Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy

Ying Hsin Wang, Hsien Wei Yeh, Hsiao Wen Wang, Chia Chun Yu, Jih Hwa Guh, Der Zen Liu, Pi Hui Liang

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Naturally occurring spirostanol saponins bear a chacotriose, α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)] -β-d-glucopyranose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2′ and/or 4′ positions of chacotriose is described and the structure-activity relationships of the glycone part at 3-OH of chlorogenin investigated. These compounds were found to be weakly-cytotoxic toward leukemia cell lines CCRF and HL-20, indicating that the chacotriose moiety is important for anticancer activity.

Original languageEnglish
Pages (from-to)118-135
Number of pages18
JournalCarbohydrate Research
Volume375
DOIs
Publication statusPublished - 2013

Keywords

  • Chacotriose
  • Cytotoxicity
  • Dioscin
  • Glycoside

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

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