Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue

Peng Wang, Chunxia Li, Jing Zang, Ni Song, Xiuli Zhang, Yingxia Li

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

The focus of this work was on the synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Therefore, 3-O-{[β-d-glucopyranosyl-(1→2)]-[α-l-arabinopyranosyl-(1→3) ]-α-l-arabinopyranosyl}ursolic acid-28-O-[β-d-glucopyranosyl] ester 1 was concisely synthesized by two strategies in 22% and 41% overall yield, respectively, and another congener 3-O-{[β-d-xylopyranosyl-(1→2)]- [β-d-glucopyranosyl-(1→3)]-α-l-arabinopyranosyl}ursolic acid-28-O-[β-d-glucopyranosyl] ester 2 was also efficiently prepared in 81% overall yield. The 1H NMR and 13C NMR signals of saponin 2 are all consistent with those reported for the natural product.

Original languageEnglish
Pages (from-to)2086-2096
Number of pages11
JournalCarbohydrate Research
Volume340
Issue number13
DOIs
StatePublished - 26 Sep 2005
Externally publishedYes

Keywords

  • Glycosylation
  • Saponin
  • Synthesis
  • Ursolic acid

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