合物合成途径的文献,推测了葱莲中植物神经酰胺类成分可能的生物合成途径。
运用MTT试验方法对部分新化合物进行了初步的细胞毒活性筛选,结果表明,这些化学成分具有弱的抑制肿瘤细胞的药理活性,为葱莲作为药用植物开发提供了科学依据。
Zephyranthes candida (Lindl.) Herb belongs to the genus Zephyranthes Herb and family Amaryllideceae, and it is a common perennial plant and used as a horticultural and traditional medicinal plant with its bulbs in many countries. The genus Zephyranthes Herb is a big genus containing about60species, mainly distributes in the warm temperate regions of west global, especially in the countries of South America.
Only two species of the genus Zephyranthes Herb, Zephyranthes candida and Zephyranthes carinata grow in China, and they were early introduced from South America only for horticultural purpose, and have not being occupied an important place in the Chinese traditional medicines from then on. At present, Zephyranthes candida is widely planted in many areas in Chinese cities, mainly the South area of Yangtse River for horticultural or ornamental utilization. Both the previous investigations and the present works on chemical constituents of the plants from the genus Zephyranthes Herb mainly focused on some alkaloids and a few flavans in foreign countries.In China, phytochemical works on Zephyranthes candida have not been attached importance to and there are no reports on chemical composition and pharmacological activity to date, and even the genus Zephyranthes Herb or family Amaryllidaceae.
In order to furtherly understand the pharmacological value of Zephyranthes candida, studies were carried systematically on the chemical constituents and pharmacological activities of this plant collected in the nursery of Nanjing Agricultural University.
On account of this, we undertook a thorough chemical investigation of the methanol extract of the plant, using macroreticular resin, sephadex LH-20,ODS, and silica gel chromatography. Forty compounds were isolated and identified and the structures of them were elucidated by chemical and spectural technology (infrared spectroscopy IR, mass spectroscopy MS,nuclear magnetic resonance NMR, ultraviolet spectroscopy UV).
These novel ceramides and known compounds are listed as follows:
Zec-1:lycorine;Zec-2:β-daucosterin;Zec-3:β-sitosterol;
Zec-4:benzo[1,3]dioxol-5-y]-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-methanol;
Zec-7:pseudolycorine;
Zec-8:(2S,3S,4R,8E,2'R)-2-[N-(2'-hydroxyoctadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol;
Zec-9:1,3,5,6-tetrahydroxy-2-(2'-hydroxytetracosanoylamino)-8-(E)-octadecadiene;
Zec-10:(Z)-9'-octadecenoie acid;
Zee-11a:(2S)-3',7-dihydroxy-4'-methoxyflavan;
Zec-11b:(2S)-4'-hydroxy-7-methoxyflavan;
Zec-11c:(2S)-4',7-dihydroxy-8-methoxyflavan;
Zec-11d:(2S)-4',7-dihydroxy-8-methoxyflavan;
Zec-11e:(2S)-4',7-dihydroxyflavan;
Zec-12:haemanthidine;Zec-14:O-methyllycorenine;
Zec-15:(1S,4R,6S)-1-(benzo[1,3]dioxol-5-yl)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-cyclohexen-l-ol;
Zec-16:(+)-5-Methoxy-9-O-demethylhomolycorine;
Zec-17:(2S,3S,4R)-1,3,4-trihydroxy-2-octacosanoylamino-hexadecene;
Zec-18:1,3,4,5,6-pentahydroxy-2-(2'-hydroxytetracosanoylamino)-7-(E)-tetracosene;
Zec-19:stigmasta-5,22-dien-3β-ol; Zec-20:9-demethylhomolycorine;
Zec-21:stigmasterol; Zec-23:stearic acid; Zec-24:butylisobutyl phthalat;
Zec-25:ambrettolide; Zec-26:heptacosane; Zec-28:linoleic Acid;
Zec-29:3β-acetoxyurs-11-en-28,13-olide;
Zec-31:(2S,6E,1"E,13R,16R,2'R)-39-methyl-3,4,5-hydroxymethyl-2-[N-(2'-hydroxyhexadecanoyl)-N-(3",4"-dihydroxyethyl)-amino]-6,13,16,1"-tetraconta-1,8,10,21-triol;
Zec-32:(2S,3S,4R,513E)-1,3,4-trihydroxy-2-[(2'R)-2'-hydroxytetracosanoylamino]-13-octadecene;
Zec-33:(2S,3S,4R,21E,2'R)-2-[N-(2'-hydroxynonadecanoyl)-N-(1",2"-dihydroxyethyl)-amino]-21-hexacosene-1,3,4-triol;
Zec-36:vanillic acid;
Zec-37:1,3,4,5,6-pentahydroxy-2-(2'-hydroxyhexacosanoylamino)-18-(E)-tetracosene;
Zec-38:lycoramine; Zec-39:galanthamine; Zec-40:α-Tocopherol;
Zec-41:2-hydroxy-4-methoxyphenyl)ethanol; Zec-50:rutin; Zec-51:pancratistatin;
Zec-53:3,11-O-(3',3"-dihydroxybutanoyl)hamayne o
Among them, compounds8、9、17、18、31、32、33、37are8novel ceramides,and they are isolated from the genus Zephyranthes and family Amaryllideceae for the first time. compounds4、15are2new natural compounds.compounds lla、11b、11c、111d、11e are5flavans. And there are10Amaryllideceae alkaloids numbered as1、12、14、16、2038、39、51、53. Apart from compound1, all these compounds were isolated from this herb for the first time.
Ceramides are a unique class of secondary metabolites, and various ceramides have been isolated from a number of marine organisms, fungi, and some plants, some of which exhibit cytotoxic, antifungal, antimicrobial, antileishmanial and immunomodulatory, and cytostatic activities. Due to their promising biological and pharmacological activities, they have aroused much increasing research interest. It is a challenging task for pharmaceutical researchers to isolate and identify the ceramides from the plants.
A significant review on the isolation, purification, structure analysis and pharmacological activities of the phyto-ceramides and cerebrosides were given on the basis of the references of recent ten years and our own study work. In addition, the presumed biosynthesis pathway of phyto-ceramides and cerebrosides in this plant was discussed according to the references reported previously.
Also, MTT method were used to screen effective activities of some novel ceramides, mainly for their cytotoxic activity. The pharmacological experiments showed weak activity in inhibiting Hela carcinoma cell line. This study will be the basis of a better medicinal research and development of the plant Zephyr anthes candida (Lindl.) Herb.
引文
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