Antiproliferative Triterpenoid Saponins from Leptaulus citroides Baill. from the Madagascar Rain Forest

doi:10.1007/s13659-015-0083-1

应用天然产物 ›› 2016, Vol. 6 ›› Issue (1): 31-39.DOI: 10.1007/s13659-015-0083-1

Antiproliferative Triterpenoid Saponins from Leptaulus citroides Baill. from the Madagascar Rain Forest

Qingxi Su¹, Peggy J. Brodie¹, Yixi Liu¹, James S. Miller², Naina M. Andrianjafy³, Rabodo Antsiferana⁴, Vincent E. Rasamison⁵, David G. I. Kingston¹

1. Department of Chemistry, Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg VA, 24061, USA;
2. Missouri Botanical Garden, P. O. Box 299, St. Louis, MO 63166-0299, USA;
3. Missouri Botanical Garden, B. P 3391, 101 Antananarivo, Madagascar;
4. Centre National d'Application des Recherches Pharmaceutiques, B. P 702, 101 Antananarivo, Madagascar

收稿日期:2015-10-12 修回日期:2015-12-19 出版日期:2016-02-24 发布日期:2018-02-08
通讯作者: David G. I. Kingston,e-mail:dkingston@vt.edu

Antiproliferative Triterpenoid Saponins from Leptaulus citroides Baill. from the Madagascar Rain Forest

Qingxi Su¹, Peggy J. Brodie¹, Yixi Liu¹, James S. Miller², Naina M. Andrianjafy³, Rabodo Antsiferana⁴, Vincent E. Rasamison⁵, David G. I. Kingston¹

1. Department of Chemistry, Virginia Tech Center for Drug Discovery, M/C 0212, Virginia Tech, Blacksburg VA, 24061, USA;
2. Missouri Botanical Garden, P. O. Box 299, St. Louis, MO 63166-0299, USA;
3. Missouri Botanical Garden, B. P 3391, 101 Antananarivo, Madagascar;
4. Centre National d'Application des Recherches Pharmaceutiques, B. P 702, 101 Antananarivo, Madagascar

Received:2015-10-12 Revised:2015-12-19 Online:2016-02-24 Published:2018-02-08

摘要/Abstract

摘要： Bioassay-guided fractionation of EtOH extracts obtained from the roots and wood of the Madagascan plant Leptaulus citroides Baill. (Cardiopteridaceae) led to the isolation of ethyl esters of three new triterpenoid saponins (1-3) and the known sesquiterpenoid cinnamosmolide (4). The structures of 1-3 were elucidated by extensive 1D and 2D NMR experiments and mass spectrometry. Compounds 1, 2, and 4 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line with IC₅₀ values of 2.8, 10.2 and 2.0 lM, respectively.

关键词: Antiproliferative activity, Triterpenoid saponins, Leptaulus citroides (Cardiopteridacea)

Abstract: Bioassay-guided fractionation of EtOH extracts obtained from the roots and wood of the Madagascan plant Leptaulus citroides Baill. (Cardiopteridaceae) led to the isolation of ethyl esters of three new triterpenoid saponins (1-3) and the known sesquiterpenoid cinnamosmolide (4). The structures of 1-3 were elucidated by extensive 1D and 2D NMR experiments and mass spectrometry. Compounds 1, 2, and 4 showed moderate cytotoxicity against the A2780 human ovarian cancer cell line with IC₅₀ values of 2.8, 10.2 and 2.0 lM, respectively.

Key words: Antiproliferative activity, Triterpenoid saponins, Leptaulus citroides (Cardiopteridacea)

Qingxi Su, Peggy J. Brodie, Yixi Liu, James S. Miller, Naina M. Andrianjafy, Rabodo Antsiferana, Vincent E. Rasamison, David G. I. Kingston. Antiproliferative Triterpenoid Saponins from Leptaulus citroides Baill. from the Madagascar Rain Forest[J]. 应用天然产物, 2016, 6(1): 31-39.

