(25R)-5α-spirostan-3β-yl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (25R)-5α-spirostan-3β-yl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
• 英文别名: tiogenin 3-O-β-D-glucopyranosyl-(1-2)-β-D-glycopyranosyl-(1-4)-β-D-galactopyranoside；tigogenin 3-O-β-lucotrioside；atroposide E；(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₄₅H₇₄O₁₈
• 分子量: 903.072
• InChiKey: JNTJNUDLVQQYGM-SSAIJFDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  63
• 可旋转键数：
  9
• 环数：
  9.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  276
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  (2S,3R,4S,5R)-2-[(2S,3R,4R,5R,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxyoxane-3,4,5-triol 生成 (25R)-5α-spirostan-3β-yl O-β-D-glucopyranosyl-(1->2)-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
  参考文献：
  名称：

  NAKANO, KIMIKO;MATSUDA, EMI;TSURUMI, KAORI;YAMASAKI, TOKUSHI;MURAKAMI, KO+, PHYTOCHEMISTRY, 27,(1988) N 10, C. 3235-3239

  摘要：

  DOI：

文献信息

• The steroidal glycosides of the flowers of Yucca gloriosa
  作者：Kimiko Nakano、Emi Matsuda、Kaori Tsurumi、Tokushi Yamasaki、Kotaro Murakami、Yoshihisa Takaishi、Toshiaki Tomimatsu

  DOI：10.1016/0031-9422(88)80033-5

  日期：1988.1

  Abstract Four steroidal compounds were isolated from the fresh flowers of Yucca gloriosa and their structures were elucidated as tigogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, gitogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, gitogenin 3-O-α- l -rhamnopyranosyl-β-lycotetraoside and proto-type of gitogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, on the basis of physical and chemical investigations

  摘要 从兰兰鲜花中分离得到4种甾体化合物，并阐明了其结构为：tigogenin 3-O-β-d-吡喃木糖基-β-lycotetraoside、gitogenin 3-O-β-d-xylopyranosyl-β-lycotetraoside、gitogenin 3-O-α-l -rhamnopyranosyl-β-lycotetraoside 和 gitogenin 3-O-β-d -xylopyranosyl-β-lycotetraoside 的原型，基于物理和化学研究。
• Steroidal saponins from the whole plants of Agave utahensis and their cytotoxic activity
  作者：Akihito Yokosuka、Yoshihiro Mimaki

  DOI：10.1016/j.phytochem.2009.02.013

  日期：2009.4

  Phytochemical investigation of the whole plants of Agave utahensis Engelm. (Agavaceae) has resulted in the isolation of 15 steroidal saponins (1-15), including five spirostanol saponins (1-5) and three furostanol saponins (11-13). Structures of compounds 1-5 and 11-13 were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells. (C) 2009 Elsevier Ltd. All rights reserved.