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Literature summary for 1.14.13.43 extracted from

  • Shaaban, M.; Abdel-Razek, A.S.; Previtali, V.; Clausen, M.H.; Gotfredsen, C.H.; Laatsch, H.; Ding, L.
    Sulochrins and alkaloids from a fennel endophyte Aspergillus sp. FVL2 (2021), Nat. Prod. Res., 2021, 1-11 .
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
DNA and amino acid sequence determination and analysis, phylogenetic analysis and tree Aspergillus sp. FVL2

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Aspergillus sp. FVL2 questin and 7-demethyl-neosulochrin are detected in strain FVL2, the latter is another isomer arising from ring cleavage between C-10/C-10a at the other side of the anthraquinone, forming the carboxylic group at ring A ?
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questin + NADPH + H+ + O2 Aspergillus sp. FVL2
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demethylsulochrin + NADP+
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?

Organism

Organism UniProt Comment Textmining
Aspergillus sp. FVL2
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isolated from the traditional medicinal fennel plant, Foeniculum vulgare, Egypt, MW281863
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information questin and 7-demethyl-neosulochrin are detected in strain FVL2, the latter is another isomer arising from ring cleavage between C-10/C-10a at the other side of the anthraquinone, forming the carboxylic group at ring A Aspergillus sp. FVL2 ?
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questin + NADPH + H+ + O2
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Aspergillus sp. FVL2 demethylsulochrin + NADP+
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?

Cofactor

Cofactor Comment Organism Structure
NADPH
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Aspergillus sp. FVL2

General Information

General Information Comment Organism
metabolism the organism is cultured on rice medium, and the secondary metabolites are analysed by chromatographic separation delivering three newly identified natural products, 7-demethyl-neosulochrin, fumigaclavine, and N-benzoyl-tryptophan together with further 14 metabolites, 1-O-methyl-sulochrin-4'-sulfate, questin, laccaic acid, isorhodoptilometrin, fumigaclavine A, fumigaclavine C, fumitremorgin C, fumigaquinazoline C, tryptoquivaline J, trypacidin, 3'-O-demethyl-sulochrin, 1-O-methyl-sulochrin, protocatechuic acid, and vermelone. The chemical structures of the three newly identified metabolites are determined by NMR spectroscopy and ESI HR mass spectrometry. The discovery of the seco-anthraquinone 7-demethyl-neosulochrin reveals a second type of ring cleavage by a questin oxygenase. Except for the moderate activity of trypacidin against Staphylococcus aureus, 7-demethyl-neosulochrin, 1-O-methyl-sulochrin, 1-O-methyl-sulochrin-4'-sulfate, isorhodoptilometrin, fumigaclavine A, fumigaclavine C, fumigaquinazoline C, tryptoquivaline J, 3'-O-demethyl-sulochrin and vermelone are inactive in the agar diffusion assay against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Candida albicans. Demethylneosulochrin, 1-O-methyl-sulochrin-4'-sulfate, 1-O-methyl-sulochrin, fumigaclavine I, and 3-O-demethyl-sulochrin are tested additionally against the human leukemia HL-60 cell line but display no cytotoxicity Aspergillus sp. FVL2