A glycosylphosphatidylinositol-anchoring inhibitor with an unusual tetracarbocyclic sesterterpene skeleton from the fungus Codinaea simplex

✍ Scribed by Ying Wang; Michael Dreyfuss; Monique Ponelle; Lukas Oberer; Howard Riezman

• Book ID: 104208603
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 608 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00322-6

✦ Synopsis

A novel sesterterpene, YW3699, was isolated from fermentation of the fungus Codinaea simplex. Based on spectroscopic evidence, including I/V, IR, FAB-MS, ESI-HRMS, IH and 13C NMR, DQ-COSY, HQSC and HMBC, YW3699 was shown to have an unusual tetracarboeyelie sesterterpene skeleton. Its relative stereoehemistry and solution conformation were elucidated with IH-IH coupling constants and detailed analysis of its ROESY spectrum, in conjunction with inspection of Dreiding stereomodels. A possible biosynthetic route for YW3699 via the mevalonate pathway is proposed and discussed. YW3699 was found to be an inhibitor of glycosylphosphatidylinositol (GPI) synthesis with a MIC of 3.5 ~tM.