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PubMed2001

Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique.

A fast and easy method was sought for determination of the iridoid glycosides catalpol, ketologanin, verbenalin, loganin, 8-epi-loganic acid, geniposidic acid and 10-cinnamoyl catalpol in plant samples. The method involved micellar electrokinetic capillary chromatography (MEKC) coupled on-line to mass spectrometry. The partial filling technique and electrospray ionization were used. Seven iridoid glycosides could be separated with use of MEKC under basic conditions. However, 8-epi-loganic acid and geniposidic acid could not be detected simultaneously with the five neutral iridoid glycosides by mass spectrometry. Therefore, only the neutral iridoid glycosides were screened from plant samples. Catalpol, verbenalin, loganin and possibly 10-cinnamoyl catalpol were found in an examination of seven plant species in the genera Plantago, Veronica, Melampyrum, Succisa, and Valeriana. Aucubin, which was not included in the sample mixture used in method development because of overlapping with catalpol in MEKC, was also detected. The limits of detection for the iridoid glycosides, both at the UV and at the mass spectrometer, are given.

Chromatography, Micellar Electrokinetic Capillary↗
PubMed2002

Systemic, genotype-specific induction of two herbivore-deterrent iridoid glycosides in Plantago lanceolata L. in response to fungal infection by Diaporthe adunca (Rob.) Niessel.

Iridoid glycosides are a group of terpenoid secondary plant compounds known to deter generalist insect herbivores. In ribwort plantain (Plantago lanceolata), the iridoid glycosides aucubin and catalpol can be induced following damage by insect herbivores. In this study, we investigated whether the same compounds can be induced following infection by the fungal pathogen Diaporthe adunca, the causal agent of a stalk disease in P. lanceolata. Significant induction of aucubin and catalpol was observed in two of the three plant genotypes used in this study following inoculation with the pathogen. In one of the genotypes, induction occurred within 6 hr after inoculation, and no decay was observed within 8 days. The highest level of induction was observed in reproductive tissues (spikes and stalks) where infection took place. In these tissues, iridoid glycoside levels in infected plants were, on average, 97% and 37% higher than the constitutive levels in the corresponding control plants, respectively. Significant induction was also observed in leaves (24%) and roots (17%). In addition to significant genotypic variation in the level of induction, we found genetic variation for the tissue-specific pattern of induction, further broadening the scope for evolutionary fine-tuning of induced responses. Recent studies have revealed a negative association between iridoid glycoside levels in P. lanceolata genotypes and the amount of growth and reproduction of D. adunca that these genotypes support. However, for the three genotypes used in the present study, differences in resistance were not related to their constitutive or induced levels of iridoid glycosides, suggesting that additional resistance mechanisms are important in this host-pathogen system. We conclude that iridoid glycosides in P. lanceolata can be induced both by arthropods and pathogenic micro-organisms. Pathogen infection could, therefore, potentially enhance resistance to generalist insect herbivores in this species.

Adaptation, Physiological↗
PubMed2003

Determination of iridoid glycosides in larvae and adults of butterfly Melitaea cinxia by partial filling micellar electrokinetic capillary chromatography-electrospray ionisation mass spectrometry.

The iridoid glycosides, methyl catalpol, asperuloside, verbenalin, cinnamoyl catalpol, catalpol and aucubin, were studied from both larvae and adults of butterfly Melitaea cinxia. Special emphasis in the study was put on finding a correlation between the iridoid glycoside content in butterflies and plants. An optimised partial filling micellar electrokinetic capillary chromatographic-electrospray ionisation mass spectrometric (PF-MECC-ESI-MS) method was employed for the separation and identification of the six iridoid glycosides. In this work, the isolation and determination of catalpol and aucubin from extracts of both larvae and adults of Melitaea cinxia butterflies is demonstrated. The PF-MECC-ESI-MS method, using the [M+Na]+, [M+Li]+ and/or [M+NH(4)]+ adducts in ESI-MS, was used for quantification of aucubin and catalpol in the insects. In addition, the identification of all analytes was attempted by direct infusion MS/MS analysis. LOQ values for the iridoid glycosides varied between 10 mg/l (for verbenalin) to 50 mg/l (for catalpol and aucubin) corresponding to 0.1% of the samplés dry mass. A correlation was noticed between the concentrations of iridoid glycosides in plants and the concentrations in larvae feeding on them.

Aging↗
PubMed2006

Lonicera Implexa leaves bearing naturally laid eggs of the specialist herbivore Euphydryas Aurinia have dramatically greater concentrations of iridoid glycosides than other leaves.

