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Paper | Regular issue | Vol 63, No. 6, 2004, pp.1375-1392
Published online, 9th April, 2004
DOI: 10.3987/COM-04-10060
Kwakhurin, a Unique Isoflavone with Rejuvenating Activity from “Kwao Keur”: Further Characterization by 2D-NMR Spectrometry and Synthesis of Triisopropylkwakhurin

Misako Iwasaki, Toshiko Watanabe,* Tsutomu Ishikawa, Sunee Chansakaow, Yoshihiro Higuchi, and Satoshi Tahara

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Kwakhurin (5), a characteristic isoflavone component of Pueraria mirifica which has been used in folk medicine as “kwao keur” for rejuvenating purpose, was structurally approached by 2D-NMR experiments. Furthermore, the synthesis of kwakhurin (5) was attempted starting from the methyl ketone (12). Thus, deoxybenzoin derivative (22) was prepared by Friedel-Crafts acylation after protection of the phenolic function with a triisopropyl group. Modification of the substituents, O-prenylation, prenyl 1,3-rearrangement, and O-methylation afforded kwakhurin triisopropyl ether (38).