Next Article in Journal
Gas Phase Thermal Reactions of exo-8-Cyclopropyl-bicyclo[4.2.0]oct-2-ene (1-exo)
Previous Article in Journal
Cross-Talk of Phosphorylation and Prolyl Isomerization of the C-terminal Domain of RNA Polymerase II
Molecules 2014, 19(2), 1512-1526; doi:10.3390/molecules19021512
Article

Synthesis of Linear Geranylphenols and Their Effect on Mycelial Growth of Plant Pathogen Botrytis cinerea

1,* , 1
, 1
, 2
 and 3
Received: 9 December 2013; in revised form: 4 January 2014 / Accepted: 15 January 2014 / Published: 27 January 2014
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [526 KB, uploaded 18 June 2014]   |   Browse Figures
Abstract: Natural geranyl compounds are known to exhibit important biological activities. In this work a series of geranylphenols were synthesized to evaluate their effect on the mycelial growth of Botrytis cinerea. Geranyl derivatives were synthesized by direct geranylation reactions between the corresponding phenol derivatives and geraniol, using BF3.OEt2 as catalyst and AgNO3 as secondary catalyst. Previously reported molecules [geranylhydroquinone (2), geranylhydroquinone diacetate (6) and geranylphloroglucinol (9)], and new substances [(E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,2,3-triol (geranyl-pyrogallol, 7), (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,2,3-triyl triacetate (8), (E)-2-(3,7-dimethylocta-2,6-dienyl)benzene-1,3,5-triyl triacetate geranylphloroglucinol triacetate (10), 2,4-bis((E)-3,7-dimethylocta-2,6-dienyl)benzene-1,3,5-triyl triacetate (11), 2,6-bis((E)-3,7-dimethylocta-2,6-dienyl)-3,5-dihydroxyphenyl acetate (12)], were obtained. All compounds were characterized by IR, HRMS and NMR spectroscopic data. The inhibitory effect of the synthesized compounds on the mycelial growth of Botrytis cinerea was tested in vitro. Excepting compound 11, all substances constrained the mycelial growth of Botrytis cinerea. The antifungal activity depends on the chemical structure of geranylphenol derivatives. Compounds 2 and 9 were the more effective substances showing inhibition degrees higher than those obtained with the commercial fungicide Captan, even at lower concentrations. Monosubstitution on the aromatic nucleus by a geranyl chain seems to be more effective for the inhibition of mycelial growth than a double substitution. These results suggest that the new derivatives of geranylphenols have the ability to block the mycelial development of the plant pathogen B. cinerea and that this capacity depends strongly on the structural features and lipophilicity of the compounds.
Keywords: synthesis; linear geranylphenols; antifungal activity; Botrytis cinerea synthesis; linear geranylphenols; antifungal activity; Botrytis cinerea
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.

Export to BibTeX |
EndNote


MDPI and ACS Style

Espinoza, L.; Taborga, L.; Díaz, K.; Olea, A.F.; Peña-Cortés, H. Synthesis of Linear Geranylphenols and Their Effect on Mycelial Growth of Plant Pathogen Botrytis cinerea. Molecules 2014, 19, 1512-1526.

AMA Style

Espinoza L, Taborga L, Díaz K, Olea AF, Peña-Cortés H. Synthesis of Linear Geranylphenols and Their Effect on Mycelial Growth of Plant Pathogen Botrytis cinerea. Molecules. 2014; 19(2):1512-1526.

Chicago/Turabian Style

Espinoza, Luis; Taborga, Lautaro; Díaz, Katy; Olea, Andrés F.; Peña-Cortés, Hugo. 2014. "Synthesis of Linear Geranylphenols and Their Effect on Mycelial Growth of Plant Pathogen Botrytis cinerea." Molecules 19, no. 2: 1512-1526.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert