Facile synthesis of trisaccharide moiety corresponding to antitumor activity in triterpenoid saponins isolated from Pullsatilla roots.
A trisaccharide found in triterpenoid saponins isolated from Pullsatilla roots appears as an important promoiety for the enhancement of anticancer activity of their aglycones. Thus a facile synthetic method for a trisaccharide moiety, allyl-2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1-->2)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->4)]-3-O-benzoyl-beta-L-arabinopyranoside (3), has been firstly developed through the regio- and stereoselective glycosylations from arabinose in total 16% yield via route 2 (eight steps). In this synthetic procedure, the protection of anomeric -OH of L-arabinose with equatorially oriented allyl group unlike with the axial 4-methoxybenzyl protecting group well promoted glycosyl bond formation between alpha-L-rhamnopyranosyl trichloroacetimidate and 2-OH of arabinose. As expected, the synthesized trisaccharide moiety 3 has no cytotoxicity (ED50: >100 microM) against three human cancer cell lines (A-549, SK-OV-3, and SK-MEL-2), respectively.
Bang
Seong-Cheol
SC
College of Pharmacy, Chungnam National University, Daejon 305-764, Korea.
Seo
Hyun-Hee
HH
Yun
Hwi-Yeol
HY
Jung
Sang-Hun
SH
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D018517:Plant Roots / Q000737:chemistry; D029626:Ranunculaceae / Q000737:chemistry*; D012503:Saponins / Q000138:chemical synthesis* / Q000494:pharmacology*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000494:pharmacology*; D014315:Triterpenes / Q000138:chemical synthesis* / Q000494:pharmacology*
D000972:Antineoplastic Agents, Phytogenic; D007202:Indicators and Reagents; D012503:Saponins; D014312:Trisaccharides; D014315:Triterpenes