Iridoid glucosides of Linaria clementei

From an acetone extract of the whole plant of Linaria clementei, besides antirride and antirrinoside, the new iridoid glucosides 6-senecioyl- and 6-angeloylantirrinoside were isolated.     

Iridoid glucosides from Phlomis rotata

Two new iridoid glucosides, dehydropentstemoside and 7-epiphlomiol have been isolated from the aerial parts of Phlomis rotata and their structures elucidated by means of chemical and spectral methods. Shanzhiside methyl ester and barlerin have also been isolated and identified     

Two new iridoid glucosides from Osmanthus fragrans

Two new iridoid glucosides, 10-acetoxyligustroside and 10-acetoxyoleuropein, along, with two known glucosides, acteoside and phillyrin, have been isolated from the leaves of Osmanthus fragrans Lour and their structures have been determined.     

Iridoid glucosides from Parentucellia Viscosa

From Parentucellia viscosa a new glucosidic iridoid, gardoside methyl ester, was isolated along with bartioside, aucubin, melampyroside, shanzhiside methyl ester and 8-epiloganin. The structure of the new glucoside was confirmed by its chemical conversion into 8-epiloganin.     

Iridoid glucosides from Melampyrum

Melampyrum arvense and M. cristatum contain, besides aucubin, 8-epiloganin and melampyroside, a new natural iridoid glucoside: gardoside methyl ester. In addition, M. arvense contains mussaenoside and M. cristatum mussaenosidic acid, another novel iridoid glucoside.     

Iridoid glucosides of Odontites verna

Five iridoids have been identified in the whole plant of Odontites verna.     

Iridoid glucosides from Utricularia australis and Pinguicula vulgaris (lentibulariaceae)

Utricularia australis contained 6-deoxycatalpol, a new iridoid glucoside, besides aucubin, gardoside and mussaenosidic acid. From Pinguicula vulgaris was isolated catalpol, globularin and 10-(Z)-cinnamoyl-catalpol, the latter being a new compound. Thus, the iridoids found in Lentibulariaceae belong to structural types which are common in Scrophulariaceae and related families.     

Iridoids from Galium mollugo

From Galium mollugo, two new iridoids, gardenosidic acid and 10-hydroxymorroniside as well as 10-hydroxyloganin have been isolated, along with seven known iridoids, secogalioside, asperuloside, asperulosidic acid, daphylloside, monotropein, scandoside and scandoside methyl ester. 10-Hydroxyloganin, a compound which was previously considered to be the key biosynthetic intermediate of secoiridoids, was obtained for the first time from a natural source.     

Iridoid glucosides from Satureja Vulgaris

Satureja vulgaris was shown to contain two new iridoid glucosides, 5-deoxylamiol and 4-methylantirrhinoside, as well as the known iridoid glucosides lamiol and 5-deoxylamioside. The structures of the new glucosides were established by spectroscopic studies and chemical evidence.     

Iridoid glucosides from roots of Vietnamese Paederia scandens

Four iridoid glucosides, three of which are dimeric were isolated from the methanol extract of roots of Vietnamese Paederia scandens (Lour) Merrill together with the five known glucosides, paederoside, asperuloside, paederosidic acid, asperulosidic acid and geniposide. Seven sulfur-containing iridoid glucosides were also isolated. The structures of the iridoid glucosides were determined by a combination of high-resolution NMR, MS, IR and UV spectra, and chemical reaction such as acetylation.     

Two new iridoid glucosides from Gardenia jasminoides fruits

From the fruits of Gardenia jasminoides which have been employed as Chinese crude drug “Shan-zhii”, two further new iridoid glucosides, gardoside (8,10-dehydrologanic acid) and scandoside methyl ester have been isolated and their structures have been established.     

The genus Comus: Non-flavonoid glucosides as taxonomic markers

Previous proposals for subdivision of the genus Cornus are reviewed. Twenty-seven authenticated Cornus species have been studied for their content of non-flavonoid glucosides. Two distinct groups of taxa can be distinguished on this basis: one, containing a hydroxycyclohexadienone glucoside, along with salidroside, its reduced counterpart, and the second, characterized by containing various iridoid glucosides. The two types of glucosides are apparently mutually exclusive.     

