Synthesis of New Hydrated Geranylphenols and in Vitro Antifungal Activity against Botrytis cinerea.
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.
Departamento de Qu&#237;mica, Universidad T&#233;cnica Federico Santa Mar&#237;a, Valpara&#237;so 2340000, Chile. mauricio.sotoc.13@sansano.usm.cl.
Mauricio
M
Soto
Departamento de Qu&#237;mica, Universidad T&#233;cnica Federico Santa Mar&#237;a, Valpara&#237;so 2340000, Chile. luis.espinozac@usm.cl.
Luis
L
Espinoza
Departamento de Qu&#237;mica, Universidad T&#233;cnica Federico Santa Mar&#237;a, Valpara&#237;so 2340000, Chile. maria.chavez@usm.cl.
María I
MI
Chávez
Departamento de Qu&#237;mica, Universidad T&#233;cnica Federico Santa Mar&#237;a, Valpara&#237;so 2340000, Chile. katy.diaz@usm.cl.
Katy
K
Díaz
Instituto de Ciencias Qu&#237;micas Aplicadas, Facultad de Ingenier&#237;a, Universidad Aut&#243;noma de Chile, Santiago 8910339, Chile. andres.olea@uautonoma.cl.
Andrés F
AF
Olea
Departamento de Qu&#237;mica, Universidad T&#233;cnica Federico Santa Mar&#237;a, Valpara&#237;so 2340000, Chile. lautaro.taborga@usm.cl.
Lautaro
L
Taborga
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020171:Botrytis / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology
D000935:Antifungal Agents; D010636:Phenols; D010936:Plant Extracts
Botrytis cinerea; fungicide; geranylated phenol derivatives; growth inhibition effect; hydrated geranyl; structural elucidation; synthesis