Two New Compounds from <i>Schisandra propinqua</i> var. <i>propinqua</i>

doi:10.1007/s13659-017-0129-7

Natural Products and Bioprospecting

2017, Vol. 7

Issue (3) : 257-262 DOI: 10.1007/s13659-017-0129-7

Two New Compounds from Schisandra propinqua var. propinqua

Miao Liu^1,2, Zheng-Xi Hu³, Yuan-Qing Luo^1,2, Min Zhou^1,2, Wei-Guang Wang¹, Xiao-Nian Li¹, Xue Du¹, Jian-Xin Pu¹, Han-Dong Sun¹

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. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China

Abstract
References
Related Articles
Metrics

Download: PDF(1065 KB) HTML ()
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract Schisanpropinoic acid (1), a new bergamotane sesquiterpenoid, and schisanpropinin (2), a new tetrahydrofuran lignan with a rare epoxyethane unit, were identified from the stems and leaves of Schisandra propinqua var. propinqua. Their structures were determined based on comprehensive spectroscopic and mass spectrometric analysis. The absolute configuration of 1 was determined by X-ray analysis. Compounds 1 and 2 were tested for their cytotoxic activity against five human tumor cell lines.

Keywords Schisandra propinqua var. propinqua Bergamotane-type sesquiterpenoid Lignan Absolute configuration Cytotoxicity

Fund:This project was supported financially by the National Natural Science Foundation of China (81373290 and 21322204).

Issue Date: 06 February 2018

	Service

	E-mail this article
	E-mail Alert
	RSS
	Articles by authors

	Miao Liu
	Zheng-Xi Hu
	Yuan-Qing Luo
	Min Zhou
	Wei-Guang Wang
	Xiao-Nian Li
	Xue Du
	Jian-Xin Pu
	Han-Dong Sun

Trendmd:

Cite this article:

Miao Liu,Zheng-Xi Hu,Yuan-Qing Luo, et al. Two New Compounds from Schisandra propinqua var. propinqua[J]. Natural Products and Bioprospecting, 2017, 7(3): 257-262.

URL:

http://npb.kib.ac.cn/EN/10.1007/s13659-017-0129-7 OR http://npb.kib.ac.cn/EN/Y2017/V7/I3/257

1. Y.W. Law, Flora Repubulicae Popularis Sinicae, vol. 30 (Science Press, Beijing, 1996), pp. 231-273
2. W.L. Xiao, R.T. Li, S.X. Huang, J.X. Pu, H.D. Sun, Nat. Prod. Rep. 25, 871-891 (2008)
3. R.T. Li, Q.S. Zhao, S.H. Li, Q.B. Han, H.D. Sun, Y. Lu, L.L. Zhang, Q.T. Zheng, Org. Lett. 5, 1023-1026 (2003)
4. Y.M. Shi, W.L. Xiao, J.X. Pu, H.D. Sun, Nat. Prod. Rep. 32, 367-410 (2015)
5. C. Lei, S.X. Huang, J.J. Chen, L.B. Yang, W.L. Xiao, Y. Chang, Y. Lu, H. Huang, J.X. Pu, H.D. Sun, J. Nat. Prod. 71, 1228-1232 (2008)
6. C. Lei, J.X. Pu, S.X. Huang, J.J. Chen, J.P. Liu, L.B. Yang, Y.B. Ma, W.L. Xiao, X.N. Li, H.D. Sun, Tetrahedron 65, 164-170 (2009)
7. C. Lei, S.X. Huang, J.X. Pu, J.P. Liu, G.Y. Yang, L.B. Yang, Y. Lu, J.J. Chen, Y. Lu, W.L. Xiao, H.D. Sun, Planta Med. 74, 292-295 (2008)
8. C. Lei, S.X. Huang, J.J. Chen, J.X. Pu, L.B. Yang, Y. Zhao, J.P. Liu, X.M. Gao, W.L. Xiao, H.D. Sun, Chem. Pharm. Bull. 55, 1281-1283 (2007)
9. M. Liu, J. Wan, Y.Q. Luo, X.N. Li, X. Du, J.X. Pu, H.D. Sun, Nat. Prod. Commun. 11, 925-929 (2016)
10. M.W. Lodewyk, C. Soldi, P.B. Jones, M.M. Olmstead, J. Rita, J.T. Shaw, D.J. Tantillo, J. Am. Chem. Soc. 134, 18550-18553 (2012)
11. Z.X. Hu, Y.M. Shi, W.G. Wang, J.W. Tang, M. Zhou, X. Du, Y.H. Zhang, J.X. Pu, H.D. Sun, Org. Lett. 18, 2284-2287 (2016)
12. A. Chandra, L.N. Misra, R.S. Thakur, Phytochemistry 26, 3077-3078 (1987)
13. R.M. Coates, J.F. Denissen, J.A. Juvik, B.A. Babka, J. Org. Chem. 53, 2186-2192 (1988)
14. H.D. Flack, Acta Crystallogr. A 39, 876-881 (1983)
15. R.W.W. Hooft, L.H. Straver, A.L. Spek, J. Appl. Crystallogr. 41, 96-103 (2008)
16. K.S. Kulkarni, S.K. Paknikar, A.S. Vaidya, G.R. Kelkar, R.B. Bates, S.C. Bhattacharyya, Tetrahedron Lett. 8, 505-511 (1963)
17. N.B. Perry, E.J. Burgess, L.M. Foster, P.J. Gerard, Tetrahedron Lett. 44, 1651-1653 (2003)
18. N.B. Perry, E.J. Burgess, L.M. Foster, M. Toyota, Y. Asakawa, J. Nat. Prod. 71, 258-261 (2008)
19. M. Massias, S. Rebuffat, L. Molho, A. Chiaroni, C. Riche, B. Bodo, J. Am. Chem. Soc. 112, 8112-8115 (1990)
20. Y.S. Che, J.B. Gloer, B. Koster, D. Malloch, J. Nat. Prod. 65, 916-919 (2002)
21. Z. Guo, F.X. Ren, Y.S. Che, G. Liu, L. Liu, Molecules 20, 14611-14620 (2015)
22. H. Oh, J.B. Gloer, C.A. Shearer, J. Nat. Prod. 62, 497-501 (1999)
23. F.A. Macias, R.M. Varela, A.M. Simonet, H.G. Cutler, S.J. Cutler, R.A. Hill, Tetrahedron Lett. 44, 941-943 (2003)
24. L.H. Zhang, B.M. Feng, G. Chen, S.G. Li, Y. Sun, H.H. Wu, J. Bai, H.M. Hua, H.F. Wang, Y.H. Pei, RSC Adv. 6, 42361-42366 (2016)
25. Y.M. Ying, C.A. Fang, F.Q. Yao, Y. Yu, Y. Shen, Z.N. Hou, Z. Wang, W. Zhang, W.G. Shan, Z.J. Zhan, Chem. Biodivers. (2017). doi:10.1002/cbdv.201600184
26. Y. Wang, D.H. Li, Z.L. Li, Y.J. Sun, H.M. Hua, T. Liu, J. Bai, Molecules 21, 31-36 (2016)
27. J.X. Pu, X.M. Gao, C. Lei, W.L. Xiao, R.R. Wang, L.B. Yang, Y. Zhao, L.M. Li, S.X. Huang, Y.T. Zheng, H.D. Sun, Chem. Pharm. Bull. 56, 1143-1146 (2008)
28. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo, M. Boyd, J. Natl. Cancer 83, 757-766 (1991)
29. M. Zhou, K. Zhou, X.M. Gao, Z.Y. Jiang, J.J. Lv, Z.H. Liu, G.Y. Yang, M.M. Miao, C.T. Che, Q.F. Hu, Org. Lett. 17, 2638-2641 (2015)
30. M. Zhou, M.M. Miao, G. Du, X.N. Li, S.Z. Shang, W. Zhao, Z.H. Liu, G.Y. Yang, C.T. Che, Q.F. Hu, X.M. Gao, Org. Lett. 16, 5016-5019 (2014)
31. L.J. Reed, H. Muench, Am. J. Hyg. 27, 493-497 (1938)

