coussaric acid

• 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: coussaric acid
• 英文别名: (1S,4aR,6aR,6aS,6bR,8aR,9S,10R,12aR,14bS)-1,10-dihydroxy-9-(hydroxymethyl)-1,6a,6b,9,12a-pentamethyl-2-methylidene-4,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-3H-picene-4a-carboxylic acid
• 化学式: C₃₀H₄₆O₅
• 分子量: 486.692
• InChiKey: GNUFXZJKHUYVFB-HIABBIIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 coussaric acid 以 甲醇 、 乙醚 、 氯仿 为溶剂， 生成 coussaric acid methyl ester
  参考文献：
  名称：

  Isolation and absolute stereochemistry of coussaric acid, a new bioactive triterpenoid from the stems of Coussarea brevicaulis

  摘要：

  Coussaric acid (1), a triterpenoid based on an ursane skeleton, and an oleanane-type triterpene acid, 3-epi-spathodic acid (2), as well as four known compounds, barbinervic acid, scutellaric acid, stigmasterol and stigmasterol glucoside, have been isolated from an EtOAc-soluble extract of the stems of Coussarea brevicaulis. The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic investigation, and single-crystal X-ray crystallography was used to confirm the structure of 1. The absolute stereochemistry of 1 was established by chemical transformations and by the Mosher ester procedure. The potential of the isolates and chemical transformation products to induce quinone reductase was evaluated in mouse Hepa lclc7 hepatoma cells. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00268-1

文献信息

• Isolation and absolute stereochemistry of coussaric acid, a new bioactive triterpenoid from the stems of Coussarea brevicaulis
  作者：Bao-Ning Su、Young-Hwa Kang、Rosa Elena Pinos、Bernard D. Santarsiero、Andrew D. Mesecar、D.Doel Soejarto、Harry H.S. Fong、John M. Pezzuto、A.Douglas Kinghorn

  DOI：10.1016/s0031-9422(03)00268-1

  日期：2003.9

  Coussaric acid (1), a triterpenoid based on an ursane skeleton, and an oleanane-type triterpene acid, 3-epi-spathodic acid (2), as well as four known compounds, barbinervic acid, scutellaric acid, stigmasterol and stigmasterol glucoside, have been isolated from an EtOAc-soluble extract of the stems of Coussarea brevicaulis. The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic investigation, and single-crystal X-ray crystallography was used to confirm the structure of 1. The absolute stereochemistry of 1 was established by chemical transformations and by the Mosher ester procedure. The potential of the isolates and chemical transformation products to induce quinone reductase was evaluated in mouse Hepa lclc7 hepatoma cells. (C) 2003 Elsevier Ltd. All rights reserved.

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