restrytisol B

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: restrytisol B
• 英文别名: 5-[(2R,3R,4R,5S)-4-(3,5-dihydroxyphenyl)-2,5-bis(4-hydroxyphenyl)oxolan-3-yl]benzene-1,3-diol
• 化学式: C₂₈H₂₄O₇
• 分子量: 472.494
• InChiKey: IRMTUHFNJGIEEV-LAJGZZDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  白藜芦醇 在 Botrytis cinerea ATCC 11542 作用下， 反应 48.0h， 生成 pallidol 、 (1R,2S,3R)-2-(3,5-Dihydroxy-phenyl)-1-[hydroxy-(4-hydroxy-phenyl)-methyl]-3-(4-hydroxy-phenyl)-indan-4,6-diol 、 restrytisol B 、 restrytisol A
  参考文献：
  名称：

  Dimerization of Resveratrol by the Grapevine Pathogen Botrytis cinerea

  摘要：

  Resveratrol (trans-3,4',5-trihydroxystilbene) is produced by grapes (Vitis spp.) in response to microbial attack by the fungal grapevine pathogen Botrytis cinerca. Several reports indicate that pathogenic B. cinerca strains are capable of biotransforming resveratrol into an assortment of unidentified oxidized metabolites as a means of reducing the antifungal effects of resveratrol and facilitating Botrytis invasion into host-plant tissues. Studies utilizing growing incubations of Botrytis cinerea ATCC 11542 with resveratrol resulted in the production of three new (restrytisols A-C) (1-3) and three known (resveratrol trans-dehydrodimer, leachinol F, and pallidol) oxidized resveratrol dimers. All of the metabolites were evaluated for their anti-HIV-1, cytotoxic, and cyclooxygenase (COX) I and COX II inhibitory activities.

  DOI：

  10.1021/np990266n

文献信息

• Generation of Antifungal Stilbenes Using the Enzymatic Secretome of <i>Botrytis cinerea</i>
  作者：Katia Gindro、Sylvain Schnee、Davide Righi、Laurence Marcourt、Samad Nejad Ebrahimi、Josep Massana Codina、Francine Voinesco、Emilie Michellod、Jean-Luc Wolfender、Emerson Ferreira Queiroz

  DOI：10.1021/acs.jnatprod.6b00760

  日期：2017.4.28

  The protein secretome of Botrytis cinerea was used to perform the biotransformation of resveratrol, pterostilbene, and a mixture of both. Metabolite profiling by UHPLC-HRMS revealed the presence of compounds with unusual molecular formula, suggesting the existence of new products. To isolate these products, the reactions were scaled up, and 21 analogues were isolated and fully characterized by NMR and HRESIMS analyses. The reaction with pterostilbene afforded five new compounds, while the reaction with-a mixture Of pterostilbene and resveratrol afforded seven unusual stilbene dimers: The antifungal propertieS of these compounds were evaluated using in vitro bioassays against Plasmopara viticola. The cytological effects of the isolated antifungal compounds on the ultrastructure of P. viticola were also evaluated.
• Dimerization of Resveratrol by the Grapevine Pathogen <i>Botrytis cinerea</i>
  作者：Robert H. Cichewicz、Samir A. Kouzi、Mark T. Hamann

  DOI：10.1021/np990266n

  日期：2000.1.1

  Resveratrol (trans-3,4',5-trihydroxystilbene) is produced by grapes (Vitis spp.) in response to microbial attack by the fungal grapevine pathogen Botrytis cinerca. Several reports indicate that pathogenic B. cinerca strains are capable of biotransforming resveratrol into an assortment of unidentified oxidized metabolites as a means of reducing the antifungal effects of resveratrol and facilitating Botrytis invasion into host-plant tissues. Studies utilizing growing incubations of Botrytis cinerea ATCC 11542 with resveratrol resulted in the production of three new (restrytisols A-C) (1-3) and three known (resveratrol trans-dehydrodimer, leachinol F, and pallidol) oxidized resveratrol dimers. All of the metabolites were evaluated for their anti-HIV-1, cytotoxic, and cyclooxygenase (COX) I and COX II inhibitory activities.