Constituents of the seeds of Hernandia ovigera with inhibitory activity against cyclooxygenase-2.
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.
Jang
Dae Sik
DS
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.
Cuendet
Muriel
M
Su
Bao-Ning
BN
Totura
Steven
S
Riswan
Soedarsono
S
Fong
Harry H
HH
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
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
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