Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin “Julibroside J28” from Albizia julibrissin
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Simple and convergent synthesis of a tetra- and a trisaccharide portions of an antitumor compound Julibroside J28, 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.
KeywordsSaponin Synthesis H2SO4-silica Growth-inhibitory
We thank SAIF (CDRI) for instrumental facility. BR is thankful to CSIR, New Delhi, India for fellowship. The work is funded by DST, New Delhi, India through SERC Fast-Track Grant SR/FTP/CS-110/2005.
Supporting Information Available
Experimental details and Copies of 1H and 13C spectra of all new compounds.
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