Fungi isolated from packaging materials: Their role in the production of 2, 4, 6‐trichloroanisole

Tindale, C Ross; Whitfield, Frank B.; Levingston, Shona D; Nguyen, Thao V.

doi:10.1002/jsfa.2740490406

Cited by 50 publications

(28 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Including the Rio flavor of Brazilian coffee, chlorophenol, bromophenol, chloroanisole and bromoanisole are responsible for claims of off-flavors in drinks and foods, and can cause economic losses. We cannot rule out any possibility that Rio flavor of Brazilian coffee is caused by the decomposition of 2,4,6-TCP and PCP, which has been reported previously, and by disinfection using chlorine (Buser et al, 1982;Chatonnet et al, 2004;Curtis et al, 1974;Fukaya et al, 1994;Goldenberg and Matheson, 1975;Griffith, 1977;Montiel et al, 1999;Ogiwara et al, 2003;Saxby and Wagg, 1985;Tindale et al, 1989;Whitfield et al, 1985;Whitfield et al, 1997).…”

Section: Description By Coffee Tasting Panelists Of Off-flavor Causedmentioning

confidence: 87%

“…Both 2,4,6-TCA and 2,6-DCP have a low threshold and cause off-flavors in drinks and foods even at very low concentrations. It should be noted that almost anyone can sense mustiness at high concentrations (Buser et al, 1982;Curtis et al, 1974;Griffith, 1977;Tindale et al, 1989;Whitfield et al, 1985). 2,6-DCP is detected by most persons as a chlorine or disinfection flavor even in minute quantities, and is supposed to be a causal substance of the chlorine odor in Rio flavor.…”

Section: Description By Coffee Tasting Panelists Of Off-flavor Causedmentioning

confidence: 99%

See 1 more Smart Citation

Analysis of Iodine-like (Chlorine) Flavor-causing Components in Brazilian Coffee with Rio Flavor

Kato

Sato

Takui

2011

FSTR

View full text Add to dashboard Cite

Green beans and roasted beans of coffee with Rio flavor were analyzed by gas chromatographyolfactometry to clarify the causal substances of Rio flavor in Brazilian coffee. In addition to 2,4,6-trichloroanisole (TCA) and 2,4,6-trichlorophenol (TCP), which are known as the main causal substances of Rio flavor, a new iodine-like flavor-causing compound, 2,6-dichlorophenol (DCP), was detected. The detected amounts of 2,6-DCP and 2,4,6-TCA were less than 0.1 and 0.1 ppb in Rio flavor-free coffee beans, 0.8 and 1.2 ppb in weak Rio flavored beans, and 3.0 and 2.6 ppb in strong Rio flavored beans, respectively. Musty and chlorine flavors were sensed more strongly in model coffee containing both 2,4,6-TCA and 2,6-DCP than in the coffee containing them individually. In the present study, 2,6-DCP was identified as a new causal substance of Rio flavor, and it was found that the presence of 2,4,6-TCA intensifies Rio flavor, as a synergy effect.

show abstract

Section: Description By Coffee Tasting Panelists Of Off-flavor Causedmentioning

confidence: 87%

Section: Description By Coffee Tasting Panelists Of Off-flavor Causedmentioning

confidence: 99%

Analysis of Iodine-like (Chlorine) Flavor-causing Components in Brazilian Coffee with Rio Flavor

Kato

Sato

Takui

2011

FSTR

View full text Add to dashboard Cite

show abstract

“…Chloroanisoles that cause unpleasant aromas and tastes are not associated solely with wines. In fact, 2,3,4,6-TeCA causes musty taint in chickens (7,13), and other chloroanisoles, including 2,4,6-TCA, also produce off-odor problems in potato chips (6), dried fruit (33,35), coffee (31), and drinking water (25).…”

Section: Discussionmentioning

confidence: 99%

“…Thus, O methylation of pentachlorophenol (PCP) by Trichoderma virgatum (6), production of 2,3,4,6-TeCA by several fungi (13), and S methylation of several phenolic compounds by the yeast Saccharomycopsis lipolytica (10) and by the protozoans Euglena gracilis (8) and Tetrahymena thermophila (9) have been reported. Also, the ability of some fungal strains isolated from food-packaging materials (33,35) and of several fungi and actinomycetes isolated from drinking water (25) to methylate 2,4,6-trichlorophenol (2,4,6-TCP) to produce 2,4,6-TCA has also been documented.…”

mentioning

confidence: 99%

Cork Taint of Wines: Role of the Filamentous Fungi Isolated from Cork in the Formation of 2,4,6-Trichloroanisole by O Methylation of 2,4,6-Trichlorophenol

