Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596483
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Triterpene glycosides from plants for antibody recognition

E Peroni
1   Laboratory of Peptide and Protein Chemistry and Biology, University of Florence, 50019 Sesto Fiorentino, Italy
3   Laboratory of Chemical Biology EA 4505 & PeptLab@UCP, Université de Cergy-Pontoise, 95031 Cergy-Pontoise cedex, France
,
F Real Fernández
1   Laboratory of Peptide and Protein Chemistry and Biology, University of Florence, 50019 Sesto Fiorentino, Italy
2   Department of Chemistry “Ugo Schiff” and NEUROFARBA Department, section of Pharmaceutical Sciences and Nutraceutics, University of Florence, 50019 Sesto Fiorentino, Italy
,
C Gheri
1   Laboratory of Peptide and Protein Chemistry and Biology, University of Florence, 50019 Sesto Fiorentino, Italy
2   Department of Chemistry “Ugo Schiff” and NEUROFARBA Department, section of Pharmaceutical Sciences and Nutraceutics, University of Florence, 50019 Sesto Fiorentino, Italy
,
F Nuti
1   Laboratory of Peptide and Protein Chemistry and Biology, University of Florence, 50019 Sesto Fiorentino, Italy
2   Department of Chemistry “Ugo Schiff” and NEUROFARBA Department, section of Pharmaceutical Sciences and Nutraceutics, University of Florence, 50019 Sesto Fiorentino, Italy
,
AC Mitaine-Offer
4   Laboratoire de Pharmacognosie, EA 4267 FDE, Université de Bourgogne-Franche-Comté, 21079 Dijon cedex, France
,
F Lolli
1   Laboratory of Peptide and Protein Chemistry and Biology, University of Florence, 50019 Sesto Fiorentino, Italy
5   Department of Biomedical, Experimental and Clinical Sciences, University of Florence, 50134 Firenze, Italy
,
MA Lacaille-Dubois
4   Laboratoire de Pharmacognosie, EA 4267 FDE, Université de Bourgogne-Franche-Comté, 21079 Dijon cedex, France
,
AM Papini
1   Laboratory of Peptide and Protein Chemistry and Biology, University of Florence, 50019 Sesto Fiorentino, Italy
2   Department of Chemistry “Ugo Schiff” and NEUROFARBA Department, section of Pharmaceutical Sciences and Nutraceutics, University of Florence, 50019 Sesto Fiorentino, Italy
3   Laboratory of Chemical Biology EA 4505 & PeptLab@UCP, Université de Cergy-Pontoise, 95031 Cergy-Pontoise cedex, France
› Author Affiliations
Further Information

Publication History

Publication Date:
14 December 2016 (online)

 

Multiple sclerosis is an autoimmune disease that affects the central nervous system. The key role of glycosylation in disease pathogenesis has been studied previously and the synthetic N-glucosylated peptide CSF114 (Glc) proved its efficiency in autoantibody recognition in sera of multiple sclerosis patients [1]. Therefore, it was interesting to test natural compounds such as triterpene glycosides from plants, possessing a wide variety of glycosyl moieties for autoantibody recognition. Five molecules, isolated from different plants were tested in sera from multiple sclerosis patients to better understand the role of glycosylation: two presenegenin glycosides from the Polygalaceae family [2], two sulfated quinovic acid glycosides from the Zygophyllaceae family [3], and one cycloartane glycoside from the Asteraceae family [4]. The interaction between these glycosides and autoantibodies was evaluated by ELISA measuring IgG and IgM levels in multiple sclerosis patients and healthy blood donors, and results were compared with those for CSF114(Glc). The ursolic acid was chosen to evaluate the activity of the aglycon only and thus the role of the oligosaccharidic part of the molecule. The five natural triterpene glycosides showed good capacity to recognize IgMs (sensitivity up to 38%) with high specificity (88.9%) for multiple sclerosis patients [5]. According to the biological results, the best structures to be selected have been deduced: monodesmosidic triterpene glycosides with only one glucopyranosyl moiety in position C-3 or bidesmosidic with one sugar, sulfated or not, at the C-3 position and a substitution with only one glucopyranosyl moiety at the C-24 or C-28 position. The ursolic acid presenting the scaffold of the five glycosides but lacking the glycosyl moieties was not able to identify specific MS antibodies.

Keywords: Multiple sclerosis, triterpene glycosides, autoimmune disease, biomarkers, autoantibody recognition.

References:

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[2] Lacaille-Dubois M-A, Mitaine-Offer A-C. Triterpene saponins from Polygalaceae. Phytochemistry Rev 2005; 4: 139 – 149

[3] Smati D, Mitaine-Offer A-C, Miyamoto T, Hammiche V, Lacaille-Dubois M-A. Ursane-type triterpene saponins from Zygophyllum geslini. Helv Chim Acta 2007; 90: 712 – 719

[4] Mitaine-Offer A-C, Miyamoto T, Semmar N, Jay M, Lacaille-Dubois M-A. A new oleanane glycoside from the roots of Astragalus caprinus. Magn Reson Chem 2006; 44: 713 – 716

[5] Peroni E, Real Fernández F, Gheri C, Nuti F, Mitaine-Offer A-C, Lolli F, Lacaille-Dubois M-A, Papini AM. Natural triterpene glycosides for antibody recognition. Planta Med Lett 2016; 3: e1-e6