We tested in the field the hypothesis that the specialist butterfly Euphydryas aurinia (Lepidoptera: Nymphalidae, Melitaeinae) lays eggs on leaves of Lonicera implexa (Caprifoliaceae) plants with greater iridoid concentrations. We conducted our investigations in a Mediterranean site by analyzing leaves with and without naturally laid egg clusters. There were no significant differences in iridoid glycoside concentrations between leaves from plants that did not receive eggs and the unused leaves from plants receiving eggs, a fact that would seem to indicate that E. aurinia butterflies do not choose plants for oviposition by their iridoid content. However, the leaves of L. implexa that bore egg clusters had dramatically greater (over 15-fold) concentrations of iridoid glycosides than the directly opposite leaves on the same plant. These huge foliar concentrations of iridoids (15% leaf dry weight) may provide specialist herbivores with compounds that they either sequester for their own defense or use as a means of avoiding competition for food from generalist herbivores. Nevertheless, it may still be possible that these high concentrations are detrimental to the herbivore, even if the herbivore is a specialist feeder on the plant.

Animals↗
PubMed2002

Analysis of eleven iridoid glycosides by micellar electrokinetic capillary chromatography (MECC) and screening of plant samples by partial filling (MECC)-electrospray ionisation mass spectrometry.

Of ammonium, lithium and sodium salts of dodecyl sulfate studied as surfactants in the separation of iridoid glycosides by micellar electrokinetic capillary chromatography (MECC), the last one gave the best results. Eleven neutral iridoid glycosides were separated by MECC with sodium dodecyl sulfate as surfactant, and the water-micelle partition coefficients of the compounds were calculated. The separation system was coupled via a coaxial sheath flow electrospray interface to a mass spectrometer, and the partial filling technique was used in the on-line analysis. Seven plant species belonging to five genera (Plantago, Veronica, Melampyrum, Succisa and Valeriana) were screened for the iridoid glycosides by the new method that was developed. The findings confirmed those of an earlier study on five of the iridoid glycosides. Some new iridoid glycosides were found in Plantago lanceolata, Veronica spicata and V. chamaedrys.

Carbohydrate Conformation↗
PubMed2000

Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides.

Data for 34 species of Plantago (Plantaginaceae), including subgen. Littorella (= Littorella uniflora), have been collected with regard to their content of iridoid glucosides and caffeoyl phenylethanoid glycosides (CPGs). In the present work, 21 species were investigated for the first time and many known compounds were found together with three new iridoid glucosides. Of these, arborescoside and arborescosidic acid, both of the uncommon type with an 8,9-double bond, were present in several species, while 6-deoxymelittoside was found only in P. subulata. The known compounds deoxyloganic acid, caryoptoside and rehmannioside D were isolated from the genus for the first time. The earlier reported occurrence of sorbitol in the family was confirmed, and this compound was shown by NMR spectroscopy to be the main sugar in the three species investigated for this. The combined data show that CPGs are present in all species investigated. With regard to the iridoids, the distribution patterns showed a good correlation with the classification of Rahn. Thus, aucubin is typical for the whole genus, while bartsioside and catalpol as well as 5-substituted iridoids are each characteristic for a subgenus in the family. Finally, the close relationship between Plantago and Veronica suggested by chloroplast DNA sequence analysis. could be corroborated by the common occurrence of the rare 8,9-unsaturated iridoids in these two genera.

Glucosides↗
PubMed2000

The distribution of iridoids in Bignoniaceae.

The distribution of iridoids among the tribes of Bignoniaceae is shown. In the present work, 18 species from the tribes Bignonieae and Tecomeae as well as one from Eccremocarpeae have been investigated. These data combined with those obtained through a literature review were analysed and showed that iridoids occur predominantly in the tribe Tecomeae. In this tribe, a chemical distintion between the genera Tabebuia and Tecoma was observed: The iridoids in Tabebuia are decarboxylated whereas in Tecoma they are C-4 formylated. The species from Bignonieae are poorly investigated and only few reports have been published, however, the iridoids found are mainly C-4 carboxylated. The only exception, Dolichandra cynanchoides (=Macfadyena cynanchoides), with decarboxylated iridoids, is also morphologically abnormal in Bignonieae.

Journal Article↗
PubMed1998

Trans-fused iridoid glycosides from Penstemon mucronatus.

Two new trans-fused iridoid glycosides (5 alpha H)-6 alpha-8-epidihydrocornin and (5 alpha H)-6 alpha-8-hydroxy-8-epiloganin, were isolated from Penstemon mucronatus, along with cornin, penstemoside and three hastatosides. The trans-fused iridoids are only the second and third known among over 900 described cis-fused iridoid glycosides. Two pairs of iridoids, identical except for the stereochemistry at C-8, were found. Structures were determined by spectroscopic methods.

