title: Antifouling properties of simple indole and purine alkaloids from the Mediterranean gorgonian Paramuricea clavata.
abstract: Chemical investigation of the Mediterranean gorgonian Paramuricea clavata resulted in the isolation of two new alkaloids, 2-bromo-N-methyltryptamine (1) and 3-bromo-N-methyltyramine (2), together with nine known compounds (3-10 and linderazulene). The bromoindole derivative 3 is reported herein for the first time from a natural source. The chemical structures of these compounds were assigned by spectroscopic analyses and comparison with literature values. The antifouling activity and toxicity of compounds 1-10 were assessed using three marine biofilm bacteria and the Microtox assay. In contrast to commercial antifoulants, bufotenine (5) and 1,3,7-trimethylisoguanine (10) showed significant antiadhesion activity against one bacterial strain while being nontoxic.
authors.affiliation: Laboratoire MAPIEM, EA 4323, Biofouling et Substances Naturelles Marines, Université du Sud Toulon-Var, Avenue de l'Université, BP 20132, F-83957 La Garde Cedex, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Pénez
authors.forename: Gérald
authors.initials: G
authors.lastname: Culioli
authors.forename: Thierry
authors.initials: T
authors.lastname: Pérez
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Briand
authors.forename: Olivier P
authors.initials: OP
authors.lastname: Thomas
authors.forename: Yves
authors.initials: Y
authors.lastname: Blache
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D057219:Biofouling / Q000517:prevention & control*; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D011687:Purines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014363:Tryptamines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D014439:Tyramine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: C568804:2-bromo-N-methyltryptamine; C568805:3-bromo-N-methyltyramine; D026121:Indole Alkaloids; D011687:Purines; D014363:Tryptamines; D014439:Tyramine