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

• Main Authors: Mauricio Soto, Luis Espinoza, María I. Chávez, Katy Díaz, Andrés F. Olea, Lautaro Taborga
• Format: Article
• Language: English
• Published: MDPI AG 2016-06-01
• Series: International Journal of Molecular Sciences
• Subjects: geranylated phenol derivatives; hydrated geranyl; synthesis; structural elucidation; growth inhibition effect; Botrytis cinerea; fungicide
• Online Access: http://www.mdpi.com/1422-0067/17/6/840

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.