New triterpenoid saponins from the leaves of Cyclocarya paliurus

Bao-Song Cui Shuai Li

Citation:  Bao-Song Cui, Shuai Li. New triterpenoid saponins from the leaves of Cyclocarya paliurus[J]. Chinese Chemical Letters, 2015, 26(5): 585-589. doi: 10.1016/j.cclet.2014.11.033 shu

New triterpenoid saponins from the leaves of Cyclocarya paliurus

    通讯作者: Shuai Li,
  • 基金项目:

    Technology Project of China (No. 2012ZX09301002001003). (No. 2012ZX09301002001003)

摘要: Two new secodammarane triterpenoid saponins, cyclocariosides I and J (1 and 2), and a new epoxydammarane triterpenoid saponin, cyclocarioside K (3) were isolated from the ethanol extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic techniques.

English

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    1. [1] Editor Committee for Flora of China of the Chinese Academy of Science, Flora of China, vol. 21, Science Publishing House, Beijing, 1979, pp. 18-19.[1] Editor Committee for Flora of China of the Chinese Academy of Science, Flora of China, vol. 21, Science Publishing House, Beijing, 1979, pp. 18-19.

    2. [2] The Editorial Committee of the Administration Bureau of Traditional Chinese Medicine, Chinese Materia Medica, vol. 2, Shanghai Science and Technology Publishing House, Shanghai, 1999, pp. 370-371.[2] The Editorial Committee of the Administration Bureau of Traditional Chinese Medicine, Chinese Materia Medica, vol. 2, Shanghai Science and Technology Publishing House, Shanghai, 1999, pp. 370-371.

    3. [3] H. Kurihara, S. Asami, H. Shibata, H. Fukami, T. Tanaka, Hypolipemic effect of Cyclocarya paliurus (Batal) Iljinskaja in lipid-loaded mice, Biol. Pharm. Bull. 26 (2003) 383-385.[3] H. Kurihara, S. Asami, H. Shibata, H. Fukami, T. Tanaka, Hypolipemic effect of Cyclocarya paliurus (Batal) Iljinskaja in lipid-loaded mice, Biol. Pharm. Bull. 26 (2003) 383-385.

    4. [4] R.G. Shu, C.R. Xu, L.N. Li, Studies on the sweet principles from the leaves of Cyclocarya paliurus (Batal.) Iljinsk, Acta Pharm. Sin. 30 (1995) 757-761.[4] R.G. Shu, C.R. Xu, L.N. Li, Studies on the sweet principles from the leaves of Cyclocarya paliurus (Batal.) Iljinsk, Acta Pharm. Sin. 30 (1995) 757-761.

    5. [5] R.G. Shu, C.R. Xu, L.N. Li, Z.L. Yu, Cyclocariosides II and III: two secodammarane triterpenoid saponins from Cyclocarya paliurus, Planta Med. 61 (1995) 551-553.[5] R.G. Shu, C.R. Xu, L.N. Li, Z.L. Yu, Cyclocariosides II and III: two secodammarane triterpenoid saponins from Cyclocarya paliurus, Planta Med. 61 (1995) 551-553.

    6. [6] E.J. Kennelly, L.N. Cai, L.N. Long, et al., Novel highly sweet secodammarane glycosides from Pterocarya puliurus, J. Agric. Food Chem. 43 (1995) 2602-2607.[6] E.J. Kennelly, L.N. Cai, L.N. Long, et al., Novel highly sweet secodammarane glycosides from Pterocarya puliurus, J. Agric. Food Chem. 43 (1995) 2602-2607.

    7. [7] Z.Y. Jiang, X.M. Zhang, J. Zhou, S.X. Qiu, J.J. Chen, Two new triterpenoid glycosides from Cyclocarya paliurus, J. Asian Nat. Prod. Res. 8 (2006) 93-98.[7] Z.Y. Jiang, X.M. Zhang, J. Zhou, S.X. Qiu, J.J. Chen, Two new triterpenoid glycosides from Cyclocarya paliurus, J. Asian Nat. Prod. Res. 8 (2006) 93-98.

    8. [8] D.J. Yang, Z.C. Zhong, Z.M. Xie, Studies on the sweet principles from the leaves of Cyclocarya paliurus (Batal.) Iljinskaya, Acta Pharm. Sin. 27 (1992) 841-844.[8] D.J. Yang, Z.C. Zhong, Z.M. Xie, Studies on the sweet principles from the leaves of Cyclocarya paliurus (Batal.) Iljinskaya, Acta Pharm. Sin. 27 (1992) 841-844.

    9. [9] R.J. Zhong, R.G. Shu, X.L. Ni, C.R. Xu, L.N. Li, Studies on the chemical structure of Cyclocaric acid A, Acta Pharm. Sin. 31 (1996) 398-400.[9] R.J. Zhong, R.G. Shu, X.L. Ni, C.R. Xu, L.N. Li, Studies on the chemical structure of Cyclocaric acid A, Acta Pharm. Sin. 31 (1996) 398-400.

