{"title":"Phorbol Derivatives of Croton Oil","authors":"Xiao-Lei Huang, Xu-Sheng Huang, Qi-Run Li, Liu-Meng Yang, Ya-Dong Cui, Yong-Tang Zheng, Jian Zhang","doi":"10.1007/s10600-024-04298-3","DOIUrl":null,"url":null,"abstract":"<p>One new seco-cyclic phorbol derivative and one new phorbol 12-monoester, named 13-oxo-14-isopropylphorbol (<b>2</b>), 12-angelylphorbol (<b>5</b>), together with four known compounds, named 4a-deoxyphorbol, 13-oxo-14-isopropenylphorbol, 12-isobutyrylphorbol, and phorbol-12-(2-methylbutyrate) were obtained by hydrolyzing croton oil. The structures of the compounds were elucidated by spectroscopic analysis. These compounds showed no cytotoxicity (CC<sub>50</sub> > 200 μM). Phorbol-12-monoesters <b>4</b>–<b>6</b> showed the weak inhibitory activities on syncytia formation induced by HIV-1IIIB (<b>4</b>, EC<sub>50</sub> = 56.05 μM; <b>5</b>, EC<sub>50</sub> = 72.97 μM; <b>6</b>, EC<sub>50</sub> = 52.58 μM). The seco-cyclic phorbol derivatives (<b>2</b>, <b>3</b>) showed no anti-HIV-1 activities (EC<sub>50</sub> > 200 μM), which indicated that chemical cleavage of cyclopropanols might affect anti-HIV-1 activity.</p>","PeriodicalId":514,"journal":{"name":"Chemistry of Natural Compounds","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry of Natural Compounds","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s10600-024-04298-3","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0
Abstract
One new seco-cyclic phorbol derivative and one new phorbol 12-monoester, named 13-oxo-14-isopropylphorbol (2), 12-angelylphorbol (5), together with four known compounds, named 4a-deoxyphorbol, 13-oxo-14-isopropenylphorbol, 12-isobutyrylphorbol, and phorbol-12-(2-methylbutyrate) were obtained by hydrolyzing croton oil. The structures of the compounds were elucidated by spectroscopic analysis. These compounds showed no cytotoxicity (CC50 > 200 μM). Phorbol-12-monoesters 4–6 showed the weak inhibitory activities on syncytia formation induced by HIV-1IIIB (4, EC50 = 56.05 μM; 5, EC50 = 72.97 μM; 6, EC50 = 52.58 μM). The seco-cyclic phorbol derivatives (2, 3) showed no anti-HIV-1 activities (EC50 > 200 μM), which indicated that chemical cleavage of cyclopropanols might affect anti-HIV-1 activity.
期刊介绍：
Chemistry of Natural Compounds publishes reviews and general articles about the structure of different classes of natural compounds, the chemical characteristics of botanical families, genus, and species, to establish the comparative laws and connection between physiological activity and the structure of substances.
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