title: (S)-13-hydroxygeranylgeraniol-derived furanoditerpenes from Bifurcaria bifurcata.
abstract: Two new diterpenes were isolated from a sample of the brown alga Bifurcaria bifurcata collected from Brittany on the Atlantic coast and their structures established by spectroscopic methods. The new diterpenes are derived from (S)-13-hydroxygeranylgeraniol by terminal cyclization and oxidation leading to a furan-3-yl ring or a beta,gamma-epoxy-gamma-lactone. One of them showed a cytotoxic effect to fertilized sea urchin eggs. The chemical shifts of the methyl groups and quaternary carbons in (S)-13-hydroxygeranylgeraniol have been revised to take account of the results obtained in a 2D NMR long-range C-H correlation experiment and the absolute configuration at C-13 determined for the first time. The geographical variation in the diterpenoid composition of B. bifurcata was also studied.
authors.affiliation: Laboratoire d'Analyse et de Valorisation des Biomolécules, I.U.T. de Saint-Jérôme, Université d'Aix-Marseille III, France.
authors.forename: R
authors.initials: R
authors.lastname: Valls
authors.forename: L
authors.initials: L
authors.lastname: Piovetti
authors.forename: B
authors.initials: B
authors.lastname: Banaigs
authors.forename: A
authors.initials: A
authors.lastname: Archavlis
authors.forename: M
authors.initials: M
authors.lastname: Pellegrini
mesh_terms: D000818:Animals; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D010063:Ovum / Q000187:drug effects; D000459:Phaeophyceae / Q000737:chemistry*; D012617:Sea Urchins / Q000196:embryology
chemical_list: D004224:Diterpenes