Álvarez-Rodríguez

López-Ocaña

López-Coronado

et al. 2002

Appl Environ Microbiol

133

103

View full text Add to dashboard Cite

Cork taint is a musty or moldy off-odor in wine mainly caused by 2,4,6-trichloroanisole (2,4,6-TCA). We examined the role of 14 fungal strains isolated from cork samples in the production of 2,4,6-TCA by O methylation of 2,4,6-trichlorophenol (2,4,6-TCP). The fungal strains isolated belong to the genera Penicillium (four isolates); Trichoderma (two isolates); and Acremonium, Chrysonilia, Cladosporium, Fusarium, Mortierella, Mucor, Paecilomyces, and Verticillium (one isolate each). Eleven of these strains could produce 2,4,6-TCA when they were grown directly on cork in the presence of 2,4,6-TCP. The highest levels of bioconversion were carried out by the Trichoderma and Fusarium strains. One strain of Trichoderma longibrachiatum could also efficiently produce 2,4,6-TCA in liquid medium. However, no detectable levels of 2,4,6-TCA production by this strain could be detected on cork when putative precursors other than 2,4,6-TCP, including several anisoles, dichlorophenols, trichlorophenols, or other highly chlorinated compounds, were tested. Time course expression studies with liquid cultures showed that the formation of 2,4,6-TCA was not affected by a high concentration of glucose (2% or 111 mM) or by ammonium salts at concentrations up to 60 mM. In T. longibrachiatum the O methylation of 2,4,6-TCP was catalyzed by a mycelium-associated S-adenosyl-L-methionine (SAM)-dependent methyltransferase that was strongly induced by 2,4,6-TCP. The reaction was inhibited by S-adenosyl-Lhomocysteine, an inhibitor of SAM-dependent methylation, suggesting that SAM is the natural methyl donor. These findings increase our understanding of the mechanism underlying the origin of 2,4,6-TCA on cork, which is poorly understood despite its great economic importance for the wine industry, and they could also help us improve our knowledge about the biodegradation and detoxification processes associated with chlorinated phenols.

show abstract

“…In fact, 2,4,6-TCA has been reported to be responsible for at least 80% of the cases of cork taint (8), and in a recent study Pollnitz and colleagues reported that 2,4,6-TCA could be detected in 100% of tainted wines (23). The role of chloroanisoles as contaminant agents is not restricted to wine, since the presence of these compounds is well documented in other food materials, such as eggs and poultry (12), chickens (11), pulp chips (10), dried fruits (30), Brazilian coffee (29), and drinking water (21).…”

mentioning

confidence: 99%

Characterization of an Inducible Chlorophenol O -Methyltransferase from Trichoderma longibrachiatum Involved in the Formation of Chloroanisoles and Determination of Its Role in Cork Taint of Wines

Coque

Álvarez-Rodríguez

Larriba

2003

Appl Environ Microbiol

View full text Add to dashboard Cite

A novel S-adenosyl-L-methionine (SAM)-dependent methyltransferase catalyzing the O methylation of several chlorophenols and other halogenated phenols was purified 220-fold to apparent homogeneity from mycelia of Trichoderma longibrachiatum CECT 20431. The enzyme could be identified in partially purified protein preparations by direct photolabeling with [methyl-3 H]SAM, and this reaction was prevented by previous incubation with S-adenosylhomocysteine. Gel filtration indicated that the M r was 112,000, and sodium dodecyl sulfate-polyacrylamide gel electrophoresis showed that the enzyme was composed of two subunits with molecular weights of approximately 52,500. The enzyme had a pH optimum between 8.2 and 8.5 and an optimum temperature of 28°C, with a pI of 4.9. The K m values for 2,4,6-trichlorophenol and SAM were 135.9 ؎ 12.8 and 284.1 ؎ 35.1 M, respectively. S-Adenosylhomocysteine acted as a competitive inhibitor, with a K i of 378.9 ؎ 45.4 M. The methyltransferase was also strongly inhibited by low concentrations of several metal ions, such as Cu 2؉ , Hg 2؉ , Zn 2؉ , and Ag ؉ , and to a lesser extent by p-chloromercuribenzoic acid, but it was not significantly affected by several thiols or other thiol reagents. The methyltransferase was specifically induced by several chlorophenols, especially if they contained three or more chlorine atoms in their structures. Substrate specificity studies showed that the activity was also specific for halogenated phenols containing fluoro, chloro, or bromo substituents, whereas other hydroxylated compounds, such as hydroxylated benzoic acids, hydroxybenzaldehydes, phenol, 2-metoxyphenol, and dihydroxybenzene, were not methylated.

show abstract

Fungi isolated from packaging materials: Their role in the production of 2, 4, 6‐trichloroanisole

Abstract: Fungi isolated >om fibreboard cartons

Cited by 50 publications

References 12 publications

Analysis of Iodine-like (Chlorine) Flavor-causing Components in Brazilian Coffee with Rio Flavor

Analysis of Iodine-like (Chlorine) Flavor-causing Components in Brazilian Coffee with Rio Flavor

Cork Taint of Wines: Role of the Filamentous Fungi Isolated from Cork in the Formation of 2,4,6-Trichloroanisole by O Methylation of 2,4,6-Trichlorophenol

Characterization of an Inducible Chlorophenol O -Methyltransferase from Trichoderma longibrachiatum Involved in the Formation of Chloroanisoles and Determination of Its Role in Cork Taint of Wines

Contact Info

Product

Resources

About