摘要
目的:研究手参属药用植物手参Gymnadenia conopsea的化学成分。方法:用乙醇提取后通过大孔树脂、硅胶、凝胶Sephadex LH-20、反相闪式快速分离、中压液相色谱和高效制备液相色谱分离纯化;运用光谱数据解析鉴定化合物结构。结果:从手参药用部位块茎的乙醇提取物中分离鉴定了34个化合物,其中包括6个2-异丁基酒石酸苄酯苷:凹舌兰素A,B,E和D(1-4),dactylorhin B(5)和loroglossin(6);3个2-异丁基苹果酸苄酯苷:dactylorhin A(7),dactylorhin E(8)和militarine(9);3个木脂素类:牛蒡酚(10),lappaol A(11)和lappaol F(12);6个芳香酸(或醛或醇)衍生物酚苷类:4-β-D-吡喃葡萄糖氧基反式苯丙稀酸(13)、4-β-D-吡喃葡萄糖氧基顺式苯丙稀酸(14)、天麻素(15)、4-(β-D-吡喃葡萄糖)苯甲醛(16)、4-(β-D-吡喃葡萄糖)苄基甲基醚(17)、4-(β-D-吡喃葡萄糖)苄基乙基醚(18)和双(4-羟基苄基)醚单β-D-葡萄糖苷(19);4个环二肽:环(L-亮氨酸-L-酪胺酸)(20)、环(L-亮氨酸-L-脯胺酸)(21)、环(L-缬氨酸-L-酪胺酸)(22)和环(L-丙氨酸-L-苯丙胺酸)(23);1个N6-取代的腺苷类:N6-(4-羟基苄基)-腺苷(24);1个酰胺类:N-trans-阿魏酰色胺(25);9个芳香酸(或醛或醇)衍生物:3-羟基苯甲酸(26)、4-羟基异肽酸(27)、4-羟基苯甲醇(28)、4-羟基苄甲醚(29)、4-羟基苯甲醛(30)、4-羟基苯甲酸(31)、3-甲氧基-4-羟基苯甲酸(32)、反式-对羟基苯丙烯酸(33)和顺式-对羟基苯丙烯酸(34)。除化合物57,9,15,2834外,其他化合物均为从手参属植物中首次分离得到;1012对Fe2+-Cys诱导大鼠肝微粒体丙二醛(MDA)的生成有抑制作用,在1×10^-6mol.L^-1浓度下抑制率分别为53%,59%,52%,阳性对照药VE的抑制率为35%。
Objective: To investigate the chemical constituents of tuber of Gymnadenia conopsea.Method: The constituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel,Sephadex LH-20,and C-18,as well as reversed-phase HPLC.Structures of the isolates were identified by spectroscopic data analysis.Result: Thirty-four compounds were isolated.Their structures were identified as six 2-isobutyltartrate benzyl ester glucosides: coelovirin A(1),coelovirin B(2),coelovirin E(3),coelovirin D(4),dactylorhin B(5) and loroglossin(6).Three 2-isobutylmalate benzyl ester glucosides: dactylorhin A(7),dactylorhin E(8) and militarine(9).Three lignans: arctigenin(10),lappaol A(11) and lappaol F(12).Six aromatic acid(alhyde or alcohol) derivatives: 4-β-D-glucopyranosyloxyl-trans-phenylpropenoic acid(13),4-β-D-glucopyranosyloxyl-cis-phenylpropenoic acid(14),gastrodin(15),4-β-D-glucopyranosyloxylphenylaldehyde(16),4-β-D-glucopyranosyloxylbenzyl methyl ether(17),4-β-D-glucopyranosyloxylbenzyl ethyl ether(18),and bis(4-hydroxybenzyl) ether mono 4-O-β-D-glucopyranoside(19).Four cyclodipeptides: cyclo(L-Leu-L-Tyr)(20),cyclo(L-Leu-L-Pro)(21),cyclo(L-Val-L-Tyr)(22),and cyclo(L-Ala-D-Phe)(23).One N6-substituted andenosine: N6-(4-hydroxybenzyl)-adenine riboside(24).An aromatic amide: N-trans-feruloyltyramine(25).Nine aromatic acids(or aldehyde or alcohol): 3-hydroxybenzoic acid(26),4-hydroxyisophthalic acid(27),4-hydroxybenzyl alcohol(28),4-hydroxybenzyl methyl ether(29),4-hydroxybenzylaldehyde(30),4-hydroxybenzoic acic(31),4-hydroxy-3-methoxybenzoic acid(32),trans-p-hydroxyphenylpropenoic acid(33),and cis-p-hydroxyphenylpropenoic acid(34).At a concentration of 1.0×10^-6 mol·L^-1,compounds 10-12 showed antioxidative activity inhibiting Fe+2-cystine induced rat liver microsomal lipid peroxidation with inhibitory rates of 53%,59%,and 52%,respectively(positive control VE with 35% inhibition).Conclusion: These compounds were obtained from the genus Gymnadenia for the first time except for 5-7,9,15,28-34.Compounds 10-12 possess antioxidant activity.
出处
《中国中药杂志》
CAS
CSCD
北大核心
2010年第21期2852-2861,共10页
China Journal of Chinese Materia Medica
基金
国家自然科学基金项目(30825044
20932007)
教育部长江学者和创新团队支持计划项目(IRT0514)
关键词
手参
手参属
兰科
化学成分
活性筛选
Gymnadenia
Gymnadenla conopsea
chemical constituents
antioxidant activity