Structural characterization and cytotoxic properties of a 4-O-methylglucuronoxylan from castanea sativa. 2. Evidence of a structure-activity relationship.

Aline Barbat-Rogeon (1) , Vincent Gloaguen (1) , Charlotte Moine , Odile Sainte-Catherine , Michel Kraemer , Hélène Rogniaux , David Ropartz , Pierre Krausz (1)

1 LCSN - Laboratoire de Chimie des Substances Naturelles

Xylans were purified from delignified holocellulose alkaline extracts of Castanea sativa (Spanish chestnut) and Argania spinosa (Argan tree) and their structures analyzed by means of GC of their per-trimethylsilylated methylglycoside derivatives and (1)H NMR spectroscopy. The structures deduced were characteristic of a 4-O-methylglucuronoxylan (MGX) and a homoxylan (HX), respectively, with degrees of polymerization ranging from 182 to 360. In the case of MGX, the regular or random distribution of 4-O-methylglucuronic acid along the xylosyl backbone--determined by MALDI mass spectrometry after autohydrolysis of the polysaccharide--varied and depended both on the botanical source from which they were extracted and on the xylan extraction procedure. The MGX also inhibited in different ways the proliferation as well as the migration and invasion capability of A431 human epidermoid carcinoma cells. These biological properties could be correlated with structural features including values of the degree of polymerization, 4-O-MeGlcA to xylose ratios, and distribution of 4-O-MeGlcA along the xylosyl backbone, giving evidence of a defined structure-activity relationship.

Domaines: Chimie organique

Aline Barbat-Rogeon, Vincent Gloaguen, Charlotte Moine, Odile Sainte-Catherine, Michel Kraemer, et al.. Structural characterization and cytotoxic properties of a 4-O-methylglucuronoxylan from castanea sativa. 2. Evidence of a structure-activity relationship.. Journal of Natural Products, 2008, 71 (8), pp.1404-1409. ⟨10.1021/np800207g⟩. ⟨hal-00686412⟩