Five new cytotoxic triterpenoid saponins from the roots of Symplocos chinensis.
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, 3beta-O-{[beta- D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3-O-acetyl)-glucuronopyranosyl}-21beta- O-[(2 Z)-3,7-dimethyl-2,6-octadienoyl]-22 alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide H, 3beta-O-{[beta-D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]- beta-D-(3-O-acetyl)-glucuronopyranosyl}-21beta-O-[(2E)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide I, 3beta-O-{[beta-D-glucopyranosyl(1-->2)][ alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3- O-acetyl-6-O-methyl)-glucuronopyranosyl}-21beta-O-[(2 Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-(2-methylbutanoyl)-R1-barrigenol, symplocososide J, 3 beta-O-{[ beta-D-glucopyranosyl(1-->2)][alpha-L-arabinofuranosyl(1-->4)]-beta-D-(3- O-acetyl)-glucuronopyranosyl}-21beta-O-[(2 Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-O-benzoyl-R1-barrigenol, and symplocososide K, 3beta-O-{[beta-D-glucopyranosyl (1-->2)][alpha-L-arabinofuranosyl(1-->4)]- beta-D-(3-O-acetyl-6-O-methyl)-glucuronopyranosyl}-21beta-O-[(2Z)3,7-dimethyl-2,6-octadienoyl]-22alpha-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 microM to 5.09 microM, 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 microM.
Fu
Guang-Miao
GM
Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, People's Republic of China.
Wang
Ying-Hong
YH
Gao
Song
S
Tang
Mei-Jun
MJ
Yu
Shi-Shan
SS
D000972:Antineoplastic Agents, Phytogenic / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D045744:Cell Line, Tumor / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells / Q000187:drug effects; D019684:Magnoliopsida; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D018517:Plant Roots; D012503:Saponins / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D014315:Triterpenes / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use
D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D012503:Saponins; D014315:Triterpenes