Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin "Julibroside J28" from Albizia julibrissin.

Abstract

Simple and convergent synthesis of a tetra- and a trisaccharide portions of an antitumor compound Julibroside J(28), isolated from Albizia julibrissin, that showed significant in vitro antitumor activity against HeLa, Bel-7402 and PC-3M-1E8 cancer cell lines is reported. The tetrasaccharide has been synthesized as its p-methoxyphenyl glycoside starting from commercially available D-glucose, L-rhamnose and L-arabinose. The trisaccharide part has been synthesized from commercially available N-acetyl D-glucosamine, D-fucose and D-xylose using simple protecting group manipulations. Sulfuric acid immobilized on silica has been used successfully as a Brönsted acid catalyst for the crucial glycosylation steps.

• Authors: Bimalendu Roy, Kausikisankar Pramanik, Balaram Mukhopadhyay
• Journal: Glycoconjugate journal (Glycoconj J) Vol. 25 Issue 2 Pg. 157-66 (Feb 2008) ISSN: 0282-0080 [Print] United States
• PMID: 17701454 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents, Phytogenic
• Saponins
• Trisaccharides
• Triterpenes
• julibroside J28

Topics

• Albizzia (chemistry)
• Antineoplastic Agents, Phytogenic (chemical synthesis, pharmacology)
• Carbohydrate Sequence
• HeLa Cells
• Humans
• Molecular Sequence Data
• Saponins (chemistry, pharmacology)
• Trisaccharides (chemical synthesis, pharmacology)
• Triterpenes (chemistry, pharmacology)