A New Alkaloid from the Aerial Parts of Bupleurum chinense DC.
Zong-Yu Xiao
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Zong-Yu Xiao and Yan Liu contributed equally to this work.
Search for more papers by this authorYan Liu
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Zong-Yu Xiao and Yan Liu contributed equally to this work.
Search for more papers by this authorYan-Ping Sun
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Search for more papers by this authorYuan Liu
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Search for more papers by this authorCorresponding Author
Bing-You Yang
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Search for more papers by this authorCorresponding Author
Hai-Xue Kuang
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Search for more papers by this authorZong-Yu Xiao
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Zong-Yu Xiao and Yan Liu contributed equally to this work.
Search for more papers by this authorYan Liu
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Zong-Yu Xiao and Yan Liu contributed equally to this work.
Search for more papers by this authorYan-Ping Sun
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Search for more papers by this authorYuan Liu
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Search for more papers by this authorCorresponding Author
Bing-You Yang
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Search for more papers by this authorCorresponding Author
Hai-Xue Kuang
Key Laboratory of Chinese Materia Medica, Heilongjiang University of Chinese Medicine, Ministry of Education, Harbin, 150040 P. R. China
Search for more papers by this authorAbstract
A new isoalloxazine alkaloid, named bupleurine A (1), along with five known compounds (2–6), were isolated from the aerial parts of Bupleurum chinense DC. The structure elucidation of the new alkaloid (1) was employed by combining NMR and HR-MS data with comparison of reference in the literature. Five known compounds (2–6) were isolated from Bupleurum genus for the first time. Additionally, their antiproliferative activities on HeLa cells were evaluated by MTT assay and IC50 of compounds 1 and 4–6 were below 10 μm after treatment for 24 h.
Graphical Abstract
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References
- 1D. Q. Li, J. Wu, L. Y. Liu, Y. Y. Wu, L. Z. Li, X. X. Huang, Q. B. Liu, J. Yu. Yang, S. J. Song, C. F. Wu, ‘Cytotoxic triterpenoid glycosides (saikosaponins) from the roots of Bupleurum chinense’, Bioorg. Med. Chem. Lett. 2015, 25, 3887–3892.
- 2L. Zhu, Z. T. Liang, T. Yi, Y. Ma, Z. Z. Zhao, B. L. Guo, J. Y. Zhang, H. B. Chen, ‘Comparison of chemical profiles between the root and aerial parts from three Bupleurum species based on a UHPLC-QTOF-MS metabolomics approach’, BMC Complementary Altern. Med. 2017, 17, 2–12.
- 3H. X. Kuang, S. W. Sun, B. Y. Yang, Y. G. Xia, W. S. Feng, ‘New megastigmane sesquiterpene and indole alkaloid glucosides from the aerial parts of Bupleurum chinense DC.’, Fitoterapia 2009, 80, 35–38.
- 4H. C. Kwon, K. R. Kim, S. D. Zee, S. Y. Cho, K. R. Lee, ‘A new indolinepeptide from Paecilomyces sp. J300’, Arch. Pharmacal Res. 2004, 27, 604–609.
- 5D. Osei-Safo, G. A. Dziwornu, R. A. Opong, M. A. Chama, I. Tuffour, R. Waibel, R. Amewu, I. A. Mensah, ‘Constituents of the roots of Dichapetalum pallidum and their anti-proliferative activity’, Molecules 2017, 22, 532.
- 6W. S. Li, J. D. McChesney, F. S. El-feraly, ‘Carbazole alkaloids from Clausena lansium’, Phytochemistry 1991, 30, 343–346.
- 7S. S. Kang, J. S. Kim, Y. N. Xu, Y. H. Kim, ‘Isolation of a new cerebroside from the root bark of Aralia elata’, J. Nat. Prod. 1999, 62, 1059–1060.
- 8G. R. N. Rathnayake, N. S. Kumar, L. Jayasinghe, H. Araya, Y. Fujimoto, ‘Chemical investigation of metabolites produced by an endophytic fungi Phialemonium curvatum from the leaves of Passiflora edulis’, Nat. Prod. Lett. 2018, 32, 2483–2486.
