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Planta Med 2018; 84(09/10): 721-728
DOI: 10.1055/a-0590-5223
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Integration of Biochemometrics and Molecular Networking to Identify Antimicrobials in Angelica keiskei

Lindsay K. Caesar
1   Department of Chemistry and Biochemistry, The University of North Carolina at Greensboro, Greensboro, North Carolina
,
Joshua J. Kellogg
1   Department of Chemistry and Biochemistry, The University of North Carolina at Greensboro, Greensboro, North Carolina
,
Olav M. Kvalheim
2   Department of Chemistry, University of Bergen, Bergen, Norway
,
Richard A. Cech
3   Strictly Medicinal Seeds, Williams, Oregon
,
Nadja B. Cech
1   Department of Chemistry and Biochemistry, The University of North Carolina at Greensboro, Greensboro, North Carolina
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 27. November 2017
revised 03. März 2018

accepted 08. März 2018

Publikationsdatum:
23. März 2018 (online)

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Abstract

Botanical medicines have been utilized for centuries, but it remains challenging to identify bioactive constituents from complex botanical extracts. Bioassay-guided fractionation is often biased toward abundant or easily isolatable compounds. To comprehensively evaluate active botanical mixtures, methods that allow for the prioritization of active compounds are needed. To this end, a method integrating bioassay-guided fractionation, biochemometric selectivity ratio analysis, and molecular networking was devised and applied to Angelica keiskei to comprehensively evaluate its antimicrobial activity against Staphylococcus aureus. This approach enabled the identification of putative active constituents early in the fractionation process and provided structural information for these compounds. A subset of chalcone analogs were prioritized for isolation, yielding 4-hydroxyderricin (1, minimal inhibitory concentration [MIC] ≤ 4.6 µM, IC50 = 2.0 µM), xanthoangelol (2, MIC ≤ 4.0 µM, IC50 = 2.3) and xanthoangelol K (4, IC50 = 168 µM). This approach allowed for the identification of a low-abundance compound (xanthoangelol K) that has not been previously reported to possess antimicrobial activity and facilitated a more comprehensive understanding of the compounds responsible for A. keiskei’s antimicrobial activity.

Key words

biochemometrics - chalcones - selectivity ratio - molecular networking - mass spectrometry - Angelica keiskei - Apiaceae

Supporting Information

    The isolation scheme, workflow, NMR spectra, and dose response curves are available as Supporting Information.

  • Supporting Information
 

  • References

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