Benzyl Derivatives with in Vitro Binding Affinity for Human Opioid and Cannabinoid Receptors from the Fungus Eurotium repens

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• 作者：Jiangtao Gao ; Francisco Leo虂n ; Mohamed M. Radwan ; Olivia R. Dale ; Afeef S. Husni ; Susan P. Manly ; Shari Lupien ; Xiaoning Wang ; Robert A. Hill ; Frank M. Dugan ; Horace G. Cutler ; Stephen J. Cutler
• 刊名：Journal of Natural Products
• 出版年：2011
• 出版时间：July 22, 2011
• 年：2011
• 卷：74
• 期：7
• 页码：1636-1639
• 全文大小：714K
• 年卷期：v.74,no.7(July 22, 2011)
• ISSN：1520-6025

文摘

Bioassay-guided fractionation of the fungus Eurotium repens resulted in the isolation of two new benzyl derivatives, (E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol (1) and (E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol (2), along with seven known compounds (3鈥?b>9) including five benzaldehyde compounds, flavoglaucin (3), tetrahydroauroglaucin (4), dihydroauroglaucin (5), auroglaucin (6), and 2-(2鈥?3-epoxy-1鈥?3鈥? heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (7), one diketopiperazine alkaloid, echinulin (8), and 5,7-dihydroxy-4-methylphthalide (9). The chemical structures of these compounds were established on the basis of extensive 1D and 2D NMR and HRMS data. Compounds 1鈥?b>4 and 6 showed good binding affinity for human opioid or cannabinoid receptors. These findings have important implications for psychoactive studies with this class of compounds.