Controlins I-X, Resin Glycosides from the Seeds of Convolvulus tricolor and Their Biological Activities

Ten new resin glycosides, controlins I-X (1-10), were isolated from the seeds of Convolvulus tricolor. Their structures were established by spectroscopic analysis as well as by chemical means. Compounds were identified as glycosidic acid methyl esters, considered as artifacts generated via transesterification with MeOH from natural resin glycosides. Compound 1 is the first nonasaccharide resin glycoside, while compounds 2-7 are rare octasaccharide resin glycosides. Compounds 5, 6, and 8 could inhibit the nitric oxide production in lipopolysaccharide-induced BV-2 cells, while compounds 3, 5, and 7 exhibited neuroprotective effects on H₂O₂-induced damage in PC12 cells. Compounds 6 and 7 could dose-dependently alleviate the dyskinesia in the UM0001 strain of Caenorhabditis elegans, a double transgenic line of Aβ and pro-aggregation tau, suggesting an anti-Alzheimer's activity, reported for resin glycosides for the first time.