参考文献

1. Y. Liu, C.H. Wiedle, P.J. Brodie, M.W. Callmander, R. Rakotondrajaona, E. Rakotobe, V.E. Rasamison. D.G.I. Kingston, Nat. Prod. Commun. 10, 1509-1512 (2015)
2. D.G.I. Kingston, J. Nat. Prod. 74, 496-511 (2010)
3. Y. Liu, L.H. Rakotondraibe, P.J. Brodie, J.D. Wiley, M.B. Cassera, J.S. Miller, F. Ratovoson, E. Rakotobe, V.E. Rasamison, D.G.I. Kingston, J. Nat. Prod. 78, 1330-1338 (2015)
4. I.I. Mahmoud, A.D. Kinghorn, G.A. Cordell, N.R. Farnsworth, J. Nat. Prod. 43, 365-371 (1980)
5. S. Cao, P. Brodie, M. Callmander, R. Randrianaivo, J. Razafitsalama, E. Rakotobe, V.E. Rasamison, K. TenDyke, Y. Shen, E.M. Suh, J. Nat. Prod. 72, 1705-1707 (2009)
6. M. Yoshikawa, T. Morikawa, N. Li, A. Nagatomo, X. Li, H. Matsuda, Chem. Pharm. Bull. 53, 1559-1564 (2005)
7. M. Yoshikawa, E. Harada, T. Murakami, H. Matsuda, J. Yamahara, N. Murakami, Chem. Pharm. Bull. 42, 742-744 (1994)
8. K. Foubert, F. Cuyckens, A. Matheeussen, A. Vlietinck, S. Apers, L. Maes, L. Pieters, Phytochemistry 72, 1414-1423 (2011)
9. T. Morikawa, N. Li, A. Nagatomo, H. Matsuda, X. Li, M. Yoshikawa, J. Nat. Prod. 69, 185-190 (2006)
10. T. Murakami, J. Nakamura, H. Matsuda, M. Yoshikawa, Chem. Pharm. Bull. 47, 1759-1764 (1999)
11. K. Kobayashi, T. Teruya, K. Suenaga, Y. Matsui, H. Masuda, H. Kigoshi, Phytochemistry 67, 1385-1389 (2006)
12. T. Tanaka, T. Nakashima, T. Ueda, K. Tomii, I. Kuono, Chem. Pharm. Bull. 55, 899-901 (2007)
13. T. Morikawa, H. Matsuda, N. Li, S. Nakamura, X. Li, M. Yoshikawa, Heterocycles 68, 1139-1148 (2006)
14. V.T. Amiguet, P. Petit, C.A. Ta, R. Nunez, P. Sanchez-Vindas, L.P. Alvarez, M.L. Smith, J.T. Arnason, T. Durst, J. Nat. Prod. 69, 1005-1009 (2006)
15. L. Harinantenaina, K. Matsunami, H. Otsuka, M. Kawahata, K. Yamaguchi, Y. Asakawa, J. Nat. Prod. 71, 123-126 (2008)
16. P.K. Chan, Biochem. Pharmacol. 73, 341-350 (2007)
17. T. Ikeda, S. Fujiwara, K. Araki, J. Kinjo, T. Nohara, T. Miyoshi, J. Nat. Prod. 60, 102-107 (1997)
18. T. Ogino, T. Hayasaka, S. Ito, T. Takahashi, Chem. Pharm. Bull. 16, 1846-1847 (1968)
19. S. Cao, P.J. Brodie, J.S. Miller, R. Randrianaivo, F. Ratovoson, C. Birkinshaw, R. Andriantsiferana, V.E. Rasamison, D.G.I. Kingston, J. Nat. Prod. 70, 679-681 (2007)
20. E. Pan, L. Harinantenaina, P.J. Brodie, J.S. Miller, M.W. Callmander, S. Rakotonandrasana, E. Rakotobe, V.E. Rasamison, D.G.I. Kingston, J. Nat. Prod. 73, 1792-1795 (2010)

[1]	Kittiwan Sresuksai, Sasiphimol Sawadsitang, Phongphan Jantaharn, Pakin Noppawan, Audomsak Churat, Nuttika Suwannasai, Wiyada Mongkolthanaruk, Thanaset Senawong, Sarawut Tontapha, Pairot Moontragoon, Vittaya Amornkitbamrung, Sirirath McCloskey. Antiproliferative polyketides from fungus Xylaria cf. Longipes SWUF08-81 in different culture media[J]. 应用天然产物, 2024, 14(1): 6-6.
[2]	Jing Lu, Xing-Rong Peng, Da-Shan Li, Qiang-Qiang Shi, Ming-Hua Qiu. Cytotoxic Cycloartane Triterpenoid Saponins from the Rhizomes of Cimicifuga foetida[J]. 应用天然产物, 2019, 9(4): 303-310.
[3]	Jin-Tang Cheng, Shi-Tao Chen, Cong Guo, Meng-Jiao Jiao, Wen-Jin Cui, Shu-Hui Wang, Zhe Deng, Chang Chen, Sha Chen, Jun Zhang, An Liu. Triterpenoid Saponins from the Seeds of Aesculus chinensis and Their Cytotoxicities[J]. 应用天然产物, 2018, 8(1): 47-56.

Antiproliferative Triterpenoid Saponins from Leptaulus citroides Baill. from the Madagascar Rain Forest

Antiproliferative Triterpenoid Saponins from Leptaulus citroides Baill. from the Madagascar Rain Forest

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 3

编辑推荐

Metrics

本文评价