2α,7β,13(S)-trihydroxystemodane | 137035-97-3

• 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: 2α,7β,13(S)-trihydroxystemodane
• 英文别名: 2α,7β,13-trihydroxystemodane；7β-Hydroxystemodin；(1R,2S,4S,7S,9S,10S,12S,13S)-2,6,6,13-tetramethyltetracyclo[10.3.1.01,10.02,7]hexadecane-4,9,13-triol
• CAS: 137035-97-3
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: XQVVNUQPNCRRAK-NKYOLRSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2α,7β,13(S)-trihydroxystemodane 在 jones reagent 作用下， 生成 (4aS,6aS,8S,9S,11aR,11bS)-9-hydroxy-4,4,9,11b-tetramethyldodecahydro-8,11a-methanocyclohepta[a]naphthalene-2,6-dione
  参考文献：
  名称：

  Stemodia 二萜类 Stemodin 的微生物转化

  摘要：

  筛选研究表明，许多微生物能够转化茎油烷二萜类油菜素。使用 Cunninghamella echinulata ATCC 9244 和 Polyangium cellulosum ATCC 29610 进行放大发酵产生了五种主要代谢物，这些代谢物已使用 2D NMR 技术进行表征。这些代谢物已被鉴定为 7β-羟基 Stemodin、7β-hydroxystemodin、14α-hydroxystemodin、19-hydroxystemodin 和 17,19-dihydroxystemodin。

  DOI：

  10.1016/0031-9422(91)83626-v
• 作为产物：
  描述：

  stemodinone 在 Cunninghamella echinulata var. elegans ATCC 8688a 、 Phanerochaete chrysosporium ATCC 24725 作用下， 以 乙醇 为溶剂， 反应 120.0h， 生成 2α,7β,13(S)-trihydroxystemodane
  参考文献：
  名称：

  Cunninghamella echinulata var. 对 Stemodia maritima 二萜及其衍生物的生物转化。线虫和 Phanerochaete chrysosporium

  摘要：

  从植物 Stemodia maritima 中分离出的 Stemodane 和 Stemarane 二萜及其二甲基氨基甲酸酯衍生物被喂养到真菌 Cunninghamella echinulata var. 的生长培养物中。elegans ATCC 8688a 和 Phanerochaete chrysosporium ATCC 24725。C. echinulata 将 Stemodin (1) 转化为它的 7alpha-hydroxy- (2)、7beta-hydroxy- (3) 和 3beta-hydroxy- (4) 类似物。2alpha-(N,N-Dimethylcarbamoxy)-13-hydroxystemodane (6) 得到 2alpha-(N,N-dimethylcarbamoxy)-6alpha,13-dihydroxystemodane (7) 和 2alpha-(N

  DOI：

  10.1016/j.phytochem.2006.04.001

文献信息

• Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145
  作者：Glenroy D.A. Martin、William F. Reynolds、Paul B. Reese

  DOI：10.1016/j.phytochem.2004.01.011

  日期：2004.3

  A new stemodinoside, stemodin-a-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(S)-trihydroxystemodane (17) and 2alpha,3beta,13(S),16alpha-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6alpha,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2beta,13(S)-dihydroxystemodane (10) by the fungus yielded 2beta,7beta,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7beta,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion. (C) 2004 Elsevier Ltd. All rights reserved.
• Microbial transformations of stemodin, a Stemodia diterpene
  作者：Farid A. Badria、Charles D. Hufford

  DOI：10.1016/0031-9422(91)83626-v

  日期：1991.1

  Screening studies have shown a number of microorganisms capable of transforming the stemodane diterpene, stemodin. Scale-up fermentation with Cunninghamella echinulata ATCC 9244 and Polyangium cellulosum ATCC 29610 have resulted in the production of five major metabolites that have been characterized with the use of 2D NMR techniques. These metabolites have been identified as 7β-hydroxystemodin, 7β-hydroxystemodin

  筛选研究表明，许多微生物能够转化茎油烷二萜类油菜素。使用 Cunninghamella echinulata ATCC 9244 和 Polyangium cellulosum ATCC 29610 进行放大发酵产生了五种主要代谢物，这些代谢物已使用 2D NMR 技术进行表征。这些代谢物已被鉴定为 7β-羟基 Stemodin、7β-hydroxystemodin、14α-hydroxystemodin、19-hydroxystemodin 和 17,19-dihydroxystemodin。
• Bioconversion of Stemodia maritima diterpenes and derivatives by Cunninghamella echinulata var. elegans and Phanerochaete chrysosporium
  作者：A LAMM、W REYNOLDS、P REESE

  DOI：10.1016/j.phytochem.2006.04.001

  日期：2006.6

  chrysosporium ATCC 24725. C. echinulata transformed stemodin (1) to its 7alpha-hydroxy- (2), 7beta-hydroxy- (3) and 3beta-hydroxy- (4) analogues. 2alpha-(N,N-Dimethylcarbamoxy)-13-hydroxystemodane (6) gave 2alpha-(N,N-dimethylcarbamoxy)-6alpha,13-dihydroxystemodane (7) and 2alpha-(N,N-dimethylcarbamoxy)-7alpha,13-dihydroxystemodane (8). Stemodinone (9) yielded 14-hydroxy-(10) and 7beta-hydroxy- (11)

  从植物 Stemodia maritima 中分离出的 Stemodane 和 Stemarane 二萜及其二甲基氨基甲酸酯衍生物被喂养到真菌 Cunninghamella echinulata var. 的生长培养物中。elegans ATCC 8688a 和 Phanerochaete chrysosporium ATCC 24725。C. echinulata 将 Stemodin (1) 转化为它的 7alpha-hydroxy- (2)、7beta-hydroxy- (3) 和 3beta-hydroxy- (4) 类似物。2alpha-(N,N-Dimethylcarbamoxy)-13-hydroxystemodane (6) 得到 2alpha-(N,N-dimethylcarbamoxy)-6alpha,13-dihydroxystemodane (7) 和 2alpha-(N