Analytical tools for accessing phenylacrylamides from Swinglea glutinosa and new metabolites from Penicillium setosum, its associated fungus

The chemical study of Swinglea glutinosa (Rutaceae) and Penicillium setosum, its
endophytic fungus are being conducted. For accessing the metabolites, we are employing
dereplication approaches through hyphenated techniques, specially UHPLC-HRMS. Our
strategies allowed the isolation of four unrelated phenylacrylamides to the S. glutinosa:
Lansamide I, Lansiumamide B, N-(2-phenylethyl)-cinnamamide and Lansiumamide C (Figure
1). Besides that, five acridonic alkaloids were also isolated (Citrusinine I, Citibrasine,
Pyranofoline, 5-hydroxynoracronicine and Glicotricine IV) from the plant. All isolated compounds
were obtained from cytotoxic fractions against human leukemia cells.
Simultaneously, the OSMAC approaches1 have been used to prioritize the study of P.
setosum, a recently discovered fungus2. Thus, it becomes very important to explore its
metabolism. Penicillium setosum was grown in six different media: BDA, YES, rice, hominy,
YES (with HBr) and CYA. The extract obtained from rice growth showed cytotoxic activity
against human leukemia cell lines. In addition, the mass spectrum obtained showed a
characteristic profile of halogenated compounds (Figure 2). The corresponding masses (m/z
333.9870 and m/z 390.2522) were consulted in databases (Antibase 2012 and Dictionary of
Natural Products) and no corresponding compounds were found, indicating the presence of
potentially unpublished compounds. The extract obtained from YES (with HBr) media presented
mass spectra that suggests the presence of bromide compounds pattern; also not found at
databases. After using dereplication strategies the fungus has been grown on large-scale in
order to isolate the metabolites. Thus, this work aims to contribute to the discovery of new
substances with cytotoxic action, besides enriching the knowledge of the chemical profile of the
genus Swinglea and also to explore the Penicillium setosum’s metabolism.