铁皮石斛化学成分的研究
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摘要
铁皮石斛(Dendrobium candidum)是兰科珍稀名贵药用植物,目前已开始人工栽培,但未见该植物化学成分的研究报道,为深入了解该植物药理作用的物质基础、并为栽培品的质量评价提供参考,本论文主要完成了以下工作。
利用多种色谱方法,从铁皮石斛药材分离出单体化合物72个;通过现代波谱技术鉴定了63个,发现新化合物18个;所得化合物的结构类型如下。
芪类及其衍生物共27个:铁皮石斛素A(1),铁皮石斛素B(11),铁皮石斛素C(2),铁皮石斛素D(3),铁皮石斛素E(4),铁皮石斛素F(5),铁皮石斛素G(6),铁皮石斛素H(9),铁皮石斛素I(15),铁皮石斛素J(7),铁皮石斛素K(8),铁皮石斛素L(10),铁皮石斛素M(12),铁皮石斛素N(13),铁皮石斛素O(14),铁皮石斛素P(16),铁皮石斛素Q(17),4,4′-二羟基-3,5-二甲氧基联苄(19),3,4-二羟基-5,4′-二甲氧基联苄(20),3′-羟基-3,4,5′-三甲氧基联苄(21),4,4′-二羟基-3,3′,5-三甲氧基联苄(22),3,4′-二羟基-5-甲氧基联苄(23),3′,4-二羟基-3,5′-二甲氧基联苄(24),二氢白藜芦醇(25),dendromoniliside E(26),denbinobin(27),2,4,7-三羟基-9,10-二氢菲(28)。
酚类化合物12个:N-p-香豆酰酪胺(29),反-N-(4-羟基苯乙基)阿魏酸酰胺(30),二氢松柏醇二氢对羟基桂皮酸酯(31),二氢阿魏酸酪胺(32),对羟基苯丙酰酪胺(33),丁香酸(34),丁香醛(35),香草酸(36),对羟基苯丙酸(37),对羟基桂皮酸(38),阿魏酸(39),对羟基苯甲酸(40)。
木脂素类化合物4个:(+)-丁香脂素-O-β-D-吡喃葡萄糖苷(41),icariolA_2-4-O-β-D-glucopyranoside(42),(+)-lyoniresinol-3a-O-β-D-glucopyranoside(43),及裂异落叶松脂醇(44)。
内酯类化合物2个:钩状石斛素(46)和洋地黄内酯(47)。二氢黄酮类化合物2个:柚皮素(48)和3′,5,5′,7-四羟基二氢黄酮(49)。其他类型化合物16个:铁皮石斛素R(18),erigesideⅡ(45),腺苷(50),尿苷(51),蔗糖(52),5-羟甲基糠醛(53),koaburaside(54),反式阿魏酸二十八烷基酯(55),对羟基反式肉桂酸三十烷基酯(56),对羟基顺式肉桂酸三十烷基酯(57),胡萝卜苷(58),β-谷甾醇(59),十六烷酸(60),十七烷(61),三十一烷醇(62),及十七烷酸(63)。
18个新化合物为:铁皮石斛素A(1),铁皮石斛素B(11),铁皮石斛素C(2),铁皮石斛素D(3),铁皮石斛素E(4),铁皮石斛素F(5),铁皮石斛素G(6),铁皮石斛素H(9),铁皮石斛素I(15),铁皮石斛素J(7),铁皮石斛素K(8),铁皮石斛素L(10),铁皮石斛素M(12),铁皮石斛素N(13),铁皮石斛素O(14),铁皮石斛素P(16),铁皮石斛素Q(17),及铁皮石斛素R(18)。
并对部分单体化合物进行了抗氧化和抗肿瘤活性初筛,发现大多数联苄类化合物具有抗氧化活性;有2个联苄类化合物具有抗肿瘤活性;并对活性筛选结果结合化合物的结构进行了初步的分析。还对石斛属植物中联苄类化学成分的结构特征及波谱规律进行了总结和探讨。
This paper reported the phytochemical investigation systematically on Dendrobium candidum,and bio-active screening results of the part chemical constituents isolated from Dendrobium candidum.In the meantime,this paper reported the progress of phytochemical studies on Dendrobium genus.
By using the chromatography techniques,72 compounds were isolated from the EtOAc and EtOH extrats of this plant's stems.On the basis of chemical methods and spectroscopic techniques,63 of these compounds were elucidated as follows:
27 stilbenoids:dendrocandin A(1),dendrocandin B(11),dendrocandin C(2), dendrocandin D(3),dendrocandin E(4),dendrocandin F(5),dendrocandin G(6), dendrocandin H(9),dendrocandin I(15),dendrocandin J(7),dendrocandin K(8), dendrocandin L(10),dendrocandin M(12),dendrocandin N(13),dendrocandin O(14), dendrocandin P(16),dendrocandin Q(17),4,4'-dihyxroxy-3,5-dimethoxybibenzyl(19), 3,4-dihydroxy-5,4'-dimethoxybibenzyl(20),3'-hydroxy-3,4,5'-trimethoxybibenzyl(21),4,4'-dihydroxy-3,3',5-trimethoxybibenzyl(22),3,4'-dihydroxy-5-methoxybibenzyl(23),3',4-dihydroxy-3,5'-dimethoxybibenzyl(24),dihydroresveratrol(25),dendromoniliside E(26), denbinobin(27),2,4,7-trihydroxy-9,10-dihydrophenanthrene(28).
