ABSTRACT
A new resin glycoside, named calysolin XVIII (1), was isolated from the leaves, stems and roots of Calystegia soldanella Roem. et Schult. (Convolvulaceae). The structure of 1 was defined as 11S-jalapinolic acid 11-O-ß-d-glucopyranosyl-(1 â 3)-O-(2-O-2S-methylbutyryl,4-O-3-hydroxy-2-methylenebutyryl)-α-l-rhamnopyranosyl-(1 â 2)-[O-ß-d-glucopyranosyl-(1 â 6)-O-(34-di-O-2S-methylbutyryl)-ß-d-glucopyranosyl-(1 â 3)]-O-ß-d-glucopyranosyl-(1 â 2)-ß-d-quinovopyranoside, intramolecular 1,2â³'â³'-ester on the basis of spectroscopic data. Compound 1 is the first known resin glycoside to feature 3-hydroxy-2-methylenebutyric acid as a component organic acid. In addition, 1 demonstrated an antiviral activity against herpes simplex virus type 1, with an IC50 value 2.3 µM.
Subject(s)
Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Calystegia/chemistry , Herpesvirus 1, Human/drug effects , Resins, Plant/chemistry , Animals , Chlorocebus aethiops , Drug Evaluation, Preclinical/methods , Glycosides/chemistry , Glycosides/pharmacology , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Leaves/chemistry , Plant Roots/chemistry , Vero CellsABSTRACT
Five new resin glycosides having macrolactone structures (jalapins), named calysolins V-IX (1-5), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The isolated compounds could be classified into two macrolactone types-one having a 22-membered ring (1-4) and the other with a 27-membered ring (5). The sugar moieties of 1-5 were found to exist in partially acylated forms comprising 2S-methylbutyric acid and tiglic acid. Compounds 4 and 5 are the first representatives of the calysolic acid C as the component glycosidic acid. Additionally, the antiviral activity of 1-5, together with calysolins I-IV and soldanelline B, which are previously isolated jalapins from this plant, toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.
