Triterpenoid Saponins from Ardisia pusilla and their Cytotoxic Activity

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.

Ardisia pusilla - Myrsinaceae - triterpenoid saponin - cytotoxicity - glioblastoma

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