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Metabolomics

, Volume 10, Issue 4, pp 574–588 | Cite as

Metabolite profiling and fingerprinting of Hypericum species: a comparison of MS and NMR metabolomics

  • Andrea Porzel
  • Mohamed A. Farag
  • Julia Mülbradt
  • Ludger A. Wessjohann
Original Article

Abstract

Hypericum perforatum, commonly known as St. John’s wort, is a popular herbal supplement used for the treatment of mild to moderate depression. The major secondary metabolites of St. John’s wort extracts include phenylpropanoids, flavonoids, xanthones, phloroglucinols, and naphthodianthrones. There are over 400 species in the genus Hypericum world-wide, most of which are little or not characterized in terms of phytochemical or pharmacological properties. Metabolomics techniques were used to investigate the natural product diversity within the genus Hypericum (Hypericaceae) and its correlation to bioactivity, exemplified by cytotoxic properties. Utilizing nuclear magnetic resonance (NMR) fingerprinting and mass spectrometry (MS) metabolic profiling techniques, MS and NMR spectra of extracts from H. perforatum, H. polyphyllum, H. tetrapterum, H. androsaemum, H. inodorum, H. undulatum and H. kouytchense were evaluated and submitted to statistical multivariate analyses. Although comparable score plots in principal component analysis were derived from both MS and NMR datasets, loading plots reveal, that different set of metabolites contribute for species segregation in each dataset. Major peaks in 1H NMR and MS spectra contributing to species discrimination were assigned as those of hyperforins, lipids, chlorogenic and shikimic acid. Shikimic acid and its downstream phenylpropanoids were more enriched in H. perforatum, H. androsaemum, H. kouytchense and H. inodorum extracts; whereas a novel hyperforin was found exclusively in H. polyphyllum. Next to H. perforatum, H. polyphyllum and H. tetrapterum show the highest levels of hypericins, and H. perforatum and H. polyphyllum are highest in phloroglucinols, suggesting that the latter species might be used as an alternative to St. John’s wort. However, the major hyperforin-type compound in H. polyphyllum possesses a novel constitution of yet unknown bioactivity. Anti-cancer in vitro assays to evaluate the ability of extracts from Hypericum species in inhibiting prostate and colon cancer growth suggest that such bioactivity might be predicted by gross metabolic profiling.

Keywords

H. perforatum H. polyphyllum 1H NMR-based metabolomics LC–MS Hyperforin Anticancer activity prediction 

Abbreviations

ESI

Electrospray ionisation

LC

Liquid chromatography

MS

Mass spectrometry

MSn

Tandem mass spectrometry

NMR

Nuclear magnetic resonance

PDA

Photodiode array detection

PCA

Principal component analysis

HCA

Hierarchical cluster analysis

Notes

Acknowledgments

Mohamed A. Farag thanks the Alexander von Humboldt-Foundation, Germany for financial support. We also thank Christoph Böttcher for assistance with the UPLC–MS. We are grateful to Steffen Neumann and Tilo Lübken for providing R scripts for NMR and MS data analysis.

Supplementary material

11306_2013_609_MOESM1_ESM.pdf (542 kb)
Supplementary material 1 (PDF 543 kb)

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Andrea Porzel
    • 1
  • Mohamed A. Farag
    • 1
    • 2
  • Julia Mülbradt
    • 1
    • 3
  • Ludger A. Wessjohann
    • 1
  1. 1.Department of Bioorganic ChemistryLeibniz Institute of Plant BiochemistryHalle (Saale)Germany
  2. 2.Pharmacognosy Department, College of PharmacyCairo UniversityCairoEgypt
  3. 3.FB Biologie/ChemieUniversität BremenBremenGermany

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