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Carthorquinosides A and B, Quinochalcone C-Glycosides with Diverse Dimeric Skeletons from Carthamus tinctorius

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† Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization and Jiangsu Key Laboratory for High Technology Research of TCM Formulae, Nanjing University of Chinese Medicine, Nanjing 210023, People’s Republic of China
‡ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, People’s Republic of China
*Tel/Fax: 86-25-85811695. E-mail: [email protected] (Y.-P. Tang).
*Tel/Fax: 86-25-85811916. E-mail: [email protected] (J.-A. Duan).
Cite this: J. Nat. Prod. 2016, 79, 10, 2644–2651
Publication Date (Web):October 17, 2016
https://doi.org/10.1021/acs.jnatprod.6b00561
Copyright © 2016 The American Chemical Society and American Society of Pharmacognosy
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Abstract

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Two novel quinochalcone C-glycosides, carthorquinosides A (1) and B (2), were isolated from the florets of Carthamus tinctorius. Their structures, including the absolute configurations, were established by analysis of NMR and MS data, together with chemical degradation and electronic circular dichroism spectra. Compound 1 has an unprecedented quinochalcone–flavonol structure linked via a methylene bridge, and compound 2 comprises two glucopyranosylquinochalcone moieties linked via the formyl carbon of an acyclic glucosyl unit. A potential biosynthesis pathway is also proposed. Compounds 1 and 2 exhibited anti-inflammatory activities in LPS-stimulated HUVEC cells by regulating IL-1, IL-6, IL-10, and IFN-γ mRNA expression at concentrations as low as 4 μM, and compound 2 also showed inhibitory activity against topoisomerase I at100 μM.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.6b00561.

  • 1H NMR, 13C NMR, HSQC, COSY, HMBC, ROESY, HRESIMS, and ECD spectra of compounds 1 and 2 (PDF)

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