17-hydroxyisosteviol | 114414-69-6

• 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: 17-hydroxyisosteviol
• 英文别名: (1R,4S,5R,9S,10R,13S)-13-(hydroxymethyl)-5,9-dimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS: 114414-69-6
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: AHYPILJMTQMLLD-ABYZYQIESA-N

物化性质

• 熔点：
  229.2-231.4 °C
• 沸点：
  502.9±35.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  2
• 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 盐酸 、 lithium hydroxide monohydrate 、 碘苯二乙酸 、 sodium acetate 、 palladium diacetate 、 sodium hydride 、 乙硫醇 作用下， 以 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 129.0h， 生成 17-hydroxyisosteviol
  参考文献：
  名称：

  复杂天然 ent-Kauranes 和 ent-Beyeranes 合成中的选择性氧化

  摘要：

  首次使用区域和非对映选择性氧化描述了从对映-贝壳杉烯贝壳酸衍生的两种天然产物的合成。钯和锰介导的氧化用于完成两种 ent-拜亚烷代谢物的合成。White-Gormisky-Zhao 催化剂 Mn(CF 3 -PDP) 的使用使非定向金属催化氧化首次应用于全合成中未活化的 C-H 键。

  DOI：

  10.1021/acs.joc.2c01051

文献信息

• Biotransformation of the diperpenoid, isosteviol, by Aspergillus niger, Penicillium chrysogenum and Rhizopus arrhizus
  作者：B de Oliveira

  DOI：10.1016/s0031-9422(99)00058-8

  日期：1999.7

  The biotransformation of isosteviol (ent-16-ketobeyeran-19-oic acid) by three fungi is described. Aspergillus niger produced the 7 beta-OH derivative, ent-7 alpha-hydroxy-16-ketobeyeran-19-oic, and the 1 alpha, 7 beta-diOH derivative, ent-1 beta, 7 alpha-dihydroxy-16-ketobeyeran-19-oic acid. The 17-OH compound, ent-17-hydroxy-16-ketobeyeran-19-oic acid, was obtained with Penicillium chrysogenum. Rhizopus

  描述了三种真菌对异甜菊醇 (ent-16-ketobeyeran-19-oic acid) 的生物转化。黑曲霉产生 7 beta-OH 衍生物 ent-7 alpha-hydroxy-16-ketobeyeran-19-oic 和 1 alpha, 7 beta-diOH 衍生物 ent-1 beta, 7 alpha-dihydroxy-16-ketobeyeran- 19-油酸。17-OH 化合物 ent-17-hydroxy-16-ketobeyeran-19-oic acid 是用 Penicillium chrysogenum 获得的。Rhizopus arrhizus 产生 7 beta-OH 衍生物，ent-7 alpha-hydroxy-16-ketobeyeran-19-oic acid。分离出的代谢物通过 IR、NMR 和 MS 进行表征。
• Avent, Anthony G.; Hanson, James R.; Hitchcock, Peter B., Journal of the Chemical Society. Perkin transactions I, 1990, # 10, p. 2661 - 2665
  作者：Avent, Anthony G.、Hanson, James R.、Hitchcock, Peter B.、Oliveira, Bras Heleno De

  DOI：——

  日期：——
• 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.
• Wagner-Meerwein rearrangement of steviol 16α,17- and 15α,16-epoxides
  作者：R. N. Khaibullin、I. Yu. Strobykina、V. E. Kataev、O. A. Lodochnikova、A. T. Gubaidullin、A. A. Balandina、Sh. K. Latypov

  DOI：10.1134/s1070428010070080

  日期：2010.7

  16 alpha,17- and 15 alpha,16-Epoxy derivatives of diterpenoid steviol having ent-kaurane structure were found for the first time to undergo Wagner-Meerwein rearrangement in alkaline medium or by the action of boron trifluoride-diethyl ether complex to give products with ent-beyerane structure. The geometric parameters of steviol 16 alpha,17- and 15 alpha,16-epoxides were determined by X-ray analysis.
• Selective Oxidations in the Synthesis of Complex Natural <i>ent</i>-Kauranes and <i>ent</i>-Beyeranes
  作者：Victor C. S. Santana、Eduardo C. S. Rocha、Julian C. S. Pavan、Vladimir C. G. Heleno、Emilio C. de Lucca

  DOI：10.1021/acs.joc.2c01051

  日期：2022.8.5

  Syntheses of two natural products derived from the ent-kaurene kaurenoic acid are described for the first time using regio- and diastereoselective oxidations. Palladium- and manganese-mediated oxidations were used to accomplish the syntheses of two ent-beyerane metabolites. The use of the White–Gormisky–Zhao catalyst Mn(CF3-PDP) enabled the first application of a nondirected metal-catalyzed oxidation

  首次使用区域和非对映选择性氧化描述了从对映-贝壳杉烯贝壳酸衍生的两种天然产物的合成。钯和锰介导的氧化用于完成两种 ent-拜亚烷代谢物的合成。White-Gormisky-Zhao 催化剂 Mn(CF 3 -PDP) 的使用使非定向金属催化氧化首次应用于全合成中未活化的 C-H 键。