11β-hydroxygedunin | 913092-22-5

• 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-hydroxygedunin
• 英文别名: 11beta-Hydroxygedunin；[(1S,2R,4S,7S,8S,10S,11R,12S,17R,19R)-7-(furan-3-yl)-10-hydroxy-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadec-13-en-19-yl] acetate
• CAS: 913092-22-5
• 化学式: C₂₈H₃₄O₈
• 分子量: 498.573
• InChiKey: CJCDIECVGAPJFT-ZINBXAAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  11β-hydroxygedunin 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以89%的产率得到7-deacetoxy-7α,11β-dihydroxygedunin
  参考文献：
  名称：

  Hydroxylated Gedunin Derivatives from Cedrela sinensis

  摘要：

  Four new limonoids, 11 alpha-hydroxygedunin ( 1), 11 beta-hydroxygedunin (2), 7-deacetoxy-7 alpha,11 alpha-dihydroxygedunin ( 3), and 7-deacetoxy-7 alpha, 11 beta-dihydroxygedunin (4), were isolated from the cortex of Cedrela sinensis, together with three known compounds, gedunin ( 5), 7-deacetoxy-7 alpha-hydroxygedunin ( 6), and 11-oxogedunin ( 7). The structures of 1-4 were determined by a combination of 2D NMR experiments and chemical methods and by X-ray crystallography of 1 and 2.

  DOI：

  10.1021/np068021f
• 作为产物：
  描述：

  葛杜宁 在 fungal whole cell of Cunninghamella echinulata 作用下， 以 aq. phosphate buffer 为溶剂， 反应 144.0h， 以8.2%的产率得到11β-hydroxygedunin
  参考文献：
  名称：

  Whole-Cell Mediated 11β-Hydroxylation on the Basic Limonoid Skeleton by Cunninghamella echinulata

  摘要：

  Regio- and stereoselective 11 beta-hydroxylation was achieved on the basic limonoid skeleton through microbial transformation. Whole cells of Cunninghamella echinulata efficiently converted basic limonoids such as epoxyazadiradione, azadiradione, and gedunin to their 11 beta-hydroxy analogues as the sole metabolite. Fermentation conditions affecting the efficiency (96%) of biotransformation including substrate concentration, incubation period, pH, and temperature were optimized. The position and stereochemistry of hydroxyl functionality on the isolated metabolites were established through extensive spectroscopic and spectrometric studies (1D, 2D NMR, ESI-MS, and MS/MS).

  DOI：

  10.1021/acs.joc.5b00417

文献信息

• Whole-Cell Mediated 11β-Hydroxylation on the Basic Limonoid Skeleton by <i>Cunninghamella echinulata</i>
  作者：Saikat Haldar、Fayaj A. Mulani、Thiagarayaselvam Aarthy、Hirekodathakallu V. Thulasiram

  DOI：10.1021/acs.joc.5b00417

  日期：2015.6.19

  Regio- and stereoselective 11 beta-hydroxylation was achieved on the basic limonoid skeleton through microbial transformation. Whole cells of Cunninghamella echinulata efficiently converted basic limonoids such as epoxyazadiradione, azadiradione, and gedunin to their 11 beta-hydroxy analogues as the sole metabolite. Fermentation conditions affecting the efficiency (96%) of biotransformation including substrate concentration, incubation period, pH, and temperature were optimized. The position and stereochemistry of hydroxyl functionality on the isolated metabolites were established through extensive spectroscopic and spectrometric studies (1D, 2D NMR, ESI-MS, and MS/MS).
• Hydroxylated Gedunin Derivatives from <i>Cedrela </i><i>sinensis</i>
  作者：Kumiko Mitsui、Hiroaki Saito、Ryota Yamamura、Haruhiko Fukaya、Yukio Hitotsuyanagi、Koichi Takeya

  DOI：10.1021/np068021f

  日期：2006.9.1

  Four new limonoids, 11 alpha-hydroxygedunin ( 1), 11 beta-hydroxygedunin (2), 7-deacetoxy-7 alpha,11 alpha-dihydroxygedunin ( 3), and 7-deacetoxy-7 alpha, 11 beta-dihydroxygedunin (4), were isolated from the cortex of Cedrela sinensis, together with three known compounds, gedunin ( 5), 7-deacetoxy-7 alpha-hydroxygedunin ( 6), and 11-oxogedunin ( 7). The structures of 1-4 were determined by a combination of 2D NMR experiments and chemical methods and by X-ray crystallography of 1 and 2.