姜勇, 王乃利, 姚新生, 北中进. 薤中抗凝和抗癌活性成分的结构鉴定J. 药学学报, 1998, 33(5): 355-361.
引用本文: 姜勇, 王乃利, 姚新生, 北中进. 薤中抗凝和抗癌活性成分的结构鉴定J. 药学学报, 1998, 33(5): 355-361.
Jiang Yong, Wang Naili, Yao Xinsheng, Kitanaka Susumu, . STRUCTURAL ELUCIDATION OF THE ANTICOAGULATION AND ANTICANCER CONSTITUENTS FROM ALLIUM CHINENSEJ. Acta Pharmaceutica Sinica, 1998, 33(5): 355-361.
Citation: Jiang Yong, Wang Naili, Yao Xinsheng, Kitanaka Susumu, . STRUCTURAL ELUCIDATION OF THE ANTICOAGULATION AND ANTICANCER CONSTITUENTS FROM ALLIUM CHINENSEJ. Acta Pharmaceutica Sinica, 1998, 33(5): 355-361.

薤中抗凝和抗癌活性成分的结构鉴定

STRUCTURAL ELUCIDATION OF THE ANTICOAGULATION AND ANTICANCER CONSTITUENTS FROM ALLIUM CHINENSE

  • 摘要: 从百合科葱属植物薤(Alium chinense)鳞茎的抗凝和抗癌活性部位中,分离得到了6个化合物。经过化学方法和光谱分析(IR,EI-MS,1HNMR,13HNMR,1H-1HCOSY,HMBC,HMQC和NOESY谱),鉴定它们的结构分别为(25R,S)-5α-spirostane-3β-ol 3-O-{β-D-glucopyranosyl-(1→2)-β-D-glucopyra-nosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}(1),(25R,S)-5α-spirostane-3β-ol 3-O-{β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)(6-acetyl-β-D-glucopyranosyl)-(1→4)-β-D-galac-topyranoside}(2),(25R,S)-5α-spirostane-2α,3β-diol3-O-{β-D-glucopyranosyl-(1→2)-O-β-D-glucopyra-nosyl-(1→4)-β-D-galactopyranoside}(3),(25S)-24-O-β-D-glucopyranosyl3β,24β-dihydroxy-5α-spirost-3-O-α-arabinopyranosyl-(1→6)-β-D-glucopyranoside(4),chinenosideI(5)及2,3,4,9-tetrahydro-1-methyl-1H-pyrido3,4-bindole-3-carboxylicacid(6)。化合物4为一新的甾体皂甙,命名为chinenosideVI。化合物1~3为3对甾体皂甙差向异构体。其中,化合物2的25S型异构体为首次报道;25R型异构体和化合物6为首次从本种植物中分得。此外,通过NOESY谱还首次确定了化合物6的相对构型,并对其C和H信号进行了确切归属。

     

    Abstract: 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)-5α-spirostane-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1), (25R,S)-5α-spirostane-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)(6-acetyl-β-D-glucopyranosyl)-(1→4)-β-D-galactopyranoside (2), (25R,S)-5α-spirostane-2α,3β-diol-3-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (3), (25S)-24-O-β-D-glucopyranosyl-3β,24β-dihydroxy-5α-spirost-3-O-α-arabinopyranosyl-(1→6)-β-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.

     

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