C(15) Acetogenins from the red alga Laurencia obtusa.
Four C(15) acetogenins, 13-epilaurencienyne (3Z) (1), 13-epipinnatifidenyne (3E) (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(*), 12R(*))-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.
Iliopoulou
Dimitra
D
Department of Pharmacy, Division of Pharmacognosy, University of Athens, Panepistimioupolis Zografou, 157 71, Athens, Greece.
Vagias
Constantinos
C
Harvala
Catherine
C
Roussis
Vassilios
V
D000818:Animals; D001000:Ants / Q000187:drug effects; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000461:Rhodophyta / Q000737:chemistry*
C450179:13-epilaurencienyne; C450180:9-chloro-13-bromo-6,12-epoxy-7,10-diacetoxypentadec-3-en-1-yne; D006573:Heterocyclic Compounds, 1-Ring; D007306:Insecticides