14-apo-arabidiol | 1429984-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 14-apo-arabidiol
• 英文别名: 14-Apo-arabidiol；1-[(3R,3aR,5aR,7S,9aR,9bR)-7-hydroxy-3a,6,6,9a-tetramethyl-1,2,3,4,5,5a,7,8,9,9b-decahydrocyclopenta[a]naphthalen-3-yl]ethanone
• CAS: 1429984-04-2
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: XVVLVNIOQHUWFO-USOAJAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  arabidiol 在 JBY₅₇₅[pMDK_3.6, pDCR_4.1, pDCR_9.3] 作用下， 生成 14-apo-arabidiol
  参考文献：
  名称：

  An Effective Strategy for Exploring Unknown Metabolic Pathways by Genome Mining

  摘要：

  Plants allocate an estimated 15-25% of their proteome to specialized metabolic pathways that remain largely uncharacterized. Here, we describe a genome mining strategy for exploring such unknown pathways and demonstrate this approach for triterpenoids by functionally characterizing three cytochrome P450s from Arabidopsis thaliana. Building on proven methods for characterizing oxidosqualene cyclases, we heterologously expressed in yeast known cyclases with candidate P450s chosen from gene clustering and microarray coexpression patterns. The yeast cultures produced mg/L amounts of plant metabolites in vivo without the complex phytochemical background of plant extracts. Despite this simplification, the product multiplicity and novelty overwhelmed analytical efforts by MS methods. HSQC analysis overcame this problem. Side-by-side HSQC comparisons of crude P450 extracts against a control resolved even minor P450 products among similar to 100 other yeast metabolites spanning a dynamic range of >10 000:1. HSQC and GC-MS then jointly guided purification and structure determination by classical NMR methods. Including our present results for P450 oxidation of thalianol, arabidiol, and marneral, the metabolic fate for most of the major triterpene synthase products in Arabidopsis is now at least partially known.

  DOI：

  10.1021/ja401535g

文献信息

• An Effective Strategy for Exploring Unknown Metabolic Pathways by Genome Mining
  作者：Dorianne A. Castillo、Mariya D. Kolesnikova、Seiichi P. T. Matsuda

  DOI：10.1021/ja401535g

  日期：2013.4.17

  Plants allocate an estimated 15-25% of their proteome to specialized metabolic pathways that remain largely uncharacterized. Here, we describe a genome mining strategy for exploring such unknown pathways and demonstrate this approach for triterpenoids by functionally characterizing three cytochrome P450s from Arabidopsis thaliana. Building on proven methods for characterizing oxidosqualene cyclases, we heterologously expressed in yeast known cyclases with candidate P450s chosen from gene clustering and microarray coexpression patterns. The yeast cultures produced mg/L amounts of plant metabolites in vivo without the complex phytochemical background of plant extracts. Despite this simplification, the product multiplicity and novelty overwhelmed analytical efforts by MS methods. HSQC analysis overcame this problem. Side-by-side HSQC comparisons of crude P450 extracts against a control resolved even minor P450 products among similar to 100 other yeast metabolites spanning a dynamic range of >10 000:1. HSQC and GC-MS then jointly guided purification and structure determination by classical NMR methods. Including our present results for P450 oxidation of thalianol, arabidiol, and marneral, the metabolic fate for most of the major triterpene synthase products in Arabidopsis is now at least partially known.