Exploring unusual antioxidant activity in a benzoic acid derivative: a proposed mechanism for citrinin

Heider, E.; Harper, James K.; Grant, David M.; Hoffman, Angela; Dugan, Frank M.; Tomer, David P.; O’Neill, Kim L.

doi:10.1016/j.tet.2005.10.066

Cited by 28 publications

(14 citation statements)

References 67 publications

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“…In this case the citrinin molecule apparently absorbs a high amount of the energy of the blue light which may result in a protective mechanism. It was further recently shown that citrinin also has antioxidative properties [24]. Light induces oxidative stress [22] and an antioxidative activity of citrinin is a further hint for the protective status of citrinin under light conditions.…”

Section: Discussionmentioning

confidence: 99%

Wavelength-Dependent Degradation of Ochratoxin and Citrinin by Light in Vitro and in Vivo and Its Implications on Penicillium

Schmidt‐Heydt

Cramer

Graf

et al. 2012

Toxins

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It has previously been shown that the biosynthesis of the mycotoxins ochratoxin A and B and of citrinin by Penicillium is regulated by light. However, not only the biosynthesis of these mycotoxins, but also the molecules themselves are strongly affected by light of certain wavelengths. The white light and blue light of 470 and 455 nm are especially able to degrade ochratoxin A, ochratoxin B and citrinin after exposure for a certain time. After the same treatment of the secondary metabolites with red (627 nm), yellow (590 nm) or green (530 nm) light or in the dark, almost no degradation occurred during that time indicating the blue light as the responsible part of the spectrum. The two derivatives of ochratoxin (A and B) are degraded to certain definitive degradation products which were characterized by HPLC-FLD-FTMS. The degradation products of ochratoxin A and B did no longer contain phenylalanine however were still chlorinated in the case of ochratoxin A. Citrinin is completely degraded by blue light. A fluorescent band was no longer visible after detection by TLC suggesting a higher sensitivity and apparently greater absorbance of energy by citrinin. The fact that especially blue light degrades the three secondary metabolites is apparently attributed to the absorption spectra of the metabolites which all have an optimum in the short wave length range. The absorption range of citrinin is, in particular, broader and includes the wave length of blue light. In wheat, which was contaminated with an ochratoxin A producing culture of Penicillium verrucosum and treated with blue light after a pre-incubation by the fungus, the concentration of the preformed ochratoxin A reduced by roughly 50% compared to the control and differed by > 90% compared to the sample incubated further in the dark. This indicates that the light degrading effect is also exerted in vivo, e.g., on food surfaces. The biological consequences of the light instability of the toxins are discussed.

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Section: Discussionmentioning

confidence: 99%

Wavelength-Dependent Degradation of Ochratoxin and Citrinin by Light in Vitro and in Vivo and Its Implications on Penicillium

Schmidt‐Heydt

Cramer

Graf

et al. 2012

Toxins

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“…Flavonoids are the major secondary metabolites of fungi [33,34]. ey are polyphenolic compounds recognized because of their antioxidant properties and free-radical scavenging potential [35].…”

Section: Total Flavonoids Content (Tfc)mentioning

confidence: 99%

Mycochemical Screening and Analysis, Antioxidant Activity, and Biochemical Composition of Fermentation Strain Snef1216 (Penicillium chrysogenum)

Sikandar

Zhang

Wang

et al. 2020

Journal of Analytical Methods in Chemistry

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Antioxidants are the radical scavengers that inhibit peroxidation and other free-radical processes, which in return safeguard different organisms from various diseases attributed to radical reactions. Synthetic antioxidants inhibit free radicals, but they also have harmful side effects. However, mycochemicals of natural fungal origin are safe and best substitutes for harmful synthetic chemical antioxidants. The prime objectives of the study include appropriate qualitative and quantitative mycochemical screening, antioxidant potential, and chemical composition of Snef1216 (Penicillium chrysogenum). The study has used aluminium chloride colourimetric method, Folin–Ciocalteu reagent assay, and DPPH (1,1-diphenyl-1-picrylhydrazyl) for analysis of total flavonoid content and phenol content and antioxidant activity, respectively. However, the presence of biologically active compounds was screened through gas chromatography-mass spectrometry (GC-MS). Quantitative analysis demonstrated the existence of flavonoids, glycosides, flavones, saponins, phenols, and catecholic tannins excluding alkaloids, terpenoids, steroids, and gallic tannins. The outcomes exposed total flavonoid content and phenolic content in P. chrysogenum were 85.31 ± 1.23 mg·QE/g and 135.77 ± 1.14 mg·GAE/g, respectively. Snef1216 (P. chrysogenum) displayed the highest free-radical scavenging activity with 63.86% inhibition of DPPH. The analysis confirms that Snef1216 (P. chrysogenum) is an alternative source of natural antioxidants. The obtained data have provided the foundation for its use in agricultural, environmental, and pharmaceutical industries.

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“…Under conditions, which impose oxidative stress, like for example under intense light conditions (field conditions), P. verrucosum shifts its secondary metabolite profile towards citrinin [14]. Citrinin is supposed to be a light protectant [20] and a potent antioxidant [21] and in fact, in certain cereal samples the contamination with citrinin was more pronounced than with ochratoxin A [22,23]. On the other hand, on substrates with increased concentrations of NaCl, the secondary metabolite profile of P. verrucosum is shifted towards ochratoxin A [15].…”

Section: Discussionmentioning

confidence: 99%

Differences in the Regulation of Ochratoxin A by the HOG Pathway in Penicillium and Aspergillus in Response to High Osmolar Environments

Stoll

Schmidt‐Heydt

Geisen

2013

Toxins

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Penicillium verrucosum, P. nordicum and Aspergillus carbonarius are three important ochratoxin A producing species. P. verrucosum is in addition able to produce citrinin. It has been shown earlier that P. nordicum is adapted to NaCl rich environments like salt rich dry cured foods or even salines. In this organism, the biosynthesis of ochratoxin A plays an adaptive role in this habitat. P. verrucosum generally can be found on cereals, but occasionally also on salt rich dry cured foods. In contrast A. carbonarius usually cannot be found in NaCl rich environments, but it occurs in another environment with high concentration of solutes, e.g., in sugar rich substrates like grapes and grape juices. Usually osmotic challenging conditions activate the HOG MAP kinase signal cascade, which in turn activates various osmo-regulated genes. In the current analysis, it could be demonstrated that in case of P. nordicum and P. verrucosum the NaCl induced production of ochratoxin A is correlated to the phosphorylation status of the HOG MAP kinase. Just the opposite was true for A. carbonarius. In this case, also higher amounts of NaCl in the medium lead to an increased phosphorylation status of HOG, but no increase in ochratoxin biosynthesis was observed. In contrast to the Penicillia, higher NaCl concentrations lead to a rapid cessation of growth by A. carbonarius. High glucose concentrations have much less impact on growth and the phosphorylation of HOG.

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Exploring unusual antioxidant activity in a benzoic acid derivative: a proposed mechanism for citrinin

Cited by 28 publications

References 67 publications

Wavelength-Dependent Degradation of Ochratoxin and Citrinin by Light in Vitro and in Vivo and Its Implications on Penicillium

Wavelength-Dependent Degradation of Ochratoxin and Citrinin by Light in Vitro and in Vivo and Its Implications on Penicillium

Mycochemical Screening and Analysis, Antioxidant Activity, and Biochemical Composition of Fermentation Strain Snef1216 (Penicillium chrysogenum)

Differences in the Regulation of Ochratoxin A by the HOG Pathway in Penicillium and Aspergillus in Response to High Osmolar Environments

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