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来自胀果黍(Panicum turgidum Forssk.)的细胞毒性甾体皂苷

Cytotoxic steroidal saponins from Panicum turgidum Forssk.

作者信息

Zaki Ahmed A, Ali Zulfiqar, Wang Yan-Hong, El-Amier Yasser A, Khan Shabana I, Khan Ikhlas A

机构信息

Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt; National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USA.

National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USA.

出版信息

Steroids. 2017 Sep;125:14-19. doi: 10.1016/j.steroids.2017.06.003. Epub 2017 Jun 17.

DOI:10.1016/j.steroids.2017.06.003
PMID:28629616
Abstract

Three new bidesmosidic cholestane-type steroidal glycosides, 16-O-β-d-glucopyranosyl-cholest-5-en-3β,16β-diol-22-one-3-O-α-l-rhamnopyranosyl-(1→2)-O-[(β-d-glucopyranosyl(1→4)]-O-β-d-glucopyranoside (1), 16-O-β-d-glucopyranosylcholest-5-en-3β,16β-diol-22-one-3-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranoside (2), and 16-O-β-d-glucopyranosylcholestan-3β,16β-diol-6,22-dione-3-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranoside (3) were isolated from a methanolic extract of Panicum turgidum. In addition four known compounds, pennogenin 3β-O-α-l-rhamnopyranosyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)-O-α-l-rhamnopyranosyl-(1→4)]-O-β-d-glucopyranoside (4), yamogenin 3β-O-α-l-rhamnopyranosyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)]-O-β-d-glucopyranoside (5), yamogenin 3β-O-α-l-rhamnopyranosyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)-O-α-l-rhamnopyranosyl-(1→4)]-O-β-d-glucopyranoside (6), and pennogenin 3β-O-α-l-rhamnopyranosyl-(1→2)-O-[α-l-rhamnopyranosyl-(1→4)]-O-β-d-glucopyranoside (7) were also isolated and characterized. Their structures were established using extensive spectroscopic methods including 1D and 2D NMR and HRESIMS. The isolated compounds were screened for cytotoxicity towards a panel of mammalian cell lines and 4-7 were found to be cytotoxic.

摘要

从胀果黍的甲醇提取物中分离出三种新的双糖苷甾体胆甾烷型糖苷,分别为16 - O - β - d - 吡喃葡萄糖基 - 胆甾 - 5 - 烯 - 3β,16β - 二醇 - 22 - 酮 - 3 - O - α - l - 吡喃鼠李糖基 - (1→2) - O - [(β - d - 吡喃葡萄糖基(1→4)] - O - β - d - 葡萄糖苷(1)、16 - O - β - d - 吡喃葡萄糖基胆甾 - 5 - 烯 - 3β,16β - 二醇 - 22 - 酮 - 3 - O - α - l - 吡喃鼠李糖基 - (1→2) - O - β - d - 葡萄糖苷(2)以及16 - O - β - d - 吡喃葡萄糖基胆甾烷 - 3β,16β - 二醇 - 6,22 - 二酮 - 3 - O - α - l - 吡喃鼠李糖基 - (1→2) - O - β - d - 葡萄糖苷(3)。此外,还分离并鉴定了四种已知化合物,分别为偏诺皂苷元3β - O - α - l - 吡喃鼠李糖基 - (1→2) - O - [α - l - 吡喃鼠李糖基 - (1→4) - O - α - l - 吡喃鼠李糖基 - (1→4)] - O - β - d - 葡萄糖苷(4)、薯蓣皂苷元3β - O - α - l - 吡喃鼠李糖基 - (1→2) - O - [α - l - 吡喃鼠李糖基 - (1→4)] - O - β - d - 葡萄糖苷(5)、薯蓣皂苷元3β - O - α - l - 吡喃鼠李糖基 - (1→2) - O - [α - l - 吡喃鼠李糖基 - (1→4) - O - α - l - 吡喃鼠李糖基 - (1→4)] - O - β - d - 葡萄糖苷(6)以及偏诺皂苷元3β - O - α - l - 吡喃鼠李糖基 - (1→2) - O - [α - l - 吡喃鼠李糖基 - (1→4)] - O - β - d - 葡萄糖苷(7)。使用包括一维和二维核磁共振以及高分辨电喷雾电离质谱等多种光谱方法确定了它们的结构。对分离得到的化合物针对一组哺乳动物细胞系进行了细胞毒性筛选,发现4 - 7具有细胞毒性。

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