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DOI: 10.1055/s-0028-1088369
© Georg Thieme Verlag KG Stuttgart · New York
Triterpenoid Saponins from Ardisia pusilla and their Cytotoxic Activity
Publication History
Received: July 20, 2008
Revised: September 10, 2008
Accepted: September 12, 2008
Publication Date:
27 November 2008 (online)
Abstract
Three new triterpenoid saponins 3, 4 and 5, together with two known saponins, ardisiacrispin B (1) and ardisiacrispin A (2), were isolated from the whole plants of Ardisia pusilla A. DC. Their structures were elucidated by extensive spectral analysis and chemical evidence. Compound 3 is a hexaglycoside with a 13,28-epoxyoleanane type aglycone, while both 4 and 5 are triterpenoid tetraglycosides related to the olean-12-ene skeleton. Saponins 1 – 4 exhibited significant cytotoxicity against human glioblastoma U251MG cells, but did not affect the growth of primary cultured human astrocytes.
Key words
Ardisia pusilla - Myrsinaceae - triterpenoid saponin - cytotoxicity - glioblastoma
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References
- 1 Jiangsu College of New Medicine. Dictionary of Chinese Materia Medica. Shanghai; Shanghai People’s Publishing House 1977: 892
- 2 Perry L M, Metager J. Medicinal plants of East and South-east Asia. Cambridge; MIT Press 1980
- 3 Zhang Q H, Wang X J, Miao Z C, Feng R. Studies on the saponin constituents of Jiu Jielong (Ardisia pusilla). Acta Pharm Sin. 1993; 28 673-8
- 4 Miao Z C, Feng R, Zhou Y X, Li G Y, Zhang Q H. NMR and chemical structure of a new saponin from Jiu Jielong (Ardisia pusilla). Chin J Org Chem. 2000; 20 361-6
- 5 Tao X J, Wang P X, Yang X J, Yao H P, Liu J, Cao Y X. Inhibitory effect of ardipusilloside-I on Lewis pulmonary carcinoma and hepatocarcinoma SMMC-7721. Zhong Yao Cai (J Chin Med Mater). 2005; 28 574-7
- 6 Tang H F, Yi Y H, Li L, Sun P, Zhang S Q, Zhao Y P. Three new asterosaponins from the starfish Culcita novaeguineae and their bioactivity. Planta Med. 2005; 71 458-63
- 7 Tang H F, Yi Y H, Li L, Sun P, Zhang S Q, Zhao Y P. Bioactive asterosaponins from the starfish Culcita novaeguineae. J Nat Prod. 2005; 68 337-41
- 8 Tang H F, Yi Y H, Zhang S Y, Sun P, Li L, Zhou D Z. A new cyclic bisdesmoside from tubers of Bolbostemma paniculatum. Chin Chem Lett. 2005; 16 479-82
- 9 Cheng G, Zhang X, Tang H F, Zhang Y, Zhang X H, Cao W D. et al . Asterosaponin 1, a cytostatic compound from the starfish Culcita novaeguineae, fuctions by inducing apoptosis in human glioblastoma U87MG cells. J Neurooncol. 2006; 79 235-41
- 10 Lin H, Zhang X, Cheng G, Tang H F, Zhang W, Zhen H N. et al . Apoptosis induced by ardipusilloside III through BAD dephosphorylation and cleavage in human glioblastoma U251MG cells. Apoptosis. 2008; 13 247-57
- 11 Denizot F, Lang R. Rapid colorimetric assay for cell growth and survival, modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods. 1986; 89 271-7
- 12 Jia Z H, Koike K, Ohmoto T, Ni M. Triterpenoid saponins from Ardisia crenata. Phytochemistry. 1994; 37 1389-96
- 13 Jansakul C, Baumann H, Kenne L, Samuelsson G. Ardisiacrispin A and B, two utero-contracting saponins from Ardisia crispa. Planta Med. 1987; 53 405-9
- 14 De Marino S, Borbone N, Iorizzi M, Esposito G, McClintock J B, Zollo F. Bioactive asterosaponins from the starfish Luidia quinaria and Psilaster cassiope, isolation and structure characterization by two-dimensional NMR spectroscopy. J Nat Prod. 2003; 66 515-9
- 15 De Tommasi N, Piacente S, De Simone F, Pizza C, Zhou Z L. Characterization of three new triterpenoid saponins from Ardisia japonica. J Nat Prod. 1993; 56 1669-75
- 16 Chang X L, Li W, Jia Z H, Satou T, Fushiya S, Koike K. Biological active triterpenoid saponins from Ardisia japonica. J Nat Prod. 2007; 70 179-87
- 17 Akai E, Takeda T, Kobayashi Y, Chen Y J, Ogihara Y. Minor triterpenoid saponins from the leaves of Bupleurum rotundifolium L. Chem Pharm Bull. 1985; 33 4685-90
- 18 Takahashi H, Iuchi M, Fujita Y, Minami H, Fukuyama Y. Coumaroyl triterpenes from Casuarina equisetifolia. Phytochemistry. 1999; 51 543-50
Dr. Hai-Feng Tang
Department of Pharmacy
Xijing Hospital
Fourth Military Medical University
15 Changle West Road
Xi’an 710032
People’s Republic of China
Phone: +86-29-8477-5471
Fax: +86-29-8477-5471
Email: tanghaifeng71@163.com
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