Natural Products and Bioprospecting    2019, Vol. 9 Issue (4) : 287-295     DOI: 10.1007/s13659-019-0211-4
ORIGINAL ARTICLES |
Anti-inflammatory and Cytotoxic Triterpenes from the Rot Roots of Panax notoginseng
Jia-Huan Shang1,2, Guo-Wei Xu1,2, Hong-Tao Zhu1,3, Dong Wang1,3, Chong-Ren Yang1, Ying-Jun Zhang1,3
1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3 Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China
Download: PDF(4533 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
Abstract  Four new protopanaxatriol-type triterpenes (1-2) and glucosides (3-4), were isolated from the rot roots of Panax notoginseng (Burk.) Chen, along with four known ones (5-8). Their structures were elucidated on the basis of extensive spectroscopic analysis (HRESIMS, NMR, UV, IR, and OR) and acidic hydrolysis. The possible transformation pathway of these compounds were also speculated from ginsenoside Rg1. Compound 1, with a unique α,β-unsaturated ketene in its side chain, showed significant inhibitory effects against NO production on Murine macrophage cells (IC50=4.12 ±0.20 μM) and comparable cytotoxicities against five human cancer cell lines (myeloid leukemia HL-60, lung cancer A-549 cells, hepatocellular carcinoma SMMC7721, breast cancer MCF-7, and colon cancer SW480) to positive control, cisplatin (DDP).
Keywords Panax notoginseng      Rot root      Triterpenes and saponins      Inhibition on NO production      Cytotoxicity     
Fund:The authors are grateful to the members of the analytical and bioactivity screening groups at the State Key Laboratory of Phytochemistry and Plant Resources in West China, KIB, CAS, for measuring the spectroscopic data and cytotoxic assay. This work was supported by the Major Science and Technique Programs in Yunnan Province (2016ZF001-001), the Science and Technology Planning Project of Yunnan Province (2013FC008) and Yung-Chi Cheng academician workstation of Yunnan provincial academy of science and technology (2015IC017).
Corresponding Authors: Ying-Jun Zhang     E-mail: zhangyj@mail.kib.ac.cn
Issue Date: 09 August 2019
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
Jia-Huan Shang
Guo-Wei Xu
Hong-Tao Zhu
Dong Wang
Chong-Ren Yang
Ying-Jun Zhang
Trendmd:   
Cite this article:   
Jia-Huan Shang,Guo-Wei Xu,Hong-Tao Zhu, et al. Anti-inflammatory and Cytotoxic Triterpenes from the Rot Roots of Panax notoginseng[J]. Natural Products and Bioprospecting, 2019, 9(4): 287-295.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-019-0211-4     OR     http://npb.kib.ac.cn/EN/Y2019/V9/I4/287
1. Y.J. Qiao, J.H. Shang, D. Wang, H.T. Zhu, C.R. Yang, Y.J. Zhang, Nat. Prod. Bioprospect. 8, 245-263 (2018)
2. P.G. Xia, S.C. Zhang, Z.S. Liang, Z.H. Qi, Chin. Tradit. Herb. Drugs. 45, 2564-2570 (2014)
3. N. Jiang, L.Y. Qin, Y.F. Ye, J. South. Agric. 42, 1070-1074 (2011)
4. X.T. Sun, L. Li, G.Q. Long, G.H. Zhang, Z.G. Meng, S.C. Yang, J.W. Chen, Chin. J. Ecol. 34, 885-893 (2015)
5. Z.S. Mao, Y.J. Long, S.S. Zhu, Z.J. Chen, F.G. Wei, Y.X. Zhu, X.H. He, Chin. Med. Mater. 36, 2051-2054 (2013)
6. T. Wang, R. Guo, G. Zhou, X. Zhou, Z. Kou, F. Sui, C. Li, L. Tang, Z. Wang, J. Ethnopharmacol. 188, 234-258 (2016)
7. R.Q. Tai, W.Z. Tan, E. Yang, Y. Feng, H.Z. Li, J. Kunming. Univ. Sci. Technol. (Nat. Sci) 40, 85-88 (2015)
