Anti-Proliferative Effect of Triterpenoidal Glycosides from the Roots of Anemone vitifolia through a Pro-Apoptotic Way
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Identification of Compounds 1–6
2.2. Inhibitory Effect on Proliferation of HepG2 Cells
2.3. Flow Cytometry Analysis
2.4. Preliminary Structure-Activity Relationship Analysis
3. Experimental Section
3.1. General Procedure
3.2. Plant Material
3.3. Isolation of Compounds
3.4. Cytotoxicity Assay
3.5. Flow Cytometry Analysis
3.6. Data Analysis
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
- Chinese Academy of Science Flora. Flora of China; Science Press: Beijing, China, 1980; Volume 28, p. 1. [Google Scholar]
- Wang, M.K.; Wu, F.E.; Chen, Y.Z. Triterpenoid saponins from Anemone hupehensis. Phytochemistry 1997, 44, 333–335. [Google Scholar] [CrossRef]
- Sun, Y.X.; Liu, J.C.; Liu, D.Y. Phytochemicals and bioactivities of Anemone raddeana Regel: A review. Pharmazie 2011, 66, 813–821. [Google Scholar] [PubMed]
- Wei, S.H.; He, W.F.; Lu, J.C.; Wang, Z.G.; Yamashita, K.; Yokoyama, M.; Kodama, H. Effects of five oleanolic acid triterpenoid saponins from the rhizome of Anemone raddeana on stimulus-induced superoxide generation, phosphorylation of proteins and translocation of cytosolic compounds to cell membrane in human neutrophils. Fitoterapia 2012, 83, 402–407. [Google Scholar] [CrossRef] [PubMed]
- Mimaki, Y.; Yokosuka, A.; Hamanaka, M.; Sakuma, C.; Yamori, T.; Sashida, Y. Triterpenoid saponins from the roots of Clematis chinensis. J. Nat. Prod. 2004, 67, 1511–1516. [Google Scholar] [CrossRef] [PubMed]
- Yan, L.H.; Xu, L.Z.; Lin, J.; Yang, S.L.; Feng, Y.L. Triterpenoid saponins from the stems of Clematis parviloba. J. Asian Nat. Prod. Res. 2009, 11, 332–338. [Google Scholar] [CrossRef] [PubMed]
- State Administration of Traditional Chinese Medicine. Chinese Materia Medica; Shanghai Science and Technology Press: Shanghai, China, 1999; p. 166.
- Li, Y.X. Dehong Minority Drug List; Dehong National Publishing House: Luxi, Yunnan, China, 1990; p. 173. [Google Scholar]
- Zhu, Z.Y. Dali Traditional Chinese Materia Resources; Yunnan National Publishing House: Kunming, Yunnan, China, 1991; p. 181. [Google Scholar]
- Zou, Z.J.; Liu, H.X.; Yang, J.S. Chemical constituents and pharmacological activities of genus Anemone. Chin. Pharm. J. 2004, 39, 493–495. [Google Scholar]
- Lv, C.N.; Li, Y.J.; Wang, J.; Qin, R.L.; Lei, T.L.; Lu, J.C. Chemical constituents from rhizome of Anemone amurensis. J. Asian Nat. Prod. Res. 2016, 18, 648–655. [Google Scholar] [CrossRef] [PubMed]
- Chang, C.I.; Chiang, T.I.; Lo, C.; Lai, Y.H.; Yue, C.H.; Liu, J.Y.; Hsu, L.S.; Lee, C.J. Anemone altaica induces apoptosis in human osteosarcoma cells. Am. J. Chin. Med. 2015, 43, 1031–1042. [Google Scholar] [CrossRef] [PubMed]
- Lv, C.N.; Fan, L.; Wang, J.; Qin, R.L.; Xu, T.Y.; Lei, T.L.; Lu, J.C. Two new triterpenoid saponins from rhizome of Anemone amurensis. J. Asian Nat. Prod. Res. 2015, 17, 132–137. [Google Scholar] [CrossRef] [PubMed]
- Tanaka, T.; Nakashima, T.; Ueda, T.; Tomii, K.; Kouno, I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem. Pharm. Bull. 2007, 55, 899–901. [Google Scholar] [CrossRef] [PubMed]
