Effect of secochiliolide acid isolated from the Patagonian shrub Nardophyllum bryoides as active component in antifouling paints

Pérez, María Emilia; Garcia, Marie-Carmen; Sánchez, Marianela; Stupak, Mirta Elena; Mazzuca, Marcia; Palermo, Jorge Alejandro; Blustein, Guillermo

doi:10.1016/j.ibiod.2014.01.009

Cited by 16 publications

(13 citation statements)

References 73 publications

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“…Antifouling paints were prepared with the addition of one of the tested compounds; acrylic tiles were then painted and tested in the sea at Mar del Plata harbor. Although this assay was originally designed to test the efficacy of antifouling coatings, it is one of the most realistic tests for antifouling activity, since the abiotic and biotic factors are not regulated, and the test surfaces are offered to a diverse fouling community, which has various settlement trends . Settlement of foulers on the experimental paints occurs under natural conditions of flow and diffusion while being exposed to a natural supply of larvae and algal spores.…”

Section: Resultsmentioning

confidence: 99%

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

Cano

Manfredi

Pérez

et al. 2017

Chemistry & Biodiversity

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Three azulenoid sesquiterpenes (1 -3) were isolated from the Antarctic gorgonian Acanthogorgia laxa collected by bottom trawls at À343 m. Besides linderazulene (1), and the known ketolactone 2, a new brominated C 16 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.

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Section: Resultsmentioning

confidence: 99%

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

Cano

Manfredi

Pérez

et al. 2017

Chemistry & Biodiversity

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“…Terrestrial plants produce secondary metabolites that exhibit a variety of biological activities, and there are reports of the use of plant extracts as antifoulants . Some plant bioactive compounds have shown antifouling properties in previous studies …”

Section: Introductionmentioning

confidence: 99%

“…[15,16] Some plant bioactive compounds have shown antifouling properties in previous studies. [17][18][19][20][21][22][23][24][25][26] In this work is studied the antifouling activity of five alkaloids: three indole alkaloids from the bark of A. australe and two furoquinoline alkaloids from the bark of B. riedelianum by laboratory and field assays. These compounds, which have been known for several decades, fulfill the following criteria used for sample selection: previous reports of biological activity for compounds of the same family, high yields of extraction from their biological sources and simple purification protocols.…”

Section: Introductionmentioning

confidence: 99%

Isolation and Antimacrofouling Activity of Indole and Furoquinoline Alkaloids from ‘Guatambú’ Trees (Aspidosperma australe and Balfourodendron riedelianum)

Pérez

Diez

Valdez

et al. 2019

Chemistry & Biodiversity

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In this work, the antifouling activity of five alkaloids, isolated from trees of the Atlantic rainforest, was studied. The tested alkaloids were olivacine (1), uleine (2) and N‐methyltetrahydroellipticine (3) from Aspidosperma australe (‘yellow guatambú’) and the furoquinoline alkaloids kokusaginine (4) and flindersiamine (5) from Balfourodendron riedelianum (‘white guatambú’). All these compounds can be isolated from their natural sources in high yields in a sustainable way. The five compounds were subjected to laboratory tests (attachment test of the mussel Mytilus edulis platensis) and field trials, by incorporation into soluble matrix paints, and 45 days of exposure of the painted panels in the sea. The results show that compound 3 is a very potent antifoulant, and that compounds 4 and 5 are also very active, while compounds 1 and 2 did not show any significant antifouling activity. These results open the way for the development of environmentally friendly antifouling agents, based on abundant and easy‐to‐purify compounds that can be obtained in a sustainable way.

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“…Por otra parte, ciertos metabolitos secundarios de plantas terrestres demostraron actividad antiincrustante [7]. Entre los metabolitos más comunes obtenidos de plantas se encuentran las cumarinas, benzo α pironas derivadas del metabolismo de la fenilalanina.…”

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Protección antiincrustante de estructuras sumergidas mediante recubrimientos formulados con 7-hidroxi-4-metilcumarina

et al. 2018

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RESUMENLa fijación de micro y macroorganismos sobre estructuras sumergidas como embarcaciones, boyas, granjas de cultivo, plataformas offshore acarrea enormes pérdidas económicas como consecuencia del deterioro de materiales y el retiro de servicio. Dado que las regulaciones vigentes apuntan a la utilización de productos "amigables con el medio ambiente" para reemplazar los biocidas metálicos altamente contaminantes empleados en pinturas antiincrustantes, existe un creciente interés por hallar compuestos que resulten eficaces sin que alteren los ecosistemas.Con esta finalidad, se sintetizó el compuesto 7-hidroxi-4-metilcumarina aplicando procedimientos de la Química Verde, esto es, en ausencia de solvente y usando ácidos sólidos recuperables, y se lo caracterizó por medio de análisis orgánicos corrientes.En laboratorio se evaluó la actividad antiincrustante de esta cumarina mediante test de asentamiento exponiendo al mejillón Mytilus edulis platensis a distintas concentraciones. Los resultados indicaron que la cumarina fue efectiva tanto en la inhibición del asentamiento como en la producción de hebras del biso. Asimismo, se realizaron ensayos de recuperación de los organismos en agua de mar sin el agregado del compuesto comprobándose que el efecto inhibidor de la cumarina es transitorio dado que recuperaron rápidamente sus funciones vitales.Posteriormente, se formuló una pintura de matriz soluble conteniendo este compuesto y se aplicó sobre paneles que se expusieron en el puerto de Mar del Plata por 45 y 90 días. Esta formulación demostró un marcado efecto antiincrustante sobre las especies más conspicuas de la comunidad.El compuesto 7-hidroxi-4-metilcumarina obtenido por síntesis sustentable resulta promisorio para su utilización en pinturas antiincrustantes no solo por la eficiencia demostrada sino también por su baja toxicidad.Palabras clave: incrustaciones biológicas, cumarinas, pinturas antiincrustantes. ABSTRACTBiofouling settlement on submerged structures such as ships, buoys, farms, off-shore platforms and meteorological stations induces economic losses as a consequence of material deterioration and withdraw from service.Environmental regulations focus on the use of environmental friendly products to replace metallic biocides included in antifouling paints which are highly pollutant. A growing interest for searching and identifying efficient and benign antifoulants has being carried out.For this reason, the compound 7-hydroxy-4-methylcoumarin was synthesized following Green Chemistry

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Effect of secochiliolide acid isolated from the Patagonian shrub Nardophyllum bryoides as active component in antifouling paints

Cited by 16 publications

References 73 publications

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

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

Isolation and Antimacrofouling Activity of Indole and Furoquinoline Alkaloids from ‘Guatambú’ Trees (Aspidosperma australe and Balfourodendron riedelianum)

Protección antiincrustante de estructuras sumergidas mediante recubrimientos formulados con 7-hidroxi-4-metilcumarina

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