The crystal and molecular structure of citrinin

Rodig, Oscar R.; Shiro, Motoo; Fernaǹdo, Quintus

doi:10.1039/c29710001553

Cited by 14 publications

(10 citation statements)

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“…The action of anthracyclic antibiotics like adriamycin and aclacinomycin on PM2 phage DNA has been described by Someya and Tanaka (30), and that of dnacin B1, a benzoquinone antibiotic, has been described by Tanida et al (33). Citrinin can be formulated as p-quinone or as o-quinone when complexed with copper ions (27). The in vivo effects of the antibiotics mentioned also showed some similarities with the citrinin action; e.g., adriamycin also interacts with cell membranes (34).…”

Section: Discussionmentioning

confidence: 99%

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Action of citrinin on bacterial chromosomal and plasmid DNA in vivo and in vitro

Martin¹,

Lorkowski²,

Creppy³

et al. 1986

Appl Environ Microbiol

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Citrinin, a mycotoxin of Penicillium citrinum and other species of the genera Penicillium and Aspergillus, caused the following effects at different concentrations in Escherichia coli. In vivo at 100 ,ug/mI single-strand breaks were caused in the chromosomal DNA. In the presence of 100 ,ug/ml, UV (254 nm)-induced DNA damage was repaired in the bacterial cells without need for a complete growth medium. At 300 ,ug/ml lambda ts prophage was induced in a lysogenic E. coli strain. In an E. coli strain carrying a F' lac plasmid, 4.7% of the cells displayed the Lac-phenotype after treatment with 200 ,ug of citrinin per ml, suggesting elimination of the F' factor. In vitro, DNA repair synthesis was observed at 5 ,ug of citrinin per ml in permeabilized cells, and replicative DNA synthesis was inhibited at 200 ,ug/ml. In these systems synthesis of stable RNAs was slightly diminished at 300 ,ug/mI, and protein synthesis was not affected at concentrations up to 450 ,ug/ml. Lambda and ColEl plasmid DNA were cleaved in vitro when small amounts of copper ions were present. This DNA-attacking activity was prevented by NADPH, catalase, and superoxide dismutase and by higher concentrations of hydroxyl radical scavengers, suggesting the involvement of free radicals in the mechanism of action of citrinin on DNA.

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Section: Discussionmentioning

confidence: 99%

“…Its occurrence in feed and food is generally regarded as being of minor importance compared with ochratoxin A (29), with which it is occasionally associated in these commodities. Chemically it was formulated as a quinone methide (27).…”

mentioning

confidence: 99%

Action of citrinin on bacterial chromosomal and plasmid DNA in vivo and in vitro

Martin¹,

Lorkowski²,

Creppy³

et al. 1986

Appl Environ Microbiol

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“…Its relative peak intensity is increased with increase in the concentration of the solution and with decrease in temperature with a simultaneous decrease in the intensity of the high-frequency band on account of displacement of the equilibrium toward the dimer (Fig. 4, curves 4,5). In addition to these two clearly defined bands, the spectrum of the solution of maltol in dichloroethane at 298 K contains three weaker bands.…”

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confidence: 90%

“…4, curves [3][4][5], in addition to the absorption band of the sp-conformer, there is an absorption band for the dimer 1d (3250 cm -1 ), shifted toward lower frequencies in relation to the spectrum of the vapor. Its relative peak intensity is increased with increase in the concentration of the solution and with decrease in temperature with a simultaneous decrease in the intensity of the high-frequency band on account of displacement of the equilibrium toward the dimer (Fig.…”

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confidence: 97%

“…In chloroform solution these dimers dissociate with the formation of monomers, which are characterized by a strong intramolecular hydrogen bond accompanied by resonance [4]. In nonpolar carbon tetrachloride citrinin, the molecules of which in the solid phase contain two intramolecular hydrogen bonds, exists in the form of an equilibrium mixture of monomeric forms with two and one hydrogen bond [5]. The conformational isomer of 2,5-dihydroxy-1,4-benzoquinone with two intramolecular hydrogen bonds is stable in the gas phase and in chloroform solution.…”

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Molecular structure of complexes with a bifurcated hydrogen bond. 5. Dimers of 3-hydroxy-2-methyl-4-pyrone in inert media

Mukha

Chípanina

Sterkhova

et al. 2006

Chem Heterocycl Compd

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According to the data from IR spectroscopy and quantum-chemical calculations (B3LYP/6-31G**, B3LYP/6-311G*), in the vapor and in dichloroethane the synperiplanar conformer of 3-hydroxy-2-methyl-4-pyrone (maltol) exists in equilibrium with two types of dimers. The hydrogen atom of the hydroxy group of one them participates in the formation of a three-center bifurcated hydrogen bond. The second isomer is formed by means of two such H bonds, the intramolecular component of which is substantially weakened while the intermolecular component is so strong that it approximates in character to a two-center hydrogen bond.

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Enantioselective synthesis of the polyketide antibiotic (3R,4S)‐(−)‐citrinin

Rödel

Gerlach

1995

Liebigs Ann./Recl.

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The fungal metabolite (−)‐citrinin (1) was synthesized for the first time. Reaction of the Grignard reagent of 2,4‐bis(benzyloxy)‐6‐bromotoluene (3) with (2S)‐trans‐(−)‐2,3‐dimethyloxirane (6) in the presence of 1,5‐cyclooctadienecopper(I) chloride as catalyst leads to the formation of (2S,3S)‐(−)‐7 with erythro configuration. Compound (−)‐7 could be transformed into (2R,3S)‐(−)‐9 with threo configuration via the formate (1R,2S)‐(+)‐8 by a Mitsunobu reaction. Reaction of the Grignard reagent of 3 with the achiral cis‐2,3‐dimethyl‐oxirane yielded directly (±)‐9. The starting material 3 was readily available from 1,3‐bis(benzyloxy)‐5‐bromobenzene (4). Formylation of 4 furnished the aldehyde 5 which could be reduced to 3 with borane. Hydrogenolysis of the benzyl ether groups in (−)‐9 gave (−)‐2 with threo configuration. The remaining steps to produce citrinin [(−)‐1] from (−)‐2 required carboxylation to 11, formylation and in situ ring closure with ethyl orthoformate to produce the required quinomethide structure. Application of the same reactions to (±)‐9 and (±)‐2 afforded (±)‐citrinin in 40% overall yield.

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The crystal and molecular structure of citrinin

Cited by 14 publications

References 0 publications

Action of citrinin on bacterial chromosomal and plasmid DNA in vivo and in vitro

Action of citrinin on bacterial chromosomal and plasmid DNA in vivo and in vitro

Molecular structure of complexes with a bifurcated hydrogen bond. 5. Dimers of 3-hydroxy-2-methyl-4-pyrone in inert media

Enantioselective synthesis of the polyketide antibiotic (3R,4S)‐(−)‐citrinin

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