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 CdC 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.
Structure and absolute stereochemistry of fusaproliferin, a toxic metabolite from Fusarium proliferatum / Antonello, Santini; Alberto, Ritieni; Vincenzo, Fogliano; Giacomino, Randazzo; Mannina, Luisa; Antonio, Logrieco; Ettore, Benedetti. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - ELETTRONICO. - 59:2(1996), pp. 109-112. [10.1021/np960023k]
Structure and absolute stereochemistry of fusaproliferin, a toxic metabolite from Fusarium proliferatum
MANNINA, LUISA;
1996
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 CdC 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.