title: Constituents of the seeds of Hernandia ovigera with inhibitory activity against cyclooxygenase-2.
abstract: A new dibenzylbutyrolactone lignan, (2 R,3 R)-5'-methoxyguayarol (1), was isolated from an EtOAc-soluble extract of the seeds of Hernandia ovigera using an in vitro activity-guided fractionation procedure based on the inhibition of cyclooxygenase-2. Also obtained were three known fatty acid derivatives, (S)-coriolic acid, (+/-)-12,13-epoxyoleic acid, and (+/-)-glycerol 1-monolinolate, and seven known lignans, epiashantin, dehydrodesoxypodophyllotoxin, dehydropodophyllotoxin, (-)-hernolactone, (-)-pinoresinol, (-)-syringaresinol, and (-)-yatein. The structure, including absolute stereochemistry, of compound 1 was determined using spectroscopic methods. All isolates were tested for their inhibitory effects against both cyclooxygenases-1 and -2, with (S)-coriolic acid and (+/-)-glycerol 1-monolinolate shown to have selective inhibitory activity with cyclooxygenase-2.
authors.affiliation: Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, IL, USA.
authors.forename: Dae Sik
authors.initials: DS
authors.lastname: Jang
authors.forename: Muriel
authors.initials: M
authors.lastname: Cuendet
authors.forename: Bao-Ning
authors.initials: BN
authors.lastname: Su
authors.forename: Steven
authors.initials: S
authors.lastname: Totura
authors.forename: Soedarsono
authors.initials: S
authors.lastname: Riswan
authors.forename: Harry H
authors.initials: HH
authors.lastname: Fong
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D006801:Humans; D020128:Inhibitory Concentration 50; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D019770:Lauraceae; D008565:Membrane Proteins; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D011451:Prostaglandin-Endoperoxide Synthases; D012639:Seeds
chemical_list: D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D007527:Isoenzymes; D008565:Membrane Proteins; D010936:Plant Extracts; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; C496511:PTGS1 protein, human; C496540:PTGS2 protein, human; D011451:Prostaglandin-Endoperoxide Synthases