title: Two new prenylated 3-benzoxepin derivatives as cyclooxygenase inhibitors from Perilla frutescens var. acuta.
abstract: Two novel prenyl 3-benzoxepin derivatives, perilloxin (1) and dehydroperilloxin (2), were isolated from the dichloromethane extract of the stems of Perilla frutescens var. acuta. Their structures were elucidated as (-)-(R)-5-methoxy-2,3-dihydrofuro[2, 3-g][3]benzoxepin and 5-methoxyfuro[2,3-g][3]benzoxepin, respectively, based on UV, MS, (1)H and (13)C NMR, NOE, (1)H-(13)C COSY, and HMBC spectral data. They were isolated following bioassay-guided fractionation, using an in vitro cyclooxygenase-1 test. Compounds 1 and 2 possess inhibitory activities, with IC(50) values of 23.2 microM and 30.4 microM, respectively.
authors.affiliation: Department of Chemistry, Columbia University, New York, New York 10027, USA.
authors.forename: J
authors.initials: J
authors.lastname: Liu
authors.forename: A
authors.initials: A
authors.lastname: Steigel
authors.forename: E
authors.initials: E
authors.lastname: Reininger
authors.forename: R
authors.initials: R
authors.lastname: Bauer
mesh_terms: D000818:Animals; D001584:Benzoxepins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D019686:Lamiaceae / Q000737:chemistry*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D012756:Sheep
chemical_list: D001584:Benzoxepins; D016861:Cyclooxygenase Inhibitors