8. S.R. Ko, K.J. Choi, K. Suzuki, Y. Suzuki, Chem. Pharm. Bull. 51, 404-408 (2003)
9. J. Asakawa, R. Kasai, K. Yamasaki, O. Tanaka, Tetrahedron 33, 1935-1939 (1997)
10. S. Fujita, R. Kasai, K. Ohtani, K. Yamasaki, M.H. Chiu, R.L. Nie, O. Tanaka, Phytochemistry 39, 591-602 (1995)
11. J.L. Yang, T.K.Q. Ha, B. Dhodary, K.H. Kim, J. Park, C.H. Lee, Y.C. Kim, W.K. Oh, J. Nat. Prod. 77, 1615-1623 (2014)
12. L.P. Christensen, Advances in Food and Nutrition Research (Elsevier, Cambridge, 2008), pp. 1-99
13. E. Bedir, N.J. Toyang, I.A. Khan, L.A. Walker, A.M. Clark, J. Nat. Prod. 64, 95-97 (2001)
14. L.W. Qi, C.Z. Wang, C.S. Yuan, Nat. Prod. Rep. 28, 467-495 (2011)
15. D.Y. Lee, B.J. Cha, Y.S. Lee, G.S. Kim, H.J. Noh, S.Y. Kim, H.C. Kang, H.K. Jin, N.I. Baek, Int. J. Mol. Sci. 16, 1677 (2015)
16. R.T. Teng, H.Z. Li, J.T. Chen, D.Z. Wang, Y.E. He, C.R. Yang, Magn. Reson. Chem. 40, 483-488 (2002)
17. L.B. Vinh, Y. Lee, Y.K. Han, J.S. Kan, J.U. Park, Y.R. Kim, S.Y. Yang, Y.H. Kim, Bioorg. Med. Chem. Lett. 27, 5149-5153 (2017)
18. Y.W. Zhang, Q.D. De, Y.J. Chen, X.S. Yao, Chin. Tradit. Herb. Drugs. 49, 442-446 (2001)
19. J. Zhang, H. Guo, Y. Tian, P. Liu, N. Li, J. Zhou, D. Guo, Phytochemistry 68, 2523-2530 (2007)
20. X. Liu, L.R. Qiao, D. Xie, J.G. Dai, J. Asian Nat. Prod. Res. 13, 652-658 (2011)
21. Q. Zhang, W.Q. Zhao, F. Meng, Y.X. Zhang, Chin. J. Antibiot. 37, 49-75 (2012)
22. M. Miyazawa, H. Ando, Y. Okuno, J. Mol. Catal B 27, 91-95 (2004)
23. Y.H. Pyo, T.C. Lee, Y.C. Lee, Food Res. Int. 38, 551-559 (2005)
24. W.Z. Yang, T. Bo, S. Ji, X. Qiao, D.A. Guo, M. Ye, Food Chem. 139, 762-769 (2013)
25. W.Z. Yang, J.X. Zhang, C.J. Yao, S. Qiu, M. Chen, H.Q. Pan, X.J. Shi, W.Y. Wu, D. Guo, J. Pharm. Biomed. Anal. 128, 322-332 (2016)
26. A. Rhule, S. Navarro, J.R. Smith, D.M. Shepherd, J. Ethnopharmacol. 106, 121-128 (2006)
27. S. Ahn, M.H. Siddiqi, H.Y. Noh, Y.J. Kim, Y.J. Kim, C.G. Jin, D.C. Yang, Sci. Bull. 60, 773-784 (2015)
28. N.W. He, Y. Zhao, L. Guo, J. Shang, X.B. Yang, J. Med. Food 15, 350-359 (2012)
29. D.F. Toh, D.N. Patel, E.C.Y. Chan, A. Teo, S.Y. Neo, H.L. Koh, Chin. Med. 6, 1-9 (2011)
30. P. Wang, J. Cui, X. Du, Q. Yang, C. Jia, M. Xiong, X. Yu, L. Li, W. Wang, Y. Chen, T. Zhang, J. Ethnopharmacol. 154, 663-671 (2014)
31. V.M. Dirsch, H. Stuppner, A.M. Vollmar, Planta Med. 64, 423-426 (1998)
32. D.W. Reif, S.A. Mccreedy, Arch. Biochem. Biophys. 320, 170-176 (1995)
33. K. Berg, L. Zhai, M. Chen, A. Kharazmi, T.C. Owen, Parasitol. Res. 80, 235-239 (1994)
[1] Cheng-Ji Li, Fan Xia, Rong Wu, Hong-Sheng Tan, Hong-Xi Xu, Gang Xu, Hong-Bo Qin. Synthesis and Cytotoxicities of Royleanone Derivatives[J]. Natural Products and Bioprospecting, 2018, 8(6): 453-456.
[2] Wen-Jie Sun, Hong-Tao Zhu, Tian-Yuan Zhang, Meng-Yue Zhang, Dong Wang, Chong-Ren Yang, Yi-Xuan Zhang, Ying-Jun Zhang. Two New Alkaloids from Fusarium tricinctum SYPF 7082, an Endophyte from the Root of Panax notoginseng[J]. Natural Products and Bioprospecting, 2018, 8(5): 391-396.
[3] Yang Tang, Zhen-Zhu Zhao, Zheng-Hui Li, Tao Feng, He-Ping Chen, Ji-Kai Liu. Irpexoates A-D, Four Triterpenoids with Malonyl Modifications from the Fruiting Bodies of the Medicinal Fungus Irpex lacteus[J]. Natural Products and Bioprospecting, 2018, 8(3): 171-176.
