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At least 163 records · Page 9Linked to original sources
PubMed2000

Extraction of iridoid glycosides and their determination by micellar electrokinetic capillary chromatography.

Several methods for the extraction of two iridoid glycosides, catalpol and aucubin, from the plant matrix (Veronica longifolia leaves) were compared. Pressurized hot water extraction and hot water extraction were the most efficient isolation techniques for both. Pressurized liquid extraction and maceration with various organic solvents were also tested. Relative to the amounts extracted with hot water, ethanol extracted only 22% of catalpol and 25% of aucubin and pressurized hot water extracted 83% of catalpol and 92% of aucubin. The lowest relative standard deviations, 22% for catalpol and 8% for aucubin, were achieved with hot water extraction (13 repetitions), and the highest relative standard deviations, 76% for catalpol and 73% for aucubin, with pressurized liquid extraction (five repetitions). A fast capillary electrophoretic method was developed for the quantitative determination of catalpol and aucubin.

Chromatography, Micellar Electrokinetic Capillary↗
PubMed1988

Iridoids and secoiridoids from Guettarda platypoda.

A reinvestigation of the roots of Guettarda platypoda afforded in addition to morronoside and sweroside isolated previously further two iridoids, loganic acid and loganin and a rare secoiridoid, secoxyloganin. The structures were elucidated by NMR techniques. This is the first report of the isolation of such compounds from G.platypoda. Some chemotaxonomic conclusion can be drawn.

Chemical Phenomena↗
PubMed2002

Iridoid glucosides from Thunbergia laurifolia.

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

Acanthaceae↗
PubMed2002

Iridoid and phenolic diglycosides from Canthium berberidifolium.

An iridoid diglycoside, 6-O-beta-D-apiofuranosyl-mussaenosidic acid, and four phenolic diglycosides, canthosides A-D, were isolated from the aerial part of Canthium berberidifolium, along with seven known compounds. Structural elucidations were based on analyses of spectroscopic data.

Disaccharides↗
PubMed2005

LC-DAD-MS/SPE-NMR hyphenation. A tool for the analysis of pharmaceutically used plant extracts: identification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens.

LC-DAD-MS monitored fractionation of a Harpagophytum procumbens DC. (Pedaliaceae) root extract was combined with a hyphenated LC-DAD-MS/SPE-NMR technique, thus providing the spectral data needed for structure elucidation. This approach allowed the characterization of isobaric iridoid glycoside regioisomers present only as minor constituents. The analytes were identified as the (E/Z) pairs of 6'-O-(p-coumaroyl)harpagide (6'-PCHG) and 8-O-(p-coumaroyl)-harpagide (8-PCHG). The fact that 8-(Z)-PCHG constitutes a new natural product underlines the analytical power of this combined approach. Furthermore, derivatives 6'-(Z)- and 6'-(E)-PCHG are new constituents for H. procumbens.

Glycosides↗
PubMed2004

Iridoid glycosides from Eremostachys glabra.

Reversed-phase preparative HPLC of a methanol extract of the rhizomes of Eremostachys glabra yielded three new iridoid glycosides, namely, 6,9-epi-8-O-acetylshanziside methyl ester, 5,9-epi-penstemoside, and 5,9-epi-7,8-didehydropenstemoside. Their structures were elucidated on the basis of spectroscopic data interpretation. The free-radical scavenging activity of these compounds was assessed using the DPPH assay.

Chromatography, High Pressure Liquid↗
PubMed1994

Inerminosides A and B, two novel complex iridoid glycosides from Clerodendrum inerme.

The leaves of Clerodendrum inerme have yielded two new iridoid biglycosides which have been characterized as 2'-O-[5"-O-(8-hydroxy-2,6-dimethyl-2(E)-octenoyl)-beta-D-apiofuranosy l]- mussaenosidic acid (inerminoside A) [1], and 2'-O-[5"-O-(8-hydroxy-2,6-dimethyl-2(E),6(E)-octadienoyl)-beta-D- apiofuranosyl]-8-epi-loganic acid (inerminoside B [2]), respectively. Structure elucidation was carried out both chemically and spectroscopically.

Africa↗
PubMed2000

Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks.

The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.

Aza Compounds↗
PubMed1991

Pharmacokinetic study of an iridoid glucoside: aucubin.

