Jiang Y, Wang N, Yao X, Susumu K
Department of Natrual Products Chemistry, Shenyang Pharmaceutical University, Shenyang, 110015.
Yao Xue Xue Bao. 1998 May;33(5):355-61.
Six compounds were isolated from the anticoagulation and anticancer fractions of the bulbs of Allium chinense G. Don. On the basis of chemical evidence and spectral analysis (IR, EI-MS, 1HNMR, 13CNMR, 1H-1H COSY, HMBC, HMQC and NOESY), their structures were established as (25R, S)-5 alpha-spirostane-3 beta-ol 3-O-(beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-beta-D- glucopyranosyl-(1-->4)-beta-D-galactopyranoside) (1), (25R, S)-5 alpha-spirostane-3 beta-ol 3-O-(beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl-(1-->3)- (1-->4)-beta-D-galactopyranoside) (2), (25R, S)-5 alpha-spirostane-2 alpha, 3 beta-diol 3-O-(beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->4)-beta-D- galactopyranoside) (3), (25S)-24-O-beta-D-glucopyranosyl-3 beta, 24 beta-dihydroxy-5 alpha-spirost-3-O-alpha-arabinopyranosyl-(1-->6)-beta-D-glucopyranoside (4), chinenoside II (5) and 2,3,4,9-tetrahydro-1-methyl-1H-pyrido [3,4-b] indole-3-carboxylic acid (6). 4 is a new steroidal saponin, named chinenoside VI. Compounds 1 to 3 are three pairs of steroidal saponin epimers. Among them, the 25S epimer of 2 is first reported, the 25R epimer of 2 and compound 6 were isolated from this title plant for the first time. The relative configuration of compound 6 was firstly determined by NOESY spectrum, and signals of C, H were assigned definitely.
从薤白鳞茎的抗凝和抗癌部位分离得到6种化合物。基于化学证据和光谱分析(红外光谱、电子轰击质谱、核磁共振氢谱、核磁共振碳谱、氢-氢化学位移相关谱、异核多键相关谱、异核单量子关系谱和核欧沃豪斯效应谱),确定它们的结构分别为(25R, S)-5α-螺旋甾烷-3β-醇3-O-(β-D-吡喃葡萄糖基-(1→2)-[β-D-吡喃葡萄糖基-(1→3)]-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃半乳糖苷)(1)、(25R, S)-5α-螺旋甾烷-3β-醇3-O-(β-D-吡喃葡萄糖基(1→2)-β-D-吡喃葡萄糖基-(1→3)-(1→4)-β-D-吡喃半乳糖苷)(2)、(25R, S)-5α-螺旋甾烷-2α, 3β-二醇3-O-(β-D-吡喃葡萄糖基-(1→2)-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃半乳糖苷)(3)、(25S)-24-O-β-D-吡喃葡萄糖基-3β, 24β-二羟基-5α-螺旋甾-3-O-α-L-阿拉伯吡喃糖基-(1→6)-β-D-吡喃葡萄糖苷(4)、薤白皂苷II(5)和2,3,4,9-四氢-1-甲基-1H-吡啶并[3,4-b]吲哚-3-羧酸(6)。化合物4是一种新的甾体皂苷,命名为薤白皂苷VI。化合物1至3是三对甾体皂苷差向异构体。其中,化合物2的25S差向异构体为首次报道,化合物2的25R差向异构体和化合物6为首次从该植物中分离得到。化合物6的相对构型首次通过核欧沃豪斯效应谱确定,并明确归属了碳、氢信号。