3β-O-(8-hydroxyoctanoyl)-12-oleanene | 1221592-92-2

• 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: 3β-O-(8-hydroxyoctanoyl)-12-oleanene
• 英文别名: [(3S,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl] 8-hydroxyoctanoate
• CAS: 1221592-92-2
• 化学式: C₃₈H₆₄O₃
• 分子量: 568.924
• InChiKey: PHCZGDLRLHOTIB-XJEZUUIPSA-N

物化性质

• 沸点：
  604.7±55.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 3β-O-(8-hydroxyoctanoyl)-12-oleanene 在 盐酸 作用下， 以 水 为溶剂， 反应 18.0h， 生成 8-羟基辛酸甲酯 、 β-香树精
  参考文献：
  名称：

  New Triterpenoids and Other Constituents from a Special Microbial-Fermented Tea—Fuzhuan Brick Tea

  摘要：

  Fuzhuan brick tea, a special microbial-fermented tea prepared from the leaves of Camellia sinensis var. sinensis, is a traditional beverage used in China throughout history. Phytochemical investigation of this material led to the identification of three new triterpenoids, 3 beta,6 alpha,13 beta-trihydroxyolean-7-one (1), 3 beta-acetoxy-6 alpha,13 beta-dihydroxyolean-7-one (2), and 3 beta-O-(8-hydroxyoctanoyl)-12-oleanene (3), together with 11 known compounds, friedelin (4), beta-amyrone (5), beta-amyrin (6), alpha-spinasterone (7), alpha-spinasterol (8), 22,23-dihydro-alpha-spinasterone (9), 22,23-dihydro-alpha-spinasterol (10), alpha-phytol (11), alpha-tocopherol (12), alpha-tocoquinone (13), and caffeine (14). The structures of 1-13 were determined by spectroscopic and chemical methods. Compounds 1 and 2 are the first two examples of triterpenoids possessing a 6-hydroxy-7-one function. All of the compounds, except 6, 8, 10, 11, and 14, were isolated from tea and Camellia spp. for the first time. The antibacterial activities of 1 were assessed against some enteric pathogenic microbes. Compound 1 showed no cytotoxic activity against A-549, Bel-7402, and HCT-8 cell lines.

  DOI：

  10.1021/jf9043524

文献信息

• New Triterpenoids and Other Constituents from a Special Microbial-Fermented Tea—Fuzhuan Brick Tea
  作者：Tie-Jun Ling、Xiao-Chun Wan、Wei-Wei Ling、Zheng-Zhu Zhang、Tao Xia、Da-Xiang Li、Ru-Yan Hou

  DOI：10.1021/jf9043524

  日期：2010.4.28

  Fuzhuan brick tea, a special microbial-fermented tea prepared from the leaves of Camellia sinensis var. sinensis, is a traditional beverage used in China throughout history. Phytochemical investigation of this material led to the identification of three new triterpenoids, 3 beta,6 alpha,13 beta-trihydroxyolean-7-one (1), 3 beta-acetoxy-6 alpha,13 beta-dihydroxyolean-7-one (2), and 3 beta-O-(8-hydroxyoctanoyl)-12-oleanene (3), together with 11 known compounds, friedelin (4), beta-amyrone (5), beta-amyrin (6), alpha-spinasterone (7), alpha-spinasterol (8), 22,23-dihydro-alpha-spinasterone (9), 22,23-dihydro-alpha-spinasterol (10), alpha-phytol (11), alpha-tocopherol (12), alpha-tocoquinone (13), and caffeine (14). The structures of 1-13 were determined by spectroscopic and chemical methods. Compounds 1 and 2 are the first two examples of triterpenoids possessing a 6-hydroxy-7-one function. All of the compounds, except 6, 8, 10, 11, and 14, were isolated from tea and Camellia spp. for the first time. The antibacterial activities of 1 were assessed against some enteric pathogenic microbes. Compound 1 showed no cytotoxic activity against A-549, Bel-7402, and HCT-8 cell lines.