Aucubin, a promising hepatoprotecting iridoid glucoside, was given intravenously (iv), orally (po), intraperitoneally (ip), and hepatoportally (pv) to rats. A linear pharmacokinetic behavior was obtained after iv administation of 400-400 mg/kg of aucubin. The half-life of aucubin in the postdistributive phase (t1/2, beta), total-body plasma clearance (CLt), and volume of distribution (Vdss) were 42.5 min, 7.2 ml/min/kg, and 346.9 ml/kg, respectively, for a 40 mg/kg dose. There was no significant difference in the parameters as a reult of increasing dose. The partition coefficients of aucubin between n-octanol and buffers of pH 3.0-10.0 were low, while 18.5 +/- 1.3% of aucubin in whole blood partitioned into the blood cells. Plasma protein binding of aucubin was only 9%. The bioavailabilites of aucubin after administration at a dose of 100 mg/kg through pv, ip, and po routes were 83.5, 76.8, and 19.3%, respectively. The pH-stability profile indicated rapid degradation of aucubin at pH 1.2, 1.6, and 2.0, with degradation half-lives of 5.1, 5.8, and 14.8 hr, respectively, at 37 degrees C. Therefore, the low oral bioavailability of aucubin may be attributed to pH-instability in the gastric fluid, poor GI absorption due to low lipophilicity, and the possible metabolism in the GI mucosa and liver (so called first-pass effect).

Animals↗
PubMed2001

Chemistry of plants from Crete: stachyspinoside, a new flavonoid glycoside and iridoids from Stachys spinosa.

The new flavonoid glycoside stachyspinoside (1), and the three iridoids, 7-O-acetyl-8-epi-loganic acid (2), ajugol (3) and harpagide (4) were isolated from Stachys spinosa. The structures of these compounds were established on the basis of mass spectrometry (ESMS and tandem MS), one- and two-dimensional nuclear magnetic resonance experiments (COSY, COSY LR, HMQC, TOCSY and HMBC) as well as simple chemical derivatization.

Antioxidants↗
PubMed1999

[A study on chemical composition of Gardenia sootepensis Hutch--quantitative determination of iridoid compounds by RP-HPLC].

OBJECTIVE: To determine the iridoid contents in Gardenia sootepensis. METHODS: Using RP-HPLC with geniposidic acid, geniposide and scandoside methyl ether as standards. RESULT: According to the selected chromatographic conditions, the linear ranges of geniposidic acid, geniposide and scandoside methyl ether were 0.097-0.606 microgram, 0.0638-3.990 micrograms and 0.198-1.239 micrograms, respectively. The average recoveries of these three compounds were 100.0%, 99.9% and 100.1%, and RSD 1.23%, 1.38% and 1.53% (n = 5) respectively. CONCLUSION: The method is easy, rapid, and reproducible.

Chromatography, High Pressure Liquid↗
PubMedDate not supplied

The structural elucidation of a novel iridoid derivative from Tachiadenus longiflorus (Gentianaceae) using the LSD programme and quantum chemical computations.

Oleanolic acid, scoparone, scopoletin and a novel iridoid derivative, angelone, were isolated from Tachiadenus longiflorus (Gentianaceae). The structure of angelone was determined from NMR data, given as input to the Logic for Structure Determination Programme, and was finally confirmed by comparison of experimental 13C-NMR chemical shifts with those obtained by quantum mechanical calculations.

Gentianaceae↗
PubMed2005

11-Methoxyviburtinal, a new iridoid from Valeriana jatamansi.

Five compounds of iridoids, lignan and phenylpropanoid glycosides were isolated from the roots of Valeriana jatamansi by column chromatography. Their structures were elucidated as 11-methoxyviburtinal (1), baldrinal (2), prinsepiol-4-omicron-beta-D-glucoside (3), coniferin (4), and hexacosanic acid (5) by spectroscopic analysis. 11-Methoxyviburtinal was a new compound, and others were isolated from the plant for the first time.

Iridoids↗
PubMed1999

Iridoid compounds from Boschniakia rossica.

Four iridoid compounds were isolated from methanol extract of Boschniakia rossica by repeated column chromatography. Their structures were determined as boschnaloside (1), boschnarol (2), bosnarol methylether (3), and 7-deoxy 8-epiloganic acid (4), respectively. Compound 2, 3, and 4 were isolated for the first time from this plant.

Glucosides↗