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Planta Med 2018; 84(03): 182-190
DOI: 10.1055/s-0043-118807
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Metabolomic-Guided Isolation of Bioactive Natural Products from Curvularia sp., an Endophytic Fungus of Terminalia laxiflora

Ahmed F. Tawfike
1   Strathclyde Institute of Pharmacy and Biomedical Science, University of Strathclyde, United Kingdom
2   Department of Pharmacognosy, Faculty of Pharmacy, Helwan University, Egypt
,
Grainne Abbott
1   Strathclyde Institute of Pharmacy and Biomedical Science, University of Strathclyde, United Kingdom
,
Louise Young
1   Strathclyde Institute of Pharmacy and Biomedical Science, University of Strathclyde, United Kingdom
,
RuAngelie Edrada-Ebel
1   Strathclyde Institute of Pharmacy and Biomedical Science, University of Strathclyde, United Kingdom
› Author Affiliations
Further Information

Publication History

received 10 May 2017
revised 11 August 2017

accepted 21 August 2017

Publication Date:
28 August 2017 (online)

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Abstract

Endophytic fungi associated with medicinal plants are a potential source of novel chemistry and biology. Metabolomic tools were successfully employed to compare the metabolite fingerprints of solid and liquid culture extracts of endophyte Curvularia sp. isolated from the leaves of Terminalia laxiflora. Natural product databases were used to dereplicate metabolites in order to determine known compounds and the presence of new natural products. Multivariate analysis highlighted the putative metabolites responsible for the bioactivity of the fungal extract and its fractions on NF-κB and the myelogenous leukemia cell line K562. Metabolomic tools and dereplication studies using high-resolution electrospray ionization mass spectrometry directed the fractionation and isolation of the bioactive components from the fungal extracts. This resulted in the isolation of N-acetylphenylalanine (1) and two linear peptide congeners of 1: dipeptide N-acetylphenylalanyl-L-phenylalanine (2) and tripeptide N-acetylphenylalanyl-L-phenylalanyl-L-leucine (3).

Key words

metabolomics - dereplication - endophytic fungi - Curvularia - Terminalia laxiflora - Combretaceae

Supporting Information

    1D and 2D NMR, MS spectra of compounds 1, 2, and 3, as well as part of the experimental methods that includes the taxonomical identification of the fungi by molecular biological methods, Marfeyʼs derivatization, and bioscreening of the isolated compounds are available as Supporting Information.

  • Supporting Information
 

  • References

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