Carbohydrate Conformation↗
PubMed2001

Iridoid glycosides from Globularia trichosantha.

A new iridoid glycoside, deacetylalpinoside (2), was isolated from the aerial parts of Globularia trichosantha together with nine known iridoid glycosides: catalpol, 10-O-benzoyl-catalpol, aucubin, asperuloside, deacetylasperuloside, asperulosidic acid, scandoside, geniposidic acid, and alpinoside (1). From the underground parts of the same plant, two new bisiridoid glycosides, globulosides A (3) and B (4); a known iridoid glycoside, globularidin; a lignan glycoside, liriodendrin; and seven phenylethanoid glycosides, arenarioside, verbascoside (= acteoside), isoacteoside, crenatoside, isocrenatoside, and trichosanthosides A and B, were isolated. Compounds 2-4 are new iridoids containing an 8,9 double bond representing a rare carbon skeleton. Their structures were established by spectroscopic methods.

Glucosides↗
PubMed2004

Effects of iridoid total glycoside from Cornus officinalis on prevention of glomerular overexpression of transforming growth factor beta 1 and matrixes in an experimental diabetes model.

The present study was conducted to determine whether iridoid total glycoside from Cornus officinalis was effective in regulating expression of transforming growth factor beta 1 (TGF-beta1) and preventing overdeposition of extracellular matrix (ECM) in a diabetes state. An experimental rat model of diabetic nephropathy (DN) was successfully induced by one intraperitoneal injection of streptozotocin at a dose of 60 mg x kg(-1) and maintained for 12 weeks. All rats had free access to standard chow and water. Four groups: normal control, diabetic control, diabetic rats with aminoguanidine treatment and diabetic rats with iridoid total glycoside treatment were used in this experiment. All treatments were administered by intragastric gavage (ig). At the end of the experiment, serum was collected for ELISA determination of TGF-beta1 protein level; renal cortex was dissected for reverse transcription polymerase chain reaction (RT-PCR) analysis of its mRNA expression; and immunohistochemistry was introduced to observe ECM deposition. A significantly higher level of protein and mRNA expression of TGF-beta1, and also overdeposition of fibronectin and laminin was found in diabetic rats. Both iridoid total glycoside and aminoguanidine were effective in decreasing serum protein level and glomerular mRNA expression of TGF-beta1, and in preventing renal overdeposition of fibronectin and laminin. This study suggests that iridoid total glycoside is a beneficial agent for prevention and therapy of DN.

Animals↗
PubMed2006

Iridoid glucosides from the aerial parts of Globularia alypum L. (Globulariaceae).

From the hydromethanolic extract of the aerial parts of Globularia alypum grown in Morocco, a new chlorinated iridoid glucoside, globularioside has been isolated beside 5 known iridoid glycosides, globularin, globularicisin, globularidin, globularinin and globularimin. This is the first report of a chlorinated iridoid in G. alypum and in the Globulareaceae. Unlike all other known 7-chlorinated iridoid glucosides where the chlorine atom exhibits an alpha configuration, globularioside incorporate the chlorine atom as a 7beta substituent. The structures of the isolated compounds were established on the basis of ESI-MS, MS-MS, 1D and 2D NMR spectral analysis.

Antioxidants↗
PubMed2000

HPLC analysis of the seasonal and diurnal variation of iridoids in cultivars of Antirrhinum majus.

In this paper we show the seasonal and diurnal variation in the content of the four iridoids found in cultivars of Antirrhinum majus, antirrhinoside, antirrhide, 5-glucosyl-antirrhinoside and linarioside. The seasonal variation in total iridoid content showed a marked bimodal distribution with high total values (around 100mg/g dry matter) early and late in the season and a very low content of all iridoids coinciding with the onset of flowering at the beginning of August. The relative contribution of antirrhinoside was significantly higher before flowering than after bud break. The relative decrease in antirrhinoside was counteracted by an increase of antirrhide, which was significantly higher after the onset of flowering than before. This pattern indicates a change in biosynthesis, although no explanation can be given to the phenomenon. The diurnal variation showed a variation between 20 and 60mg/g dry weight, but there was no relation to light/darkness conditions, temperature patterns or water content. The analyses were performed by HPLC. The applied method has not previously been used in the quantification of iridoids, but was developed specifically for the analyses of cultivars of Antirrhinum majus. We have fully validated the method during its development. The limit of detection was calculated to 0.004mg/ml and the limit of quantification was 0.01mg/ml.

Journal Article↗
PubMed2006

Antiamoebic activity of iridoids from Morinda morindoides leaves.

An aqueous decoction (dried extract), an 80 % methanolic extract from Morinda morindoides (Rubiaceae) leaves, and five iridoids isolated from the 80 % methanolic extract were evaluated in vitro for their activity against Entamoeba histolytica and their cytotoxicity. The aqueous decoction and the 80 % methanolic extract exhibited a promising antiamoebic activity with IC (50) values of 3.1 +/- 1.7 and 1.7 +/- 0.6 microg/mL, respectively. All tested iridoids displayed antiamoebic activity, the most active being epoxygaertneroside (IC (50): 1.3 +/- 0.4 microg/mL) and methoxygaertneroside (IC (50): 2.3 +/- 0.7 microg/mL) followed by gaertneroside, acetylgaertneroside and gaertneric acid with IC (50) values of 4.3 +/- 1.8, 5.4 +/- 1.4 and 7.1 +/- 1.4 microg/mL, respectively. Synergistic effects between the iridoids tested, or with other constituents, may explain the high activity of the extracts. All extracts and iridoids were devoid of any cytotoxic effect against MT-4 cells at the highest test concentration of 250 microg/mL. These findings support at least in part the traditional use of Morinda morindoides leaves for the treatment of amoebiasis in the Democratic Republic of Congo.

Amebiasis↗
PubMedDate not supplied

Iridoid patterns of genus Plantago L. and their systematic significance.

The distribution of 14 iridoid glucosides in 14 Plantago L. species (44 samples corresponding to 18 taxa) was shown. P. tenuiflora and P. gentianoides were studied for iridoids for the first time. The iridoid patterns showed a good correlation with morphological and other chemical features of the representatives of genus Plantago. The studied species are grouped together according to the iridoid patterns: species containing mainly aucubin (P. major, P. cornuti, P. gentianoides); species containing aucubin and aucubin derivatives (P. subulata, P. media); species containing aucubin and catalpol (P. lanceolata, P. altissima, P. argentea, P. lagopus, P. atrata); species containing aucubin and plantarenaloside (P. afra, P. scabra).

Bulgaria↗
PubMed2006

Effect on capillary permeability in rabbits of iridoids from Buddleia scordioides.

The methanol soluble fraction of the leaves of Buddleia scordioides after column chromatography resulted in the isolation of two known iridoid glucosides, catalpol and methylcatalpol. The structures were elucidated by extensive 1D-2D-NMR spectroscopy. The structure of methylcatalpol was confirmed by single-crystal x-ray diffraction. These compounds showed protective activity against increased (both chloroform and histamine) skin vascular permeability in rabbits. The protective effect was measured as the reduction in leakage of Evans blue. The results showed that the iridoids produced a significant inhibition of microvascular permeability. A comparison was made between the action of the iridoids and a known inhibitor of vascular permeability, troxerutin (50 mg/kg). Methylcatalpol and catalpol were found to be less effective than troxerutin.

Animals↗
PubMed2003

seco-iridoids from Calycophyllum spruceanum (Rubiaceae).

Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml).

Animals↗
PubMed2002

Caudatosides A-F: new iridoid glucosides from Citharexylum caudatum.

Six new iridoid glucosides, caudatosides A-F (2-7), and one known iridoid glucoside, 5-deoxypulchelloside I (1), were isolated from the fruits of Citharexylum caudatum. The structures of these compounds were elucidated by various one- and two-dimensional NMR techniques as well as high-resolution negative-ion ESIMS. Other plant parts were extracted on a small scale, and TLC of these extracts revealed the presence of the same iridoids.

Chromatography, Thin Layer↗
PubMed2003

Colorimetric estimation of total iridoid content of Picrorhiza kurrooa.

A colorimetric method has been developed for the selective analysis of the total iridoid content of the rhizomes of Picrorhiza kurrooa in terms of catalpol. The method of analysis is based on the reaction between iridoid compounds and primary amine. The iridoid glycosides present in P. kurrooa are mainly the esters of catalpol, and can be easily converted into catalpol by saponification. Catalpol thus obtained by hydrolysis is treated with glycine in acidic medium to give a purple color with a maxmimum absorption of 542 nm. The method was validated as per the ICH guidelines for linearity, accuracy and precision. Several other rhizome samples of the plant were also assayed using this method. The method developed is precise, sensitive, reproducible and easy to perform and can be used for the standardization of crude drug.

Colorimetry↗