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: 3.11). 04/2005; 53(5):1769-75. DOI: 10.1021/jf048575t
Source: PubMed

ABSTRACT 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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    • "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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    • "In the present study, the vanillin antimicrobial effect was also dependent on time, temperature, culture medium, and the microorganism target. Fitzgerald et al. (2005) investigated the relationship between the structure of vanillin and its antimicrobial activity and found that the aldehyde group in vanillin is the main responsible for its antimicrobial effect despite the influence of the type and position of some of the lateral groups in the benzene ring. Due to their hydrophobic nature, the vanillin antimicrobial mechanism is mainly based on its ability to destroy the plasmatic membrane of the microbial cells through interaction with the lipids or proteins, or with both structures, with a subsequent loss of the ionic gradient and inhibition of the respiratory activity. "
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