Meroditerpenoids and derivatives from the brown alga Cystoseira baccata and their antifouling properties.
The brown alga Cystoseira baccata harvested along the Atlantic coasts of Morocco yielded seven new meroditerpenoids (1-4) and derivatives (5-7), whose chemical structures were elucidated mainly by 2D NMR and mass spectrometry. Surprisingly, for all these compounds, which possess a bicyclo[4.3.0]nonane ring system, a trans fusion of the bicyclic system was deduced by stereochemical studies even though such compounds isolated from Cystoseira species are known to have a typical cis orientation for the bridgehead methyls. The antifouling and antibacterial activities of compounds 1-5 and 7 were evaluated, as well as their toxicity toward nontarget species. Compounds 4, 5, and 7 showed antifouling activities against growth of microalgae, macroalgal settlement, and mussel phenoloxidase activity, while being nontoxic to larvae of sea urchins and oysters.
Mokrini
Redouane
R
Laboratoire MAPIEM, Université du Sud Toulon-Var, Avenue de l'Université, BP 20132, F-83957 La Garde Cedex, France.
Mesaoud
Mohammed Ben
MB
Daoudi
Mohammed
M
Hellio
Claire
C
Maréchal
Jean-Philippe
JP
El Hattab
Mohamed
M
Ortalo-Magné
Annick
A
Piovetti
Louis
L
Culioli
Gérald
G
D000818:Animals; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009018:Morocco; D019906:Nuclear Magnetic Resonance, Biomolecular; D010125:Ostreidae / Q000187:drug effects; D000459:Phaeophyceae / Q000737:chemistry*; D012617:Sea Urchins / Q000187:drug effects; D013237:Stereoisomerism
D004224:Diterpenes