Structure and absolute stereochemistry of fusaproliferin, a toxic metabolite from Fusarium proliferatum

Antonello Santini*, Alberto Ritieni, Vincenzo Fogliano, Giacomino Randazzo, Luisa Mannina, Antonio Logrieco, Ettore Benedetti

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

44 Citations (Scopus)

Abstract

Fusaproliferin is a toxic sesterterpene isolated from Fusarium proliferatum, a widespread pathogen of cereals. Its absolute configuration has been determined by single crystal X-ray diffraction analysis. Fusaproliferin is considered to be a sesterterpene with a new ring skeleton having four C=C double bonds and four chiral atoms. The configurations of the four chiral atoms C10, C14, C15, and C19 are (R), (S), (R), and (S), respectively. In the solid state the macrolide Shows a concave hydrophobic surface and hydrophilic convex face. The absolute configuration of C14 and C15 is the same as that observed for retigeranic acid, consistent with fusaproliferin being formed via a sesterterpenic-type biosynthetic pathway.

Original languageEnglish
Pages (from-to)109-112
Number of pages4
JournalJournal of Natural Products
Volume59
Issue number2
DOIs
Publication statusPublished - Jan 1996
Externally publishedYes

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