Chinese Journal of Organic Chemistry >
Triterpenoid Glycosides from the Leaves of Lyonia ovalifolia var. hebecarpa and Their Antitumor Activities
Received date: 2017-05-03
Revised date: 2017-05-19
Online published: 2017-05-25
Supported by
Project supported by the Fundamental Research Funds for the Central Universities (No. 2016YXMS148).
Three triterpenoid glycosides were isolated from the leaves of Lyonia ovalifolia var. hebecarpa by separation techniques such as column chromatograph and HPLC, and their structures were determined to be 3β-O-α-L-arabinopyranosyloxy-olean-12-ene-23,25-diol (1), 3β-O-α-L-arabinopyranosyloxy-olean-12-ene-1β,23-diol (2), and 3α-[(β-D-glucopyranosyl)-oxy]-24α-[(α-L-arabinopyranosyl)-oxy]-25-hydroxy-9,10-seco-cycloaran-1(10)-en-30-oic acid (3), respectively, by HRESIMS and NMR data analysis, as well as chemical methods. Compound 1 and its aglycone are new compounds, and compounds 2 and 3 were isolated from Lyonia ovalifolia var. hebecarpa for the first time. This is the first report of the NMR data assignment of compound 2 and its aglycone. The in vitro anti-tumor activities of compounds 1~3 were evaluated, and compound 2 showed anti-proliferation activities against five cancer cell lines HL-60, MCF-7, SMMC-7221, A-549 and SW480 with IC50 values of (16.35±0.25), (17.05±0.52), (17.66±0.21), (15.87±0.26) and (12.30±0.36) μmol·L-1, respectively, and showed more potent anti-proliferation than the positive control, cis-platin, against MCF-7, A-549, and SW480 cell lines.
Teng Yang , Zhang Hanqi , Zhou Junfei , Li Yongji , Yao Guangmin . Triterpenoid Glycosides from the Leaves of Lyonia ovalifolia var. hebecarpa and Their Antitumor Activities[J]. Chinese Journal of Organic Chemistry, 2017 , 37(9) : 2416 -2422 . DOI: 10.6023/cjoc201705007
[1] Fang, M.; Fang, R.; He, M.; Hu, L.; Yang, H.; Qin, H.; Min, T.; Chamberlain, D. F.; Stevens, P. F.; Wallace, G. D.; Anderberg, A. Ericaceae. In Flora of China, Vol. 14, Eds.:Wu, Z. Y.; Raven, P. H.; Hong, D. Y., Science Press, Beijing & Missouri Botanical Garden Press, St. Louis, 2005, p. 242.
[2] Yasue, M.; Kato, Y. Yakugaku Zasshi 1959, 79, 403.
[3] Kato, Y. Phytochemistry 1973, 12, 2302.
[4] Kato, Y.; Yasue, M. Shoyakugaku Zasshi 1983, 37, 412.
[5] Kato, Y.; Kato, N.; Baba, M. Pharmazie 1984, 39, 425.
[6] Ohta, T.; Hikino, H. Chem. Pharm. Bull. 1981, 29, 280.
[7] Sakakibara, J.; Ikai, K.; Yasue, M. Yakugaku Zasshi 1974, 94, 1534.
[8] Sakakibara, J.; Hotta, Y.; Yasue, M. Yakugaku Zasshi 1975, 95, 911.
[9] Sakakibara, J.; Hotta, Y.; Yasue, M. Yakugaku Zasshi 1974, 94, 170.
[10] Lv, X. J.; Li, Y.; Ma, S. G.; Qu, J.; Liu, Y. B.; Li, L.; Wang, R. B.; Yu, S. S. Tetrahedron 2017, 73, 776.
[11] Lv, X. J.; Li, Y.; Ma, S. G.; Qu, J.; Liu, Y. B.; Li, Y. H.; Zhang, D.; Li, L.; Yu, S. S. J. Nat. Prod. 2016, 79, 2824.
[12] Wu, Z. Y.; Li, H. Z.; Wang, W. G.; Li, H. M.; Chen, R.; Li, R. T.; Luo, H. R. Chem. Biodiversity 2011, 8, 1182.
[13] Kashima, K.; Sano, K.; Yunity, Y. S.; Ina, H.; Kunugi, A.; Inoue, H. Chem. Pharm. Bull. 2010, 58, 191.
[14] Rahman, M. A.; Katayama, T.; Suzuki, T.; Nakagawa, T. J. Wood Sci. 2007, 53, 161.
[15] Subramanian, S. S.; Kotiyal, J. P. Indian J. Pharm. Sci. 1978, 40, 131.
[16] Yasue, M.; Sakakibara, J.; Nakagami, J. Yakugaku Zasshi 1974, 94, 1349.
[17] Wang, C.; Liu, Y.; Li, C.; Chen, S.; Qin, G. J. Henan Med. Univ. 2001, 36, 743(in Chinese). (王彩芳, 刘延泽, 李灿军, 陈绍农, 秦国伟, 河南医科大学学报, 2001, 36, 743.)
[18] Wang, K. W.; Sun, H, X. Wu, B.; Pan, Y. J. Helv. Chim. Acta 2005, 88, 990.
[19] Xiong, J.; Huang, Y.; Tang, N.; You, M.; Hu, J. Chin. J. Org. Chem. 2013, 33, 1304(in Chinese). (熊娟, 黄亚, 唐宁, 尤梅, 胡金锋, 有机化学, 2013, 33, 1304.)
[20] Zheng, H.; Chen, Q.; Zhang, M.; Lai, Y.; Lei, L.; Shu, P.; Xue, Y.; Luo, Z.; Zhang, J.; Li, Y.; Yao, G.; Zhang, Y. J. Nat. Prod. 2013, 76, 2253.
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