arabidiol | 845796-91-0

• 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: arabidiol
• 英文别名: (3R,3aR,5aR,7S,9aR,9bR)-3-[(2R,5E)-2-hydroxy-6,10-dimethylundeca-5,9-dien-2-yl]-3a,6,6,9a-tetramethyl-1,2,3,4,5,5a,7,8,9,9b-decahydrocyclopenta[a]naphthalen-7-ol
• CAS: 845796-91-0
• 化学式: C₃₀H₅₂O₂
• 分子量: 444.742
• InChiKey: KCSCTOANDBOIGV-ZFAZNOKVSA-N

物化性质

• 沸点：
  535.6±30.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  squalene 2,3(S)-oxide 在 arabidiol synthase 作用下， 生成 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

• A New Triterpene Synthase from <i>Arabidopsis </i><i>t</i><i>haliana</i> Produces a Tricyclic Triterpene with Two Hydroxyl Groups
  作者：Ting Xiang、Masaaki Shibuya、Yuji Katsube、Takehiko Tsutsumi、Miyuki Otsuka、Hong Zhang、Kazuo Masuda、Yutaka Ebizuka

  DOI：10.1021/ol060973p

  日期：2006.6.1

  transformant accumulated tricyclic triterpene, (3S,13R)-malabarica-17,21-dien-3,14-diol (arabidiol), whose structure was determined by NMR and MS analyses. Its epoxide analogue, (3S,13R,21S)-malabarica-17-en-20,21-epoxy-3,14-diol (arabidiol 20,21-epoxide), was also isolated from the transformed yeast. This is the first example of a triterpene synthase that yields a tricyclic triterpene with two hydroxyl groups

  [结构：见正文]拟南芥基因组中存在13种氧化角鲨烯环化酶同源物。这些基因之一At4g15340通过PCR扩增并在酵母中表达。酵母转化体积累了三环三萜，（3S，13R）-malabarica-17,21-dien-3,14-二醇（阿拉伯糖），其结构通过NMR和MS分析确定。还从转化酵母中分离出其环氧类似物，（3S，13R，21S）-malabarica-17-en-20,21-环氧-3,14-二醇（阿拉伯糖20,21-环氧）。这是三萜合酶的第一个实例，其产生具有两个羟基的三环三萜。
• Stereochemistry of Water Addition in Triterpene Synthesis:  The Structure of Arabidiol
  作者：Mariya D. Kolesnikova、Allie C. Obermeyer、William K. Wilson、David A. Lynch、Quanbo Xiong、Seiichi P. T. Matsuda

  DOI：10.1021/ol070709b

  日期：2007.5.1

  An oxidosqualene cyclase from Arabidopsis thaliana makes arabidiol, a tricyclic triterpene reported with indeterminate side-chain stereochemistry. We established the full structure of arabidiol through chemical degradation, NOE experiments, and molecular modeling. By examining the mechanistic constraints that govern water addition in triterpene synthesis, we further show how the stereochemistry of hydroxylation can generally be deduced a priori, why deprotonation is more common than hydroxylation, and why cyclases that perform hydroxylation also generate olefinic byproducts.
• 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.