Elucidation of the biosynthetic origin of the anti-inflammatory pseudopterosins

摘要: The pseudopterosins are a family of diterpene glycosides isolated from the gorgonian coral Pseudopterogorgia elisabethae. These metabolites exhibit potent anti-inflammatory activity, and this review describes our efforts to elucidate their biosynthetic origin. A radioactivity-guided isolation was used identify terpene cyclase product. In addition, detailed NMR-guided search for potential intermediates identified which were tested by incubating 3H-labeled analogues with cell-free extract coral. All labeled generated biosynthetically, radiochemical purity established combination HPLC purification derivatization. summary, produced cyclization geranylgeranyl diphosphate elisabethatriene, aromatization erogorgiaene, two successive oxidations 7,8-dihydroxyerogorgiaene glycosylation afford seco-pseudopterosin as key intermediate. dehydrogenation leads amphilectosins undergo ring closures yield pseudopterosins.