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MALDI-HRMS Imaging Maps the Localization of Skyrin the Precursor of Hypericin and Pathway Intermediates in Leaves of

机译：Maldi-Hrms成像地图柿子的定位血清胰蛋白酶的前体叶片中的途径中间体

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摘要

Hypericum perforatum and related species (Hypericaceae) are a reservoir of pharmacologically important secondary metabolites, including the well-known naphthodianthrone hypericin. However, the exact biosynthetic steps in the hypericin biosynthetic pathway, vis-à-vis the essential precursors and their localization in plants, remain unestablished. Recently, we proposed a novel biosynthetic pathway of hypericin, not through emodin and emodin anthrone, but skyrin. However, the localization of skyrin and its precursors in Hypericum plants, as well as the correlation between their spatial distribution with the hypericin pathway intermediates and the produced naphthodianthrones, are not known. Herein, we report the spatial distribution of skyrin and its precursors in leaves of five in vitro cultivated Hypericum plant species concomitant to hypericin, its analogs, as well as its previously proposed precursors emodin and emodin anthrone, using MALDI-HRMS imaging. Firstly, we employed HPLC-HRMS to confirm the presence of skyrin in all analyzed species, namely H. humifusum, H. bupleuroides, H. annulatum, H. tetrapterum, and H. rumeliacum. Thereafter, MALDI-HRMS imaging of the skyrin-containing leaves revealed a species-specific distribution and localization pattern of skyrin. Skyrin is localized in the dark glands in H. humifusum and H. tetrapterum leaves together with hypericin but remains scattered throughout the leaves in H. annulatum, H. bupleuroides, and H. rumeliacum. The distribution and localization of related compounds were also mapped and are discussed concomitant to the incidence of skyrin. Taken together, our study establishes and correlates for the first time, the high spatial distribution of skyrin and its precursors, as well as of hypericin, its analogs, and previously proposed precursors emodin and emodin anthrone in the leaves of Hypericum plants.
机译：金丝桃属植物和相关物种（二氧化纤维）是药理学上重要的二级代谢物储层，包括众所周知的萘丙酮化素。然而，HyperIcIN生物合成途径中的确切生物合成步骤，Vis-is-植物中必需的前体和它们的本地化仍然未完成。最近，我们提出了一种新型的高霉素的生物合成途径，而不是通过大蛋白和大黄素蒽酮，但潜水。然而，柿子局部的定位及其在金属化植物中的前体以及与丙晶菌途径中间体和产生的萘酮的空间分布之间的相关性尚不清楚。在此，我们报告了使用MALDI-HRMS成像的五种体外培养的金刚晶植物物种中睾丸的空间分布及其前体的五种体外培养的金刚晶植物物种以及先前提出的前体，其先前提出的前体和大黄素蒽酮。首先，我们使用HPLC-HRMS确认所有分析的物种中的睾丸存在，即H. humfuSum，H.Bupleuroides，H. uchulatum，H.Tetraentum和H. Rumeliacum。此后，含臭叶片的MALDI-HRMS成像揭示了锆的物种特异性分布和定位模式。苏里林在H. HumfuSum和H.Tetraentum的暗腺中定位在HumfuSum和H. Tetraentum叶子，但在H. Chululatum，H.Bupleuroides和H. Rumeliacum的H. Chululatum和H. Rumeliacum仍然散落。还映射了相关化合物的分布和定位，并伴随着柿子的发生率。我们的研究占据了第一次建立和关联，柿子的高空间分布及其前体，以及金刚素植物叶片中的预先提出的前体鸟嘌呤和引起的前体植物中的前体和大黄素蒽酮。

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