Mapping the structural requirements of inducers and substrates for decarboxylation of weak acid preservatives by the food spoilage mould Aspergillus niger

International Journal of Food Microbiology

Volumn 157, Issue 3, 2012, Pages 375-383

  Stratford, Malcolm ^a   Plumridge, Andrew ^a,c   Pleasants, Mike W ^b   Novodvorska, Michaela ^a   Baker Glenn, Charles A G ^a,d   Pattenden, Gerald ^a   Archer, David B ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

^c Molecular Profiles   (United Kingdom)

^d BioFocus DPI   (United Kingdom)

Author keywords

Cinnamic acid; Decarboxylation; OHBA1; PADA1; Sorbic acid; Spoilage

Indexed keywords

2,3,4,5,6 PENTAFLUOROCINNAMIC ACID; ALKENYL GROUP; CARBOXYLIC ACID; CARBOXYLYASE; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; COUMARIC ACID; FERULIC ACID; FOOD PRESERVATIVE; HEXANOIC ACID; PADA1 DECARBOXYLASE; PHENYL GROUP; SORBIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS NIGER; CHEMICAL BOND; DECARBOXYLATION; ENZYME SUBSTRATE; FOOD SPOILAGE; MASS FRAGMENTOGRAPHY; MOLECULAR SIZE; NONHUMAN; PROTEIN STRUCTURE; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; TRANSCRIPTION INITIATION;

ACIDS; ALKADIENES; ASPERGILLUS NIGER; CARBOXY-LYASES; CINNAMATES; DECARBOXYLATION; FOOD PRESERVATIVES; FUNGI; GERMINATION; PENTANES; SORBIC ACID; SPORES, FUNGAL; TRANSCRIPTION, GENETIC;

ASPERGILLUS NIGER;

EID: 84863882491     PISSN: 01681605     EISSN: 18793460     Source Type: Journal    
DOI: 10.1016/j.ijfoodmicro.2012.06.007     Document Type: Article

References (40)

