Lactam Triterpenoids from the Bark of Toona sinensis

doi:10.1007/s13659-016-0108-4

应用天然产物 ›› 2016, Vol. 6 ›› Issue (5): 239-245.DOI: 10.1007/s13659-016-0108-4

Lactam Triterpenoids from the Bark of Toona sinensis

Qian-Qian Meng^1,2, Xing-Rong Peng^1,3, Shuang-Yang Lu^1,2, Luo-Sheng Wan^1,3, Xia Wang^1,2, Jin-Run Dong^1,2, Rui Chu^1,2, Lin Zhou^1,3, Xiao-Nian Li^1,3, Ming-Hua Qiu^1,2,3

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 the Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Yunnan University of Traditional Chinese Medicine, Kunming 650500, People's Republic of China

收稿日期:2016-07-29 修回日期:2016-09-22 出版日期:2016-10-24 发布日期:2018-02-08
通讯作者: Ming-Hua Qiu,e-mail:mhchiu@mail.kib.ac.cn
基金资助:
This project was financially supported by Major Program of the National Knowledge Innovation of CAS (No.KSCX2-YW-G-038);and the Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China (P2015-ZZ09);Authors also were particularly grateful to Research Group of Prof.Yan Li for bioassay tests

Lactam Triterpenoids from the Bark of Toona sinensis

Qian-Qian Meng^1,2, Xing-Rong Peng^1,3, Shuang-Yang Lu^1,2, Luo-Sheng Wan^1,3, Xia Wang^1,2, Jin-Run Dong^1,2, Rui Chu^1,2, Lin Zhou^1,3, Xiao-Nian Li^1,3, Ming-Hua Qiu^1,2,3

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 the Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3. Yunnan University of Traditional Chinese Medicine, Kunming 650500, People's Republic of China

Received:2016-07-29 Revised:2016-09-22 Online:2016-10-24 Published:2018-02-08
Supported by:
This project was financially supported by Major Program of the National Knowledge Innovation of CAS (No.KSCX2-YW-G-038);and the Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China (P2015-ZZ09);Authors also were particularly grateful to Research Group of Prof.Yan Li for bioassay tests

摘要/Abstract

摘要： Three new limonoid-type triterpenoids, namely toonasins A-C (1-3) with a rare lactam E ring, along with six known compounds (4-9) were isolated from the barks of Toona sinensis. The structures of new compounds were elucidated by interpretation of spectroscopic data, and the relative configuration of compound 1 was further characterized by X-ray crystallographic analyses. The isolated compounds were evaluated for their cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480), and compounds 3 and 5 showed weak cytotoxicities.

关键词: Toona sinensis, Limonoids, Lactam triterpenoids, Cytotoxicity

Abstract: Three new limonoid-type triterpenoids, namely toonasins A-C (1-3) with a rare lactam E ring, along with six known compounds (4-9) were isolated from the barks of Toona sinensis. The structures of new compounds were elucidated by interpretation of spectroscopic data, and the relative configuration of compound 1 was further characterized by X-ray crystallographic analyses. The isolated compounds were evaluated for their cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480), and compounds 3 and 5 showed weak cytotoxicities.

Key words: Toona sinensis, Limonoids, Lactam triterpenoids, Cytotoxicity

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]. 应用天然产物, 2016, 6(5): 239-245.

