Phenolic Glucosides from the Leaves of Vitex negundo var. cannabifolia
Jing Sun
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, 100193 China
Search for more papers by this authorManman Li
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorYongru Wang
Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, 100193 China
Search for more papers by this authorChuang Chang
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorYujie Pei
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorKewu Zeng
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing, 100191 P. R. China
Search for more papers by this authorYunfang Zhao
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorJiao Zheng
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorYuelin Song
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorPengfei Tu
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorCorresponding Author
Huixia Huo
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorCorresponding Author
Jun Li
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorJing Sun
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, 100193 China
Search for more papers by this authorManman Li
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorYongru Wang
Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences, Beijing, 100193 China
Search for more papers by this authorChuang Chang
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorYujie Pei
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorKewu Zeng
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing, 100191 P. R. China
Search for more papers by this authorYunfang Zhao
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorJiao Zheng
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorYuelin Song
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorPengfei Tu
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorCorresponding Author
Huixia Huo
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorCorresponding Author
Jun Li
Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029 P. R. China
Search for more papers by this authorAbstract
Four new phenolic glucosides, cannabifolins G–J (1–4), together with four known ones (5–8), were isolated from the leaves of Vitex negundo var. cannabifolia. Their structures were established by comprehensive analysis of 1D and 2D NMR data and comparison of their spectroscopic and physical data with the literature values. Compound 7 exhibited weak inhibition of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC50 value of 132.8 μM.
Graphical Abstract
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available on request from the corresponding author. The data are not publicly available due to privacy or ethical restrictions.
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References
- 1J. Pei, S. L. Chen, ‘Flora Reipublicae Popularis Sinicae’, Science Press 1982, 65, 143–145.
- 2Editorial Committee of the Administration Bureau of Traditional Chinese Medicine, ‘Chinese Materia Medica (Zhong Hua Ben Cao)’, Shanghai Science and Technology Press 1999, 18, 599–604.
- 3China Pharmacopoeia Committee, ‘Chinese Pharmacopoeia’, Chemical Industry Press 2005, 1, 276.
- 4E. Nyiligira, A. M. Viljoen, F. R. Van Heerden, R. L. Van Zyl, S. F. Van Vuuren, P. A. Steenkamp, ‘Phytochemistry and In Vitro pharmacological activities of South African Vitex (Verbenaceae) species’, J. Ethnopharmacol. 2008, 119, 680–685.
- 5M. M. Li, X. Q. Su, J. Sun, Y. F. Gu, Z. Huang, K. W. Zeng, Q. zhang, Y. F. Zhao, D. Ferreira, J. K. Zjawiony, J. Li, P. F. Tu, ‘Anti-inflammatory ursane- and oleanane-type triterpenoids from Vitex negundo var. cannabifolia’, J. Nat. Prod. 2014, 77, 2248–2254.
- 6H. Taguchi, ‘Studies on the constituents of Vitex cannabifolia’, Chem. Pharm. Bull. 1976, 24, 1668–1670.
- 7Y. J. Chen, C. M. Li, W. W. Ling, X. C. Wan, T. Xia, X. F. Du, Z. Z. Zhang, T. J. Ling, ‘A rearranged labdane-type diterpenoid and other constituents from Vitex negundo var. cannabifolia’, Biochem. Syst. Ecol. 2012, 40, 98–102.
- 8T. Yamasaki, T. Kawabata, C. Masuoka, J. Kinjo, T. Ikeda, T. Nohara, M. Ono, ‘Two new lignan glucosides from the fruit of Vitex cannabifolia’, J. Nat. Med. 2008, 62, 47–51.
- 9T. J. Ling, W. W. Ling, Y. J. Chen, X. C. Wan, T. Xia, X. F. Du, Z. Z. Zhang, ‘Antiseptic activity and phenolic constituents of the aerial parts of Vitex negundo var. cannabifolia’, Molecules 2010, 15, 8469–8477.
- 10M. M. Li, Z. Huang, H. X. Huo, J. Zhang, J. Zheng, Q. Zhang, J. Li, P. F. Tu, ‘Chemical constituents from Vitex negundo L. var. cannabifolia’, Modern. Tradit. Chin. Med. Mater. Med.-World Sci. Technol. 2015, 17, 578–582.
- 11M. M. Li, Y. T. Li, Z. Huang, J. Zhang, H. X. Huo, D. R. Pang, J. Zheng, Q. Zhang, Y. F. Zhao, J. Li, ‘A new flavonoid glycoside from leaves of Vitex negundo var. cannabifolia’, Chin. Tradit. Herb Drugs 2015, 46, 1723–1726.
- 12E. Okuyama, S. Fujimori, M. Yamazaki, T. Deyama, ‘Pharmacologically active components of Viticis fructus (Vitex rotundifolia). II. The components having analgesic effects’, Chem. Pharm. Bull. 1998, 46, 655–662.
- 13K. Machida, M. Ando, Y. Yaoita, R. Kakuda, M. Kikuchi, ‘Phenolic compounds of the leaves of Catalpa ovata G. DON’, Nat. Med. 2001, 55, 64–67.
- 14H. M. Tao, L. S. Wang, D. Q. Zhao, Q. H. Zhu, Y. H. Liu, ‘Phenolic compounds from roots of Asparagus filicinus’, Chin. Tradit. Herb Drugs 2011, 42, 2181–2185.
- 15H. Kirmizibekmez, D. Demir, ‘Iridoid glycosides and phenolic compounds from the flowers of Vitex agnus-castus’, Helv. Chim. Acta 2016, 99, 1–5.
- 16L. L. Gao, X. D. Xu, H. J. Nan, J. S. Yang, S. L. Chen, ‘Chemical constituents in Rheum tanguticum’, Chin. Tradit. Herb Drugs 2011, 42, 443–446.
- 17J. Li, K. W. Zeng, S. P. Shi, Y. Jiang, P. F. Tu, ‘Anti-neuroinflammatory constituents from Polygala tricornis Gagnep’, Fitoterapia 2012, 83, 896–900.
- 18Z. Huang, Z. X. Zhu, Y. T. Li, D. R. Pang, J. Zheng, Q. Zhang, Y. F. Zhao, D. Ferreira, J. K. Zjawiony, P. F. Tu, J. Li, ‘Anti-inflammatory labdane diterpenoids from Leonurus macranthus’, J. Nat. Prod. 2015, 78, 2276–2285.
