11β-hydroxyisosteviol

• 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: 11β-hydroxyisosteviol
• 英文别名: 11beta-Hydroxyisosteviol；(1R,4S,5R,9R,10R,11S,13R)-11-hydroxy-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: SJSXVMKVEKHZPQ-RBLOAEQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异甜菊醇 在 fungus Aspergillus niger IFO 4414 作用下， 生成 ent-12α-hydroxy-16-ketobeyeran-19-oic acid 、 ent-7α-hydroxy-16-ketobeyeran-19-oic acid 、 11β-hydroxyisosteviol
  参考文献：
  名称：

  Structural analysis of isosteviol and related compounds as DNA polymerase and DNA topoisomerase inhibitors

  摘要：

  Isosteviol (ent-16-ketobeyeran-19-oic acid) is a hydrolysis product of stevioside, which is a natural sweetener produced in the leaves of Stevia rebaudiana (Bertoni) Bertoni. In this report, we prepared isosteviol and related compounds from stevioside by microbial transformation and chemical conversion and assayed the inhibitory activities toward DNA metabolic enzymes and human cancer cell growth. Among twelve compounds obtained, only isosteviol (compound 3) potently inhibited both mammalian DNA polymerases (pols) and human DNA topoisomerase II (topo II), and IC50 value for pol alpha was 64.0 mu M. This compound had no inhibitory effect on higher plant (cauliflower) pols, prokaryotic pols, human topo I, and DNA metabolic enzymes such as human telomerase, T7 RNA polymerase, and bovine deoxyribonuclease I. With pol alpha, isosteviol acted non-competitively with the DNA template-primer and nucleotide substrate. Isosteviol prevented the growth of human cancer cells, with LD50 values of 84-167 mu M, and 500 mu g of the compound caused a marked reduction in TPA (12-O-tetradecanoylphorbol-13-acetate)-induced inflammation (inhibitory effect, 53.0%). The relationship between the structure of stevioside-based compounds and these activities were discussed. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2005.03.022

文献信息

• Structural analysis of isosteviol and related compounds as DNA polymerase and DNA topoisomerase inhibitors
  作者：Yoshiyuki Mizushina、Toshihiro Akihisa、Motohiko Ukiya、Yusuke Hamasaki、Chikako Murakami-Nakai、Isoko Kuriyama、Toshifumi Takeuchi、Fumio Sugawara、Hiromi Yoshida

  DOI：10.1016/j.lfs.2005.03.022

  日期：2005.9

  Isosteviol (ent-16-ketobeyeran-19-oic acid) is a hydrolysis product of stevioside, which is a natural sweetener produced in the leaves of Stevia rebaudiana (Bertoni) Bertoni. In this report, we prepared isosteviol and related compounds from stevioside by microbial transformation and chemical conversion and assayed the inhibitory activities toward DNA metabolic enzymes and human cancer cell growth. Among twelve compounds obtained, only isosteviol (compound 3) potently inhibited both mammalian DNA polymerases (pols) and human DNA topoisomerase II (topo II), and IC50 value for pol alpha was 64.0 mu M. This compound had no inhibitory effect on higher plant (cauliflower) pols, prokaryotic pols, human topo I, and DNA metabolic enzymes such as human telomerase, T7 RNA polymerase, and bovine deoxyribonuclease I. With pol alpha, isosteviol acted non-competitively with the DNA template-primer and nucleotide substrate. Isosteviol prevented the growth of human cancer cells, with LD50 values of 84-167 mu M, and 500 mu g of the compound caused a marked reduction in TPA (12-O-tetradecanoylphorbol-13-acetate)-induced inflammation (inhibitory effect, 53.0%). The relationship between the structure of stevioside-based compounds and these activities were discussed. (c) 2005 Elsevier Inc. All rights reserved.