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J. Biochem, 1983, Vol. 94, No. 1 149-154
© 1983 Japanese Biochemical Society

research-article

Physiological Activity of Warburganal and Its Reactivity with Sulfhydryl Groups

Makoto TANIGUCHI*, Takeshi ADACHI*, Hiroyuki HARAGUCHI*, Susumu OI* and Isao KUBO**

*Department of Biology, Faculty of Science, Osaka City University Sumiyoshi-ku, Osaka, Osaka 558
**Division of Entomology and Parasitology, College of Natural Resources, University of California Berkeley, California 94720, U.S.A.

Warburganal, a unique dialdehyde sesquiterpene isolated from East African Warburgia plants, showed a strong antifungal activity. However, this growth inhibition in Saccharomyces cerevisiae was reversed with L-cysteine. In addition, warburganal inhibited the alcoholic fermentation of S. cerevisiae while L-cysteine reversed this inhibiton. When alcohol dehydrogenase, a sulfhydryl enzyme, was incubated with warburganal, the enzyme activity decreased with time. The decrease was more rapid at alkaline pH. L-Cysteine prevented this enzyme inhibition by warburganal but could not restore the enzyme activity lost already due to warburganal. Warburganal lost its characteristic ultraviolet absorption spectrum in the presence of L-cysteine. The change in absorbance was favored at alkaline pH, indicating Michael reaction type addition of L-cysteine to warburganal. Based on these observations, a variety of physiological activities due to warburganal appear to result from its irreversible reactivity with sulfhydryl groups.


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