Two new isoflavones from Ceiba pentandra and their effect on cyclooxygenase-catalyzed prostaglandin biosynthesis
1998 (English)In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 61, no 1, 8-12 p.Article in journal (Refereed) Published
The new isoflavone glucoside vavain 3'-O-beta-d-glucoside (1) and its aglycon, vavain (2), were isolated from the bark of Ceiba pentandra, together with the known flavan-3-ol, (+)-catechin, These novel structures were elucidated by one- and two-dimensional NMR experiments and by MS, IR, and UV spectroscopy as 5-hydroxy-7,4',5'-trimethoxyisoflavone 3'-O-beta-D-glucoside (1) and 5,3'-dihydroxy-7,4',5'-trimethoxyisoflavone (2), respectively. The compounds were isolated following bioactivity-directed fractionation, using a cyclooxygenase-1-catalyzed prostaglandin biosynthesis assay in vitro, in which compounds 1 and 2 and (+)-catechin exhibited IC50 values of 381, 97, and 80 microM, respectively (standard: indomethacin, IC50 1,1 microM). When further tested for their inhibitory effects on cyclooxygenase-2-catalyzed prostaglandin biosynthesis, 1 and 2 were found to be inactive (IC50 > 1200 and > 900 microM, respectively).
Place, publisher, year, edition, pages
1998. Vol. 61, no 1, 8-12 p.
IdentifiersURN: urn:nbn:se:uu:diva-50639DOI: 10.1021/np970198+ISI: 000071728100002PubMedID: 9461647OAI: oai:DiVA.org:uu-50639DiVA: diva2:78547