Natural Products and Bioprospecting    2014, Vol. 4 Issue (4) : 233-242     DOI: 10.1007/s13659-014-0026-2
Original article |
Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus
Jian-Qiang Zhao1,2, Yan-Ming Wang1,2, Hong-Tao Zhu1, Dong Wang1, Sheng-Hong Li1, Rong-Rong Cheng1, Chong-Ren Yang1, Yi-Fei Wang3, Min Xu1, Ying-Jun Zhang1
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. Guangzhou Jinan Biomedicine Research and Development Center, Guangzhou 510632, People's Republic of China
Download: PDF(701 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
Abstract  Two new highly oxygenated limonoids, flexuosoids A(1) and B(2), and three new arylnaphthalene lignan glycosides, phyllanthusmins D-F(3-5), were isolated from the roots of Phyllanthus flexuosus, in addition to three known lignans, phyllanthusmin C, arabelline, and(+)-diasyringaresinol. Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods. Compounds 1 and 2, two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1, C-2, C-3, C-7, C-11, C-17, and C-30, represent the second example of limonoids in the Euphorbiaceae family. Most of the isolates were tested for their antifeedant, anti-herpes simplex virus 1, and cytotoxic activities. The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm(Spodoptera exigua) with EC50 values of 25.1 and 17.3 μg/cm2, respectively. In addition, both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line, along with the known lignan glycoside, phyllanthusmin C, with the IC50 values of 11.5(1), 8.5(2), and 7.8(phyllanthusmin C) μM, respectively.
Keywords Phyllanthus flexuosus      Euphorbiaceae      Limonoids      Lignan glycosides      Antifeedant      Antiviral      Cytotoxicity     
Fund:We are grateful to the members of the analytical group of our institute for the measurement of spectroscopic data. This work was supported by the NSFC 21002105, the 973 Program of Science and Technology of P. R. China(2011CB915503), the Fourteenth Batch Candidates of the Young Academic Leaders of Yunnan Province(Min XU, 2011CI044) and by West Light Foundation of the Chinese Academy of Sciences.
Issue Date: 11 February 2018
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
Jian-Qiang Zhao
Yan-Ming Wang
Hong-Tao Zhu
Dong Wang
Sheng-Hong Li
Rong-Rong Cheng
Chong-Ren Yang
Yi-Fei Wang
Min Xu
Ying-Jun Zhang
Trendmd:   
Cite this article:   
Jian-Qiang Zhao,Yan-Ming Wang,Hong-Tao Zhu, et al. Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus[J]. Natural Products and Bioprospecting, 2014, 4(4): 233-242.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-014-0026-2     OR     http://npb.kib.ac.cn/EN/Y2014/V4/I4/233
1. D.W. Unander, G.L. Webster, B.S. Blumberg, J. Ethnopharmacol. 45, 1-18 (1995)
2. Y.J. Zhang, T. Abe, T. Tanaka, C.R. Yang, I. Kouno, J. Nat. Prod. 64, 1527-1532 (2001)
3. Y.J. Zhang, T. Tanaka, Y. Iwamoto, C.R. Yang, I. Kouno, J. Nat. Prod. 63, 1507-1510 (2000)
4. R. Ratnayake, D. Covell, T.T. Ransom, K.R. Gustafson, J.A. Beutler, Org. Lett. 11, 57-60 (2009)
5. G.R. Pettit, D.E. Schaufel-berger, R.A. Nieman, C. Dufresne, J.A. Saenz-Renauld, J. Nat. Prod. 53, 1406-1413 (1990)
6. Q. Liu, Y.F. Wang, R.J. Chen, M.Y. Zhang, Y.F. Wang, C.R. Yang, Y.J. Zhang, J. Nat. Prod. 72, 969-972 (2009)
7. Y.J. Zhang, T. Nagao, T. Tanaka, C.R. Yang, H. Okabe, I. Kouno, Biol. Pharm. Bull. 27, 251-255 (2004)
8. B.T. Li, Flora of China, vol. 44. (Science Press, Beijing, 1994), pp. 86
9. R. Tanaka, Y. Kinouchi, S. Wada, H. Tokuda, Planta Med. 70, 1234-1236 (2004)