参考文献

1. J.M. Edmonds, M. Staniforth, Curtis's Bot. Mag. 15, 186-193 (1998)
2. Y.C. Chen, Y.L. Liang, Y.L. Huang, B.M. Huang, J. Funct. Foods 14, 318-323 (2015)
3. H.L. Chang, H.K. Hsu, J.H. Su, P.H. Wang, Y.F. Chung, Y.C. Chia, L.Y. Tsai, Y.C. Wu, S.S. Yuan, Gynecol. Oncol. 102, 309-314 (2006)
4. Y.Y.J.Wang,Z.E.Xing, Y.Q.Dai, Food Chem. 128, 831-838(2011)
5. W.J. Yu, C.C. Chang, T.F. Kuo, Food Chem. Toxicol. 50, 1860-1865 (2012)
6. P.H. Wang, M.J. Tsai, C.Y. Hsu, Food Chem. Toxicol. 46, 2554-2560 (2008)
7. C.Y. Hsiang, Y.C. Hseu, Y.C. Chang, Food Chem. 136, 426-434 (2013)
8. J.G. Wu, W. Peng, J. Yi, Y.B. Wu, T.Q. Chen, K.H. Wong, J.Z. Wu, J. Ethnopharmacol. 154, 198-205 (2014)
9. Y.F. Su, Y.C. Yang, H.K. Hsu, S.L. Hwang, K.S. Lee, A.S. Lieu, T.F. Chan, C.L. Lin, BMC Complement Altern. Med. 15, 1 (2015). doi:10.1186/s12906-015-0599-2
10. J. Tang, X. Jian, J. Zhang, W.Y. Liu, N. Xie, L. Chen, F. Feng, W. Qu, Fitoterapia 112, 97-103 (2016)
11. X.J. Dong, Y.F. Zhu, G.H. Bao, F.L. Hu, G.W. Qin, Molecules 18, 2840-2850 (2013)
12. K. Mitsui, M. Maejima, H. Saito, H. Fukaya, Y. Hitotsuyanagi, K. Takeya, Tetrahedron 61, 10569-10582 (2005)
13. I.S. Lee, H.I. Kim, U.J. Youn, Q.C. Chen, J.P. Kim, D.T. Ha, T.M. Ngoc, B.S. Min, S.M. Lee, H.J. Jung, M.K. Na, K.H. Bae, Helv. Chim. Acta 93, 272-276 (2010)
14. J.C. Park, Y.B. Yu, J.H. Lee, J.S. Choi, K.D. Ok, Korea J. Pharmacognosy 27, 219-223 (1996)
15. J.J. Xia, X.Y. Li, S.Z. Zhang, J.Q. Liu, W.M. Zhang, Y.X. Yan, Z.T. Ding, M.H. Qiu, Tetrahedron Lett. 55, 2104-2106 (2014)
16. J.J. Chen, S.S. Huang, C.H. Liao, D.C. Wei, P.J. Sung, T.C. Wang, M.J. Cheng, Food Chem. 120, 379-384 (2010)
17. T.R. Govindachari, G. Suresh, B. Banumathy, S. Masilamani, G. Gopalakrishnan,G.N.K. Kumari, J. Chem. Ecol. 25, 923-933 (1999)
18. S. Falah, T. Suzuki, T. Katayama, Park. J. Biol. Sci. 11, 2007-2012 (2008)
19. R. Fowles, B. Mootoo, R. Ramsewak, A. Khan, A. Ramsubhag, W. Reynolds, M. Nair, Pest Manage. Sci. 66, 1298-1303 (2010)
20. J.Q. Liu, X.R. Peng, W.M. Zhang, L. Shi, X.Y. Li, J.C. Chen, M.H. Qiu, RSC Adv. 3, 4890-4893 (2013)
21. W.M. Zhang, J.Q. Liu, D.Y. Deng, J.J. Xia, Z.R. Zhang, Z.R. Li, M.H. Qiu, Nat. Prod. Bioprospect. 4, 53-57 (2014)
22. C.L. Cespedes, J.S. Calderon, B. King-Diaz, B. Lotina-Hennsen, J. Agric. Food Chem. 46, 2810-2816 (1998)
23. G.J.W. Breen, E. Ritchie, W.T.L. Sidwell, W.C. Taylor, Australian J. Chem. 19, 455-481 (1966)
24. C.P. Reyes, M.J. Nunez, L.A. Jimenez, J. Busserolles, M.J. Alcaraz, I.L. Bazzocchi, Bioorg. Med. Chem. 14, 1573-1579 (2006)
25. X.H. Zheng, L.Z. Zhen, K. Chohachi, D.D. Soejarto, G.A. Cordell, H.H.S. Fong, W. Hodgson, Phytochemistry 27, 233-235 (1988)
26. J.J. Xu, J.T. Fan, G.Z. Zeng, N.H. Tan, Helv. Chim. Acta 94, 842-846 (2011)
27. J.J. Chen, H.C. Hung, P.J. Sung, I.S. Chen, W.L. Kuo, Phytochemistry 72, 523-532 (2011)
28. W. Zhang, C. Li, L.J. You, X. Fu, Y.S. Chen, Y.Q. Luo, J. Funct. Foods 10, 427-435 (2014)
29. C.L. Wang, J.X. Shi, Y. Wu, Asian J. Chem. 26, 2557-2560 (2014)
30. K. Akinori, N. Masayuki, E. Mai, A. Morina, H. Masahiro, T. Kaori, K. Mamoru, Bioorg. Med. Chem. Lett. 24, 4286-4290 (2014)
31. J. Hu, Y. Song, X. Mao, Z.J. Wang, Q.J. Zhao, J. Funct. Foods 20, 1-9 (2016)

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Lactam Triterpenoids from the Bark of Toona sinensis

Lactam Triterpenoids from the Bark of Toona sinensis

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