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Int. J. Mol. Sci. 2016, 17(6), 840; doi:10.3390/ijms17060840

Synthesis of New Hydrated Geranylphenols and in Vitro Antifungal Activity against Botrytis cinerea

1
Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso 2340000, Chile
2
Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, Santiago 8910339, Chile
*
Author to whom correspondence should be addressed.
Academic Editor: Zdenek Wimmer
Received: 18 April 2016 / Revised: 12 May 2016 / Accepted: 25 May 2016 / Published: 3 June 2016
(This article belongs to the Section Green Chemistry)
View Full-Text   |   Download PDF [2771 KB, uploaded 3 June 2016]   |  

Abstract

Geranylated hydroquinones and other geranylated compounds isolated from Aplydium species have shown interesting biological activities. This fact has prompted a number of studies where geranylated phenol derivatives have been synthesized in order to assay their bioactivities. In this work, we report the synthesis of a series of new hydrated geranylphenols using two different synthetic approaches and their inhibitory effects on the mycelial growth of Botrytis cinerea. Five new hydrated geranylphenols were obtained by direct coupling reaction between geraniol and phenol in dioxane/water and using BF3·Et2O as the catalyst or by the reaction of a geranylated phenol with BF3·Et2O. Two new geranylated quinones were also obtained. The synthesis and structural elucidation of all new compounds is presented. All hydrated geranylphenols efficiently inhibit the mycelial growth of B. cinerea. Their activity is higher than that observed for non-hydrated compounds. These results indicate that structural modification on the geranyl chain brings about an enhancement of the inhibition effect of geranylated phenol derivatives. View Full-Text
Keywords: geranylated phenol derivatives; hydrated geranyl; synthesis; structural elucidation; growth inhibition effect; Botrytis cinerea; fungicide geranylated phenol derivatives; hydrated geranyl; synthesis; structural elucidation; growth inhibition effect; Botrytis cinerea; fungicide
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Soto, M.; Espinoza, L.; Chávez, M.I.; Díaz, K.; Olea, A.F.; Taborga, L. Synthesis of New Hydrated Geranylphenols and in Vitro Antifungal Activity against Botrytis cinerea. Int. J. Mol. Sci. 2016, 17, 840.

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