12 phenols:paprazine(29),moupinamide(30),dihydroconiferyl dihydro-p -cumarate(31),dihydro-feruloyltyramine(32),p-hydroxyphenylpropionyl tyramine(33), syringic acid(34),syringaldehyde(35),vanillic acid(36),p-hydroxy-phenylpropionic acid(37),p-hydroxy cinnamic acid(38),ferulic acid(39),and 4-hydroxybenzoic acid (40).
4 lignans:(+)-syringaresinol-β-D-glucopyranoside(41),icariol A_2-4-O-β-D-glucopyranoside (42),(+)-lyoniresinol-3a-O-β-D-glucopyranoside(43),and(-)-secoisolariciresinol (44).
2 lactones:aduncin(46),and digiprolactone(47);2 flavanones:naringenin(48),and 3',5,5',7-tetrahydroxyflavanone(49).16 other compounds:dendrocandin R(18),erigesideⅡ(45),adenosine(50),uridine(51),sucrose(52),5-hydroxymethyl-furaldehyde(53), koaburaside(54),n-octacostyl ferulate(55),defuscin(56),n-triacontyl cis-p-coumarate(57), daucosterol(58),β-sitosterol(59),hexadecanoic acid(60),heptadecane(61),hentriacontane (62),heptadecanoic acid(63).
Among these compounds,18 are new ones:dendrocandin A(1),dendrocandin B (11),dendrocandin C(2),dendrocandin D(3),dendrocandin E(4),dendrocandin F(5), dendrocandin G(6),dendrocandin H(9),dendrocandin I(15),dendrocandin J(7), dendrocandin K(8),dendrocandin L(10),dendrocandin M(12),dendrocandin N(13), dendrocandin O(14),dendrocandin P(16),dendrocandin Q(17),and dendrocandin R (18).
As for the screening of antioxidant activity,most of the bibenzyls showed bio-activity;as for the screening of antitumour activity,only two compounds showed bio-activity.We concluded the relationship between the structures and the activities from the present results.
The structural and spectroscopic characteristics of bibenzyl derivatives from Dendrobium genus were concluded,and we hope that will be helpful for the structural elucidation of this type compounds.
利用多种色谱方法,从铁皮石斛药材分离出单体化合物72个;通过现代波谱技术鉴定了63个,发现新化合物18个;所得化合物的结构类型如下。
芪类及其衍生物共27个:铁皮石斛素A(1),铁皮石斛素B(11),铁皮石斛素C(2),铁皮石斛素D(3),铁皮石斛素E(4),铁皮石斛素F(5),铁皮石斛素G(6),铁皮石斛素H(9),铁皮石斛素I(15),铁皮石斛素J(7),铁皮石斛素K(8),铁皮石斛素L(10),铁皮石斛素M(12),铁皮石斛素N(13),铁皮石斛素O(14),铁皮石斛素P(16),铁皮石斛素Q(17),4,4′-二羟基-3,5-二甲氧基联苄(19),3,4-二羟基-5,4′-二甲氧基联苄(20),3′-羟基-3,4,5′-三甲氧基联苄(21),4,4′-二羟基-3,3′,5-三甲氧基联苄(22),3,4′-二羟基-5-甲氧基联苄(23),3′,4-二羟基-3,5′-二甲氧基联苄(24),二氢白藜芦醇(25),dendromoniliside E(26),denbinobin(27),2,4,7-三羟基-9,10-二氢菲(28)。
酚类化合物12个:N-p-香豆酰酪胺(29),反-N-(4-羟基苯乙基)阿魏酸酰胺(30),二氢松柏醇二氢对羟基桂皮酸酯(31),二氢阿魏酸酪胺(32),对羟基苯丙酰酪胺(33),丁香酸(34),丁香醛(35),香草酸(36),对羟基苯丙酸(37),对羟基桂皮酸(38),阿魏酸(39),对羟基苯甲酸(40)。
木脂素类化合物4个:(+)-丁香脂素-O-β-D-吡喃葡萄糖苷(41),icariolA_2-4-O-β-D-glucopyranoside(42),(+)-lyoniresinol-3a-O-β-D-glucopyranoside(43),及裂异落叶松脂醇(44)。
内酯类化合物2个:钩状石斛素(46)和洋地黄内酯(47)。二氢黄酮类化合物2个:柚皮素(48)和3′,5,5′,7-四羟基二氢黄酮(49)。其他类型化合物16个:铁皮石斛素R(18),erigesideⅡ(45),腺苷(50),尿苷(51),蔗糖(52),5-羟甲基糠醛(53),koaburaside(54),反式阿魏酸二十八烷基酯(55),对羟基反式肉桂酸三十烷基酯(56),对羟基顺式肉桂酸三十烷基酯(57),胡萝卜苷(58),β-谷甾醇(59),十六烷酸(60),十七烷(61),三十一烷醇(62),及十七烷酸(63)。
18个新化合物为:铁皮石斛素A(1),铁皮石斛素B(11),铁皮石斛素C(2),铁皮石斛素D(3),铁皮石斛素E(4),铁皮石斛素F(5),铁皮石斛素G(6),铁皮石斛素H(9),铁皮石斛素I(15),铁皮石斛素J(7),铁皮石斛素K(8),铁皮石斛素L(10),铁皮石斛素M(12),铁皮石斛素N(13),铁皮石斛素O(14),铁皮石斛素P(16),铁皮石斛素Q(17),及铁皮石斛素R(18)。
并对部分单体化合物进行了抗氧化和抗肿瘤活性初筛,发现大多数联苄类化合物具有抗氧化活性;有2个联苄类化合物具有抗肿瘤活性;并对活性筛选结果结合化合物的结构进行了初步的分析。还对石斛属植物中联苄类化学成分的结构特征及波谱规律进行了总结和探讨。
