title: Fatty acids with in vitro binding affinity for human opioid receptors from the fungus Emericella nidulans.
abstract: Bioassay-guided fractionation of the EtOAc extracts of the epiphytic fungus Emericella nidulans resulted in the isolation of a mixture of two fatty acids. This mixture showed 98% binding affinity to human δ opioid receptor. These two fatty acids were identified as palmitic (PAM), 1, and linoleic acids (LNA), 2, by 1D NMR as well as by GC/MS analysis, after their methylation. We found that different ratio mixtures of 1 and 2 showed variations in selective binding activities to human δ opioid receptors. Five more fatty acids, arachidonic acid (ARA), 3, cis-4,7,10,13,16,19-docosahexanoic acid (DHA), 4, cis-5,8,11,14,17-eicosapentaenoic acid (EPA), 5, linolenic acid (ALA), 6, and γ-linolenic acid (GLA), 7, were evaluated for their binding affinity for opioid receptors. ARA, 3, displayed affinity to δ and μ human opioid receptors with 68% and 80%, respectively. GLA, 7, showed selective binding affinity to μ receptor with a value of 55%. These findings provide fascinating insight into the use of foods with high concentrations of fatty acids.
authors.affiliation: Department of Medicinal Chemistry and ‡National Center for Natural Products Research, School of Pharmacy, The University of Mississippi , University, Mississippi 38677, United States.
authors.forename: Amer H
authors.initials: AH
authors.lastname: Tarawneh
authors.forename: Francisco
authors.initials: F
authors.lastname: León
authors.forename: Mohamed M
authors.initials: MM
authors.lastname: Radwan
authors.forename: Xiaoning
authors.initials: X
authors.lastname: Wang
authors.forename: Olivia R
authors.initials: OR
authors.lastname: Dale
authors.forename: Afeef S
authors.initials: AS
authors.lastname: Husni
authors.forename: Luiz H
authors.initials: LH
authors.lastname: Rosa
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Cutler
mesh_terms: D032842:Emericella / Q000737:chemistry / Q000378:metabolism*; D005227:Fatty Acids / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D007700:Kinetics; D019787:Linoleic Acid / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D019308:Palmitic Acid / Q000737:chemistry / Q000378:metabolism; D011485:Protein Binding; D011957:Receptors, Opioid / Q000737:chemistry* / Q000378:metabolism
chemical_list: D005227:Fatty Acids; D011957:Receptors, Opioid; D019308:Palmitic Acid; D019787:Linoleic Acid