C-15 acetogenins from the red alga Laurencia obtusa

Four C-15 acetogenins, 13-epilaurencienyne (3Z) (1), 13-epipinnatifidenyne (3,E) (2), (3E, 6S*, 7R*, 9S*, 10S*, 12R*)-9-chloro-13-bromo-6:12-epoxy-7, 10-diacetoxypentadec-3-en-1-yne (3), (3Z, 6S*, 7R*, 9S*, 10S*, 12 R *)-9-chloro-13-bromo-6:12-epoxy-7, 10-diacetoxypentadec-3-en-1-yne (4), along with the known 13-epilaurencienyne (3E) (5), have been isolated from the organic extract of the red alga Laurencia obtusa collected in the Aegean Sea, Greece. The structures of the new natural products, as well as their relative stereochemistry, were established by means of spectral data analysis, including 2D NMR spectroscopic experiments. Some of the new metabolites exhibited significant insecticidal activity. (C) 2002 Elsevier Science Ltd. All rights reserved.