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Title: Synthesis, Formulation, and Adjuvanticity of Monodesmosidic Saponins with Olenanolic Acid, Hederagenin and Gypsogenin Aglycones, and some C-28 Ester Derivatives
Contributor(s): Greatrex, Ben  (author)orcid ; Daines, Alison M (author); Hook, Sarah (author); Lenz, Dirk H (author); McBurney, Warren (author); Rades, Thomas (author); Rendle, Phillip M (author)
Publication Date: 2015
Open Access: Yes
DOI: 10.1002/open.201500149Open Access Link
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Abstract: In an attempt to discover a new synthetic vaccine adjuvant, the glycosylation of hederagenin, gypsogenin, and oleanolic acid acceptors with di- and trisaccharide donors to generate a range of mimics of natural product QS-21 was carried out. The saponins were formulated with phosphatidylcholine and cholesterol, and the structures analyzed by transmission electron microscopy. 3-O-(Man'p'(1→3)Glcp)hederagenin was found to produce numerous ring-like micelles when formulated, while C-28 choline ester derivatives preferred self-assembly and did not interact with the liposomes. When alone and in the presence of cholesterol and phospholipid, the choline ester derivatives produced nanocrystalline rods or helical micelles. The effects of modifying sugar stereochemistry and the aglycone on the immunostimulatory effects of the saponins was then evaluated using the activation markers MHC class II and CD86 in murine bone marrow dendritic cells. The most active saponin, 3-O-(Man'p'(1→3)Glcp)hederagenin, was stimulatory at high concentrations in cell culture, but this did not translate to strong responses in vivo.
Publication Type: Journal Article
Source of Publication: ChemistryOpen, 4(6), p. 740-755
Publisher: Wiley-VCH Verlag GmbH & Co KGaA
Place of Publication: Germany
ISSN: 2191-1363
Field of Research (FoR) 2008: 030502 Natural Products Chemistry
030503 Organic Chemical Synthesis
030401 Biologically Active Molecules
Socio-Economic Objective (SEO) 2008: 970103 Expanding Knowledge in the Chemical Sciences
970106 Expanding Knowledge in the Biological Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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School of Rural Medicine

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