Phenylpolyenes d'Aspergillus niger: structure et proprietes de l'asperrubrol

Rabache, Maurice; Neumann, J.; Lavollay, J

doi:10.1016/s0031-9422(00)91366-9

Cited by 9 publications

(7 citation statements)

References 11 publications

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“…These results support the structure of asperrubrol reported by Rabache et al 20 Labeling in Fusarium spp. The compound YWA1 is known to be a biosynthetic precursor of several compounds including nor-rubrofusarin, rubrofusarin, fuscofusarin, and aurofusarin in fusaria.…”

supporting

confidence: 92%

“…These results suggest that asperrubrol is indeed biosynthesized from benzoic acid, which may in turn be synthesized from cinnamic acid in a different compartment. These results support the structure of asperrubrol reported by Rabache et al…”

Section: Results and Discussionmentioning

confidence: 99%

“…A. niger is a producer of numerous PKs including asperrubrol ( 7 ) . It has previously been hypothesized that cinnamic acid is a precursor to asperrubrol .…”

mentioning

confidence: 99%

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Combining UHPLC-High Resolution MS and Feeding of Stable Isotope Labeled Polyketide Intermediates for Linking Precursors to End Products

et al. 2015

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We present the results from stable isotope labeled precursor feeding studies combined with ultrahigh performance liquid chromatography-high resolution mass spectrometry for the identification of labeled polyketide (PK) end-products. Feeding experiments were performed with (13)C8-6-methylsalicylic acid (6-MSA) and (13)C14-YWA1, both produced in-house, as well as commercial (13)C7-benzoic acid and (2)H7-cinnamic acid, in species of Fusarium, Byssochlamys, Aspergillus, and Penicillium. Incorporation of 6-MSA into terreic acid or patulin was not observed in any of six evaluated species covering three genera, because the 6-MSA was shunted into (2Z,4E)-2-methyl-2,4-hexadienedioic acid. This indicates that patulin and terreic acid may be produced in a closed compartment of the cell and that (2Z,4E)-2-methyl-2,4-hexadienedioic acid is a detoxification product toward terreic acid and patulin. In Fusarium spp., YWA1 was shown to be incorporated into aurofusarin, rubrofusarin, and antibiotic Y. In A. niger, benzoic acid was shown to be incorporated into asperrubrol. Incorporation levels of 0.7-20% into the end-products were detected in wild-type strains. Thus, stable isotope labeling is a promising technique for investigation of polyketide biosynthesis and possible compartmentalization of toxic metabolites.

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supporting

confidence: 92%

Section: Results and Discussionmentioning

confidence: 99%

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Combining UHPLC-High Resolution MS and Feeding of Stable Isotope Labeled Polyketide Intermediates for Linking Precursors to End Products

et al. 2015

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“…Literature search on asperenone showed that it has been isolated independently by two other groups [17,18] however this major yellow intermycelial pigment was characterized as a methyl derivative of 13-phenyl tri-deca-4,6,8,10,12-penta-3-one and was given the trivial name as asperenone by Jefferson [14]. Biological benefi ciary activities of asperenone is not known much except for showing an antifungal activity [18] and lipoxygenase and human platelet aggregation inhibition [13].…”

Section: Resultsmentioning

confidence: 99%

Strain improvement of Aspergillus niger for the enhanced production of asperenone

2008

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The enhancement of production of asperenone ( Fig. 1), an inhibitor of lipoxygenase and human platelet aggregation from Aspergillus niger CFTRI 1105, was achieved by UV and nitrous acid mutagenesis. Nitrous acid mutants exhibited increased inhibitor production when compared with UV irradiated mutants. I N 41 a fi rst-generation nitrous acid mutant produced 5.1 fold increased asperenone over parent strain. Mutant II N 31 obtained by second-generation nitrous acid treatment produced 60.3 mg asperenone/g biomass, which was 131 fold increase when compared to fi rst generated mutant I N 41 and 670 fold increase over the parent strain. This mutant was stable for several generations on production medium.

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“…89 This pigment and another yellow pigment named asperrubrol (158) were biosynthesized by an A. niger strain cultured on synthetic medium containing toxic concentrations of Zn +2 and Cd +2 and high concentration of Mg +2 . 90 In addition, the deep green color pigment cycloleucomelone (159) was identified in the mycelium of a marine strain associated to the Mediterranean sponge Axinella damicornis. 70…”

Section: Pigmentsmentioning

confidence: 99%

Aspergillus niger: A Hundred Years of Contribution to the Natural Products Chemistry

Lima¹,

Oliveira²,

Pimenta³

et al. 2019

J. Braz. Chem. Soc.

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Aspergillus niger is a phytopathogenic fungus responsible for the plant disease called "black mold", and it is considered the most versatile microorganism for producing acids, proteins, and enzymes of industrial value, besides a variety of compounds of pharmacological interest. This review presents a century of contribution of A. niger in the natural products chemistry under two different perspectives: (i) an overview of the structural diversity of secondary metabolites produced by A. niger from different habitats and their biological activities; (ii) a general discussion of the enzymatic potential of A. niger on the selective biotransformation of terpenes, highlighting the most uncommon microbial transformations.

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Phenylpolyenes d'Aspergillus niger: structure et proprietes de l'asperrubrol

Cited by 9 publications

References 11 publications

Combining UHPLC-High Resolution MS and Feeding of Stable Isotope Labeled Polyketide Intermediates for Linking Precursors to End Products

Combining UHPLC-High Resolution MS and Feeding of Stable Isotope Labeled Polyketide Intermediates for Linking Precursors to End Products

Strain improvement of Aspergillus niger for the enhanced production of asperenone

Aspergillus niger: A Hundred Years of Contribution to the Natural Products Chemistry

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