    10. [10] R.J. Zhong, Y.H. Gao, C.R. Xu, L.N. Li, Pentacyclic triterpenoids from Rounduingfruit Cyclocarya (Cyclocarya paliurus), Chin. Trad. Herbal Drugs 27 (1996) 387-388.[10] R.J. Zhong, Y.H. Gao, C.R. Xu, L.N. Li, Pentacyclic triterpenoids from Rounduingfruit Cyclocarya (Cyclocarya paliurus), Chin. Trad. Herbal Drugs 27 (1996) 387-388.

    11. [11] R.G. Shu, Z.R. Song, J.C. Shu, Study on the chemical constituents of the butanol extraction of Cyclocarya paliurus (Batal.) Iljinsk, J. Chin. Med. Mater. 29 (2006) 1304-1307.[11] R.G. Shu, Z.R. Song, J.C. Shu, Study on the chemical constituents of the butanol extraction of Cyclocarya paliurus (Batal.) Iljinsk, J. Chin. Med. Mater. 29 (2006) 1304-1307.

    12. [12] R.G. Shu, J.C. Shu, Phenolic constituents of Cyclocarya paliurus, Chin. Trad. Herbal Drugs 38 (2007) 507-508.[12] R.G. Shu, J.C. Shu, Phenolic constituents of Cyclocarya paliurus, Chin. Trad. Herbal Drugs 38 (2007) 507-508.

    13. [13] J. Li, Y.Y. Lu, F. Li, et al., Study on chemical constituents of Cyclocarya paliurus, J. Chin. Med. Mater. 29 (2006) 441-442.[13] J. Li, Y.Y. Lu, F. Li, et al., Study on chemical constituents of Cyclocarya paliurus, J. Chin. Med. Mater. 29 (2006) 441-442.

    14. [14] B.S. Cui, S. Li, Studies on chemical constituents from the leaves of Cyclocarya paliurus, Chin. Trad. Herbal Drugs 43 (2012) 2132-2136.[14] B.S. Cui, S. Li, Studies on chemical constituents from the leaves of Cyclocarya paliurus, Chin. Trad. Herbal Drugs 43 (2012) 2132-2136.

    15. [15] S. Li, B.S. Cui, Q. Liu, et al., New Triterpenoids from the leaves of Cyclocarya paliurus, Planta Med. 78 (2012) 290-296.[15] S. Li, B.S. Cui, Q. Liu, et al., New Triterpenoids from the leaves of Cyclocarya paliurus, Planta Med. 78 (2012) 290-296.

    16. [16] C. Seger, S. Pointinger, H. Greger, O. Hofer, Isoeichlerianic acid from Aglaia silvestris and revision of the stereochemistry of foveolin B, Tetrahedron Lett. 49 (2008) 4313-4315.[16] C. Seger, S. Pointinger, H. Greger, O. Hofer, Isoeichlerianic acid from Aglaia silvestris and revision of the stereochemistry of foveolin B, Tetrahedron Lett. 49 (2008) 4313-4315.

    17. [17] T. Aoki, S. Ohta, T. Suga, Six novel secodammarane-tape triterpenes from male flower of Alnus Japonica, Phytochemistry 27 (1988) 2915-2920.[17] T. Aoki, S. Ohta, T. Suga, Six novel secodammarane-tape triterpenes from male flower of Alnus Japonica, Phytochemistry 27 (1988) 2915-2920.

    18. [18] T. Hirata, R. Ideo, T. Suga, Structure of Alnuselide, the first reported naturally occurring C31-secodammarane-type triterpene lactone from Alnus Serrulatoides, Chem. Lett. 6 (1977) 711-714.[18] T. Hirata, R. Ideo, T. Suga, Structure of Alnuselide, the first reported naturally occurring C31-secodammarane-type triterpene lactone from Alnus Serrulatoides, Chem. Lett. 6 (1977) 711-714.

    19. [19] A. Tadashi, O. Shinji, A. Satoshi, H. Toshifumi, S. Takayuki, The structures of four novel C31-secodammarane-type triterpenoid saponins from the female flowers of Alnus serrdatoides, J. Chem. Soc. Perkin Trans. 1 (1982) 1399-1403.[19] A. Tadashi, O. Shinji, A. Satoshi, H. Toshifumi, S. Takayuki, The structures of four novel C31-secodammarane-type triterpenoid saponins from the female flowers of Alnus serrdatoides, J. Chem. Soc. Perkin Trans. 1 (1982) 1399-1403.

