trans-(3S,5R,6R,9R)-megastigm-7-en-3,9-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: trans-(3S,5R,6R,9R)-megastigm-7-en-3,9-diol
• 英文别名: sarmentol F；(1S,4R,5R)-4-[(E,3R)-3-hydroxybut-1-enyl]-3,3,5-trimethylcyclohexan-1-ol
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: WIYDYJDQKNCJRC-RNKUOQLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-(3S,5R,6R,9R)-megastigm-7-en-3,9-diol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以60%的产率得到(3S,5R,6S,9R)-megastigman-3,9-diol
  参考文献：
  名称：

  Bioactive Constituents from Chinese Natural Medicines. XXII. Absolute Structures of New Megastigmane Glycosides, Sedumosides E1, E2, E3, F1, F2, and G, from Sedum sarmentosum (Crassulaceae)

  摘要：

  从景天科植物多肉植物（Sedum sarmentosum）的全株中分离出六种新的巨型萜糖苷，即 sedumosides E1、E2、E3、F1、F2 和 G。根据化学和物理化学证据阐明了新成分的结构，包括绝对构型。

  DOI：

  10.1248/cpb.55.435
• 作为产物：
  描述：

  (3S,5R,6R,7E,9R)-7-megastigmene-3,9-diol 3-O-β-D-(2'-O-β-D-apiofuranosyl)glucopyranoside 在 hesperidinase 、 β-glucosidase 作用下， 以 水 为溶剂， 反应 96.0h， 以1.1 mg的产率得到trans-(3S,5R,6R,9R)-megastigm-7-en-3,9-diol
  参考文献：
  名称：

  Crotonionosides A–G: Megastigmane glycosides from leaves of Croton cascarilloides Räuschel

  摘要：

  From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Croton cascarilloides, collected in Okinawa, Japan, seven megastigmane glycosides, named crotonionosides A-G, were isolated together with three known megastigmane glucosides, dendranthemosides A and B, and citroside A. This structures were elucidated by a combination of spectroscopic analyses, HPLC analyses, and application of the modified Mosher's method. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2010.10.003

文献信息

• Crotonionosides A–G: Megastigmane glycosides from leaves of Croton cascarilloides Räuschel
  作者：Susumu Kawakami、Katsuyoshi Matsunami、Hideaki Otsuka、Takakazu Shinzato、Yoshio Takeda

  DOI：10.1016/j.phytochem.2010.10.003

  日期：2011.1

  From the 1-BuOH-soluble fraction of a MeOH extract of leaves of Croton cascarilloides, collected in Okinawa, Japan, seven megastigmane glycosides, named crotonionosides A-G, were isolated together with three known megastigmane glucosides, dendranthemosides A and B, and citroside A. This structures were elucidated by a combination of spectroscopic analyses, HPLC analyses, and application of the modified Mosher's method. (C) 2010 Elsevier Ltd. All rights reserved.
• Bioactive Constituents from Chinese Natural Medicines. XXII. Absolute Structures of New Megastigmane Glycosides, Sedumosides E1, E2, E3, F1, F2, and G, from Sedum sarmentosum (Crassulaceae)
  作者：Toshio Morikawa、Yi Zhang、Seikou Nakamura、Hisashi Matsuda、Osamu Muraoka、Masayuki Yoshikawa

  DOI：10.1248/cpb.55.435

  日期：——

  Six new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). The structures of new constituents including the absolute configuration were elucidated on the basis of chemical and physicochemical evidence.

  从景天科植物多肉植物（Sedum sarmentosum）的全株中分离出六种新的巨型萜糖苷，即 sedumosides E1、E2、E3、F1、F2 和 G。根据化学和物理化学证据阐明了新成分的结构，包括绝对构型。