Iridoid glucosides from Thunbergia laurifolia

Two iridoid glucosides, 8-epi-grandifloric acid and 3′-O-β-glucopyranosyl-stilbericoside, were isolated from the aerial part of Thunbergia laurifolia along with seven known compounds, benzyl β-glucopyranoside, benzyl β-(2′-O-β-glucopyranosyl) glucopyranoside, grandifloric acid, (E)-2-hexenyl β-glucopyranoside, hexanol β-glucopyranoside, 6-C-glucopyranosylapigenin and 6,8-di-C-glucopyranosylapigenin. Strucural elucidation was based on the analyses of spectroscopic data.     

Intermediacy of iridodial in the biosynthesis of some iridoid glucosides

Administration of MVA-[2-¹⁴C] to Lamium applexicaule and Deutzia crenata as well as of 11-hydroxyiridodial glucoside-[10-³H] and 7-deoxyloganic acid-[10-³H] to the former plant suggested that, in contrast to secoiridoid-indole alkaloids, iridoid glucosides such as ipolamiide, lamiide, lamioside, deutzioside and scabroside in these plants are biosynthesized via iridodial. Iridodial as a precursor for the biosynthesis of asperuloside was also suggested from the results of the administration of MVA-[2-¹⁴C] to Galium spurium var. echinospermon.     

Four iridoids from Randia canthioides

Four new iridoids, 10-dehydrogardenoside, dimeric 10-dehydrogardenoside, randioside and deacetylasperulosidic acid methyl ester aglycone, have been isolated together with three known iridoid glucosides, gardenoside, deacetylasperulosidic acid methyl ester and scandoside methyl ester, from Randia canthioides. It is conceivable that dimeric 10-dehydrogardenoside could be an artefact formed during the isolation process.     

Iridoid glucosides from Kickxia abhaica D.A. Sutton from Scrophulariaceae

Two iridoid glucosides namely; 6-acetylantirrinoside (1), 6'-O-p-hydroxybenzoylantirrinoside (2) were isolated from the aerial parts of Kickxia abhaica. Beside that, three known iridoid glucosides, antirrinoside (3), antirride (4) and mussaenosidic acid (5), one flavone glycoside (6) and a hexitol, d-mannitol (7) were isolated. The structures of the iridoid glucosides 1-2 were established by 1D and 2D NMR spectral data, including COSY, HMQC and HMBC experiments, as well as HRMS.     

Iridoid glucosides of the genus Veronica s.l. and their systematic significance

 The mode of reproduction, pollen production, chromosome numbers, genetic variation (RAPD, allozymes) and overall similarity were studied in 6 species of Hieracium sect. Alpina in the Tatry Mts. (the Western Carpathians, Slovakia). All species were confirmed to be agamospermous and, except of H. krivanense and H. slovacum, lacking pollen grains. For the first time, a chromosome number is reported for H. krivanense (2n=4x=36). Considerable genetic variation was revealed in H. alpinum and a correlation between geographic and genetic distances was found in this species. Between-population variation in RAPD and allozyme phenotypes was found in H. pinetophilum and H. crassipedipilum. In all other species, allozyme and RAPD variation was low or absent. With few exceptions, the species differ in their allozyme as well as RAPD patterns. The relatedness of one population of endemic H. slovacum and H. halleri was confirmed. It is shown, that Carpathian species of the H. fritzei group are derived from at least two ancestors. Received July 3, 2000; accepted June 24, 2002 Published online: November 20, 2002 Addresses of the authors: H. Štorchová, (e-mail: storchova@ueb.cas.cz) Institute of Experimental Botany, Academy of Sciences of the Czech Republic, Rozvojová 135, CZ-165 00 Praha 6, Czech Republic. I. V. Bartish, J. Chrtek Jr., J. Kirschner, M. Tetera, J. Štěpánek, Institute of Botany, Academy of Sciences of the Czech Republic, CZ-252 43 Pruhonice, Czech Republic.