    20. [20] T. Suga, S. Ohta, E. Ohta, T. Aoki, A C31-secodammarane-type triterpenic acid, 12- deoxy alnustic acid, from the female flowers of Alnus pendula, Phytochemistry 25 (1986) 1243-1244.[20] T. Suga, S. Ohta, E. Ohta, T. Aoki, A C31-secodammarane-type triterpenic acid, 12- deoxy alnustic acid, from the female flowers of Alnus pendula, Phytochemistry 25 (1986) 1243-1244.

    21. [21] T.R. Govindachari, G. Suresh, G.N. Krishna Kumari, Triterpenoids from Dysoxylum Malabaricum, Phytochemistry 37 (1994) 1127-1129.[21] T.R. Govindachari, G. Suresh, G.N. Krishna Kumari, Triterpenoids from Dysoxylum Malabaricum, Phytochemistry 37 (1994) 1127-1129.

    22. [22] L.K. Wah, F. Abas, G.A. Cordell, H. Ito, I.S. Ismail, Steroids from Dysoxylum grande (Meliaceae) leaves, Steroids 78 (2013) 210-219.[22] L.K. Wah, F. Abas, G.A. Cordell, H. Ito, I.S. Ismail, Steroids from Dysoxylum grande (Meliaceae) leaves, Steroids 78 (2013) 210-219.

    23. [23] S. Yogendra, A. William, Dammarane triterpenoids from Dysoxylum richii, Phytochemistry 31 (1992) 4033-4035.[23] S. Yogendra, A. William, Dammarane triterpenoids from Dysoxylum richii, Phytochemistry 31 (1992) 4033-4035.

    24. [24] C.O. Esimone, G. Eck, T.N. Duong, et al., Potential anti-respiratory syncytial virus lead compounds from Aglaia species, Pharmazie 63 (2008) 768-773.[24] C.O. Esimone, G. Eck, T.N. Duong, et al., Potential anti-respiratory syncytial virus lead compounds from Aglaia species, Pharmazie 63 (2008) 768-773.

    25. [25] K. Mohamad, T. Sévenet,V. Dumontet, et al., Dammarane triterpenes and pregnane steroids from Aglaia lawii and A. tomentosa, Phytochemistry 51 (1999) 1031-1037.[25] K. Mohamad, T. Sévenet,V. Dumontet, et al., Dammarane triterpenes and pregnane steroids from Aglaia lawii and A. tomentosa, Phytochemistry 51 (1999) 1031-1037.

    26. [26] H. Desi, T. Roekmiati, S. Agus, et al., Cytotoxic triterpenoids from the bark of Aglaia smithii (Meliaceae), Phytochem. Lett. 5 (2012) 496-499.[26] H. Desi, T. Roekmiati, S. Agus, et al., Cytotoxic triterpenoids from the bark of Aglaia smithii (Meliaceae), Phytochem. Lett. 5 (2012) 496-499.

    27. [27] N. Joycharat, P. Plodpai, K. Panthong, Y. Boonek, P. Supayang, Terpenoid constituents and antifungal activity of Aglaia forbesii seed against phytopathogens, Can. J. Chem. 88 (2010) 937-944.[27] N. Joycharat, P. Plodpai, K. Panthong, Y. Boonek, P. Supayang, Terpenoid constituents and antifungal activity of Aglaia forbesii seed against phytopathogens, Can. J. Chem. 88 (2010) 937-944.

    28. [28] S. Pointinger, S. Promdang, S. Vajrodaya, et al., Silvaglins and related 2,3-secodammarane derivatives-unusual types of triterpenes from Aglaia silvestris, Phytochemistry 69 (2008) 2696-2703.[28] S. Pointinger, S. Promdang, S. Vajrodaya, et al., Silvaglins and related 2,3-secodammarane derivatives-unusual types of triterpenes from Aglaia silvestris, Phytochemistry 69 (2008) 2696-2703.

    29. [29] M.M. Rao, H. Meshulam, R. Zelnik, D. Lavie, Cabralea eichleriana DC. (Meliaceae) - I Structure and stereochemistry of wood extractives, Tetrahedron 31 (1975) 333- 339.[29] M.M. Rao, H. Meshulam, R. Zelnik, D. Lavie, Cabralea eichleriana DC. (Meliaceae) - I Structure and stereochemistry of wood extractives, Tetrahedron 31 (1975) 333- 339.

    30. [30] C.O. Esimone, G. Eck, C.S. Nworu, et al., Dammarenolic acid, a secodammarane triterpenoid from Aglaia sp. shows potent anti-retroviral activity in vitro, Phytomedicine 17 (2010) 540-547.[30] C.O. Esimone, G. Eck, C.S. Nworu, et al., Dammarenolic acid, a secodammarane triterpenoid from Aglaia sp. shows potent anti-retroviral activity in vitro, Phytomedicine 17 (2010) 540-547.

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  • 发布日期:  2014-12-04
  • 收稿日期:  2014-01-20
  • 网络出版日期:  2014-11-19
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