iridoids and patrinoside

The phytochemical examination of the polar constituents of

Topics: Glucosides; Glycosides; Iridoids; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Phytochemicals; Plant Leaves; Sambucus

The phytochemical study of the aerial parts of Viburnum chinshanense Graebn., a species growing in Western and Central China, led to the isolation of six iridoid glucosides: the novel 10,2'-diacetylpatrinoside, 1, and the known 2'-acetyldihydropenstemide, 2'-trans- p-coumaroyl-dihydropenstemide, 2'-acetylpatrinoside, decapetaloside, and patrinoside. In addition, amentoflavone and rosarin were also isolated.

Topics: Glucosides; Iridoids; Magnetic Resonance Spectroscopy; Molecular Conformation; Viburnum

Topics: Animals; Cholagogues and Choleretics; Glucosides; Glycosides; Iridoid Glycosides; Iridoids; Lymphokines; Male; Pyrans; Rats; Rats, Inbred Strains

We made a study on choleretic property and mechanism of action of iridoid compounds as well as dehydrocholate (DHC), cholate (CA), and salicylate (SA), examining their effects on factors such as bile flow, bile acids, electrolytes (Na+, K+, Cl-, and HCO3-), and their metabolites. Each sample showed a characteristic property, respectively. Genipin and patrinoside decreased biliary concentrations of bile acids, Na+, Cl-, and HCO3-, corresponding to their rapid choleretic actions which were due to bile acids independent fraction. The choleretic action of DHC is approximately twice as potent as that of CA. Their actions were due to bile acids-dependent fraction. CA gave a marked increase in Na+ concentration but DHC did not. And both compounds gave a marked diminution in Cl- concentration and weakly decreased HCO3- concentration. SA showed a weak and durable choleretic action and also gave a marked increase in HCO3- concentration. The main metabolite detected from the bile given genipin was genipin-1-O-glucuronic acid (GGA). The periodical pattern of GGA level in bile was in agreement with that of genipin- induced choleretic action, and quantitatively cation, anion gap produced was nearly compensated by biliary concentration of GGA. From out various results, the choleretic mechanism of iridoid compounds is considered to be as follows: The hemiacetal moiety of them undergoes conjugation in the liver to give glucuronide. Glucuronide thus formed is secreted into the biliary tree being coupled mainly with Na+ and water is passively excreted.

Topics: Animals; Bicarbonates; Bile Acids and Salts; Chlorides; Cholagogues and Choleretics; Cholic Acids; Dehydrocholic Acid; Glucosides; Glycosides; Iridoid Glycosides; Iridoids; Male; Plant Extracts; Potassium; Pyrans; Rats; Rats, Inbred Strains; Sodium; Sodium Salicylate

The relationship between the structures and the choleretic actions of iridoid compounds was examined. Only patrinoside and villoside accelerated bile secretion among the iridoid glucosides but all of the iridoid aglycones increased it after intravenous administration rats. The choleretic effects of villoside, patrinoside aglycone, and 11-deoxy patrinoside aglycone were far weaker in comparison with those of other active iridoid compounds. When an equimolar amount of patrinoside, its aglycone, or 11-deoxy patrinoside aglycone was administered intravenously, their periodical patterns of choleretic activities nearly paralleled with those of isovaleric acid excreted in the bile. Patrinoside was partly hydrolyzed into its aglycone by the artificial gastric juice or the intestinal content. After intraduodenal administration of patrinoside (1 g/kg), the amount of patrinoside enough to exert a choleretic action was detected in the portal blood. These findings indicate that the hemiacetal moiety of iridoid compounds plays an important role in exerting a strong choleretic action and that patrinoside shows the same action following saponification of isovalerate of C-1 position in the liver.

Topics: Animals; Bile; Cholagogues and Choleretics; Glucosides; Glycosides; Hemiterpenes; Hydrolysis; Iridoids; Male; Pentanoic Acids; Pyrans; Rats; Structure-Activity Relationship; Time Factors; Valerates