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.

金丝桃属中存在的多种化合物被列为有效的天然来源药物。几种金丝桃属植物代表的主要生物活性归因于萘二蒽酮、间苯三酚和其他不同组的次生代谢物的存在，这些代谢物协同促进其治疗效果。作为关键生物活性萘并二蒽酮的金丝桃素的生物合成调控仍不确定。在这里，我们对 17 种金丝桃属植物进行了基于液相色谱质谱的表型分析，结果表明 Skyrin 及其衍生物在导致金丝桃素形成的聚酮化合物途径中发挥着重要作用。此外，我们首次报告金丝桃属中存在与蒽醌类、其衍生物和间苯三酚类相关的新代谢物。由于skyrin等蒽醌类化合物在高等植物中很少见，但在真菌微生物中经常出现，因此所得结果表明，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，并且这些生物体之间的代谢途径可能存在一些相似性，这一事实也应该进行研究。