dolabradiene | 3650-13-3

• 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: dolabradiene
• 英文别名: Dolabradien；(2S,4aR,4bS,8aS,10aR)-2-ethenyl-2,4a,8a-trimethyl-8-methylidene-1,3,4,4b,5,6,7,9,10,10a-decahydrophenanthrene
• CAS: 3650-13-3
• 化学式: C₂₀H₃₂
• 分子量: 272.474
• InChiKey: GHYZJFFJSPZRIU-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  dolabradiene 在 甲酸 作用下， 生成 (13S,8β)-Rosa-5(10),15-dien
  参考文献：
  名称：

  多拉布拉二烯中的骨架重排

  摘要：

  在甲酸中加热多拉二烯 (1) 得到烃的混合物。从混合物中分离出的五种主链重排产物分别归属于 Δ5(10)-8β-rimuene (2)、Δ5(10)-rimuene (3)、Δ1(10)-rimuene (4)、Δ8(9)-pimaradiene ( 5), 和 Δ1(10),5-rimutriene (6a)，分别。还讨论了它们的形成机制。

  DOI：

  10.1246/cl.1974.963
• 作为产物：
  描述：

  3-methyl-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]pent-2-en-1-yl diphosphate 生成 pyrophosphoric acid 、 dolabradiene
  参考文献：
  名称：

  Discovery, Biosynthesis and Stress-Related Accumulation of Dolabradiene-Derived Defenses in Maize

  摘要：

  在10 µg mL−1时对两种病原体的生长有显著抑制作用。

  DOI：

  10.1104/pp.17.01351

文献信息

• Soman, R.; Dev, Sukh, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 10, p. 984 - 988
  作者：Soman, R.、Dev, Sukh

  DOI：——

  日期：——
• BACKBONE REARRANGEMENT IN DOLABRADIENE
  作者：Masayuki Kitadani、Chizuko Kabuto、Kunikazu Sakai、Akira Yoshikoshi、Yoshio Kitahara

  DOI：10.1246/cl.1974.963

  日期：1974.9.5

  Upon heating in formic acid dolabradiene (1) gives a mixture of hydrocarbons. Five backbone rearrangement products isolated from the mixture are assigned to Δ5(10)-8β-rimuene (2), Δ5(10)-rimuene (3), Δ1(10)-rimuene (4), Δ8(9)-pimaradiene (5), and Δ1(10),5-rimutriene (6a), respectively. Their formation mechanisms are also discussed.

  在甲酸中加热多拉二烯 (1) 得到烃的混合物。从混合物中分离出的五种主链重排产物分别归属于 Δ5(10)-8β-rimuene (2)、Δ5(10)-rimuene (3)、Δ1(10)-rimuene (4)、Δ8(9)-pimaradiene ( 5), 和 Δ1(10),5-rimutriene (6a)，分别。还讨论了它们的形成机制。
• Discovery, Biosynthesis and Stress-Related Accumulation of Dolabradiene-Derived Defenses in Maize
  作者：Sibongile Mafu、Yezhang Ding、Katherine M. Murphy、Omar Yaacoobi、J. Bennett Addison、Qiang Wang、Zhouxin Shen、Steven P. Briggs、Jörg Bohlmann、Gabriel Castro-Falcon、Chambers C. Hughes、Mariam Betsiashvili、Alisa Huffaker、Eric A. Schmelz、Philipp Zerbe

  DOI：10.1104/pp.17.01351

  日期：2018.4

  Terpenoids are a major component of maize (Zea mays) chemical defenses that mediate responses to herbivores, pathogens, and other environmental challenges. Here, we describe the biosynthesis and elicited production of a class of maize diterpenoids, named dolabralexins. Dolabralexin biosynthesis involves the sequential activity of two diterpene synthases, ENT-COPALYL DIPHOSPHATE SYNTHASE (ZmAN2) and KAURENE SYNTHASE-LIKE4 (ZmKSL4). Together, ZmAN2 and ZmKSL4 form the diterpene hydrocarbon dolabradiene. In addition, we biochemically characterized a cytochrome P450 monooxygenase, ZmCYP71Z16, which catalyzes the oxygenation of dolabradiene to yield the epoxides 15,16-epoxydolabrene (epoxydolabrene) and 3β-hydroxy-15,16-epoxydolabrene (epoxydolabranol). The absence of dolabradiene and epoxydolabranol in Zman2 mutants under elicited conditions confirmed the in vivo biosynthetic requirement of ZmAN2. Combined mass spectrometry and NMR experiments demonstrated that much of the epoxydolabranol is further converted into 3β,15,16-trihydroxydolabrene (trihydroxydolabrene). Metabolite profiling of field-grown maize root tissues indicated that dolabralexin biosynthesis is widespread across common maize cultivars, with trihydroxydolabrene as the predominant diterpenoid. Oxidative stress induced dolabralexin accumulation and transcript expression of ZmAN2 and ZmKSL4 in root tissues, and metabolite and transcript accumulation were up-regulated in response to elicitation with the fungal pathogens Fusarium verticillioides and Fusarium graminearum. Consistently, epoxydolabranol significantly inhibited the growth of both pathogens in vitro at 10 µg mL−1, while trihydroxydolabrene-mediated inhibition was specific to F. verticillioides. These findings suggest that dolabralexins have defense-related roles in maize stress interactions and expand the known chemical space of diterpenoid defenses as genetic targets for understanding and ultimately improving maize resilience.

  在10 µg mL−1时对两种病原体的生长有显著抑制作用。