Polarized epithelial cells like Madin-Darby canine kidney (MDCK) and CaCo-2 cells synthesize and secrete proteoglycans (PGs), mostly of heparan sulphate (HS) type in direction of the basal extracellular matrix, but also some in the apical direction. MDCK cells possess the capacity to synthesize chondroitin sulphate (CS) PGs that are mainly secreted into the apical medium, a process that is enhanced in the presence of hexyl-beta-D: -xyloside. We have now tested the capacity of several xylosides to enhance glycosaminoglycan (GAG) chain secretion from the human colon carcinoma cell line CaCo-2 in the differentiated and non-differentiated state. In these cells, benzyl-beta-D: -xyloside was a potent initiator of CS chains, which for these cells were predominantly secreted into the basolateral medium. Xylosides with other aglycone groups mediated only minor changes in GAG secretion. Although benzyl-beta-D: -xyloside stimulated the basolateral CS-GAG secretion in both differentiated and undifferentiated CaCo-2 cells, basolateral secretion of trypsin-like activity was dramatically enhanced in undifferentiated cells, but not significantly altered in differentiated cells.