ABSTRACT
Four new resin glycosides, named calysolins XIV (1), XV (2), XVI (3), and XVII (4) were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM.. et SCHULT. (Convolvulaceae). Their structures were determined based on spectroscopic and chemical evidence, and consisted of two different types: those (1) with a macrolactone structure and those (2-4) with a non-macrolactone structure. Their sugar moieties were partially acylated by specific organic acids, including tiglic, 2S-methylbutyric, and 2S,3S-nilic acids. Additionally, evaluation of the antiviral activity of 1-4 revealed effects against the herpes simplex virus type 1.
Subject(s)
Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Calystegia/chemistry , Glycosides/chemistry , Glycosides/pharmacology , Herpesvirus 1, Human/drug effects , Antiviral Agents/isolation & purification , Glycosides/isolation & purification , Herpes Simplex/drug therapy , HumansABSTRACT
Four new resin glycosides having macrolactone structures (jalapins), named calysolins X (1)-XIII (4), 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 sugar moieties of 1-4 were partially acylated by some organic acids, including tiglic acid, 2S-methylbutyric acid, and 2S,3S-nilic acid. Additionally, the antiviral activity of 1-4 toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.
Subject(s)
Antiviral Agents/chemistry , Calystegia/chemistry , Glycosides/chemistry , Herpesvirus 1, Human/drug effects , Lactones/chemistry , Resins, Plant/chemistry , Antiviral Agents/isolation & purification , Antiviral Agents/pharmacology , Glycosides/isolation & purification , Glycosides/pharmacology , Herpes Simplex/drug therapy , Humans , Lactones/isolation & purification , Lactones/pharmacologyABSTRACT
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.
Subject(s)
Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Calystegia/chemistry , Glycosides/chemistry , Glycosides/pharmacology , Herpesvirus 1, Human/drug effects , Lactones/chemistry , Lactones/pharmacology , Resins, Plant/chemistry , Resins, Plant/pharmacologyABSTRACT
Four new resin glycosides having intramolecular cyclic ester structures (jalapins), named calysolins I-IV (1-4), were isolated from the methanol extract of leaves, stems, and roots of Calystegia soldanella , along with one known jalapin (5) derivative. The structures of 1-4 were determined on the basis of spectroscopic data and chemical evidence. They fall into two types, one having a 22-membered ring (1 and 4) and the other with a 27-membered ring (2 and 3). The sugar moieties of 1-4 were partially acylated by some organic acids. Compound 4 is the first example of a hexaglycoside of jalapin.
Subject(s)
Calystegia/chemistry , Glycosides/isolation & purification , Resins, Plant/isolation & purification , Carbohydrate Sequence , Glycosides/analysis , Glycosides/chemistry , Molecular Structure , Plant Leaves/chemistry , Plant Roots/chemistry , Plant Stems/chemistry , Resins, Plant/analysis , Resins, Plant/chemistryABSTRACT
Alkaline hydrolysis of the crude resin glycoside fraction of the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae) gave four new glycosidic acids, named calysolic acids A, B, C, and D, along with one known glycosidic acid, soldanellic acid B, and three organic acids, 2S-methylbutyric, tiglic, and 2S,3S-nilic acids. The structures of the new glycosidic acids were characterized on the basis of spectroscopic data and chemical evidence.
Subject(s)
Acids/chemistry , Calystegia/chemistry , Acids/isolation & purification , Glycosides/chemistry , Hydrolysis , Magnetic Resonance Spectroscopy , Molecular Conformation , Plant Leaves/chemistry , Plant Roots/chemistry , Plant Stems/chemistry , Resins, Plant/chemistryABSTRACT
Treatment of the crude ether-insoluble resin glycoside (convolvulin) from seeds of Pharbitis nil (Pharbitis Semen), called pharbitin, with indium(III) chloride in methanol provided seven oligoglycosides of hydroxy fatty acid methyl esters partially acylated by 2-methyl-3-hydroxybutyric (nilic) and 2S-methylbutyric acids. Their structures were elucidated on the basis of NMR and MS data and chemical conversions.
