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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5~7,9,15,28~34外,其他化合物均为从手参属植物中首次分离得到;10~12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 study the chemical constituents of Gymnadenia conopsea Methods: The compounds were isolated and purified by macroporous resin, silica gel, Sephadex LH-20, RP-HPLC, medium pressure liquid chromatography and HPLC. The structures of the compounds were identified by spectral data analysis. Results: 34 compounds were isolated and identified from the ethanol extract of tuber of ginseng medicinal part, including 6 2-isobutylcarbosyltartrate: vimentin A, B, E and D (1-4 ), dactylorhin B (5) and loroglossin (6); three 2-isobutylcarbamases: dactylorhin A (7), dactylorhin E (15), lappaol A (11) and lappaol F (12); six aromatic acid (or aldehyde or alcohol) derivatives Phenol glycosides: 4-β-D-glucopyranosyloxy trans-styrene (14), gastrodin (15), 4- (β-D-glucopyranose) benzaldehyde (16), 4 - (β-D-glucopyranose) benzyl methyl ether (17), 4- (β-D-glucopyranose) (19); 4 cyclic dipeptides: cyclo (L-leucine-L-tyrosine) (20) (22) and cyclo (L-alanine-L-phenylalanine) (23); one N6-substituted adenosine: N6- (24); 1 amide: N-trans-ferulicitramine (25); 9 aromatic acids (or aldehyde or alcohol) derivatives: 3-hydroxybenzoic acid ), 4 Hydroxyisopenic acid (27), 4-hydroxybenzyl alcohol (28), 4-hydroxybenzyl ether (29), 4- hydroxybenzaldehyde (30), 4- hydroxybenzoic acid 4-hydroxybenzoic acid (32), trans-p-hydroxyphenyl acrylic acid (33) and cis-p-hydroxybenzene acrylic acid (34). The compounds were all isolated from the genus Panax notoginseng for the first time except for the compounds 5 ~ 7, 9, 15, 28 ~ 34. The formation of malondialdehyde (MDA) in rat liver microsomes induced by Fe2 + -Cys 10-12 The inhibitory rates were 53%, 59% and 52% at the concentration of 1 × 10-6mol.L-1, respectively. The inhibition rate of positive control drug VE was 35%.