[4] Zhen-Xiong Wang, Shen Qin, Li-Hua Xu, He-Ping Chen, Huan Sun, Rong Huang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Xylanilyticolides A-C, Three New Compounds from Cultures of the Actinomycete Promicromonospora xylanilytica YIM 61515[J]. Natural Products and Bioprospecting, 2018, 8(2): 91-95.
[5] Manar Adam, Gihan O. M. Elhassan, Sakina Yagi, Fatma Sezer Senol, Ilkay Erdogan Orhan, Abdel Azim Ahmed, Thomas Efferth. In Vitro Antioxidant and Cytotoxic Activities of 18 Plants from the Erkowit Region, Eastern Sudan[J]. Natural Products and Bioprospecting, 2018, 8(2): 97-105.
[6] Rong Chen, Jian-Wei Tang, Xing-Ren Li, Miao Liu, Wen-Ping Ding, Yuan-Fei Zhou, Wei-Guang Wang, Xue Du, Han-Dong Sun, Pema-Tenzin Puno. Secondary Metabolites from the Endophytic Fungus Xylaria sp. Hg1009[J]. Natural Products and Bioprospecting, 2018, 8(2): 121-129.
[7] Xing Yu, Kai-Ting Duan, Zhen-Xiong Wang, He-Ping Chen, Xiao-Qing Gan, Rong Huang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Anemhupehins A-C, Podocarpane Diterpenoids from Anemone hupehensis[J]. Natural Products and Bioprospecting, 2018, 8(1): 31-35.
[8] Xin Wei, Afsar Khan, Da Song, Zhi Dai, Ya-Ping Liu, Hao-Fei Yu, Bei Wang, Pei-Feng Zhu, Cai-Feng Ding, Xu-Dong Zhao, Yi-Fen Wang, Xiao-Dong Luo. Three New Pyridine Alkaloids from Vinca major Cultivated in Pakistan[J]. Natural Products and Bioprospecting, 2017, 7(4): 323-327.
[9] Xu-Jie Qin, Tong Shu, Qian Yu, Huan Yan, Wei Ni, Lin-Kun An, Pan-Pan Li, Yin-E Zhi, Afsar Khan, Hai-Yang Liu. Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus[J]. Natural Products and Bioprospecting, 2017, 7(4): 315-321.
[10] Miao Liu, Zheng-Xi Hu, Yuan-Qing Luo, Min Zhou, Wei-Guang Wang, Xiao-Nian Li, Xue Du, Jian-Xin Pu, Han-Dong Sun. Two New Compounds from Schisandra propinqua var. propinqua[J]. Natural Products and Bioprospecting, 2017, 7(3): 257-262.
[11] Li-Xia Wang, Hai-Rong Zheng, Fu-Cai Ren, Tian-Ge Chen, Xiang-Mei Li, Xian-Jun Jiang, Fei Wang. Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis[J]. Natural Products and Bioprospecting, 2017, 7(2): 201-206.
[12] Satheesh Kumar Palanisamy, N. M. Rajendran, Angela Marino. Natural Products Diversity of Marine Ascidians (Tunicates; Ascidiacea) and Successful Drugs in Clinical Development[J]. Natural Products and Bioprospecting, 2017, 7(1): 1-111.
[13] Mehtab Parveen, Faheem Ahmad, Ali Mohammed Malla, Shaista Azaz, Mahboob Alam, Omer A. Basudan, Manuela Ramos Silva, Pedro S. Pereira Silva. Acetylcholinesterase and Cytotoxic Activity of Chemical Constituents of Clutia lanceolata Leaves and its Molecular Docking Study[J]. Natural Products and Bioprospecting, 2016, 6(6): 267-278.
[14] Vincent E. Rasamison, Peggy J. Brodie, Emilio F. Merino, Maria B. Cassera, Michel A. Ratsimbason, Stephan Rakotonandrasana, Andriamalala Rakotondrafara, Elie Rafidinarivo, David G. I. Kingston, Harinantenaina L. Rakotondraibe. Furoquinoline Alkaloids and Methoxyflavones from the Stem Bark of Melicope madagascariensis (Baker) T. G. Hartley[J]. Natural Products and Bioprospecting, 2016, 6(5): 261-265.
[15] Qian-Qian Meng, Xing-Rong Peng, Shuang-Yang Lu, Luo-Sheng Wan, Xia Wang, Jin-Run Dong, Rui Chu, Lin Zhou, Xiao-Nian Li, Ming-Hua Qiu. Lactam Triterpenoids from the Bark of Toona sinensis[J]. Natural Products and Bioprospecting, 2016, 6(5): 239-245.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed