Phenotyping the genus Hypericum by secondary metabolite profiling: emodin vs. skyrin, two possible key intermediates in hypericin biosynthesis.

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  • Additional Information
    • Source:
      Publisher: Springer-Verlag Country of Publication: Germany NLM ID: 101134327 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1618-2650 (Electronic) Linking ISSN: 16182642 NLM ISO Abbreviation: Anal Bioanal Chem Subsets: MEDLINE
    • Publication Information:
      Original Publication: Heidelberg : Springer-Verlag, 2002-
    • Subject Terms:
      Hypericum* ; Secondary Metabolism*; Anthraquinones/*chemistry ; Emodin/*chemistry ; Perylene/*analogs & derivatives; Anthracenes ; Chromatography, Liquid ; Mass Spectrometry ; Perylene/chemistry ; Phenotype ; Plant Leaves/chemistry
    • Abstract:
      A wide range of compounds that occur in the genus Hypericum are listed as effective drugs of natural origin. The main biological activities of several Hypericum representatives are due to the presence of naphthodianthrones, phloroglucinols, and other diverse groups of secondary metabolites that synergistically contribute to their therapeutic effects. The regulation of biosynthesis of hypericin as the key bioactive naphthodianthrone remains uncertain. Here, we present liquid chromatography mass spectrometry-based phenotyping of 17 Hypericum species, the results of which suggest an important role for skyrin and its derivatives in the polyketide pathway that leads to hypericin formation. Moreover, we report for the first time the presence of new metabolites in the genus Hypericum that are related to classes of anthraquinones, their derivatives, and phloroglucinols. As skyrin and other species of anthraquinones are rarely found in higher plants but frequently occur in fungal microorganisms, the obtained results suggest that further research on the synthesis pathways of hypericin and the role of anthraquinone derivatives in plant metabolism should be carried out. The fact that these compounds are commonly synthesized in endophytic fungi and perhaps there is some similarity in the metabolic pathways between these organisms should also be investigated.
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    • Grant Information:
      VEGA, 1/0090/15 Scientific Grant Agency of the Slovak Republic; PAS, No. 500 0901 Research grant from the Institute of Bioorganic Chemistry; Grant No. APVV-14-0154 Slovak Research and Development Agency
    • Contributed Indexing:
      Keywords: Anthraquinones; Hypericin biosynthesis; Hypericum; Liquid chromatography mass spectrometry; Metabolite profiling; Naphthodianthrones; Phloroglucinols
    • Accession Number:
      0 (Anthracenes)
      0 (Anthraquinones)
      5QD5427UN7 (Perylene)
      7V2F1075HD (hypericin)
      KA46RNI6HN (Emodin)
      VLA1F42GXP (skyrin)
    • Publication Date:
      Date Created: 20181007 Date Completed: 20190208 Latest Revision: 20240403
    • Publication Date:
      20240403
    • Accession Number:
      PMC6244766
    • Accession Number:
      10.1007/s00216-018-1384-0
    • Accession Number:
      30291388