Abstract
Citrinin (116) (Fig. 3.1), first reported in 1931 following its isolation from Penicillium citrinum (67), was found to display a significant antibiotic activity against several Gram-positive bacteria in the 1940’s (68, 69). In the following decade (at the time of the widespread application of penicillin), there was a considerable interest in citrinin (116) and other antibacterials of fungal origin. Despite this, and its additional insecticidal properties (70), the investigation of 116 for either therapeutic or agrochemical application was abandoned due to its substantial toxicity (71), including nephrotoxicity (72).
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References
Hetherington AC, Raistrick H (1931) Biochemistry of micro-organisms. XIV. Production and chemical constitution of a new yellow coloring matter, citrinin, produced from dextrose by Penicillium citrinum, Thom. Proc R Soc Ser B 220:269
Pollock AV (1947) Production of citrinin by five species of Penicillium. Nature 160:331
Oxford AE (1942) Antibacterial substances from molds. III. The bacteriostatic powers of the mold products citrinin and penicillic acid. Chem Ind 48
Dobias J, Betina V, Nemec P (1980) Insecticidal activity of ramihyfin a, citrinin, and rugulosin. Biologia 35:431
Betina V (1989) Mycotoxins: chemical, biological, and environmental aspects. Elsevier, Amsterdam
Krogh P, Hasselager E, Friis P (1970) Fungal nephrotoxicity. 2. Isolation of Two nephrotoxic compounds from Penicillium viridicatum citrinin and oxalic acid. Acta Pathol Microbiol Scand B Microbiol Immunol 78:401
Brown JP, Cartwright NJ, Robertson A, Whalley WB (1948) Structure of Citrinin. Nature 162:72
Cram DJ (1950) Mold metabolites. V. The stereochemistry and ultraviolet absorption of citrinin. J Am Chem Soc 72:1001
Rodig OR, Shiro M, Fernando Q (1971) Crystal and molecular structure of citrinin. J Chem Soc Chem Commun 1553
Mehta PP, Whalley WB (1963) Chemistry of fungi. XLII. Absolute configuration of citrinin. J Chem Soc 3777
Hill RK, Gardella LA (1964) Absolute configuration of citrinin. J Org Chem 29:776
Cartwright NJ, Robertson A, Whalley WB (1949) Chemistry of fungi. VII. Synthesis of citrinin and dihydrocitrinin. J Chem Soc 1563
Warren HH, Dougherty G, Wallis ES (1949) Synthesis of citrinin and dihydrocitrinin. J Am Chem Soc 71:3422
Curtis RF, Hassall CH, Nazar M (1968) Biosynthesis of phenols. XV. Metabolites of Penicillium citrinum related to citrinin. J Chem Soc C 85
Hirota M, Menta AB, Yoneyama K, Kitabatake N (2002) A major decomposition product, citrinin H2, from citrinin on heating with moisture. Biosci Biotechnol Biochem 66:206–210
Trivedi AB, Hirota M, Etsushiro D, Kitabatake N (1993) Formation of a new toxic compound, citrinin H1, from citrinin on mild heating in water. J Chem Soc Perkin Trans 1:2167
Clark RC, Capon RJ, Lacey E, Tennant S, Gill JH (2006) Citrinin revisited: from monomers to dimers and beyond. Org Biomol Chem 4:1520
Barber JA, Staunton J, Wilkinson MR (1986) A diastereoselective synthesis of the polyketide antibiotic citrinin using toluate anion chemistry. J Chem Soc Perkin Trans 1:2101
Anctil EJG, Snieckus V (2004) The directed ortho-metallation (DoM) cross-coupling nexus. Synthetic methodology for the formation of aryl-aryl and aryl-heteroatom-aryl bonds. In: de Meijere A, Diederich F (eds) Metal-catalyzed cross-coupling reactions, 2nd edn. Wiley, Weinheim, p 761
Regan AC, Staunton J (1987) Asymmetric synthesis of (+)-citrinin using an ortho-toluate carbanion generated by a chiral base. J Chem Soc Chem Commun 520
Rödel T, Gerlach H (1995) Enantioselective synthesis of the polyketide antibiotic (3R,4S)-(–)-citrinin. Liebigs Ann 885
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Bräse, S. et al. (2013). Citrinin. In: The Chemistry of Mycotoxins. Progress in the Chemistry of Organic Natural Products, vol 97. Springer, Vienna. https://doi.org/10.1007/978-3-7091-1312-7_3
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DOI: https://doi.org/10.1007/978-3-7091-1312-7_3
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