massarilactone H | 1393110-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: massarilactone H
• 英文别名: (2S,3R,4S)-3,4-dihydroxy-7-methylidene-2-[(E)-prop-1-enyl]-3,4-dihydro-2H-furo[3,4-b]pyran-5-one
• CAS: 1393110-39-8
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: ZVRUDYNVKYYNCW-JZSYEIFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  massarilactone H 、 乙酸酐 在 吡啶 作用下， 以6.9 mg的产率得到
  参考文献：
  名称：

  Massarilactones D and H, phytotoxins produced by Kalmusia variispora, associated with grapevine trunk diseases (GTDs) in Iran

  摘要：

  A strain ofKalmusia variisporaassociated with grapevine trunk diseases (GTDs) was identified in Iran and induced disease symptoms on the host in greenhouse conditions. The grapevine pathogens are able to produce a plethora of toxic metabolites belonging to different classes of naturally occurring compounds. Two homogeneous compounds were isolated from the organic extract ofK. variisporaculture filtrates. They were identified by physic (specific optical rotation), and spectroscopic (essentially 1D(1)H and(13)C NMR and HR ESIMS) methods as the fungal polyketides massarilactones D and H (1and2). The unassigned absolute configuration of massarilactone D was unambiguously determined by X-ray diffractometric analysis. Massarilactones D and H showed phytotoxic activity onVitis viniferaL. at two concentrations used and depending from the days of inoculation. Phytotoxicity is also increased when the 3,4,7-O,O',O"-triacetyl derivative of massarilactone D (3) was assayed on the host plant. This is the first report on the investigation of phytotoxic metabolites produced byK. variisporaisolated from infected grapevine in Iran and they seem to be involved in the development of disease symptoms.

  DOI：

  10.1080/14786419.2020.1791116