- Zhao, M.; Ma, N.; Qiu, F.; Tian, X.R.; Zhang, Y.; Tang, H.F.; Liu, X.Y. Triterpenoid saponins from the roots of Clematis argentilucida. Fitoterapia 2014, 97, 234–240. [Google Scholar] [CrossRef] [PubMed]
- Yang, B.; Fu, Z.Z.; Zhang, Y.; Chen, Y.J. Isolation and identification of a new saponin from Dahurian patrinia root and rhizome (Patrinia scabiosaefolia). J. Chin. Med. Mater. 2000, 31, 1–2. [Google Scholar]
- Chau, T.A.M.; Nguyen, M.K.; Phuong, T.T.; In, H.H.; Dong, W.K.; MinKyun, N. A new saponin and other constituents from Anemone rivularis Buch.-Ham. Biochem. Syst. Ecol. 2012, 44, 270–274. [Google Scholar]
- Tian, X.R.; Feng, J.T.; Tang, H.F.; Zhao, M.; Li, Y.; Hai, W.L.; Zhang, X. New cytotoxic triterpenoid saponins from the whole plant of Clematis lasiandra Maxim. Fitoterapia 2013, 90, 233–239. [Google Scholar] [CrossRef] [PubMed]
- Shao, B.; Qin, G.; Xu, R.; Wu, H.; Ma, K. Triterpenoid saponins from Clematis cheinensis. Phytochemistry 1995, 38, 1473–1479. [Google Scholar] [CrossRef]
- Zhao, H.Q.; Zong, G.H.; Zhang, J.J.; Wang, D.Q.; Liang, X.M. Synthesis and anti-fungal activity of seven oleanolic acid glycosides. Molecules 2011, 16, 1113–1128. [Google Scholar] [CrossRef] [PubMed]
- Malaviya, N.; Pal, R.; Khanna, N.M. Saponins from Deutzia corymbosa. Phytochemistry 1991, 30, 2798–2800. [Google Scholar] [CrossRef]
- Ye, W.C.; Zhang, Q.W.; Zhao, S.X.; Che, C.T. Four new oleanane saponins from Anemone anhuiensis. Chem. Pharm. Bull. 2001, 49, 632–634. [Google Scholar] [CrossRef] [PubMed]
- Nicholson, D.W. From bench to clinic with apoptosis-based therapeutic agents. Nature 2000, 407, 810–816. [Google Scholar] [CrossRef] [PubMed]
- Yue, T.L.; Ohlstein, E.H.; Ruffolo, R.R. Apoptosis: A potential target for discovering novel therapies for cardiovascular diseases. Curr. Opin. Chem. Boil. 1999, 3, 474–480. [Google Scholar] [CrossRef]
- Yang, H.; Tian, S.T.; Wu, R.Y.; Chen, Y.; Mei, Z.N.; Wang, C.Y.; Yang, G.Z. Glycoborinine induces apoptosis through mitochondrial pathway in HepG2 cells. J. Asian Nat. Prod. Res. 2014, 16, 991–999. [Google Scholar] [CrossRef] [PubMed]
- Yu, X.L.; Guo, Q.; Su, G.Z.; Yang, A.L.; Hu, Z.D.; Qu, C.H.; Wan, Z.; Li, R.Y.; Tu, P.F.; Chai, X.Y. Usnic acid derivatives with cytotoxic and antifungal activities from the lichen Usnea longissima. J. Nat. Prod. 2016, 79, 1373–1380. [Google Scholar] [CrossRef] [PubMed]
Sample Availability: Samples of the compounds 1–6 are available from the authors. |
© 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Bai, C.; Ye, Y.; Feng, X.; Bai, R.; Han, L.; Zhou, X.; Yang, X.; Tu, P.; Chai, X. Anti-Proliferative Effect of Triterpenoidal Glycosides from the Roots of Anemone vitifolia through a Pro-Apoptotic Way. Molecules 2017, 22, 642. https://doi.org/10.3390/molecules22040642
Bai C, Ye Y, Feng X, Bai R, Han L, Zhou X, Yang X, Tu P, Chai X. Anti-Proliferative Effect of Triterpenoidal Glycosides from the Roots of Anemone vitifolia through a Pro-Apoptotic Way. Molecules. 2017; 22(4):642. https://doi.org/10.3390/molecules22040642
Chicago/Turabian StyleBai, Changcai, Yunyun Ye, Xiao Feng, Ruifeng Bai, Lu Han, Xiuping Zhou, Xinyao Yang, Pengfei Tu, and Xingyun Chai. 2017. "Anti-Proliferative Effect of Triterpenoidal Glycosides from the Roots of Anemone vitifolia through a Pro-Apoptotic Way" Molecules 22, no. 4: 642. https://doi.org/10.3390/molecules22040642