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Science 3 June 1983:
Vol. 220. no. 4601, pp. 1065 - 1066
DOI: 10.1126/science.220.4601.1065
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Articles

Crystallization and X-ray Analysis of Stemphyloxin I, a Phytotoxin from Stemphylium botryosum

ISAAC BARASH 1, SHULAMIT MANULIS 1, YOEL KASHMAN 2, JAMES P. SPRINGER 3, MARIE H. M. CHEN 4, JON CLARDY 4, and GARY A. STROBEL 5

1 Department of Botany, University of Tel Aviv, Tel Aviv, Israel
2 Department of Chemistry, University of Tel Aviv
3 Merck Institute for Therapeutic Research, Rahway, New Jersey 07065
4 Department of Chemistry, Cornell University, Ithaca, New York 14853
5 Department of Plant Pathology, Montana State University, Bozeman 59717

Certain isolates of the plant-pathogenic fungus Stemphylium botryosum produce a phytotoxin, stemphyloxin I. This toxin (C21H34O6) was crystallized and its structure was determined by x-ray crystallography to be a beta-ketoaldehyde trans-Decalin. This compound is a highly unusual natural product. Iron (Fe3+) controls production of toxin by this fungus. Furthermore, iron reacts with the toxin to yield a colored product which aids in its detection on chromatograms and in its quantitative estimation by colorimetry.;

Submitted on November 15, 1982
Revised on January 28, 1983

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Science. ISSN 0036-8075 (print), 1095-9203 (online)