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.

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

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