|
|
Four 14(13→12)-Abeolanostane Triterpenoids with 6/6/5/6-Fused Ring System from the Roots of Kadsura coccinea |
Hou-Chao Xu1,2, Kun Hu1, Han-Dong Sun1, Pema-Tenzin Puno1 |
1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, People's Republic of China; 2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China |
|
|
Abstract Four new rearranged 6/6/5/6-fused lanostane-type triterpenoids, kadcoccitanes A-D (1-4), were isolated from the roots of Kadsura coccinea, and their structures were mainly elucidated by comprehensive analysis of their spectroscopic data. Additionally, the structure of 1 was ambiguously verified by single-crystal X-ray diffraction, while the structure of 2, which features a novel 8,16-epoxy motif, was validated by quantum chemical calculation of NMR parameters and ECD spectrum. Moreover, 1 and 4 were found to exhibited anticoagulant activity, while 3 and 4 were found to possess anti-platelet aggregation activity.
|
Keywords
Kadsura coccinea
Lanostane triterpenoid
NMR computation
Anti-platelet aggregation
Anticoagulant
|
Fund:This project was supported financially by the National Natural Science Foundation of China (Nos. 81874298 and 81673329). |
Corresponding Authors:
Pema-Tenzin Puno
E-mail: punopematenzin@mail.kib.ac.cn
|
Issue Date: 05 June 2019
|
|
|
1. W.L. Xiao, R.T. Li, S.X. Huang, J.X. Pu, H.D. Sun, Nat. Prod. Rep. 25, 871-891 (2008) 2. Y.M. Shi, W.L. Xiao, J.X. Pu, H.D. Sun, Nat. Prod. Rep. 32, 367-410 (2015) 3. M.R. Jia, X.W. Li, Zhong Guo Min Zu Yao Zhi Yao, 1st edn. (China Medical Science and Technology Press, Beijing, 2005), p. 357 4. C.Q. Liang, Y.M. Shi, R.H. Luo, X.Y. Li, Z.H. Gao, X.N. Li, L.M. Yang, S.Z. Shang, Y. Li, Y.T. Zheng, H.B. Zhang, W.L. Xiao, H.D. Sun, Org. Lett. 14, 6362-6365 (2012) 5. C.Q. Liang, Y.M. Shi, X.Y. Li, R.H. Luo, Y. Li, Y.T. Zheng, H.B. Zhang, W.L. Xiao, H.D. Sun, J. Nat. Prod. 76, 2350-2354 (2013) 6. C.Q. Liang, Y.M. Shi, W.G. Wang, Z.X. Hu, Y. Li, Y.T. Zheng, X.N. Li, X. Du, J.X. Pu, W.L. Xiao, H.B. Zhang, H.D. Sun, J. Nat. Prod. 78, 2067-2073 (2015) 7. Z.X. Hu, Y.M. Shi, W.G. Wang, X.N. Li, X. Du, M. Liu, Y. Li, Y.B. Xue, Y.H. Zhang, J.X. Pu, H.D. Sun, Org. Lett. 17, 4616-4619 (2015) 8. Z.X. Hu, Y.H. Zhang, Z.X. Hu, K. Hu, Y.M. Shi, W.G. Wang, X. Du, Y. Li, J.X. Pu, H.D. Sun, J. Nat. Prod. 79, 2590-2598 (2016) 9. Z.X. Hu, X.N. Li, Y.M. Shi, W.G. Wang, X. Du, Y. Li, Y.H. Zhang, J.X. Pu, H.D. Sun, Tetrahedron 73, 2931-2937 (2017) 10. X.M. Gao, J.X. Pu, S.X. Huang, Y. Lu, L.G. Lou, R.T. Li, W.L. Xiao, Y. Chang, H.D. Sun, J. Nat. Prod. 71, 1182-1188 (2008) 11. X.M. Gao, J.X. Pu, W.L. Xiao, S.X. Huang, L.G. Lou, H.D. Sun, Tetrahedron 64, 11673-11679 (2008) 12. C. Bannwarth, S. Ehlert, S. Grimme, J. Chem. Theory Comput. 15, 1652-1671 (2019) 13. S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 132, 154104 (2010) 14. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09 (Gaussian Inc., Wallingford, 2010) 15. T. Lu molclus program. Version 1.6 edn. http://www.keinsci.com/research/molclus.html. Accessed 15 Feb 2019 16. P.H. Willoughby, M.J. Jansma, T.R. Hoye, Nat. Protoc. 9, 643-660 (2014) 17. M.W. Lodewyk, M.R. Siebert, D.J. Tantillo, Chem. Rev. 112, 1839-1862 (2012) 18. N. Grimblat, M.M. Zanardi, A.M. Sarotti, J. Org. Chem. 80, 12526-12534 (2015) 19. F. Jensen, Theor. Chem. Acc. 126, 371-382 (2009) 20. T. Lu, F. Chen, J. Comput. Chem. 33, 580-592 (2011) 21. L.J. Kuester, J. Filep, J.C. Froelich, Thromb. Res. 43, 425-433 (1986) 22. G.V. Born, Nature 194, 927-929 (1962) 23. M. Wu, D. Wen, N. Gao, C. Xiao, L. Yang, L. Xu, W. Lian, W. Peng, J. Jiang, J. Zhao, Eur. J. Med. Chem. 92, 257-269 (2015) |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|