Structure−Function Analysis of the Vanillin Molecule and Its Antifungal Properties

Institute of Food Research, Norwich, England, United Kingdom
Journal of Agricultural and Food Chemistry (Impact Factor: 2.91). 04/2005; 53(5):1769-75. DOI: 10.1021/jf048575t
Source: PubMed


The aim of the present study was to evaluate which structural elements of the vanillin molecule are responsible for its observed antifungal activity. MICs of vanillin, its six direct structural analogues, and several other related compounds were determined in yeast extract peptone dextrose broth against a total of 18 different food spoilage molds and yeasts. Using total mean MICs after 4 days of incubation at 25 degrees C, the antifungal activity order was 3-anisaldehyde (1.97 mM) > benzaldehyde (3.30 mM) > vanillin (5.71 mM) > anisole (6.59 mM) > 4-hydroxybenzaldehyde (9.09 mM) > phenol (10.59 mM) > guaiacol (11.66 mM). No correlation was observed between the relative antifungal activity of the test compounds and log P(o/w). Furthermore, phenol (10.6 mM) was found to exhibit a greater activity than cyclohexanol (25.3 mM), whereas cyclohexanecarboxaldehyde (2.13 mM) was more active than benzaldehyde (3.30 mM). Finally, the antifungal order of isomers of hydroxybenzaldehyde and anisaldehyde was found to be 2- > 3- > 4- and 3- > 2- > 4-, respectively. In conclusion, the aldehyde moeity of vanillin plays a key role in its antifungal activity, but side-group position on the benzene ring also influences this activity. Understanding how the structure of natural compounds relates to their antimicrobial function is fundamentally important and may help facilitate their application as novel food preservatives.

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    • "The presence of the polarized carbon-oxygen double bond of aldehyde/keto groups, which probably accounts for their activity forming covalent bonds with DNA and proteins and interfere with their metabolism (Feron et al. 1991). Our results are similar to the studies reported on vanillin (Fitzgerald et al. 2005). DZ have also shown significant antifungal activity (EC 50 86.49 "
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    ABSTRACT: Dehydrozingerone, structural half analogue of curcumin, is a phenolic compound isolated from ginger (Zingiber officinale) rhizomes. Dehydrozingerone and several of its derivatives such as glucopyranosides and its tetra acetate derivative and 4-O-acetyl and methyl derivatives of dehydrozingerone were synthesized in the present study. Dehydrozingerone, synthesised with improved yield was used for the synthesis of Dehydrozingerone 4-O-β-D-glucopyranoside (first time report) by modified Koenigs-Knorr-Zemplén method. Structures of all the compounds have been established using spectroscopic methods. These compounds were tested for radical scavenging activity by DPPH and FRAP method as well as for antibacterial and antifungal activities. The parent molecule exhibited better scavenging activity as compared to its derivatives indicating the significance of free phenolic hydroxyl group. Also, Dehydrozingerone and its derivatives exhibited antibacterial as well as antifungal activity due to the conjugation system present, which includes α,β-unsaturated carbonyl (C = O) group. This study gave an insight into structural requirements for dehydrozingerone activity.
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    • "It showed minimal inhibitory concentrations (MICs) of 1250 and 738 μg/mL and minimal fungicidal concentrations (MFCs) of 5000 and 1761 μg/mL against Candida albicans and C. neoformans, respectively [6]. Structure activity relationship studies on vanillin and related aldehydes revealed that the aldehyde moiety plays a significant role in imparting antifungal activity [7]. "
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    ABSTRACT: Vanillin oxime-N-O-alkanoates were synthesized following reaction of vanillin with hydroxylamine hydrochloride, followed by reaction of the resultant oxime with acyl chlorides. The structures of the compounds were confirmed by IR, 1H, 13C NMR and mass spectral data. The test compounds were evaluated for their in vitro antifungal activity against three phytopathogenic fungi Macrophomina phaseolina, Rhizoctonia solani and Sclerotium rolfsii by the poisoned food technique. The moderate antifungal activity of vanillin was slightly increased following its conversion to vanillin oxime, but significantly increased after conversion of the oxime to oxime-N-O-alkanoates. While vanillin oxime-N-O-dodecanoate with an EC50 value 73.1 microg/mL was most active against M. phaseolina, vanillin oxime-N-O-nonanoate with EC50 of value 66.7 microg/mL was most active against R. solani. The activity increased with increases in the acyl chain length and was maximal with an acyl chain length of nine carbons.
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    • "Not much is known about vanillin's mechanism of antifungal activity, but it has been suggested that the aldehyde moiety of vanillin plays an important role in its antifungal activity. The rationale for this is that S. cerevisiae convert vanillin into vanillic acid and vanillyl alcohol, which possess no antimicrobial activity, confirming the key-role of the aldehyde moiety (Feron et al., 1991; Fitzgerald et al., 2005). "
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