A chemotaxonomic study of phytochemicals in Hedyotis corymbosa

Li, Hongquan; Li, Chun; Xia, Bo‐Hou; Zhou, Yamin; Lin, Limei; Liao, Duan‐Fang

doi:10.1016/j.bse.2015.06.028

Cited by 10 publications

(8 citation statements)

References 30 publications

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“…A main active compound found in both O. diffusa and O. corymbosa is ursolic acid (Li et al, 2015; Chen et al, 2016). This pentacyclic triterpene shows a range of effects, including anti‐tumor, anti‐inflammatory, anti‐oxidative, antiphytol‐diabetic, and pro‐apoptotic (Iqbal et al, 2018; Seo et al, 2018; Feng and Su, 2019).…”

Section: Discussionmentioning

confidence: 99%

“…It is known that O. corymbosa contains iridoids, flavonoids, saponins, triterpenes, phenols, terpenoids, sterols, and anthraquinones (Sivaprakasam et al, 2014; Li et al, 2015). To identify the compounds conferring the anti‐cancer activity against SKBR3, we performed activity‐guided fractionation, NMR, and high‐resolution mass spectrometry, which revealed ursolic acid, oleanolic acid, pheophorbide a, phytol, and lutein in the active fractions.…”

Section: Discussionmentioning

confidence: 99%

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Genomic, transcriptomic, and metabolomic analysis of Oldenlandia corymbosa reveals the biosynthesis and mode of action of anti‐cancer metabolites

Julca

Mutwil-Anderwald

Manoj

et al. 2023

JIPB

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Plants accumulate a vast array of secondary metabolites, which constitute a natural resource for pharmaceuticals. Oldenlandia corymbosa belongs to the Rubiaceae family, and has been used in traditional medicine to treat different diseases, including cancer. However, the active metabolites of the plant, their biosynthetic pathway and mode of action in cancer are unknown. To fill these gaps, we exposed this plant to eight different stress conditions and combined different omics data capturing gene expression, metabolic profiles, and anti‐cancer activity. Our results show that O. corymbosa extracts are active against breast cancer cell lines and that ursolic acid is responsible for this activity. Moreover, we assembled a high‐quality genome and uncovered two genes involved in the biosynthesis of ursolic acid. Finally, we also revealed that ursolic acid causes mitotic catastrophe in cancer cells and identified three high‐confidence protein binding targets by Cellular Thermal Shift Assay (CETSA) and reverse docking. Altogether, these results constitute a valuable resource to further characterize the biosynthesis of active metabolites in the Oldenlandia group, while the mode of action of ursolic acid will allow us to further develop this valuable compound.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Genomic, transcriptomic, and metabolomic analysis of Oldenlandia corymbosa reveals the biosynthesis and mode of action of anti‐cancer metabolites

Julca

Mutwil-Anderwald

Manoj

et al. 2023

JIPB

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“…It is known that O. corymbosa contains iridoids, flavonoids, saponins, triterpenes, phenols, terpenoids, sterols, and anthraquinones 64,65 . To identify the compounds conferring the anti-cancer activity against SKBR3, we performed activity-guided fractionation, NMR, and high-resolution mass spectrometry, which revealed ursolic acid, oleanolic acid, pheophorbide L, phytol, and lutein in the active fractions.…”

Section: Discussionmentioning

confidence: 99%

Genomic, transcriptomic, and metabolomic analysis of Traditional Chinese Medicine plantOldenlandia corymbosareveals the biosynthesis and mode of action of anti-cancer metabolites

Julca

Mutwil-Anderwald

Manoj

et al. 2022

Preprint

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Natural products from traditional medicinal plants are valuable candidates for clinical cancer therapy. Plants from the Oldenlandia-Hedyotis complex are popular ingredients of Traditional Chinese Medicine (TCM), however a major hurdle in the plant bioprospecting process of TCM plants is that the active metabolites, their biosynthetic pathways, and mode of actions are often unknown. We show that Oldenlandia corymbosa extracts are active against breast cancer cell lines. To study the genes involved in the biosynthesis of active compounds in this medicinal plant, we assembled a high-quality genome. We show that the main active compound is ursolic acid and that abiotic stresses cause changes in anti-cancer activity, metabolite composition and gene expression of plants. To reveal the mode of action of ursolic acid, we show that cancer cells undergo mitotic catastrophe, and we identify three high-confidence protein binding targets by Cellular Thermal Shift Assay (CETSA) and reverse docking.

