Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents.
Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including d-galactopyranosides, d-glucopyranosides, d-xylopyranoses, d-arabopyranoses and d-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K(2)CO(3), Bu(4)NBr, CH(2)Cl(2)-H(2)O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1alpha, 25-dihydroxy vitamin D(3) was evaluated in a co-culture assay system. The structure-activity relationships of these compounds were also discussed.
Li
Jun-Feng
JF
Key Lab of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, PR China.
Chen
Song-Jie
SJ
Zhao
Yu
Y
Li
Jian-Xin
JX
D000818:Animals; D001854:Bone Marrow Cells / Q000187:drug effects; D002478:Cells, Cultured; D005690:Galactose / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D010010:Osteoclasts / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014807:Vitamin D / Q000031:analogs & derivatives / Q000494:pharmacology; D014994:Xylose / Q000031:analogs & derivatives / Q000737:chemistry
D005960:Glucosides; D006001:Glycoconjugates; C431715:xylopyranose; D014807:Vitamin D; D009828:Oleanolic Acid; D014994:Xylose; D005690:Galactose