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

机译:通过次级代谢产物分析对金丝桃属进行表型鉴定:大黄素与天粉金丝桃素生物合成中的两种可能的关键中间体

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摘要

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 materialThe online version of this article (10.1007/s00216-018-1384-0) contains supplementary material, which is available to authorized users.
机译:金丝桃属中存在的多种化合物被列为天然来源的有效药物。几个金丝桃属植物代表的主要生物活性是由于萘二酮,间苯三酚和其他不同种类的次级代谢产物的协同作用,从而共同促进了它们的治疗作用。金丝桃素作为关键的生物活性萘啶酮的生物合成的调控仍不确定。在这里,我们目前基于液相色谱质谱法的17种金丝桃属植物的表型分析,其结果表明Skyrin及其衍生物在聚酮化合物途径中的重要作用,导致金丝桃素的形成。此外,我们首次报道了金丝桃属中新的代谢物的存在,这些代谢物与蒽醌类,其衍生物和间苯三酚有关。由于在高等植物中很少发现Skyrin和其他种类的蒽醌,而在真菌微生物中则很常见,因此获得的结果表明,应进一步研究金丝桃素的合成途径以及蒽醌衍生物在植物代谢中的作用。这些化合物通常在内生真菌中合成,并且这些生物之间的代谢途径可能存在相似性这一事实也应进行研究。电子补充材料本文的在线版本(10.1007 / s00216-018-1384-0)包含补充剂资料,可供授权用户使用。

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