ent-12α-hydroxy-16-ketobeyeran-19-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: ent-12α-hydroxy-16-ketobeyeran-19-oic acid
• 英文别名: 12β-hydroxyisosteviol；12beta-Hydroxyisosteviol；(1R,4S,5R,9S,10R,12R,13R)-12-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: KHHQDXVAFQEBIY-WQMQNYNQSA-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：

  stevioside 在 盐酸 、 葡萄糖 、 corn steep liquor 、 yeast extract 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 98.0h， 生成 ent-12α-hydroxy-16-ketobeyeran-19-oic acid
  参考文献：
  名称：

  轮枝镰刀菌对异甜菊醇的生物转化

  摘要：

  摘要 Fusarium v​​erticilloides (Sacc.) Nirenberg I33 对异甜菊醇 (ent -16-ketobeyeran19-oic acid) 的生物转化产生了 ent -7 β -hydroxy-16-ketobeyeran-19-oic acid 和 ent -12 α -hydroxy-16-酮拜兰-19-油酸。通过光谱方法分离和表征代谢物。

  DOI：

  10.1016/0031-9422(96)00269-5

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.
• Microbial Transformations of Isosteviol
  作者：Feng-Lin Hsu、Chia-Chung Hou、Li-Ming Yang、Juei-Tang Cheng、Tzong-Cherng Chi、Pang-Chun Liu、Shwu-Jiuan Lin

  DOI：10.1021/np000622y

  日期：2002.3.1

  Microbial transformations of the tetracyclic diterpenoid isosteviol (ent-16-ketobeyeran-19-oic acid) (2) have revealed that isosteviol is metabolized by Cunninghamella, bainieri, Actinoplanes sp., Mucor recurvatus, and Cunninghamella blakesleeana to yield five new metabolites, ent-11alpha,12alpha-dihydroxy-16-ketobeyeran-19-oic acid (5), ent-11alpha,12alpha,17-trihydroxy-16-ketobeyeran-19-oic acid (6), ent-12alpha,15alpha-dihydroxy-16-ketobeyeran-19-oic acid (7), ent-7alpha,15alpha-dihydroxy-16-ketobeyeran-19-oic acid (8), and ent-9alpha-hydroxy-16-ketobeyeran-19-oic acid (9), together with three known metabolites, ent-7alpha-hydroxy-16-ketobeyeran-19-oic acid (3), ent-7beta-hydroxy-16-ketobeyeran-19-oic acid (4):, and ent-12alpha-hydroxy-16-ketobeyeran-19-oic acid (10). The structures of these metabolites were established on the basis of HRFABMS and 1D and 2D NMR spectral data. In addition, metabolites 3-10 were tested for antihypertensive activity and were found to be less active than the parent compound 2.
• Biotransformation of isosteviol by Fusarium verticilloides
  作者：Brás H. de Oliveira、Rogério A. Strapasson

  DOI：10.1016/0031-9422(96)00269-5

  日期：1996.9

  Abstract The biotransformation of isosteviol ( ent -16-ketobeyeran19- oic acid ) by Fusarium verticilloides (Sacc.) Nirenberg I33 produced ent -7 β -hydroxy-16-ketobeyeran-19-oic acid and ent -12 α -hydroxy-16-ketobeyeran-19-oic acid. The metabolites were isolated and characterized by spectroscopic methods.

  摘要 Fusarium v​​erticilloides (Sacc.) Nirenberg I33 对异甜菊醇 (ent -16-ketobeyeran19-oic acid) 的生物转化产生了 ent -7 β -hydroxy-16-ketobeyeran-19-oic acid 和 ent -12 α -hydroxy-16-酮拜兰-19-油酸。通过光谱方法分离和表征代谢物。