Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa

• Main Authors: Patiño Cano, L.P., Quintana Manfredi, R., Pérez, M., García, M., Blustein, G., Cordeiro, R., Pérez, C.D., Schejter, L., Palermo, J.A.
• Format: Journal/Newspaper
• Language: unknown
• Subjects: Acanthogorgiidae; antifouling activity; azulene sesquiterpenoids; marine natural products; octocorals; antifouling agent; azulene derivative; ketolactone; linderazulene; linderazulene derivative; paint; sesquiterpene derivative; unclassified drug; azulene; Acanthogorgia laxa; Amphibalanus amphitrite; Artemia salina; Article; biofouling; carbon nuclear magnetic resonance; controlled study; heteronuclear multiple bond correlation; heteronuclear single quantum coherence; Lindera; Lindera strychnifolia; Mannich reaction; marine species; nonhuman; nuclear magnetic resonance spectroscopy; nuclear Overhauser effect; proton nuclear magnetic resonance; thin layer chromatography; animal; Antarctica; Anthozoa; Artemia; chemical structure; chemistry; dose response; drug effects; isolation and purification; structure activity relation; Animals; Antarctic Regions; Azulenes; Dose-Response Relationship; Antarc*; Antarctic
• Online Access: https://hdl.handle.net/20.500.12110/paper_16121872_v15_n1_p_PatinoCano

Three azulenoid sesquiterpenes (1 – 3) were isolated from the Antarctic gorgonian Acanthogorgia laxa collected by bottom trawls at −343 m. Besides linderazulene (1), and the known ketolactone 2, a new brominated C16 linderazulene derivative (3) was also identified. This compound has an extra carbon atom at C(7) of the linderazulene framework. The antifouling activity of compounds 1 and 2 was assayed in the laboratory with Artemia salina larvae, and also in field tests, by incorporation in soluble-matrix experimental antifouling paints. The results obtained after a 45 days field trial of the paints, showed that compounds 1 and 2 displayed good antifouling potencies against a wide array of organisms. Compound 3, a benzylic bromide, was unstable and for this reason was not submitted to bioassays. Two known cembranolides: pukalide and epoxypukalide, were also identified as minor components of the extract. © 2018 Wiley-VHCA AG, Zurich, Switzerland