Two new prenylated 3-benzoxepin derivatives as cyclooxygenase inhibitors from Perilla frutescens var. acuta

J Liu; A Steigel; E Reininger; R Bauer

doi:10.1021/np990362o

Two new prenylated 3-benzoxepin derivatives as cyclooxygenase inhibitors from Perilla frutescens var. acuta

J Nat Prod. 2000 Mar;63(3):403-5. doi: 10.1021/np990362o.

Authors

J Liu¹, A Steigel, E Reininger, R Bauer

Affiliation

¹ Department of Chemistry, Columbia University, New York, New York 10027, USA.

PMID: 10757731
DOI: 10.1021/np990362o

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Benzoxepins / chemistry
Benzoxepins / isolation & purification
Benzoxepins / pharmacology*
Cyclooxygenase Inhibitors / chemistry
Cyclooxygenase Inhibitors / isolation & purification
Cyclooxygenase Inhibitors / pharmacology*
Lamiaceae / chemistry*
Molecular Structure
Plants, Medicinal / chemistry*
Sheep

Substances

Benzoxepins
Cyclooxygenase Inhibitors