(25S)-spirost-5-ene-3β,27-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25S)-spirost-5-ene-3β,27-diol
• 英文别名: isonarthogenin；(25s)-Spirost-5-ene-3beta,27-diol；(1S,2S,4S,5'S,6R,7S,8R,9S,12S,13R,16S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-ol
• 化学式: C₂₇H₄₂O₄
• 分子量: 430.628
• InChiKey: NZQMLFKQRZBSPM-CAKNJAFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1S,2S,4S,5'S,6R,7S,8R,9S,12S,13R,16S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol 生成 (25S)-spirost-5-ene-3β,27-diol
  参考文献：
  名称：

  MIMAKI, YOSHIHIRO;SASHIDA, YUTAKA, PHYTOCHEMISTRY, 29,(1990) N, C. 2267-2271

  摘要：

  DOI：

文献信息

• Steroidal saponins from the bulbs of Lilium longiflorum and their antitumour-promoter activity
  作者：Yoshihiro Mimaki、Osamu Nakamura、Yutaka Sashida、Yoshiko Satomi、Atsuko Nishino、Hoyoku Nishino

  DOI：10.1016/0031-9422(94)85030-5

  日期：1994.1

  3-O-(O-alpha-L-rhamnopyranosyl-(1 --> 2)- O-[beta-D-xylopyranosyl-(1 --> 3)]-beta-D-glucopyranoside). The isolated saponins and their derivatives were examined for inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to find new antitumour-promoter compounds.

  从长花百合的新鲜鳞茎中分离出两种新的螺甾醇皂苷和两种新的呋甾醇皂苷以及几种已知的皂苷。新化合物的结构被确定为 (25S)-spirost-5-ene-3 beta, 27-diol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-O- [alpha -L-阿拉伯吡喃糖基-(1-->3)]-β-D-吡喃葡萄糖苷)，(25R)-27-O-[(S)-3-羟基-3-甲基戊二酰基]-spirost-5-ene-3 β,27二醇3-O-(O-α-L-吡喃鼠李糖基-(1-->2)-O-[α-L-阿拉伯吡喃糖基-(1-->3)]-β-D-吡喃葡萄糖苷)， 22-O-甲基-26-O-β-D-吡喃葡萄糖基-(25R)-furost-5-ene-3 beta,22 xi, 26-triol 3-O-(O-alpha-L-rhamnopyranosyl-(1 -->2)-O-[α-L
• MIMAKI, YOSHIHIRO;SASHIDA, YUTAKA, CHEM. AND PHARM. BULL., 38,(1990) N1, C. 3055-3059
  作者：MIMAKI, YOSHIHIRO、SASHIDA, YUTAKA

  DOI：——

  日期：——
• Cytotoxic Steroidal Saponins from <i>Polygonatum </i><i>z</i><i>anlanscianense</i>
  作者：Jian-Ming Jin、Ying-Jun Zhang、Hai-Zhou Li、Chong-Ren Yang

  DOI：10.1021/np049897u

  日期：2004.12.1

  Four new steroidal saponins, polygonatosides A-D (1-4), were isolated from the rhizomes of Polygonatum zanlanscianense, together with six known spirostanols (5-10) and a known megastigmane glycoside (11). Their structures were elucidated on the basis of spectroscopic analysis and the results of acidic and enzymatic hydrolysis. The cytotoxic activities of 1-11 against HeLa cells are described.