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Synthesis of new hydrated geranylphenols and in vitro antifungal activity against botrytis cinerea

dc.contributor.authorSoto M.
dc.contributor.authorEspinoza L.
dc.contributor.authorChávez M.I.
dc.contributor.authorDíaz K.
dc.contributor.authorOlea A.F.
dc.contributor.authorTaborga L.
dc.date.accessioned2020-09-02T22:28:38Z
dc.date.available2020-09-02T22:28:38Z
dc.date.issued2016
dc.identifier10.3390/ijms17060840
dc.identifier.citation17, 6, -
dc.identifier.issn16616596
dc.identifier.urihttps://hdl.handle.net/20.500.12728/6279
dc.descriptionGeranylated 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. © 2016 by the authors; licensee MDPI, Basel, Switzerland.
dc.language.isoen
dc.publisherMDPI AG
dc.subjectBotrytis cinerea
dc.subjectFungicide
dc.subjectGeranylated phenol derivatives
dc.subjectGrowth inhibition effect
dc.subjectHydrated geranyl
dc.subjectStructural elucidation
dc.subjectSynthesis
dc.subject2 ((2 hydroxy 2,6,6 trimethylcyclohexyl)methyl) 5 methoxybenzene 1,4 diol
dc.subject2 (3,7 dihydroxy 3, 7 dimethyloctyl) 5 methoxybenzene 1,4 diol
dc.subject2 (3,7 dimethylocta 2,6 dien 1 yl) 5 methoxycyclohexa 2,5 diene 1,4 dione
dc.subject2 (3,7 dimethylocta 2,6 dienyl) 4 methylphenol
dc.subject2 (3,7 dimethylocta 2,6 dienyl) 4 methylphenyl acetate
dc.subject2 (3,7 dimethylocta 2,6 dienyl) 5 methoxy 1,4 phenylene diacetate
dc.subject2 (3,7 dimethylocta 2,6 dienyl) 5 methoxybenzene 1,4 diol
dc.subject2 geranylhydroquinone
dc.subject2 geranylquinone
dc.subject2,5 bisgeranylquinone
dc.subject3,5 bis( 3,7-dimethylocta 2,6 dienyl) 2 methoxycyclohexa 2,5 diene 1,4 dione
dc.subject4 (3,7 dimethylocta 2,6 dienyl) 2 methylphenol
dc.subject8 (2 hydroxy 3 methylphenyl) 2,6 dimethyloctane 2,6 diol
dc.subject8 (4 hydroxy 3 methylphenyl) 2,6 dimethyloctane 2,6 diol
dc.subjectgeranylated phenol derivative
dc.subjectphenol derivative
dc.subjectquinone derivative
dc.subjectunclassified drug
dc.subjectantifungal agent
dc.subjectphenol derivative
dc.subjectplant extract
dc.subjectantifungal activity
dc.subjectArticle
dc.subjectBotrytis cinerea
dc.subjectcarbon nuclear magnetic resonance
dc.subjectchemical structure
dc.subjectcolumn chromatography
dc.subjectcontrolled study
dc.subjectdrug synthesis
dc.subjectinfrared spectroscopy
dc.subjectnonhuman
dc.subjectnuclear Overhauser effect
dc.subjectproton nuclear magnetic resonance
dc.subjectthin layer chromatography
dc.subjectBotrytis
dc.subjectchemistry
dc.subjectdrug effects
dc.subjectmicrobial sensitivity test
dc.subjectsynthesis
dc.subjectAntifungal Agents
dc.subjectBotrytis
dc.subjectMicrobial Sensitivity Tests
dc.subjectMolecular Structure
dc.subjectPhenols
dc.subjectPlant Extracts
dc.titleSynthesis of new hydrated geranylphenols and in vitro antifungal activity against botrytis cinerea
dc.typeArticle


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