title: Structure-function analysis of the vanillin molecule and its antifungal properties.
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.
authors.affiliation: Food Safety Science Division, Institute of Food Research, Norwich Research Park, Colney Lane, Norwich, Norfolk, United Kingdom.
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Fitzgerald
authors.forename: Malcolm
authors.initials: M
authors.lastname: Stratford
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Gasson
authors.forename: Arjan
authors.initials: A
authors.lastname: Narbad
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry* / Q000494:pharmacology*; D005516:Food Microbiology; D005658:Fungi / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
chemical_list: D001547:Benzaldehydes; D005659:Fungicides, Industrial; C100058:vanillin