Syntheses and Biological Activities of Dihydro-5,6-dehydrokawain Derivatives | Zendy

Shinkichi Tawata | Zendy; Shigehiko Taira | Zendy; Naotada Kobamoto | Zendy; Masanobu Ishihara | Zendy; Seizen Toyama | Zendy

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Syntheses and Biological Activities of Dihydro-5,6-dehydrokawain Derivatives

Author(s) -

Shinkichi Tawata,

Shigehiko Taira,

Naotada Kobamoto,

Masanobu Ishihara,

Seizen Toyama

Publication year - 1996

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.60.1643

Subject(s) - antifungal , pyran , chemistry , biological activity , organic chemistry , stereochemistry , biology , microbiology and biotechnology , biochemistry , in vitro

The syntheses and biological activities of dihydro-5,6-dehydrokawain derivatives against plant pathogenic fungi and termites were investigated. Dihydro-5,6-dehydrokawain was isolated by a simple method without chromatography from the leaves of Alpinia speciosa K. SCHUM. The white crystalline compound obtained was identified as dihydro-5,6-dehydrokawain (1) by instrumental analyses. 4-Hydroxy-6-(2-phenylethyl)-2H-pyran-2-one (3) was prepared by hydrolyzing dihydro-5,6-dehydrokawain. Three dihydro-5,6-dehydrokawain derivatives were synthesized by reacting 3 with phosphoric agents. Among the synthesized compounds, dimethyl [6-(2-phenylethyl)-2-oxo-2H-pyran-4-yl]phosphorothionate (4) had the strongest antifungal activity of 91% at 100 ppm against Corticium rolfsii.

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