Non-geminal Aliphatic Dihalogenation Pattern in Dichlorinated Diaporthins from Hamigera fusca NRRL 35721

Celso Almeida, Ignacio Pérez-Victoria, Víctor González-Menéndez, Nuria De Pedro, Jesús Martín, Gloria Crespo, Thomas Mackenzie, Bastien Cautain, Fernando Reyes, Francisca Vicente, Olga Genilloud

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3 Citations (Scopus)

Abstract

Two new epimeric dihalogenated diaporthins, (9R)-8-methyl-9,11-dichlorodiaporthin (2) and (9S)-8-methyl-9,11-dichlorodiaporthin (3), have been isolated from the soil fungus Hamigera fusca NRRL 35721 alongside the known regioisomeric isocoumarin 8-methyl-11,11-dichlorodiaporthin (1). Their structures were elucidated by high-resolution mass spectrometry and NMR spectroscopy combined with molecular modeling. Compounds 1-3 are the first isocoumarins and the first halogenated metabolites ever reported from the Hamigera genus. The new compounds 2 and 3 display a non-geminal aliphatic dichlorination pattern unprecedented among known fungal dihalogenated aromatic polyketides. A bifunctional methyltransferase/aliphatic halogenase flavoenzyme is proposed to be involved in the biosynthesis of dichlorinated diaporthins 1-3. These metabolites are weakly cytotoxic.

Original languageEnglish
Pages (from-to)1488-1492
Number of pages5
JournalJournal Of Natural Products
Volume81
Issue number6
DOIs
Publication statusPublished - 22 Jun 2018

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    Almeida, C., Pérez-Victoria, I., González-Menéndez, V., De Pedro, N., Martín, J., Crespo, G., ... Genilloud, O. (2018). Non-geminal Aliphatic Dihalogenation Pattern in Dichlorinated Diaporthins from Hamigera fusca NRRL 35721. Journal Of Natural Products, 81(6), 1488-1492. https://doi.org/10.1021/acs.jnatprod.8b00041