钮子瓜和袋花忍冬的化学成分研究

钮子瓜（Zehneria maysorensis Arn.）是一种常用的中草药，其性味苦、凉，主要功效为清热利湿、散风止痛，主治膀胱炎、头痛。体外活性筛选实验表明，袋花忍冬（Lonicera saccata Rehd.）95%乙醇提取物的乙酸乙酯部分对血管紧张素转化酶显示较强的抑制活性。为明确钮子瓜的药用物质基础和袋花忍冬中具有ACE抑制活性的成分，首次对两个植物的成分进行了研究。 1. 从钮子瓜95%乙醇提取物中主要通过色谱方法首次分离了14个化合物，通过波谱方法鉴定为(2S,3S,4R,10E)-2-[(2R)-2-羟基二十四烷酰基氨基]-10-十八烷-1,3,4-三醇（1）、(2S,3S,4R)-2-二十四烷酰基氨基-十八烷-1,3,4-三醇 （2）、胡萝卜苷（3）、swertish （4）、苯甲酸（5）、水杨酸（6）、loliolide （7）、胸腺嘧啶（8）、尿嘧啶（9）、(23Z)-9,19-环阿尔廷-23-烯-3β,25-二醇（10）、(20S,22E,24R)-5α,8α-表二氧-麦角甾-6,22-二烯-3β-醇（11）、十六烷酸 1-甘油酯（12）、大豆脑苷Ⅰ（13）和(22E,24S)-24-甲基-5α-胆甾-7,22-二烯-3β,5α,6β-三醇（14）。其中化合物4为一黄酮碳苷，具有旋转异构现象，有止痛作用；化合物6具有抗炎、镇痛、减热的活性，它们可能是钮子瓜药用物质基础的一部分。 2. 从袋花忍冬95%乙醇提取物中首次分离并鉴定了16个已知化合物：胡萝卜苷（3）、(20S,22E,24R)-5α,8α-表二氧-麦角甾-6,22-二烯-3β-醇（11）、十六烷酸 1-甘油酯（12）、E-p-coumaryl behenate (15)、谷甾醇（16）、2,6-dihydroxyhumula-3(12), 7(13),9(E)-triene (17)、环阿尔廷-25-烯-3β,24ξ-二醇 (18)、二十四烷酸 (19)、2,4-二羟基-3,6-二甲基苯甲酸甲酯 (20)、乌苏酸 (21)、柚皮素 (22)、木犀草素 (23)、柏双黄酮（24）咖啡酸 (25)、洋芹素（26）和木犀草素-7-O-β-D-葡萄糖苷 (27)。其中木犀草素（23）和咖啡酸（25）含量较高，它们为抑制ACE活性的成分。 3．综述了黄酮碳苷的旋转异构现象。 Zehneria maysorensis is a folk medicine for the treatment of cystitis and headache. The ethyl acetate soluble fraction of the 95% ethanol extract of Lonicera saccata showed obvious ACE inhibitory activity in vitro. To reveal their active constitutents, they were subjected to chemically study. From the 95% ethanol extract of the whole plants of Zehneria maysroensis fourteen compounds were isolated for the first time. On the basis of spectral data and/or by comparison with authentic samples, they were characterized to be (2S,3S,4R,10E)-2-[(2R)-2-hydroxytetracosanoylamino]-10-octadecene-1,3,4-triol (1), (2S,3S,4R)-2-tetracosanoylamino-1,3,4-octadecanetriol (2), daucosterol (3), swertish (4), benzoic acid (5), salicylic acid (6), loliolide (7), thymine (8), uracil (9), (23Z)-9,19-cycloart-23-ene-3β,25-diol (10), (20S,22E,24R)-5α,8α-epidioxy-ergosta- 6,22-diene-3β-ol (11), 2,3-dihydroxypropyl hexadecoate (12), soya-cerebroside (13) and (22E,24S)-24-methyl-5α-cholesta-7,22-diene-3β,5α,6β-triol (14). Compound 4, a C-glycosylflavone, showed a very interesting rotational isomerism. Compounds 4 and 6 may be the active constituents of Zehneria maysorensis considering their sedative and anti-inflammation activity, respectively. From the whole plants of Lonicera saccata, sixteen compounds were isolated for the first time. On the basis of spectral data and/or by comparison with authentic samples, they were identified to be daucosterol (3), (20S,22E,24R)-5α,8α-epidioxy- ergosta-6,22-diene-3β-ol (11), 2,3-dihydroxypropyl hexadecoate (12), E-p-coumaryl behenate (15), β-sitosterol (16), 2,6-dihydroxyhumula-3(12),7(13),9(E)-triene (17), cycloart-25-ene-3β,24ξ-diol (18), tetracosanoic acid (19), methyl 2,4-dihydroxy- 3,6-dimethylbenzoate (20), ursolic acid (21), naringenin (22), luteolin (23), cupressuflavone (24), caffeic acid (25), apigenin (26) and luteolin-7-O-β-D- glucopyranoside (27). Luteolin (23) and caffeic acid (25) were the ACE inhibitory active constituents. Rotational isomerism for C-glycosylflavonoid was reviewed.