Two new prenylated 3-benzoxepin derivatives as cyclooxygenase inhibitors from Perilla frutescens var. acuta.
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.
Liu
J
J
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Steigel
A
A
Reininger
E
E
Bauer
R
R
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
D001584:Benzoxepins; D016861:Cyclooxygenase Inhibitors