UV-guided isolation of polyynes and polyenes from the roots of Codonopsis pilosula

Chao, Chih‐Hua; Juang, Shin‐Hun; Chan, Hsiu Hui; Shen, De Yang; Liao, Yu-Hsien; Shih, Hung Cheng; Huang, Chieh Hung; Cheng, Ju Chien; Chen, Fu An; Hung, Hsin Yi; Wu, Tian Shung

doi:10.1039/c5ra02765a

Cited by 23 publications

(11 citation statements)

References 26 publications

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“…In 2015, pilosulynes A-G, which are five polyynes and two polyenes, were first isolated from C. pilosula roots. Among them, pilosulyne F exhibited anti-HCV (hepatitis C virus) activity (Liao et al, 2015). However, lobetyolin (the standard chemical marker for Radix Codonopsis in Chinese Pharmacopoeia) and lobetyolinin, the mono-and bis-glucosylated forms of the polyacetylenic compound lobetyol, were not identified as DEMs in metabolomics analyses (He et al, 2020).…”

Section: Polyacetylenes Polyenes and Their Glycosidesmentioning

confidence: 99%

Untargeted Metabolomics Reveals Multiple Phytometabolites in the Agricultural Waste Materials and Medicinal Materials of Codonopsis pilosula

Lyu

et al. 2022

Front. Plant Sci.

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Codonopsis pilosula has been used in traditional Chinese medicine for hundreds of years, where it has been used to treat anaemia, fatigue, a weak spleen, and stomach problems, among other ailments. The roots of C. pilosula are considered medicinal, while the aerial parts are always directly discarded after harvest in autumn or winter. Some studies have shown that the stems and leaves of C. pilosula also contain a variety of active metabolites, including saponins, flavonoids, terpenoids, and polysaccharides. To efficiently utilise resources, waste products from C. pilosula leaves and stems were analysed by untargeted metabolomics and chemometrics. A total of 1508 metabolites were detected and annotated, of which 463 were identified as differentially expressed metabolites (DEMs). These DEMs were grouped into classes, such as carboxylic acids and derivatives, steroids, organic oxygen compounds, fatty acyls, prenol lipids, and flavonoids. Metabolic profiling of C. pilosula tissues showed that the contents of polyacetylenes, polyenes, flavonoids, some alkaloids, steroids, terpenoids, and organic acids were higher in stems and leaves, whereas the contents of the main lignans and some alkaloids were more enriched in roots. Moreover, C. pilosula stems and leaves also contained a lobetyolin, syringin and atractylenolide III, which were detected by LC-MS/MS and HPLC-UV. The extracts of C. pilosula aerial parts also showed stronger antioxidant properties than roots. C. pilosula stems and leaves were rich in active ingredients and might have great value for development and utilisation.

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Section: Polyacetylenes Polyenes and Their Glycosidesmentioning

confidence: 99%

Untargeted Metabolomics Reveals Multiple Phytometabolites in the Agricultural Waste Materials and Medicinal Materials of Codonopsis pilosula

Lyu

et al. 2022

Front. Plant Sci.

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“…The fragment of C 14 -diendiynetriol is confirmed by the 1 H– 1 H COSY correlations of H-1/H-2/H-3/H-4/H-5/H-6/H-7 and H-12/H-13/H-14, and by the HMBC correlations of H-6/C-7, C-8, H-7/C-8, C-9, H-12/C-10, C-11, and H-13/C-11 ( Figure 2 ). The relevant NMR data in the literature suggest that threo and erythro vic -diols with similar partial structures have coupling constants of 6.0–7.0 Hz for threo diols and 3.0–4.0 Hz for erythro diols [ 15 , 16 , 17 , 18 ]. The J H-6,H-7 (6.5 Hz) value indicates a threo configuration between H-6 and H-7.…”

Section: Resultsmentioning

confidence: 99%

Three New Polyynes from Codonopsis pilosula and Their Activities on Lipid Metabolism

Qin

et al. 2018

Molecules

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Three new polyynes, named choushenpilosulynes A–C (1–3), were isolated from an 85% aqueous EtOH extract of the roots of Codonopsis pilosula cultivated in Xundian County of Yunnan province, China. Their structures, including the absolute configuration of the glucose residue in 1 and 2, were determined by spectroscopic analysis and gas chromatography (GC). In addition, biological evaluation shows that all the compounds can inhibit the expression of the squalene monooxygenase (SQLE) gene in HepG2 cells, suggesting that these compounds may be involved in lipid metabolism.

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“…20 The 1 H spectrum of 1 (Table 1) revealed the 20 D-Glucose was obtained upon acidic hydrolysis of 1 with 5% H 2 SO 4 , as indicated by a HPLC method of its o-tolythiocarbamate. 21 The glucosyl anomeric proton configuration was concluded to be an β-axial configuration, attributed to the larger coupling constant (J = 8.3 Hz) of this proton. 22 The downfield signals at H-1 (δ H 5.88) and H 2 -6 (δ H 4.59, 4.48) were considered to be a result of a connection to galloyl ester or caffeoyl ester groups.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Hypoglycemic Constituents Isolated from Trapa natans L. Pericarps

Huang

Chao

Liaw³

et al. 2016

J. Agric. Food Chem.

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Trapa natans L., called water chestnut or water caltrop, is a floating aquarium plant. Its fruits are widely used as food. Two new tannins, 1 and 2, one new neolignan, 14, one new norlignan, 17, and 20 known compounds, 3-13, 15, 16, and 18-24 were isolated from T. natans pericarps in this study. The 1, 2, 14, and 17 structures were elucidated using a chemical method and extensive spectral evidence. A series of hydrolyzable tannins, 1-8, a lignin, 13, a flavonoid, 16, a norlignan, 17, and phenolic compounds, 18, 20, 21, and 24 resulted in the enhanced glucose uptake activity in C2C12 myotubes. Compounds 4 and 5 significantly increased GLUT4 protein expression in C2C12 myotubes. In addition, 4 and 5 improved the phosphorylation of AMPK, AKT(S473), and AKT(T308). The involvement of AMPK and PI3K in the mechanism of action of compounds 4 and 5 was confirmed by use of AMPK and PI3K inhibitors, which completely suppressed the 4- and 5-mediated activities of glucose uptake in C2C12 myotubes. We also demonstrated that 4 and 5 could increase GLUT4 protein levels in plasma membranes.

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UV-guided isolation of polyynes and polyenes from the roots of Codonopsis pilosula

Abstract: UV-guided isolation of polyacetylenes from Codonopsis pilosula has successfully led to the characterization of new polyynes and polyenes. The HCVcc infection assay was used to evaluate the anti-HCV activity of compounds 1–12.

Cited by 23 publications

References 26 publications

Untargeted Metabolomics Reveals Multiple Phytometabolites in the Agricultural Waste Materials and Medicinal Materials of Codonopsis pilosula

Untargeted Metabolomics Reveals Multiple Phytometabolites in the Agricultural Waste Materials and Medicinal Materials of Codonopsis pilosula

Three New Polyynes from Codonopsis pilosula and Their Activities on Lipid Metabolism

Hypoglycemic Constituents Isolated from Trapa natans L. Pericarps

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