Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa
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...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_16121872_v15_n1_p_PatinoCano |
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todo:paper_16121872_v15_n1_p_PatinoCano2023-10-03T16:28:00Z Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa Patiño Cano, L.P. Quintana Manfredi, R. Pérez, M. García, M. Blustein, G. Cordeiro, R. Pérez, C.D. Schejter, L. Palermo, J.A. Acanthogorgiidae antifouling activity azulene sesquiterpenoids marine natural products octocorals antifouling agent azulene derivative ketolactone linderazulene linderazulene derivative paint sesquiterpene derivative unclassified drug azulene azulene derivative 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 Anthozoa Artemia Azulenes Biofouling Dose-Response Relationship, Drug Molecular Structure Structure-Activity Relationship 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 JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_16121872_v15_n1_p_PatinoCano |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Acanthogorgiidae antifouling activity azulene sesquiterpenoids marine natural products octocorals antifouling agent azulene derivative ketolactone linderazulene linderazulene derivative paint sesquiterpene derivative unclassified drug azulene azulene derivative 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 Anthozoa Artemia Azulenes Biofouling Dose-Response Relationship, Drug Molecular Structure Structure-Activity Relationship |
| spellingShingle |
Acanthogorgiidae antifouling activity azulene sesquiterpenoids marine natural products octocorals antifouling agent azulene derivative ketolactone linderazulene linderazulene derivative paint sesquiterpene derivative unclassified drug azulene azulene derivative 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 Anthozoa Artemia Azulenes Biofouling Dose-Response Relationship, Drug Molecular Structure Structure-Activity Relationship Patiño Cano, L.P. Quintana Manfredi, R. Pérez, M. García, M. Blustein, G. Cordeiro, R. Pérez, C.D. Schejter, L. Palermo, J.A. Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa |
| topic_facet |
Acanthogorgiidae antifouling activity azulene sesquiterpenoids marine natural products octocorals antifouling agent azulene derivative ketolactone linderazulene linderazulene derivative paint sesquiterpene derivative unclassified drug azulene azulene derivative 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 Anthozoa Artemia Azulenes Biofouling Dose-Response Relationship, Drug Molecular Structure Structure-Activity Relationship |
| description |
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 |
| format |
JOUR |
| author |
Patiño Cano, L.P. Quintana Manfredi, R. Pérez, M. García, M. Blustein, G. Cordeiro, R. Pérez, C.D. Schejter, L. Palermo, J.A. |
| author_facet |
Patiño Cano, L.P. Quintana Manfredi, R. Pérez, M. García, M. Blustein, G. Cordeiro, R. Pérez, C.D. Schejter, L. Palermo, J.A. |
| author_sort |
Patiño Cano, L.P. |
| title |
Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa |
| title_short |
Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa |
| title_full |
Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa |
| title_fullStr |
Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa |
| title_full_unstemmed |
Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa |
| title_sort |
isolation and antifouling activity of azulene derivatives from the antarctic gorgonian acanthogorgia laxa |
| url |
http://hdl.handle.net/20.500.12110/paper_16121872_v15_n1_p_PatinoCano |
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