(S)-13-hydroxygeranylgeraniol-derived furanoditerpenes from Bifurcaria bifurcata.
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.
Valls
R
R
Laboratoire d'Analyse et de Valorisation des Biomolécules, I.U.T. de Saint-Jérôme, Université d'Aix-Marseille III, France.
Piovetti
L
L
Banaigs
B
B
Archavlis
A
A
Pellegrini
M
M
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
D004224:Diterpenes