title: Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
authors.forename: Jiangtao
authors.initials: J
authors.lastname: Gao
authors.forename: Francisco
authors.initials: F
authors.lastname: León
authors.forename: Mohamed M
authors.initials: MM
authors.lastname: Radwan
authors.forename: Olivia R
authors.initials: OR
authors.lastname: Dale
authors.forename: Afeef S
authors.initials: AS
authors.lastname: Husni
authors.forename: Susan P
authors.initials: SP
authors.lastname: Manly
authors.forename: Shari
authors.initials: S
authors.lastname: Lupien
authors.forename: Xiaoning
authors.initials: X
authors.lastname: Wang
authors.forename: Robert A
authors.initials: RA
authors.lastname: Hill
authors.forename: Frank M
authors.initials: FM
authors.lastname: Dugan
authors.forename: Horace G
authors.initials: HG
authors.lastname: Cutler
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Cutler
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D001555:Benzene Derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006224:Cricetinae; D003412:Cricetulus; D055325:Eurotium / Q000737:chemistry*; D005845:Georgia; D006801:Humans; D015394:Molecular Structure; D043882:Receptors, Cannabinoid / Q000187:drug effects*; D011957:Receptors, Opioid / Q000187:drug effects*; D013237:Stereoisomerism
chemical_list: C561556:(E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol; C561555:(E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol; D000470:Alkaloids; D001555:Benzene Derivatives; D001572:Benzofurans; D043882:Receptors, Cannabinoid; D011957:Receptors, Opioid