Disease relevance of Versicolorin

• Versiconal cyclase catalyzes the dehydration of versiconal to versicolorin B or versicolorin C [versicolorin B(C)] [1].
• These improved yields will facilitate attempts to accumulate enough versicolorin A and versicolorin C for toxicity and carcinogenicity testing [2].

High impact information on Versicolorin

• Isolation and characterization of the versicolorin B synthase gene from Aspergillus parasiticus. Expansion of the aflatoxin b1 biosynthetic gene cluster [3].
• Mannitol-1-phosphate dehydrogenase (EC 1.1.1.17) has been purified from Aspergillus parasiticus, a filamentous fungus which produces the polyketide mycotoxin, versicolorin A [4].
• Purification and characterization of versicolorin B synthase from Aspergillus parasiticus. Catalysis of the stereodifferentiating cyclization in aflatoxin biosynthesis essential to DNA interaction [5].
• To directly test this hypothesis, gene-1, encoding one of the eight transcripts, was disrupted in A. parasiticus CS10, which accumulates the aflatoxin precursor versicolorin A, by insertion of plasmid pAPNVES4 [6].
• The cosmid library was transformed into an Afl- mutant, A. parasiticus CS10 (ver-1 wh-1 pyrG), deficient in the conversion of the aflatoxin biosynthetic intermediate versicolorin A to sterigmatocystin [7].

Biological context of Versicolorin

• It is concluded that one or both of these compounds are intermediates in the biosynthesis of versicolorin A and therefore may possibly be involved in the biogenesis of the aflatoxins [8].
• Genotoxicity of versicolorin A and 6,8-O-dimethylversicolorin A was stronger than that of versicolorin B and 6,8-O-dimethylversicolorin B, respectively, in the HPC/DNA repair test [9].
• Six of the mycotoxins (AFB1, AFG1, AFB2, aflatoxicol, sterigmatocystin and versicolorin A) were genotoxic on PQ37 strain with and without metabolic activation [10].
• These mutants and heterozygous diploids formed by pairwise combinations of auxotrophs were assayed for aflatoxin production; norsolorinic acid and versicolorin A production were also assayed in the diploids [11].

Anatomical context of Versicolorin

• The results showed that both versicolorin A hemiacetal and versicolorin A hemiacetal acetate were converted to aflatoxin B1, whereas versicolorin A was not, even though it was added to the same cell-free system [12].

Associations of Versicolorin with other chemical compounds

• Both whole mycelium and cell-free extracts of this mutant were able to convert 14C-labeled versiconal hemiacetal acetate to versicolorin A [8].
• Their structures have been shown to be norsolorinic acid, averantin, averufin, versicolorin C, versicolorin A, versicolorin A hemiacetal and nidurufin, all of which are known anthraquinone pigments on, or associated with, the aflatoxin biosynthetic pathway in Aspergillus spp [13].
• The conversion of versiconal acetate to versicolorin C in the cell-free system is proposed to involve an esterase and an NADPH-dependent cyclase [14].

Gene context of Versicolorin

• The INDO atomic charges q and Wiberg bond indices p (in electrons) were calculated for aflatoxin B1, sterigmatocystin and versicolorin A [15].

Analytical, diagnostic and therapeutic context of Versicolorin

• Thin-layer chromatography revealed that gene-1 disruptant clones no longer accumulated versicolorin A [6].
• Effect of acetone on production of aflatoxins and versicolorin pigments by resting cell cultures of Aspergillus parasiticus [16].

References