Journal
MOLECULES
Volume 27, Issue 8, Pages -Publisher
MDPI
DOI: 10.3390/molecules27082402
Keywords
Quillaja brasiliensis; immunoadjuvant saponins; structural analysis; NMR spectroscopy; QS-21 isomer
Funding
- Agencia Nacional de Investigacion e Innovacion (ANII) [FMV_3_2018_1_149104]
- Programa de Desarrollo de las Ciencias Basicas (PEDECIBA)
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In this study, two compounds were isolated from the aqueous extract of Quillaja brasiliensis leaves, one of which is a previously undescribed triterpene saponin (Qb1) with potential vaccine adjuvant application. The structure of Qb1 and another known triterpene saponin (S13) were elucidated.
An immunoadjuvant preparation (named Fraction B) was obtained from the aqueous extract of Quillaja brasiliensis leaves, and further fractionated by consecutive separations with silica flash MPLC and reverse phase HPLC. Two compounds were isolated, and their structures elucidated using a combination of NMR spectroscopy and mass spectrometry. One of these compounds is a previously undescribed triterpene saponin (Qb1), which is an isomer of QS-21, the unique adjuvant saponin employed in human vaccines. The other compound is a triterpene saponin previously isolated from Quillaja saponaria bark, known as S13. The structure of Qb1 consists of a quillaic acid residue substituted with a beta-d-Galp-(1 -> 2)-[beta-d-Xylp-(1 -> 3)]-beta-d-GlcpA trisaccharide at C3, and a beta-d-Xylp-(1 -> 4)-alpha-l-Rhap-(1 -> 2)-[alpha-l-Arap-(1 -> 3)]-beta-d-Fucp moiety at C28. The oligosaccharide at C28 was further substituted at O4 of the fucosyl residue with an acyl group capped with a beta-d-Xylp residue.
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