This paper reported the phytochemical investigation systematically on Dendrobium candidum,and bio-active screening results of the part chemical constituents isolated from Dendrobium candidum.In the meantime,this paper reported the progress of phytochemical studies on Dendrobium genus.
By using the chromatography techniques,72 compounds were isolated from the EtOAc and EtOH extrats of this plant's stems.On the basis of chemical methods and spectroscopic techniques,63 of these compounds were elucidated as follows:
27 stilbenoids:dendrocandin A(1),dendrocandin B(11),dendrocandin C(2), dendrocandin D(3),dendrocandin E(4),dendrocandin F(5),dendrocandin G(6), dendrocandin H(9),dendrocandin I(15),dendrocandin J(7),dendrocandin K(8), dendrocandin L(10),dendrocandin M(12),dendrocandin N(13),dendrocandin O(14), dendrocandin P(16),dendrocandin Q(17),4,4'-dihyxroxy-3,5-dimethoxybibenzyl(19), 3,4-dihydroxy-5,4'-dimethoxybibenzyl(20),3'-hydroxy-3,4,5'-trimethoxybibenzyl(21),4,4'-dihydroxy-3,3',5-trimethoxybibenzyl(22),3,4'-dihydroxy-5-methoxybibenzyl(23),3',4-dihydroxy-3,5'-dimethoxybibenzyl(24),dihydroresveratrol(25),dendromoniliside E(26), denbinobin(27),2,4,7-trihydroxy-9,10-dihydrophenanthrene(28).
12 phenols:paprazine(29),moupinamide(30),dihydroconiferyl dihydro-p -cumarate(31),dihydro-feruloyltyramine(32),p-hydroxyphenylpropionyl tyramine(33), syringic acid(34),syringaldehyde(35),vanillic acid(36),p-hydroxy-phenylpropionic acid(37),p-hydroxy cinnamic acid(38),ferulic acid(39),and 4-hydroxybenzoic acid (40).
4 lignans:(+)-syringaresinol-β-D-glucopyranoside(41),icariol A_2-4-O-β-D-glucopyranoside (42),(+)-lyoniresinol-3a-O-β-D-glucopyranoside(43),and(-)-secoisolariciresinol (44).
2 lactones:aduncin(46),and digiprolactone(47);2 flavanones:naringenin(48),and 3',5,5',7-tetrahydroxyflavanone(49).16 other compounds:dendrocandin R(18),erigesideⅡ(45),adenosine(50),uridine(51),sucrose(52),5-hydroxymethyl-furaldehyde(53), koaburaside(54),n-octacostyl ferulate(55),defuscin(56),n-triacontyl cis-p-coumarate(57), daucosterol(58),β-sitosterol(59),hexadecanoic acid(60),heptadecane(61),hentriacontane (62),heptadecanoic acid(63).
Among these compounds,18 are new ones:dendrocandin A(1),dendrocandin B (11),dendrocandin C(2),dendrocandin D(3),dendrocandin E(4),dendrocandin F(5), dendrocandin G(6),dendrocandin H(9),dendrocandin I(15),dendrocandin J(7), dendrocandin K(8),dendrocandin L(10),dendrocandin M(12),dendrocandin N(13), dendrocandin O(14),dendrocandin P(16),dendrocandin Q(17),and dendrocandin R (18).
As for the screening of antioxidant activity,most of the bibenzyls showed bio-activity;as for the screening of antitumour activity,only two compounds showed bio-activity.We concluded the relationship between the structures and the activities from the present results.
The structural and spectroscopic characteristics of bibenzyl derivatives from Dendrobium genus were concluded,and we hope that will be helpful for the structural elucidation of this type compounds.
引文
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