10. R. Tanaka, M. Tabuse, S. Matsunaga, Phytochemistry 27, 3563-3567 (1988)
11. R. Tanaka, K. Masuda, S. Matsunaga, Phytochemistry 32, 472-474 (1993)
12. R. Tanaka, Y. In, T. Ishida, S. Matsunaga, J. Nat. Prod. 57, 1123-1128 (1994)
13. J.Q. Zhao, J.J. Lv, Y.M. Wang, M. Xu, H.T. Zhu, D. Wang, C.R. Yang, Y.F. Wang, Y.J. Zhang, Tetrahedron Lett. 54, 4670-4674 (2013)
14. Y. Pei, Y.F. Xiang, J.N. Chen, C.H. Lu, J. Hao, Q. Du, C.C. Lai, C. Qu, S. Li, H.Q. Ju, Z. Ren, Q.Y. Liu, S. Xiong, C.W. Qian, F.L. Zeng, P.Z. Zhang, C.R. Yang, Y.J. Zhang, J. Xu, K. Kitazato, Y.F. Wang, Antiviral Res. 89, 98-108 (2011)
15. L.W. Tian, Y. Pei, Y.J. Zhang, Y.F. Wang, C.R. Yang, J. Nat. Prod. 72, 1057-1060 (2009)
16. H.Q. Ju, S.Y. Wang, Y. Pei, Y.F. Xiang, S. Li, Y.J. Zhang, C.R. Yang, Y.F.J. Wang, Chin. Med. Mater. 34, 242-245 (2011)
17. G. Liu, S. Xiong, Y.F. Xiang, C.W. Guo, F. Ge, C.R. Yang, Y.J. Zhang, Y.F. Wang, K. Kitazato, Arch. Virol. 156, 1359-1369 (2011)
18. S.J. Wu, T.S. Wu, Chem. Pharm. Bull. 54, 1223-1225 (2006)
19. Y. Al-Abed, S. Sabri, M.A. Zarga, Z. Shah, Atta-Ur-Rahman, J. Nat. Prod. 53, 1152-1161 (1990)
20. F.R. Chang, Y.C. Chao, C.M. Teng, Y.C. Wu, J. Nat. Prod. 61, 863-866 (1998)
21. J. Polonsky, Z. Varon, B. Arnoux, C. Pascard, G.R. Pettit, J.M. Schmidt, L.M. Lange, J. Am. Chem. Soc. 22, 7731-7733 (1978)
22. T.R. Govindachari, N. Viswanathan, B.R. Pai, T.S. Savitri, Tetrahedron Lett. 16, 901-906 (1964)
23. J.C. Vardamidesa, E. Dongo, A.E. Nkengfack, Z.T. Fomum, T.M. Ngando, B. Vogler, W. Kraus, Fitoterapia 72, 386-393 (2001)
24. R.C. Huang, H. Okamura, T. Iwagawa, M. Nakatani, Bull. Chem. Soc. Jpn. 67, 2468-2472 (1994)
25. K. Takeya, Z.S. Qiao, C. Hirobe, H. Itokawa, Bioorg. Med. Chem. 4, 1355-1359 (1996)
26. I. Kitagawa, M. Saito, T. Taniyama, M. Yoshikawa, Chem. Pharm. Bull. 33, 598-608 (1985)
27. K.C. Lewis, A.R. Maxwell, S. McLean, W.F. Reynolds, R.G. Enriquez, Magn. Reson. Chem. 38, 771-774 (2000)
28. J.Y. Cai, Y. Zhang, S.H. Luo, D.Z. Chen, G.H. Tang, C.M. Yuan, Y.T. Di, S.H. Li, X.J. Hao, H.P. He, Org. Lett. 14, 2524-2527 (2012)
29. Q.G. Tan, X.D. Luo, Chem. Rev. 111, 7437-7522 (2011)
30. J.Q. Zhao, Y.M. Wang, H.P. He, S.H. Li, X.N. Li, C.R. Yang, D. Wang, H.T. Zhu, M. Xu, Y.J. Zhang, Org. Lett. 15, 2414-2417 (2013)
31. M.B. Isman, O. Koul, A. Luczynski, J. Kaminski, J. Agric. Food Chem. 38, 1406-1411 (1990)
[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] 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.
[5] 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.
[6] 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.
[7] 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.
[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] 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.
[10] 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.
[11] 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.
[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] Lai-Bin Zhang, Chun Lei, Li-Xin Gao, Jing-Ya Li, Jia Li, Ai-Jun Hou. Isoprenylated Flavonoids with PTP1B Inhibition from Macaranga denticulata[J]. Natural Products and Bioprospecting, 2016, 6(1): 25-30.
[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] Tao Feng, Juan He, Hong-Lian Ai, Rong Huang, Zheng-Hui Li, Ji-Kai Liu. Three New Triterpenoids from European Mushroom Tricholoma terreum[J]. Natural Products and Bioprospecting, 2015, 5(4): 205-208.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed