title: Implication of the stereoisomers of ginsenoside derivatives in the antiproliferative effect of HSC-T6 cells.
abstract: Two ginsenoside derivatives (9, 10) along with 10 known ginsenosides (1-8, 11, and 12) were isolated from BST204, which is a crude ginseng extract fermented by enzyme and acid hydrolysis. The two ginsenosides were determined as 12β,20(S),25-trihydroxydammara-3-O-β-D-glucopyranoside (9) and 12β,20(R),25-trihydroxydammara-3-O-β-D-glucopyranoside (10). Compounds 1-12 were categorized into stereoisomeric pairs differentiated by R- or S-configuration at C-20, the number or position of sugar residues at C-3 or C-6, and the type of derivative at C-21. Their structure-activity relationship was evaluated by the cell viability assay using HSC-T6 cells. Results showed that 20(S) (3 > 4, 7 > 8, and 9 > 10), a 2-hydroxy-2-methylbutyl moiety at C-21 (3, 7 > 9), and the number of sugar residues at C-3 (3 > 7) significantly affected the antiproliferative activity on HSC-T6 cells. The inhibition of the cell proliferation of compound 3 was assessed by annexin-V/PI staining analysis using flow cytometry.
authors.affiliation: College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Daehak-Dong, Gwanak-Gu, Seoul 151-742, Republic of Korea.
authors.forename: Heejung
authors.initials: H
authors.lastname: Yang
authors.forename: Guijae
authors.initials: G
authors.lastname: Yoo
authors.forename: Hye Seong
authors.initials: HS
authors.lastname: Kim
authors.forename: Jeom Yong
authors.initials: JY
authors.lastname: Kim
authors.forename: Sun Ok
authors.initials: SO
authors.lastname: Kim
authors.forename: Young Hyo
authors.initials: YH
authors.lastname: Yoo
authors.forename: Sang Hyun
authors.initials: SH
authors.lastname: Sung
mesh_terms: D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects*; D005285:Fermentation; D036145:Ginsenosides / Q000737:chemistry* / Q000494:pharmacology*; D055166:Hepatic Stellate Cells / Q000187:drug effects*; D008103:Liver Cirrhosis; D005894:Panax / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D036145:Ginsenosides; D010936:Plant Extracts