- 9L. Lin, Y. Fang, A. Huang, L. Chen, S. Guo, J. Chen, ‘Chemical constituents from Sedum aizoon and their hemostatic activity’, Pharm. Biol. 2014, 52, 1429–1434.
- 10R. D. Xiang, X. Y. Zhang, Y. Han, C. Xia, X. J. Yin, D. X. Liu, G. X. Huang, H. C. Wang, ‘Study on active constituents of the fruits water extract of Cnidium monnieri (L.) Cuss.’, Chin. Herb. Med. 1999, 11, 813–814.
- 11K. Isshiki, Y. Asai, S. Tanaka, M. Nishio, T. Uchida, T. Okuda, S. Komatsubara, N. Sakurai, ‘Aurantiamide acetate, a selective cathepsin inhibitor, produced by aspergillus penicilloides’, Biosci. Biotechnol. Biochem. 2001, 65, 1195–1197.
- 12J. D. Tamokou1, D. J. S. Mpetga, P. K. Lunga, M. Tene, P. Tane, J. R. Kuiate, ‘Antioxidant and antimicrobial activities of ethyl acetate extract, fractions and compounds from stem bark of Albizia adianthifolia (Mimosoideae)’, BMC. Complement. Altern. Med. 2012, 12, 99.
- 13C. S. Yoon, D. C. Kim, D. S. Lee, K. S. Kim, W. Ko, J. H. Sohn, J. H. Yim, Y. C. Kim, H. Oh, ‘Anti-neuroinflammatory effect of aurantiamide acetate from the marine fungus Aspergillus sp. SF-5921: Inhibition of NF-κB and MAPK pathways in lipopolysaccharide-induced mouse BV2 microglial cells’, Int. Immunopharmacol. 2014, 23, 568–574.
- 14X. B. Liu, B. X. Yang, L. Zhang, Y. Z. Lu, M. H. Gong, J. K. Tian, ‘An in vivo and In Vitro assessment of the anti-inflammatory, antinociceptive, and immunomodulatory activities of Clematis terniflora DC. extract, participation of aurantiamide acetate’, J. Ethnopharmacol. 2015, 169, 287–294.
- 15B. X. Zhou, Z. F. Yang, Q. T. Feng, X. L. Liang, J. Li, M. Zanin, Z. H. Jiang, N. S. Zhong, ‘Aurantiamide acetate from Baphicacanthus cusia root exhibits anti-inflammatory and anti-viral effects via inhibition of the NF-κB signaling pathway in Influenza A virus-infected cells’, J. Ethnopharmacol. 2017, 199, 60–67.
- 16T. A. Choi, R. Czerwonka, R. Forke, A. Jäger, J. Knöll, M. P. Krahl, T. Krause, K. R. Reddy, S. G. Franzblau, H. J. Knölker, ‘Transition metals in organic synthesis-Part 83#: Synthesis and pharmacological potential of carbazoles’, Med. Chem. Res. 2008, 17, 374–385.
- 17P. Rodanant, R. Surarit, S. Laphookhieo, J. Kuvatanasuchati, ‘In vitro evaluation of the antibacterial and anti-inflammation activities of Clausena lansium (Lour.) Skeels’, Songklanakarin J. Sci. Technol. 2015, 37, 43–48.
- 18H. J. Jung, H. A. Jung, S. S. Kang, J. H. Lee, Y. S. Cho, K. H. Moon, J. S. Choi, ‘Inhibitory activity of Aralia continentalis roots on protein tyrosine phosphatase 1B and rat lens aldose reductase’, Arch. Pharmacal Res. 2012, 35, 1771–1777.
- 19B. Y. Yang, Y. M. Luo, Y. Liu, X. Yin, Y. Y. Zhou, H. X. Kuang, ‘New lignans from the roots of Datura metel L’, Phytochem. Lett. 2018, 28, 8–12.