Metabolite profiling and fingerprinting of Hypericum species: a comparison of MS and NMR metabolomics

Porzel, Andrea; Farag, Mohamed A.; Mülbradt, Julia; Wessjohann, Ludger A.

doi:10.1007/s11306-013-0609-7

Cited by 95 publications

(96 citation statements)

References 46 publications

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“…A compound with an identical molecular formula was previously detected as an unidentified compound in H. perforatum [19] and in the flower extracts of six Hypericum spp. [4]. Our results confirm the presence of this compound in the leaves of the three species, H. perforatum , H. androsaemum , and H. kouytchense , along with the flowers analyzed by [4], and we report for the first time its occurrence in H. stellatum , H. annulatum , and H. monogynum.…”

Section: Discussionsupporting

confidence: 86%

“…[4]. Our results confirm the presence of this compound in the leaves of the three species, H. perforatum , H. androsaemum , and H. kouytchense , along with the flowers analyzed by [4], and we report for the first time its occurrence in H. stellatum , H. annulatum , and H. monogynum. …”

Section: Discussionsupporting

confidence: 86%

“…Similarly, R-(−)-skyrin-6-O-β-D-xylopyranoside was found in H. sampsonii [13], and skyrin-2-O-glucopyranoside was detected in the flower extracts of six Hypericum spp. by [4]. This work provides the first report of skyrin and (2) in other Hypericum spp., all of which accumulate hypericin in their leaves.…”

Section: Discussionmentioning

confidence: 54%

“…A comprehensive review by Stojanovič et al [3] concentrated on the presence of 11 main bioactive compounds including naphthodianthrones, phloroglucinols, flavonoids, and xanthones in 132 representatives of the Hypericum genus. Porzel et al [4] compared the use of two methods, liquid chromatography mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectroscopy coupled with multivariate data analysis, for profiling the floral metabolome of six Hypericum spp. ; they found 38 compounds, and some of them remain unidentified or even unknown.…”

Section: Introductionmentioning

confidence: 99%

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

Kimáková

Idkowiak

et al. 2018

Anal Bioanal Chem

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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.

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Section: Discussionsupporting

confidence: 86%

Section: Discussionsupporting

confidence: 86%

Section: Discussionmentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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

Kimáková

Idkowiak

et al. 2018

Anal Bioanal Chem

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“…Analytical methods such as thin layer chromatography (TLC) (Ferraz et al, 2002), high-performance liquid chromatography (HPLC) (Ferraz et al, 2002), liquid-chromatography mass spectrometric analyses (LC-MS as well as LC-HRMS) (Tatsis et al, 2007; Kusari et al, 2009), and nuclear magnetic resonance (NMR) (Porzel et al, 2014) have been successfully used to determine several major and minor compounds in Hypericum plants. However, there is only sporadic information about the distribution and localization (or accumulation) of the aforementioned metabolites in different tissues of plants belonging to the genus Hypericum .…”

Section: Introductionmentioning

confidence: 99%

Occurrence and Distribution of Phytochemicals in the Leaves of 17 In vitro Cultured Hypericum spp. Adapted to Outdoor Conditions

et al. 2016

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A plethora of plants belonging to the genus Hypericum have been investigated so far owing to the biological efficacies of pharmacologically important secondary metabolites produced by several Hypericum species. However, there is currently a dearth of information about the localization (accumulation) of these compounds in the plants in situ. In particular, the biosynthetic and ecological consequence of acclimatization of in vitro cultured Hypericum spp. to outdoor conditions is not fully known. Herein, we report an application of matrix-assisted laser desorption/ionization high-resolution mass spectrometry (MALDI-HRMS) to reveal the distribution of major naphthodianthrones hypericin, pseudohypericin, protohypericin, and their proposed precursor emodin as well as emodin anthrone, along with the phloroglucinol derivative hyperforin, the flavonoids quercetin, quercitrin, rutin and hyperoside (and/or isoquercitrin), and chlorogenic acid in Hypericum leaves. Plants encompassing seventeen Hypericum species classified into eleven sections, which were first cultured in vitro and later acclimatized to outdoor conditions, were studied. We focused both on the secretory (dark and translucent glands, other types of glands, and glandular-like structures) as well as the non-secretory leaf tissues. We comparatively analyzed and interpreted the occurrence and accumulation of our target compounds in different leaf tissues of the seventeen species to get an intra-sectional as well as inter-sectional perspective. The naphthodianthrones, along with emodin, were present in all species containing the dark glands. In selected species, hypericin and pseudohypericin accumulated not only in the dark glands, but also in translucent glands and non-secretory leaf tissues. Although hyperforin was localized mainly in translucent glands, it was present sporadically in the dark glands in selected species. The flavonoids quercetin, quercitrin, and hyperoside (and/or isoquercitrin) were distributed throughout the leaves. Rutin was present only within sections Hypericum, Adenosepalum, Ascyreia, and Psorophytum. Our study provides insights into the prospects and challenges of using in vitro cultured Hypericum plants, further adapted to field conditions, for commercial purposes.

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UPLC‐MS‐Based Metabolomics Profiling and Chemometric Analysis for Hypericum sinaicum Boiss and the Endophytic Aspergillus foetidus in Comparison to Hypericum perforatum L.

Sheashea,

El‐Hawary,

Ahmed

et al. 2023

Chemistry & Biodiversity

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One of the endangered plant species in Saint Catherine protectorate is Hypericum sinaicum Boiss which is endemic to Egypt, Jordan, and Saudi Arabia. The fungus‐host relationship can assist in the investigation of bioactive compounds produced by H. sinaicum paving the way for economic and medicinal implications. Therefore, a comprehensive metabolic approach via MS and chemical analysis was used to track and compare metabolites from H. sinaicum and Aspergillus foetidus var. pallidus, the endophytic fungus, with Hypericum perforatum. Metabolomics analysis revealed the presence of 25 metabolites distributed among samples and the discovery of new chemotaxonomic compounds, i.e., phloroglucinols and xanthones, allowing the discrimination between species. A. foetidus extract is considered a reliable source of furohyperforin and naphthodianthrone derivatives. In conclusion, using A. foetidus as an in vitro technique for producing potential phytoconstituents was cost effective, having easier optimization conditions and faster growth with fewer contamination rates than other in vitro methods.

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Metabolite profiling and fingerprinting of Hypericum species: a comparison of MS and NMR metabolomics

Cited by 95 publications

References 46 publications

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

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

Occurrence and Distribution of Phytochemicals in the Leaves of 17 In vitro Cultured Hypericum spp. Adapted to Outdoor Conditions

UPLC‐MS‐Based Metabolomics Profiling and Chemometric Analysis for Hypericum sinaicum Boiss and the Endophytic Aspergillus foetidus in Comparison to Hypericum perforatum L.

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