(6S)-hydroxy-29-nor-3,4-seco-cycloart-4(30),24-dien-3-oic 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: (6S)-hydroxy-29-nor-3,4-seco-cycloart-4(30),24-dien-3-oic acid
• 英文别名: 3-[(1S,4R,5R,8S,9S,11S,12S,13R)-12-ethenyl-11-hydroxy-4,8-dimethyl-5-[(2R)-6-methylhept-5-en-2-yl]-13-tetracyclo[7.5.0.01,13.04,8]tetradecanyl]propanoic acid
• 化学式: C₂₉H₄₆O₃
• 分子量: 442.682
• InChiKey: JCKMCGRZLQGGCS-IRUUMJFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (6S)-hydroxy-29-nor-3,4-seco-cycloart-4(30),24-dien-3-oic acid 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以1.9 mg的产率得到(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (2S,3S,3aR,4aS,6aR,7R,9aS,9bS)-3a-(2-carboxy-ethyl)-7-((R)-1,5-dimethyl-hex-4-enyl)-6a,9a-dimethyl-3-vinyl-dodecahydro-cyclopenta[a]cyclopropa[e]naphthalen-2-yl ester
  参考文献：
  名称：

  Cyclooxygenase-inhibitory and antioxidant constituents of the aerial parts of Antirhea acutata

  摘要：

  Two new compounds, (6S)-hydroxy-29-nor-3,4-seco-cycloart-4(30),24-dien-3-oic acid (1) and 8-[1-(3,4-dihydroxyphenyl)-3-methoxy-3-oxopropyl]epicatechin (3), were isolated by bioassay-guided fractionation from the aerial parts of Antirhea acutata (DC.) Urb. (Rubiaceae). Compound 1 showed moderate inhibitory activities in cyclooxygenase-1 and -2 assays (IC50 43.7 and 4.7 muM, respectively), while compound 3 was active in 1,1-diphenyl-2-picrylhydrazyl free-radical and cytochrome c reduction antioxidant assays (IC50 29.1 and 16.3 muM, respectively). Additionally, one further new compound was isolated, (3S,24S)-25-trihydroxy-9,19-cycloartane-29-oic acid (2), but this was inactive in the bioassay systems used. Compound 1 is based on the unprecedented 29-nor-3,4-seco-cycloartane skeleton. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00129-9

文献信息

• Cyclooxygenase-inhibitory and antioxidant constituents of the aerial parts of Antirhea acutata
  作者：Dongho Lee、Eun Jung Park、Muriel Cuendet、Franklin Axelrod、Pedro I. Chavez、Harry H.S. Fong、John M. Pezzuto、A.Douglas Kinghorn

  DOI：10.1016/s0960-894x(01)00129-9

  日期：2001.6

  Two new compounds, (6S)-hydroxy-29-nor-3,4-seco-cycloart-4(30),24-dien-3-oic acid (1) and 8-[1-(3,4-dihydroxyphenyl)-3-methoxy-3-oxopropyl]epicatechin (3), were isolated by bioassay-guided fractionation from the aerial parts of Antirhea acutata (DC.) Urb. (Rubiaceae). Compound 1 showed moderate inhibitory activities in cyclooxygenase-1 and -2 assays (IC50 43.7 and 4.7 muM, respectively), while compound 3 was active in 1,1-diphenyl-2-picrylhydrazyl free-radical and cytochrome c reduction antioxidant assays (IC50 29.1 and 16.3 muM, respectively). Additionally, one further new compound was isolated, (3S,24S)-25-trihydroxy-9,19-cycloartane-29-oic acid (2), but this was inactive in the bioassay systems used. Compound 1 is based on the unprecedented 29-nor-3,4-seco-cycloartane skeleton. (C) 2001 Elsevier Science Ltd. All rights reserved.