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“…It is a pity that it was not be detected under our experimental conditions. Similarly, (9 R ,10 S ,7 E )-6,9,10-trihydroxyoctadec-7-enoic acid, isolated with a yield of 47.9 mg from 20 kg of HC, was reported to be used to differentiate HC from HD [ 26 ]. It was not be detected under our experimental conditions either.…”

Section: Discussionmentioning

confidence: 99%

“…Several methods using various techniques have been established to distinguish between these two species, such as loop-mediated isothermal amplification technique (LAMP) [ 20 ], fluorescence microscopy [ 21 ], thin layer chromatography (TLC) [ 22 ], DNA sequencing of the complete internal transcribed spacer region and chemical analysis [ 23 ], phylogenetic utility of nuclear ribosomal DNA (nrDNA) internal transcribed spacers (ITS) [ 24 ], high-performance liquid chromatography (HPLC) [ 25 ], etc. As a result, markers such as hedyotiscone A [ 22 ], scandoside methyl ester [ 25 ], (9 R ,10 S ,7 E )-6,9,10-trihydroxyoctadec-7-enoic acid [ 26 ] for HC, 6- O -( E )- p -coumaroyl scandoside methyl ester [ 23 , 25 ], (10 S )-hydroxypheophytin a [ 23 ], 6- O -( E )- p -coumaroyl scandoside methyl ester-10-methyl ether and 6- O - p -feruloyl scandoside methyl ester [ 25 ] for HD have been found. The UPLC-UV (detection wavelength at 254 nm) fingerprint of HC was also established to distinguish it from HD [ 27 ].…”

Section: Introductionmentioning

confidence: 99%

Discovery of the Potential Biomarkers for Discrimination between Hedyotis diffusa and Hedyotis corymbosa by UPLC-QTOF/MS Metabolome Analysis

Wang

Lin

et al. 2018

Molecules

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Hedyotis diffuse Willd. (HD) and Hedyotis corymbosa (L.) Lam. (HC), two closely related species of the same genus, are both used for health benefits and disease prevention in China. HC is also indiscriminately sold as HD in the wholesale chain and food markets. This confusion has led to a growing concern about their identification and quality evaluation. In order to further understand the molecular diversification between them, we focus on the screening of chemical components and the analysis of non-targeted metabolites. In this study, UPLC-QTOF-MSE, UNIFI platform and multivariate statistical analyses were used to profile them. Firstly, a total of 113 compounds, including 80 shared chemical constituents of the two plants, were identified from HC and HD by using the UNIFI platform. Secondly, the differences between two herbs were highlighted with the comparative analysis. As a result, a total of 33 robust biomarkers enabling the differentiation were discovered by using multivariate statistical analyses. For HC, there were 18 potential biomarkers (either the contents were much greater than in HD or being detected only in HC) including three iridoids, eight flavonoids, two tannins, two ketones, one alcohol and two monoterpenes. For HD, there were15 potential biomarkers (either the contents were much greater than in HC or being detected only in HD) including two iridoids, eight flavonoids, one tannin, one ketone, and three anthraquinones. With a comprehensive consideration of the contents or the MS responses of the chemical composition, Hedycoryside A and B, detected only in HC, could be used for rapid identification of HC. The compounds 1,3-dihydroxy-2-methylanthraquinone and 2-hydroxy-3-methylanthraquinone, detected only in HD, could be used for rapid identification of that plant. The systematic comparison of similarities and differences between two confusing Chinese herbs will provide reliable characterization profiles to clarify the pharmacological fundamental substances. HC should not be used as the substitute of HD.

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A chemotaxonomic study of phytochemicals in Hedyotis corymbosa

Cited by 10 publications

References 30 publications

Genomic, transcriptomic, and metabolomic analysis of Oldenlandia corymbosa reveals the biosynthesis and mode of action of anti‐cancer metabolites

Genomic, transcriptomic, and metabolomic analysis of Oldenlandia corymbosa reveals the biosynthesis and mode of action of anti‐cancer metabolites

Genomic, transcriptomic, and metabolomic analysis of Traditional Chinese Medicine plantOldenlandia corymbosareveals the biosynthesis and mode of action of anti-cancer metabolites

Discovery of the Potential Biomarkers for Discrimination between Hedyotis diffusa and Hedyotis corymbosa by UPLC-QTOF/MS Metabolome Analysis

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