Targeted metabolomic profiling reveals interspecific variation in the genus Hypericum in response to biotic elicitors

Bálintová, Miroslava; Bruňáková, Katarína; Petijová, Linda; Čellárová, Eva

doi:10.1016/j.plaphy.2018.12.024

Cited by 19 publications

(12 citation statements)

References 54 publications

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“…Emodin (1) was detected in four samples except in H. bupleuroides (<LOD). Our results were in accordance with previous reports where emodin was not found in the Hypericum species mentioned above [ 24 , 25 ]. Conversely, emodin anthrone (2) was typically either not detected or in low abundance in the samples where emodin (1) was detected in higher abundance.…”

Section: Resultssupporting

confidence: 94%

“…Emodin anthrone (2) also exhibited a scattered distribution pattern around the dark glands, similar to emodin (1) ( Figure 5 A and Figure 6 ). Furthermore, the analogs of hypericin (6) , namely pseudohypericin (4) , protopseudohypericin (3) , and protohypericin (5) , were all found to localize in the dark glands, corroborating the previous results [ 7 , 8 , 24 ] ( Figure 6 ).…”

Section: Resultssupporting

confidence: 89%

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

et al. 2020

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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.

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Section: Resultssupporting

confidence: 94%

Section: Resultssupporting

confidence: 89%

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

et al. 2020

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“…St. John’s wort is used to treat mild to moderate depressive disorders or nervous unrest [8,9]. SJW contains a variety of bioactive constituents, of which flavonoids (rutin, quercitrin, hyperoside), phloroglucinols (hyperforin, adhyperforin), and naphtodianthrones (hypericin, pseudohypericin) are the most abundant [10,11]. There is some evidence that hyperforin (HP) and hypericin (HY), in combination with photodynamic therapy (HY-PDT), have anti-angiogenic effects and could inhibit tumor growth.…”

Section: Introductionmentioning

confidence: 99%

Novel Insights into the Effect of Hyperforin and Photodynamic Therapy with Hypericin on Chosen Angiogenic Factors in Colorectal Micro-Tumors Created on Chorioallantoic Membrane

Majerník

Jendželovský

Babinčák

et al. 2019

IJMS

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Photodynamic therapy with hypericin (HY-PDT) and hyperforin (HP) could be treatment modalities for colorectal cancer (CRC), but evidence of their effect on angiogenic factors in CRC is missing. Convenient experimental model utilization is essential for angiogenesis research. Therefore, not only 2D cell models, but also 3D cell models and micro-tumors were used and compared. The micro-tumor extent and interconnection with the chorioallantoic membrane (CAM) was determined by histological analyses. The presence of proliferating cells and HY penetration into the tumor mass were detected by fluorescence microscopy. The metabolic activity status was assessed by an colorimetric assay for assessing cell metabolic activity (MTT assay) and HY accumulation was determined by flow cytometry. Pro-angiogenic factor expression was determined by Western blot and quantitative real-time polymerase chain reaction (RT-qPCR). We confirmed the cytotoxic effect of HY-PDT and HP and showed that their effect is influenced by structural characteristics of the experimental model. We have pioneered a method for analyzing the effect of HP and cellular targeted HY-PDT on pro-angiogenic factor expression in CRC micro-tumors. Despite the inhibitory effect of HY-PDT and HP on CRC, the increased expression of some pro-angiogenic factors was observed. We also showed that CRC experimental micro-tumors created on quail CAM could be utilized for analyses of gene and protein expression.

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“…Flavonoids and their derivatives are a major group of compounds in tea 13 that are known to confer stress tolerance to tea plants during growth and development 14,15 . Polyphenols are the major flavonoids found within fresh and commercial tea leaves 16 .…”

Section: Introductionmentioning

confidence: 99%

Identification and distribution of a single nucleotide polymorphism responsible for the catechin content in tea plants

Jiang

Liu

et al. 2020

Hortic Res

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Catechins are the predominant products in tea plants and have essential functions for both plants and humans. Several genes encoding the enzymes regulating catechin biosynthesis have been identified, and the identification of single nucleotide polymorphisms (SNPs) resulting in nonsynonymous mutations within these genes can be used to establish a functional link to catechin content. Therefore, the transcriptomes of two parents and four filial offspring were sequenced using next-generation sequencing technology and aligned to the reference genome to enable SNP mining. Subsequently, 176 tea plant accessions were genotyped based on candidate SNPs using kompetitive allelespecific polymerase chain reaction (KASP). The catechin contents of these samples were characterized by highperformance liquid chromatography (HPLC), and analysis of variance (ANOVA) was subsequently performed to determine the relationship between genotypes and catechin content. As a result of these efforts, a SNP within the chalcone synthase (CHS) gene was shown to be functionally associated with catechin content. Furthermore, the geographical and interspecific distribution of this SNP was investigated. Collectively, these results will contribute to the early evaluation of tea plants and serve as a rapid tool for accelerating targeted efforts in tea breeding.

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Targeted metabolomic profiling reveals interspecific variation in the genus Hypericum in response to biotic elicitors

Cited by 19 publications

References 54 publications

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

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

Novel Insights into the Effect of Hyperforin and Photodynamic Therapy with Hypericin on Chosen Angiogenic Factors in Colorectal Micro-Tumors Created on Chorioallantoic Membrane

Identification and distribution of a single nucleotide polymorphism responsible for the catechin content in tea plants

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