Separation and structural analysis of some saponins from Quillaja saponaria Molina

• Published in: Carbohydrate research Vol. 323; no. 1; pp. 87 - 97
• Main Authors: Nyberg, Nils T., Kenne, Lennart, Rönnberg, Bengt, Sundquist, Bo G.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.01.1999
• Subjects: O-Acyl migration; Quillaic acid; Quillaja saponaria Molina; Saponins; Saponins; Quillaja saponaria Molina; Quillaic acid; O-Acyl migration
• DOI: 10.1016/S0008-6215(99)00227-X
• ISSN: 0008-6215

A fraction of saponins from Quillaja saponaria Molina, QH-B, was fractionated by consecutive separations on three different reverse-phase HPLC systems. Eight compounds were isolated and the structures of these were elucidated mainly by sugar analysis and NMR spectroscopy. The structures consisted of a quillaic acid substituted with two different trisaccharides at C-3, β- d-Gal p-(1→2)-[α- l-Rha p-(1→3)]-β- d-Glc pA and β- d-Gal p-(1→2)-[β- d-Xyl p-(1→3)]-β- d-Glc pA, and a tetra- or pentasaccharide at C-28, β- d-Xyl p-(1→4)-[β- d-Glc p-(1→3)]-α- l-Rha p-(1→2)-β- d-Fuc p and β- d-Api f-(1→3)-β- d-Xyl p-(1→4)-[β- d-Glc p-(1→3)]-α- l-Rha p-(1→2)-β- d-Fuc p. These compounds were further substituted with an acyl group either at O-3 or O-4 of the fucose residue, which is the sugar linked to C-28 of the quillaic acid.