Article

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.

2 Followers
 · 
137 Views
  • [Show abstract] [Hide abstract]
    ABSTRACT: This chapter reviews available techniques and makes recommendations for studying fungal endophytes. The current understanding of the geographic, environmental and host-mediated factors that influence the distribution of endophyte colonization of plants is summarized. Causes for the method-dependent differences in endophyte detection and recovery are discussed. Strategies, protocols and materials for observing, sampling and culturing vertically- and horizontally-transmitted plant endophytes are recommended. A protocol for a newly-developed dilution-to-extinction method for isolation and cultivation of horizontally-transmitted endophytes is detailed in the experimental procedures, and protocols for the direct observation and culturing of the vertically-transmitted endophytes are given. The book in which this chapter was published is no longer being printed. However, the book can be found on the web in google books.
    Prospects and Applications for Plant Associated Microbes: A Laboratory Manual, Part B: Fungi, Edited by Anna Maria Pirttila, Seppo Sorvari, 01/2011: chapter Isolation and identification of fungal endophytes: pages 153-164; Paimo, BBI (Biobien Innovations), Turku, Pinland., ISBN: 9789529930265
  • [Show abstract] [Hide abstract]
    ABSTRACT: Aldehydes are a class of chemicals with many industrial uses. Several aldehydes are responsible for flavors and fragrances present in plants, but aldehydes are not known to accumulate in most natural microorganisms. In many cases, microbial production of aldehydes presents an attractive alternative to extraction from plants or chemical synthesis. During the past two decades, a variety of aldehyde biosynthetic enzymes have undergone detailed characterization. Although metabolic pathways that result in alcohol synthesis via aldehyde intermediates were long known, only recent investigations in model microbes such as Escherichia coli have succeeded in minimizing the rapid endogenous conversion of aldehydes into their corresponding alcohols. Such efforts have provided a foundation for microbial aldehyde synthesis and broader utilization of aldehydes as intermediates to other synthetically challenging biochemical classes. However, aldehyde toxicity imposes a practical limit on achievable aldehyde titers and remains an issue of academic and commercial interest. In this minireview, we summarize published efforts of microbial engineering for aldehyde synthesis, with an emphasis on de novo synthesis, engineered aldehyde accumulation in E. coli, and the challenge of aldehyde toxicity. Copyright © 2015, American Society for Microbiology. All Rights Reserved.
    Applied and Environmental Microbiology 01/2015; DOI:10.1128/AEM.03319-14 · 3.95 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Vanillin, a major component of the vanilla is known to exhibit various antimicrobial properties including inhibition of bacterial biofilms. However, a systematic study on activities of vanillin against the most common fungal pathogen, Candida albicans, is lacking. In this study, broth micro dilution method was used to assess vanillin’s activity on the planktonic growth of C. albicans. Minimum inhibitory concentration (MIC) was established at 1 mg ml-1 of vanillin. Prevention of yeast to hyphae morphogenesis was evident at 500 μg ml-1 of vanillin, in standard micro plate based assay. Adhesion, biofilm development and mature biofilms were studied in an in vitro biofilm model using XTT- metabolic assay and light microscopy. Significant (p < 0.05) reduction in biofilm development was observed in presence of 500 μg ml-1 vanillin. Concentration dependent decrease of cellular ergosterol in presence of vanillin indicated that inhibition of ergosterol biosynthesis may be a probable target. Our study, for the first time reveals vanillin as a potential inhibitor of biofilm formation by C. albicans.
    04/2013; 3(2):130-138. DOI:10.1080/22311866.2013.817749