[1]	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.
[2]	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.
[3]	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.
[4]	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.
[5]	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.
[6]	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.
[7]	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.
[8]	Xiang-Mei Li, Xian-Jun Jiang, Ku Yang, Li-Xia Wang, Shi-Zhen Wen, Fei Wang. Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata[J]. Natural Products and Bioprospecting, 2016, 6(5): 233-237.
[9]	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.
[10]	Ling Ni, Xiu-Hong Zhong, Jie Cai, Mei-Fen Bao, Bing-Jie Zhang, Jing Wu, Xiang-Hai Cai. Five New Alkaloids from Cephalotaxus lanceolata and C. fortunei var. alpina[J]. Natural Products and Bioprospecting, 2016, 6(3): 149-154.
[11]	Jing-Xian Zhuo, Yue-Hu Wang, Xing-Li Su, Ren-Qiang Mei, Jun Yang, Yi Kong, Chun-Lin Long. Neolignans from Selaginella moellendorffii[J]. Natural Products and Bioprospecting, 2016, 6(3): 161-166.
[12]	Christian Bäcker, Malgorzata N. Drwal, Robert Preissner, Ulrike Lindequist. *Inhibition of DNA-Topoisomerase I by Acylated Triterpene Saponins from Pittosporum angustifolium* Lodd**[J]. Natural Products and Bioprospecting, 2016, 6(2): 141-147.
[13]	Liang-Yan Liu, Han Sun, Christian Griesinger, Ji-Kai Liu. *The Use of a Combination of RDC and Chiroptical Spectroscopy for Determination of the Absolute Configuration of Fusariumin A from the Fungus Fusarium* sp**[J]. Natural Products and Bioprospecting, 2016, 6(1): 41-48.
[14]	Fan Xia,Chun-Yan Wu,Xing-Wei Yang, Xian Li,Gang Xu. Diterpenoids from the Roots of Salvia yunnanensis[J]. Natural Products and Bioprospecting, 2015, 5(6): 307-312.
[15]	Qi-Long Zhou, Hui-Jing Wang, Pei Tang, Hao Song, Yong Qin. Total Synthesis of Lignan Lactone(-)-Hinokinin[J]. Natural Products and Bioprospecting, 2015, 5(5): 255-261.

Viewed

Full text

Abstract

Cited

Shared

Discussed