Phenotyping the genus Hypericum by secondary metabolite profiling: emodin vs. skyrin, two possible key intermediates in hypericin biosynthesis
| Autor: | Jakub Idkowiak, Łukasz Marczak, Eva Čellárová, Paweł Rodziewicz, Andrea Kimáková, K. Kimáková, Maciej Stobiecki |
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| Rok vydání: | 2018 |
| Předmět: |
0106 biological sciences
0301 basic medicine Emodin Liquid chromatography mass spectrometry Secondary Metabolism Anthraquinones Secondary metabolite 01 natural sciences Biochemistry Plant use of endophytic fungi in defense Mass Spectrometry Analytical Chemistry 03 medical and health sciences Polyketide chemistry.chemical_compound Metabolite profiling medicine Phloroglucinols Perylene Hypericin biosynthesis Anthracenes biology Chemistry biology.organism_classification Hypericin Plant Leaves Metabolic pathway 030104 developmental biology Phenotype Naphthodianthrones Hypericum 010606 plant biology & botany medicine.drug Chromatography Liquid Research Paper |
| Zdroj: | Analytical and Bioanalytical Chemistry |
| ISSN: | 1618-2650 |
| Popis: | 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. Electronic supplementary material The online version of this article (10.1007/s00216-018-1384-0) contains supplementary material, which is available to authorized users. |
| Databáze: | OpenAIRE |
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