Sulochrins and alkaloids from a fennel endophyte Aspergillus sp. FVL2

Mohamed Shaaban, Ahmed S. Abdel-Razek, Viola Previtali, Mads Hartvig Clausen, Charlotte H. Gotfredsen, Hartmut Laatsch, Ling Ding*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The fungal endophyte Aspergillus sp. strain FVL2, isolated from the traditional medicinal fennel plant, Foeniculum vulgare, was investigated for secondary metabolites. Fermentation on rice medium followed by chromatographic separation delivered three new natural products, 7-demethyl-neosulochrin (1), fumigaclavine I (3) and N-benzoyl-tryptophan (6) together with further 14 known 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 new metabolites were determined by NMR spectroscopy and ESI HR mass spectrometry. For fumigaclavine I, we observed the partial deuterium transfer from the solvent to the enol form with a remarkable high stereo selectivity. The discovery of the new seco-anthraquinone 7-demethyl-neosulochrin (1) revealed a second type of ring cleavage by a questin oxygenase. The discovery of diverse secondary metabolites broadens the chemical space of Aspergillus.
Original languageEnglish
JournalNatural Product Research
Number of pages11
ISSN1478-6419
DOIs
Publication statusAccepted/In press - 2022

Keywords

  • Aspergillus sp
  • Sulochrins
  • Fennel endophyte
  • Fumigaclavine I

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