1. Anon EC directive 95/2/EC; food additives other than colours and sweeteners. EC Official Journal 1995, (L61):1-40. (March 18th).
2. Archer, D.B., Stratford, M., Plumridge, A., 2008. Preservative. Patent number WO2008/149102 A2. PCT/GB2008/001935. Published 11/12/08.
3. Belin P., Le Du M.H., Fielding A., Lequin O., Jacquet M., Charbonnier J.-B., Lecoq A., Thai R., Courcon M., Masson C., Dugave C., Genet R., Pernodet J.-L., Gondry M. Identification and structural basis of the reaction catalysed by CYP121, an essential cytochrome P450 in Mycobacterium tuberculosis. Proceedings of the National Academy of Sciences, USA 2009, 106:7426-7431.
4. Bos C.J., Debets A.J.M., Swart K., Huybers A., Kobus G., Slakhorst S.M. Genetic analysis and construction of master strains for assignment of genes to six linkage groups in Aspergillus niger. Current Genetics 1988, 14:437-443.
5. Breeuwer P., de Reu J.-C., Drocourt J.-L., Rombouts F.M., Abee T. Nonanoic acid, a fungal self-inhibitor, prevents germination of Rhizopus oligosporus sporangiospores by dissipation of the pH gradient. Applied and Environmental Microbiology 1997, 63:178-185.
6. Burdock G.A. Fenaroli's Handbook of Flavor Ingredients 2002, CRC Press, Boca Raton, London, New York, Washington. 4th Edn.
7. Casas E., Valderrama M.J., Peinado J.M. Sorbate detoxification by spoilage yeasts isolated from marzipan products. Food Technology and Biotechnology 1999, 37:87-91.
8. Casas E., de Ancos B., Valderrama M.J., Cano P., Peinado J.M. Pentadiene production from potassium sorbate by osmotolerant yeasts. International Journal of Food Microbiology 2004, 94:93-96.
9. Cavin J.-F., Dartois V., Divies C. Gene cloning, transcriptional analysis, purification and characterization of phenolic acid decarboxylase from Bacillus subtilis. Applied and Environmental Microbiology 1998, 64:1466-1471.
10. Chitarra G.S., Abee T., Rombouts F.M., Posthumus M.A., Dijksterhuis J. Germination of Penicillium paneum conidia is regulated by 1-octen-3-ol, a volatile self-inhibitor. Applied and Environmental Microbiology 2004, 70:2823-2829.
11. Ciulli A., Abell C. Fragment-based approaches to enzyme inhibition. Current Opinions in Biotechnology 2007, 18:489-496.
12. Ciulli A., Scott D.E., Ando M., Reyes F., Saldanha S.A., Tuck K.L., Chirgadze D.Y., Blundell T.L., Abell C. Inhibition of Mycobacterium tuberculosis pantothenate synthetase by analogues of the reaction intermediate. ChemBioChem 2008, 9:2606-2611.
13. Clausen M., Lamb C.J., Megnet R., Doerner P.W. PAD1 encodes phenylacrylic acid decarboxylase which confers resistance to cinnamic acid in Saccharomyces cerevisiae. Gene 1994, 142:107-112.
14. Garrett M.K., Robinson P.M. A stable inhibitor of spore germination produced by fungi. Archives fur Mikrobiology 1969, 67:370-377.
15. Goffeau A., Park J., Paulsen I.T., Jonniaux J.-L., Dinh T., Mordant P., Saier M.H. Multidrug-resistant transport proteins in yeast: complete inventory and phylogenetic characterization of yeast open reading frames within the major facilitator superfamily. Yeast 1997, 13:43-54.
16. Gulmezian M., Hyman K.R., Marbois B.N., Clarke C.F., Javor G.T. The role of UbiX in Escherichia coli coenzyme Q biosynthesis. Archives of Biochemistry and Biophysics 2007, 467:144-153.
17. Hann M.M., Leach A.R., Harper G. Molecular complexity and its impact on the probability of finding leads for drug discovery. Journal of Chemical Information and Computer Sciences 2001, 41:856-864.
18. Hung A.W., Silvestre H.L., Wen S., Ciulli A., Blundell T.L., Abell C. Application of fragment growing and fragment linking to the discovery of inhibitors of Mycobacterium tuberculosis pantothenate synthetase. Angewandte Chemie International Edition 2009, 48:8452-8456.
19. Kinderlerler J.L., Hutton P.V. Fungal metabolites of sorbic acid. Food Additives and Contaminants 1990, 7:657-669.
20. Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. Efficient conditions for conversion of 2-substituted furans into 4-oxygenated 2-enoic acids and its application to synthesis of (+)-aspicilin. Journal of Organic Chemistry 1998, 63:7505-7515.
21. Kowlaczkowski M., Goffeau A. Active efflux by multidrug transporters as one of the strategies to evade chemotherapy and novel practical implications of yeast pleiotropic drug resistance. Pharmacology and Therapeutics 1997, 76:219-242.
22. Kurogochi S., Tahara S., Mizutani L. Fungal reduction of C6 α, β unsaturated carboxylic acids. Agricultural and Biological Chemistry 1975, 39:825-831.
23. Lachance M.-A. Yeast selection in nature. Yeast Strain Selection 1989, 21-41. Marcel Dekker Inc., New York. C.J. Panchal (Ed.).
24. Larkin A., Olivier N.B., Imperiali B. Structural analysis of WbpE from Pseudomonas aeruginosa PAO1: a nucleotide sugar aminotransferase involved in o-antigen assembly. Biochemistry 2010, 49:7227-7237.
25. Liu Z.L., Palmquist D.E., Ma M., Liu J., Alexander N.J. Application of a master equation to quantitative mRNA analysis using qRT-PCR. Journal of Biotechnology 2009, 143:10-16.
26. Lupa B., Lyon D., Gibbs M.D., Reeves R.A., Wiegel J. Distribution of genes encoding the microbial non-oxidative reversible hydroxyacrylic acid decarboxylases/phenol carboxylases. Genomics 2005, 86:342-351.
27. Marth E.H., Capp C.M., Hasenzah L., Jackson H.W., Hussong R.V. Degradation of potassium sorbate by Penicillium species. Journal of Dairy Science 1966, 49:1197-1205.
28. Mukai N., Masaki K., Fujii T., Kawamukai M., Iefuji H. PAD1 and FDC1 are essential for the decarboxylation of phenylacrylic acids in Saccharomyces cerevisiae. Journal of Bioscience and Bioengineering 2010, 109:564-569.
29. Murray C.W., Verdonk M.L. The consequences of translational and rotational entropy lost by small molecules on binding to proteins. Journal of Computer-Aided Molecular Design 2002, 16:741-753.
30. Myers H.B. An unappreciated fungicidal action of certain volatile oils. Journal of the American Medical Association 1927, 89:1834-1836.
31. Olivier N.B., Imperiali B. Crystal structure and catalytic mechanism of PglD from Campylobacter jejuni. Journal of Biological Chemistry 2008, 283:27937-27946.
32. Pinches S.E., Apps P. Production in food of 1,3-pentadiene and styrene by Trichoderma species. International Journal of Food Microbiology 2007, 116:182-185.
33. Plumridge A., Hesse S.J.A., Watson A.J., Lowe K.C., Stratford M., Archer D.B. The weak-acid preservative, sorbic acid, inhibits conidial germination and mycelial growth of Aspergillus niger through intracellular acidification. Applied and Environmental Microbiology 2004, 74:550-552.
34. Plumridge A., Stratford M., Lowe K.C., Archer D.B. The weak-acid preservative, sorbic acid, is decarboxylated and detoxified by a phenylacrylic acid decarboxylase, PadA1, in the spoilage mould Aspergillus niger. Applied and Environmental Microbiology 2008, 74:550-552.
35. Plumridge A., Melin P., Stratford M., Novodvorska M., Shunburne L., Dyer P.S., Roubos J.A., Menke H., Stark J., Stam H., Archer D.B. The decarboxylation of the weak-acid preservative, sorbic acid, is encoded by linked genes in Aspergillus spp. Fungal Genetics and Biology 2010, 47:683-692.
36. Rangarajan E.S., Li Y., Iannuzzi P., Tocilj A., Hung L.-W., Matte A., Cygler M. Crystal structure of a dodecameric FMN-dependent, UbiX-like decarboxylase (Pad1) from Escherichia coli 0157:H7. Protein Science 2004, 13:3006-3016.
37. Scott D.E., Dawes G.J., Ando M., Abell C., Ciulli A. A fragment-based approach to probing adenosine recognition sites by using dynamic combinatorial chemistry. ChemBioChem 2009, 10:2772-2779.
38. Stratford, M., Anslow, P., 1997. A preservative and flavouring system for beverages based on cinnamic acid and its derivatives. Patent application filed 28th October 1997, WO 99/21433.
39. Stratford M., Plumridge A., Archer D.B. Decarboxylation of sorbic acid by spoilage yeasts is associated with the PAD1 gene. Applied and Environmental Microbiology 2007, 73:6534-6542.
40. van Beek S., Priest F.G. Decarboxylation of substituted cinnamic acids by lactic acid bacteria isolated during malt whisky fermentation. Applied and Environmental Microbiology 2000, 66:5322-5328.