Five New Cytotoxic Triterpenoid Saponins from the Roots of Symplocos chinensis

Abstract

Five new triterpenoid saponins, named symplocososides G-K, were isolated from the roots of Symplocos chinensis. Their structures were elucidated by spectral and chemical methods as symplocososide G, 3β-O-{[β-D-glucopyranosyl(1→2)][α-L-arabinofuranosyl(1→4)]-β-D-(3-O-acetyl)-glucuronopyranosyl}-21β-O-[(2Z)-3,7-dimethyl-2,6-octadienoyl]-22α-O-(2-methylbutanoyl)-R₁-barrigenol, symplocososide H, 3β-O-{[β-D-glucopyranosyl(1→2)][α-L-arabinofuranosyl(1→4)]-β-D-(3-O-acetyl)-glucuronopyranosyl}-21 β-O-[(2E)3,7-dimethyl-2,6-octadienoyl]-22α-O-(2-methylbutanoyl)-R₁-barrigenol, symplocososide I, 3β-O-{[β-D-glucopyranosyl(1→2)][α-L-arabinofuranosyl(1→4)]-β-D-(3-O-acetyl-6-O-methyl)-glucuronopyranosyl}-21β-O-[(2Z)3,7-dimethyl-2,6-octadienoyl]-22α-O-(2-methylbutanoyl)-R₁-barrigenol, symplocososide J, 3β-O-{[β-D-glucopyranosyl(1→2)][α-L-arabinofuranosyl(1→4)]-β-D-(3-O-acetyl)-glucuronopyranosyl}-21β-O-[(2Z)3,7-dimethyl-2,6-octadienoyl]-22α-O-benzoyl-R₁-barrigenol, and symplocososide K, 3β-O-{[β-D-glucopyranosyl (1→2)][α-L-arabinofuranosyl(1→4)]-β-D-(3-O-acetyl-6-O-methyl)-glucuronopyranosyl}-21β-O-[(2Z)3,7-dimethyl-2,6-octadienoyl]-22α-O-benzoyl-R₁-barrigenol. Symplocososides G-K showed significant cytotoxicity against cancer cell lines KB, HCT-8, Bel-7402, BGC-823 and A549 with IC₅₀ values ranging from 0.82 μM to 5.09 μM, except for symplocososide I against cancer cell lines KB, BGC-823, A549 and symplocososide K against cancer cell line BGC-823 with IC₅₀ values >10.00 μM.

Key words

Symplocos chinensis - Symplocaceae - symplocososides G-K - triterpenoid saponins - cytotoxic activity

References

• 1 Jiangsu New Medical C ollege. Dictionary of the Traditional Chinese Medicines. Shanghai; Shanghai Science and Technology Press 1985: p 918
• 2 Li X H, Shen D D, Li N, Yu S S. Bioactive triterpenoids from Symplocos chinensis. J.  Asian Nat Prod Res. 2003;  5 49-56
• 3 Oshima R, Kumanotani J. Determination of configuration of monosaccharides by HPLC on diastereoisomeric 1-deoxy-1-(N-acetyl-α-methylbenzylamino)alditol acetates. Chem Lett 1981: 943-6
• 4 Olugbade T A, Ogundaini A, Birlirakis N, Pais M, Martin M -T. Petersaponins III and IV, triterpenoid saponins from Petersianthus macrocarpus. J. Nat.  Prod.. 2000;  63 716-9
• 5 Yu D Q, Yang J S. Analysis Chemistry Handbook. Chinese Chemical Industry Publishing House 1999 7: p 754
• 6 Lu Y, Umeda T, Yagi A, Sakata K, Chaudhuri T, Ganguly D K. et al . Triterpenoid saponins from the roots of tea plant (Camellia sinensis var. assamica).  Phytochemistry. 2000;  53 941-6
• 7 Konoshima T, Lee K -H. Antitumor agents, 82. cytotoxic sapogenols from Aesculus hippocastanum. J. Nat.  Prod.. 1986;  49 650-6