tricalysioside A aglycone

• 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: tricalysioside A aglycone
• 英文别名: (1R,4S,9R,12S,13S,16R,17R,18R)-17,18-dihydroxy-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadec-5-en-7-one
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: BHKIILDNBVMAHN-UQQGSFQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tricalysioside A 在 硫酸 作用下， 反应 2.0h， 以50%的产率得到tricalysioside A aglycone
  参考文献：
  名称：

  Tricalysiosides A−G:  Rearranged ent-Kauranoid Glycosides from the Leaves of Tricalysia dubia

  摘要：

  Seven rearranged ent-kaurane glycosides, named tricalysiosides A-G (1-7), were isolated from the leaves of Tricalysia dubia collected on Okinawa Island. Their C-18 and 19 methyls were found to have rearranged to form an alpha,beta-unsaturated gamma-lactone ring, with other functional groups remotely located only on C-15, -16, and -17 of the five-membered ring. Information available from various kinds of two-dimensional NMR spectra was limited and insufficient to allow total characterization of the structures. Finally, using X-ray crystallographic analysis, the structure of tricalysioside A (1) was determined to be 4-nor-18-homo-ent-kauran-4(18)-en- 15beta, 16beta, 17-triol-3beta,19-olide 16-O-beta-D-glucopyranoside (1). On the basis of the crystal structure of 1, the structures of the other tricalysiosides (2-7) were also established.

  DOI：

  10.1021/np010620t