Planta Med 2019; 85(18): 1568
DOI: 10.1055/s-0039-3400149
Main Congress Poster
Poster Session 2
© Georg Thieme Verlag KG Stuttgart · New York

Characterization of glycosylated flavonoids obtained from enzymatic reaction by matrix free laser desorption ionization mass spectrometry (LDI-MS)

S Boisard
1   University of Angers, SONAS/SFR QUASAV, Campus du Végétal,, 42 rue Georges Morel, 49070 Beaucouzé, France
,
T Brouté
1   University of Angers, SONAS/SFR QUASAV, Campus du Végétal,, 42 rue Georges Morel, 49070 Beaucouzé, France
,
J Guerry
2   University of Nantes, UFIP/ UMR CNRS 6286/UFR Sciences et Techniques,, 2, rue de la Houssinière, BP 92208/44322 NANTES Cedex 3, France
,
M Škopíková
1   University of Angers, SONAS/SFR QUASAV, Campus du Végétal,, 42 rue Georges Morel, 49070 Beaucouzé, France
,
I Freuze
3   University of Angers,, SFR MATRIX, 2 bd Lavoisier, 49045 Angers, France
,
C Solleux
2   University of Nantes, UFIP/ UMR CNRS 6286/UFR Sciences et Techniques,, 2, rue de la Houssinière, BP 92208/44322 NANTES Cedex 3, France
,
C Miral
2   University of Nantes, UFIP/ UMR CNRS 6286/UFR Sciences et Techniques,, 2, rue de la Houssinière, BP 92208/44322 NANTES Cedex 3, France
,
B Offmann
2   University of Nantes, UFIP/ UMR CNRS 6286/UFR Sciences et Techniques,, 2, rue de la Houssinière, BP 92208/44322 NANTES Cedex 3, France
,
A Schinkovitz
1   University of Angers, SONAS/SFR QUASAV, Campus du Végétal,, 42 rue Georges Morel, 49070 Beaucouzé, France
,
P Richomme
1   University of Angers, SONAS/SFR QUASAV, Campus du Végétal,, 42 rue Georges Morel, 49070 Beaucouzé, France
,
D Guilet
1   University of Angers, SONAS/SFR QUASAV, Campus du Végétal,, 42 rue Georges Morel, 49070 Beaucouzé, France
› Author Affiliations
Further Information

Publication History

Publication Date:
20 December 2019 (online)

 

Plant polyphenols such as stilbenoids and flavonoids exhibit a wide range of biological effects such as antioxidant activities and therefore represent an interesting field of research [1]. However, due to their poor solubility in water, glycosylation is generally employed to improve their bioavailability as well as biochemical and pharmaceutical properties [2]. Among different possible pathways, enzymatic glycosylation using sucrose phosphorylase from Bifidobacterium adolescentis (BaSP) as enzyme, sucrose as donnor and stilbenoids or flavonoids as polyphenolic acceptors allows the formation of α-glucosylated compounds with high yields [3].

The present study therefore focuses on two main aspects, first the formation of glycosylated flavonoids by enzymatic reactions and secondly their rapid and direct detection by matrix free laser desorption ionization mass spectrometry (LDI-MS).

The polyphenol glucosylation was carried out using engineered variants of BaSP as catalyst. For example, the resveratrol-α-glucoside was obtained with high yields using variant BaSP Q345F. Following a SPE pre-purification for eliminating sugars from the reaction medium, all target compounds were directly detected from the methanolic wash solution by LDI-MS. Next to the quasi-molecular ions [M-H]- of glycosides also those of their aglycons were systematically observed in the spectra.

Overall present results show that LDI-MS, preceding SPE separation, represents a direct and efficient technique for the rapid identification of glucosylated stilbenoids and flavonoids originating from enzymatic reactions.

 

  • References

  • 1 Quideau S, Deffieux D, Douat-Casassus C, Pouysegu L. Plant polyphenols: chemical properties, biological activities, and synthesis. Angew Chem Int Ed Engl 2011; 50: 586-621.
    CrossrefPubMedGoogle Scholar
  • 2 Gantt RW, Peltier-Pain P, Thorson JS. . Enzymatic methods for glyco(diversification/randomization) of drugs and small molecules. Nat Prod Rep 2011; 28: 1811-1853.
    CrossrefPubMedGoogle Scholar
  • 3 Kraus M, Grimm C, Seibel J. . Redesign of the Active Site of Sucrose Phosphorylase through a Clash-Induced Cascade of Loop Shifts. ChemBioChem 2016; 17: 33-36
    CrossrefPubMedGoogle Scholar