title: Neocosmospora sp.-derived resorcylic acid lactones with in vitro binding affinity for human opioid and cannabinoid receptors.
abstract: Bioassay-guided fractionation of a fungus Neocosmospora sp. (UM-031509) resulted in the isolation of three new resorcylic acid lactones, neocosmosin A (2), neocosmosin B (3), and neocosmosin C (4). Three known resorcylic acid lactones, monocillin IV (1), monocillin II (5), and radicicol (6), were also isolated and identified. The structures of these compounds were established on the basis of extensive 1D and 2D NMR spectroscopic analysis, mass spectrometric (ESIMS) data, and X-ray crystallography. Compounds 4-6 show good binding affinity for the human opioid receptors. These findings have important implications for evaluating the potential psychoactive effects with this class of compounds.
authors: Department of Medicinal Chemistry and ‡National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, United States.
authors: Jiangtao
authors: J
authors: Gao
authors: Mohamed M
authors: MM
authors: Radwan
authors: Francisco
authors: F
authors: León
authors: Olivia Reed
authors: OR
authors: Dale
authors: Afeef S
authors: AS
authors: Husni
authors: Yunshan
authors: Y
authors: Wu
authors: Shari
authors: S
authors: Lupien
authors: Xiaoning
authors: X
authors: Wang
authors: Susan P
authors: SP
authors: Manly
authors: Robert A
authors: RA
authors: Hill
authors: Frank M
authors: FM
authors: Dugan
authors: Horace G
authors: HG
authors: Cutler
authors: Stephen J
authors: SJ
authors: Cutler
mesh_terms: D018360:Crystallography, X-Ray; D004578:Electron Spin Resonance Spectroscopy; D005845:Georgia; D057809:HEK293 Cells; D006801:Humans; D006999:Hypocreales / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008968:Molecular Conformation; D015394:Molecular Structure; D043882:Receptors, Cannabinoid / Q000187:drug effects; D011957:Receptors, Opioid / Q000187:drug effects*; D012118:Resorcinols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D007783:Lactones; D043882:Receptors, Cannabinoid; D011957:Receptors, Opioid; D012118:Resorcinols; C548475:monocillin II; C116417:monocillin IV; C582805:neocosmosin A; C582806:neocosmosin B; C582807:neocosmosin C
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