Dolores Garcia Gravalos

Helioporins : bioactive diterpenes from the blue coral Heliopora coerulea

Abstract Seven new diterpenes, helioporins A-G (1–7), have been isolated from the blue coral Heliopora coerulea . The structures determined by spectroscopic data and chemical conversions are related to the aglycons of pseudopterosins and seco-pseudopterosins, which are antiinflammatory glycosides from Caribbean gorgonians. Treatment of helioporin A ( a ) with TMSI/NaI followed by Na 2 S 2 O 3 gave helioporin E ( 5 ) and an unusual product ( 11 ) resulting from CC bond cleavage. Reaction of helioporin B ( 2 ) with Tf 2 O/C 5 H 2 NMe t -Bu 2 followed by catalytic reduction gave a cyclization product ( 14 ) which was identical with a compound derived from 5 . All helioporins were chemically correlated and their relative stereochemistry was related to that of the aglycon of pseudopterosin G ( 10 ). Helioporins A and B showed antiviral activity against HSV1 and C-G cytotoxicity against P388.