Abstract
Citrinin (CIT) is a nephrotoxic mycotoxin produced by Aspergillus, Penicillium, and Monascus genera. It appears as a contaminant in grains, fruits, and spices. After oral exposure to CIT, its major urinary metabolite, dihydrocitrinone (DHC) is formed, which can be detected in human urine and blood samples. Cyclodextrins (CDs) are ring-shaped molecules built up from glucose units. CDs can form host-guest type complexes with several compounds, including mycotoxins. In this study, the complex formation of DHC with native and chemically modified beta- and gamma-cyclodextrins was tested at a wide pH range, employing steady-state fluorescence spectroscopic and modeling studies. The weakly acidic environment favors the formation of DHC-CD complexes. Among the CDs tested, the quaternary-ammonium-γ-cyclodextrin (QAGCD) formed the most stable complexes with DHC. However, the quaternary-ammonium-β-cyclodextrin (QABCD) induced the strongest enhancement in the fluorescence signal of DHC. Our results show that some of the chemically modified CDs are able to form stable complexes with DHC (logK = 3.2–3.4) and the complex formation can produce even a 20-fold increase in the fluorescence signal of DHC. Considering the above-listed observations, CD technology may be a promising tool to increase the sensitivity of the fluorescence detection of DHC.
Highlights
Citrinin (CIT) is a nephrotoxic mycotoxin produced by Penicillium, Aspergillus and Monascus species [1]
The results suggest significantly regarding summarizes the thermodynamic parameters of theare complex formation of DHC with orcavity
The synthesis of (±)-dihydrocitrinone (DHC) was performed based on the synthetic procedure for (±)-[13 C3 ]-dihydrocitrinone reported by Bergmann et al [32]
Summary
Citrinin (CIT) is a nephrotoxic mycotoxin produced by Penicillium, Aspergillus and Monascus species [1]. It occurs as a contaminant in cereals, spices, fruits, as well as in Asian foods and beverages (e.g., cheese, sake, and miso). CIT appears in red mold rice used as a red pigment in the Asian food industry [2,3]. Dry heating of CIT at 175 ◦ C results in the formation of its nontoxic degradation products, and in moist conditions, the toxicity of CIT decreases with the increase of heat [4]. At 140–160 ◦ C, toxic products (as the parent compound) are produced.
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