Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 17, Issue 14, Pages 5207-5218Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2009.05.043
Keywords
Saponins; Glycosylation; Oleanolic acid; Glycyrrhizic acid; ISCOMs; Nanostructures
Funding
- Foundation for Research Science and Technology, New Zealand [CO8X0303]
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Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.
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