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chlorination as primary hydrogens

The usage of exploratory strategies has increased notably within natural products research, including for instance, the ultrahigh performance liquid chromatography-diode array detection—high resolution mass spectrometry (UHPLC-DAD-HRMS) and tandem high resolution mass spectrometry (MS-HRMS) based dereplication Such approaches usually comprise dedicated data evaluation but often result in successful and rapid identification of known compounds, revealing secondary metabolites still untapped . In view of the foregoing outcomes, the metabolite screening of Talaromyces wortmannii (T. wortmannii) extracts was performed trough ultraviolet/visible (UV/Vis) and HRMS data analysis in combination with queries in commercial and in-house microbial databases. The strategy led to the identification of tryptophan-derived alkaloids, comprised of new halogenated rugulovasines . Rugulovasines are modified clavine alkaloids containing a singular spirolactone moiety with toxic effects observed in day-old chickens . These metabolites have been isolated as a racemic mixture ] since they may interconvert upon warming through vinylogous Mannich reaction. Due to this chemical feature, they have also attracted interest in organic synthesis studies [ The first occurrence of a halocompound derived from rugulovasines was reported by Cole in the 1970s ] and so far, the new halogenated alkaloids produced by T. wortmannii are unique representatives to be reported since Cole’s discovery.Usually, the numbering of carbons into the ergot alkaloid backbone is established according to the original ergoline system Nevertheless, in their first report, the 8-chlororugulovasines were named from a different counting system where the new halogenated rugulovasines were named on the basis of their known analogues.