Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
J Nat Prod. 2011 Jul 22;74(7):1636-9. doi: 10.1021/np200147c. Epub 2011 Jun 13.
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 (3-9) including five benzaldehyde compounds, flavoglaucin (3), tetrahydroauroglaucin (4), dihydroauroglaucin (5), auroglaucin (6), and 2-(2',3-epoxy-1',3'- 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 1-4 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.
真菌扩展青霉的生物活性导向分离得到两个新的苄基衍生物，（E）-2-（庚-1-烯基）-3-（羟甲基）-5-（3-甲基-2-丁烯基）-1,4-苯二酚（1）和（E）-4-（庚-1-烯基）-7-（3-甲基-2-丁烯基）-2,3-二氢苯并呋喃-2,5-二醇（2），以及七个已知化合物（3-9），包括五个苯甲醛化合物，黄曲霉素（3）、四氢金雀花碱（4）、二氢金雀花碱（5）、金雀花碱（6）和 2-（2'，3'-环氧-1'，3'-庚二烯基）-6-羟基-5-（3-甲基-2-丁烯基）苯甲醛（7），一个二酮哌嗪生物碱，埃奎林（8）和 5,7-二羟基-4-甲基邻苯二甲酸酐（9）。这些化合物的化学结构是基于广泛的 1D 和 2D NMR 和 HRMS 数据确定的。化合物 1-4 和 6 对人阿片类或大麻素受体表现出良好的结合亲和力。这些发现对这类化合物的精神活性研究具有重要意义。
