iridoids and catalposide

Ten new glycosides, 6,10-O-di-trans-feruloyl catalpol (1), 6,6'-O-di-trans-feruloyl catalpol (2), 3,4-dihydro-6-O-di-trans-feruloyl catalpol (10), (8R,7'S,8'R)-lariciresinol 9'-O-β-d-(6-O-trans-feruloyl)glucopyranoside (17), and ovatosides A-F (18-22, 24), were isolated from the stem bark of Catalpa ovata along with 19 known compounds. All isolates, except 6 (catalposide) and 9 (6-O-veratroyl catalpol), were found to scavenge peroxynitrite (ONOO

Topics: Bignoniaceae; Furans; Glucosides; Glycosides; Inhibitory Concentration 50; Iridoid Glucosides; Iridoids; Lignans; Molecular Structure; Peroxynitrous Acid; Plant Stems

Verproside, isovanilloylcatalpol, catalposide and 6-O-veratroyl catalpol are bioactive iridoid glucosides isolated from in a number of folk medicinal plants. A rapid, sensitive and selective liquid chromatography/mass spectrometric (LC/MS) method for the simultaneous determination of verproside, isovanilloylcatalpol, catalposide and 6-O-veratroyl catalpol in rat plasma was developed. The analytes were extracted from 50 microL of rat plasma with ethyl acetate using 7-carboxymethyloxy-3',4',5-trimethoxyflavone as internal standard and analyzed on an X-Bridge C(18) column within 6.5 min with 40% methanol in 10 mm ammonium formate (pH 3.0). The analytes were quantified using an electrospray ionization mass spectrometry in the selected ion monitoring mode. The standard curves were linear over the concentration ranges of 10-2000 ng/mL for verproside, isovanilloylcatalpol and catalposide and 20-2000 ng/mL for 6-O-veratroyl catalpol. The coefficients of variation and relative errors of verproside, isovanilloylcatalpol, catalposide and 6-O-veratroyl catalpol for intra- and inter-assay at four quality control levels were 2.5-8.0 and-4.0-6.6%, respectively. This method was successfully applied to the pharmacokinetic study of verproside and its possible metabolite isovanilloylcatalpol after intravenous administration of verproside, a candidate anti-asthma drug, in male Sprague-Dawley rats.

Topics: Animals; Area Under Curve; Calibration; Chromatography, Liquid; Glucosides; Iridoid Glucosides; Iridoids; Least-Squares Analysis; Male; Rats; Rats, Sprague-Dawley; Reproducibility of Results; Sensitivity and Specificity; Spectrometry, Mass, Electrospray Ionization

The growth and survival of the Catalpa sphinx, Ceratomia catalpae (Sphingidae), were measured on five different species of Catalpa: C. bignonioides, C. bungeii, C. fargeseii, C. ovata, and C. speciosa. Larval growth varied significantly among these host plant species; however, survival did not differ. Quantification of the iridoid glycoside content of larvae, pupae, adults, larval frass, and leaves of the larval host plant, C. bignonioides, by gas chromatography showed that leaves contained both catalpol and catalposide; larvae, pupae, and frass contained only catalpol; and the adults contained no detectable iridoid glycosides. Amounts were highest in the larvae and declined in the pupal stage. Very small amounts of catalpol were detected in adults of the parasitoid, Cotesia congregata, and in the silken cocoons. The hemolymph in which the parasitoid larvae grew contained over 50% dry weight catalpol. Larvae of C. catalpae often regurgitate when disturbed. This may serve as a defense against predators. A comparison of the growth of larvae pinched with forceps to induce regurgitation with those that were not so treated showed that larvae that were pinched, and usually regurgitated, grew significantly more slowly than those that were not.

Topics: Adaptation, Physiological; Age Factors; Animals; Chromatography, Gas; Glucosides; Hemolymph; Host-Parasite Interactions; Iridoid Glucosides; Iridoids; Larva; Moths; Plants, Edible; Predatory Behavior

1. A glycoside of the aucubin type has been isolated in crystalline form from Plantago and Buddleia species, and has been shown to be identical with catalpol (Lunn, Edward & Edward, 1962). Catalpol has not been found in the free state before, but occurs as its p-hydroxybenzoyl ester, catalposide, in the genus Catalpa. 2. A second glycoside of this type has been obtained in crystalline form from Buddleia, and has been shown to be a mono-O-methyl derivative of catalpol, for which the name ;methylcatalpol' is proposed. 3. Both Plantago and Buddleia species are known to contain aucubin. The concentrations of this glycoside and catalpol are comparable in Plantago. In Buddleia methylcatalpol predominates somewhat over catalpol. Yields of the individual glycosides were about 0.1% of the fresh weight of the leaves. 4. Bobbitt, Spiggle, Mahboob, Philipsborn & Schmid (1962) have suggested structures for catalposide and catalpol based on chemical and physical evidence, in particular on n.m.r. spectra. Reappraisal of this evidence and additional measurements have now confirmed these structures and show that the Buddleia glycoside is the 6-O-methyl derivative of catalpol.

Topics: Buddleja; Chemistry, Pharmaceutical; Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Magnetic Resonance Imaging; Magnetic Resonance Spectroscopy; Plant Leaves; Plantago; Plants, Medicinal; Research; Spectrum Analysis