orthosiphol A | 142741-25-1

• 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: orthosiphol A
• 英文别名: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,10-diacetyloxy-5-benzoyloxy-2-ethenyl-7,10a-dihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
• CAS: 142741-25-1
• 化学式: C₃₈H₄₄O₁₁
• 分子量: 676.761
• InChiKey: HIBFBUSEUDRQMX-OFUWLHILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  163
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  orthosiphol A 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以3 mg的产率得到(1S,2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-2,4b,8,8-Tetramethyl-2-vinyl-dodecahydro-phenanthrene-1,4,5,6,7,10,10a-heptaol
  参考文献：
  名称：

  Indonesian Medicinal Plants. XXII. Chemical Structures of Two New Isopimarane-Type Diterpenes, Orthosiphonones A and B, and a New Benzochromene, Orthochromene A from the Leaves of Orthosiphonaristatus (Lamiaceae).

  摘要：

  从印度尼西亚爪哇岛采集的 Orthosiphon aristatus（拉米亚种）叶片的水煎剂中分离出了两种新的异马兰萜类二萜，分别命名为 orthosiphonones A 和 B，以及一种新的苯并色烯，命名为 orthochromene A。根据物理化学和化学证据阐明了它们的化学结构。

  DOI：

  10.1248/cpb.47.695

文献信息

• Orthosiphol A and B, novel diterpenoid inhibitors of TPA (12-O-tetradecanoylphorbol-13-acetate)-induced inflammation, from Orthosiphon stamineus
  作者：Toshiya Masuda、Kazuyo Masuda、Shizuno Shiragami、Akiko Jitoe、Nobuji Nakatani

  DOI：10.1016/s0040-4020(01)89868-9

  日期：1992.1

  Two novel highly oxygenated pimarane diterpenes, orthosiphol A (1) and B (2), have been isolated from the dry leaves of Orthosiphon stamineus Benth (Labiatae). Their structures were elucidated by spectroscopic and chemical methods. Orthosiphol A and B showed potent inhibitory activity against the inflammation induced by a tumor promoter, TPA (12-O-tetradecanoylphorbol-13-acetate), on mouse ears

  两个新的高度氧化的pimarane二萜，邻苯二酚A（1）和B（2），已从Orthosiphon stamineus Benth（唇形科）的干燥叶子中分离出来。通过光谱和化学方法阐明了它们的结构。Orthosiphol A和B在小鼠耳朵上显示出对由肿瘤启动子TPA（12 - O-十四烷酰phorbol-13-乙酸盐）诱导的炎症的有效抑制作用。
• Orthosiphol A, a highly oxygenated diterpene from the leaves of orthosiphon stamineus
  作者：Toshiya Masuda、Kazuyo Masuda、Nobuji Nakatani

  DOI：10.1016/s0040-4039(00)91583-1

  日期：1992.2

  The structure of orthosiphol A (1), a highly oxygenated pimarane diterpene, has been established on the basis of spectroscopic and chemical methods.
• ORTHOSIPHON STAMINEUS EXTRACTS WITH BENEFICIAL USE AS COGNITION ENHANCER
  申请人：Biotropics Malaysia Berhad

  公开号：EP2515923A1

  公开（公告）日：2012-10-31
• EXTRACT OF ORTHOSIPHON STAMINEUS, FORMULATIONS, AND USES THEREOF
  申请人：NatureCeuticals Sdn. Bhd.

  公开号：EP3703724A1

  公开（公告）日：2020-09-09
• ORTHOSIPHON STAMINEUS EXTRACTS FOR USE AS A COGNITION ENHANCER
  申请人：GEHLING Matthias

  公开号：US20110151033A1

  公开（公告）日：2011-06-23

  The present invention relates to the use of compounds of isopimarane diterpene type, e.g. obtainable as or from extracts from Orthosiphon species, especially certain enriched or purified specific compounds therefrom, as well as said compounds or extracts for use or methods of using said compounds or extracts in the management of cognitive performance; in mammals, especially humans, respectively. The isopimarane diterpene type compounds can be of the formula wherein the symbols are as defined in the description and claims.