Monoterpene glucosides, perillosides A and C, obtained from the leaves of Perilla frutescens, were found to be inhibitors of aldose reductase (EC 1.1.1.21) which is considered to be a key enzyme in diabetic complications such as cataract. The apparent type of inhibition of rat lens aldose reductase by perillosides A and C was competitive with respect to glyceraldehyde and their K_i values were 1.4×10^<-4> and 2.3×10^<-4>M, respectively. The type of inhibition by their tetraacetates was non-competitive with respect to the same substrate, although their inhibitory effects were increased by about one order of magnitude compared with those of the perillosides and the K_i values were 2.5×10^<-5> and 7.1×10^<-5>M, respectively. We also prepared related monoterpene glucosides and their tetraacetates and determined their inhibitory activities towards aldose reductase in order to elucidate the relationship between structure and inhibitory activity.
structure-activity relationship, Perilla frutescens, monoterpene glucoside, perilloside A, perilloside C, aldose reductase inhibitor
NCBI PubMed ID: 7641310Publication DOI: 10.1248/cpb.43.920Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Department of Applied Biological Chemistry, College of Agriculture, University of Osaka Prefecture, Japan
Methods: 13C NMR, 1H NMR, IR, HPLC, UV, biological assay, SI-MS, synthesis
Found