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Two new isoflavones from Ceiba pentandra and their effect on cyclooxygenase-catalyzed prostaglandin biosynthesis
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
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
Abstract [en]

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.
National Category
Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-50639DOI: 10.1021/np970198+ISI: 000071728100002PubMedID: 9461647OAI: oai:DiVA.org:uu-50639DiVA: diva2:78547
Available from: 2008-10-17 Created: 2008-10-17 Last updated: 2017-12-05Bibliographically approved

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