SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES

Osorio, Mauricio E.; Quiroz, Karol A.; Carvajal, Marcela A.; Vergara, Alejandra P.; Sánchez, Elizabeth Y.; González, Cesar E.; Catalán, Karen S.

dc.creator	Osorio, Mauricio E.
dc.creator	Quiroz, Karol A.
dc.creator	Carvajal, Marcela A.
dc.creator	Vergara, Alejandra P.
dc.creator	Sánchez, Elizabeth Y.
dc.creator	González, Cesar E.
dc.creator	Catalán, Karen S.
dc.date	2016-09-10
dc.date.accessioned	2019-11-13T15:11:24Z
dc.date.available	2019-11-13T15:11:24Z
dc.identifier	http://www.jcchems.com/index.php/JCCHEMS/article/view/100
dc.identifier.uri	https://revistaschilenas.uchile.cl/handle/2250/112533
dc.description	The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (SEAr) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay and expressed as half maximal inhibitory concentration (IC50) values in μM concentrations. The antioxidant activity went from 27.20 μM to >100 μM. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC50 values between 250 and <3.9 μM.	en-US
dc.format	application/pdf
dc.language	eng
dc.publisher	Sociedad Chilena de Química	en-US
dc.relation	http://www.jcchems.com/index.php/JCCHEMS/article/view/100/86
dc.rights	Copyright (c) 2017 Mauricio E. Osorio, Karol A. Quiroz, Marcela A. Carvajal, Alejandra P. Vergara, Elizabeth Y. Sánchez, Cesar E. González, Karen S. Catalán	en-US
dc.rights	https://creativecommons.org/licenses/by-nc-sa/4.0	en-US
dc.source	Journal of the Chilean Chemical Society; Vol 61 No 3 (2016): Journal of the Chilean Chemical Society	en-US
dc.source	0717-9707
dc.source	0717-9324
dc.subject	C-prenylation	en-US
dc.subject	Prenylated acetophenone	en-US
dc.subject	Prenylated benzaldehyde	en-US
dc.subject	Electrophilic aromatic substitution	en-US
dc.subject	Anti-phytopathogenic	en-US
dc.subject	DPPH radical scav¬enging activity	en-US
dc.title	SYNTHESIS, ANTI-PHYTOPATHOGENIC AND DPPH RADICAL SCAVENGING ACTIVITIES OF C-PRENYLATED ACETOPHENONES AND BENZALDEHYDES	en-US
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/publishedVersion

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