In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands

International Journal of Molecular Sciences
María I ChávezLautaro Taborga

Abstract

A series of new and known geranylated phenol/methoxyphenol derivatives has been tested in vitro as inhibitor agents of mycelial growth of Phytophthora cinnamomi. The activity of tested compounds is correlated with the nature, number, and position of the substituent group on the aromatic ring. Results indicate that the most active geranylated derivatives are those having two hydroxyl groups (or one ⁻OH and one ⁻OCH₃) attached to the aromatic ring. Interestingly, these derivatives are as active as Metalaxil®, a commonly used commercial fungicide. Thus, our results suggest that some of these compounds might be of agricultural interest due to their potential use as fungicides against P. cinnamomi. The effect of structure on fungicide activity is discussed in terms of electronic distribution on both the aromatic ring and side geranyl chain. All tested compounds have been synthesized by direct coupling of geraniol and the respective phenol. Interestingly, new digeranylated derivatives were obtained by increasing the reaction time.

References

Oct 1, 2011·The Journal of Organic Chemistry·Susanna T S ChanBrent R Copp
Feb 7, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marcos DeritaSusana A Zacchino
Sep 3, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Zhe HouLe Zhou
Jan 30, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luis EspinozaHugo Peña-Cortés
Jul 22, 2015·Journal of Agricultural and Food Chemistry·Lautaro TaborgaLuis Espinoza
Aug 20, 2015·International Journal of Molecular Sciences·María I ChávezLuis Espinoza
May 22, 2017·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Lautaro TaborgaLuis Espinoza

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Citations

Nov 23, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrés F OleaKaty Díaz
Jul 8, 2020·Journal of Agricultural and Food Chemistry·Dong LiuZhimou Gao

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Methods Mentioned

BETA
geranylation
column chromatography
NMR

Software Mentioned

Statistica

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An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.