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At least 109 records · Page 6Linked to original sources
PubMed2005

Immunosuppressive iridoids from the fruits of Gardenia jasminoides.

A new iridoid, gardaloside (1), and a new safranal-type monoterpene, jasminoside G (2), together with 10 known compounds including nine iridoids and a second safranal-type monoterpene, were isolated from the fruits of Gardenia jasminoides. The structures of 1 and 2 were established on the basis of spectroscopic evidence. Of these compounds, geniposide (3), 6alpha-hydroxygeniposide (5), ixoroside (7), and shanzhiside (8) showed significant inhibition of IL-2 secretion by phorbol myristate acetate and anti-CD28 monoclonal antibody co-stimulated activation of human peripheral blood T cells.

Antibodies, Monoclonal↗
PubMed2006

Iridoid constituents of Tarenna attenuata.

Members of a rare type of iridoid with two alpha,beta-unsaturated acid units were isolated from the whole plant of Tarenna attenuata, including a new compound, tarennin (1), an extraction artifact, and seven new glucosides, tarenninosides A-G (2-8), together with two known iridoid glucosides, ixoside and 10-methylixoside. The structures of 1-8 were elucidated by analysis of spectroscopic data including HMQC, HMBC, 1H-1H COSY, and ROESY NMR spectra and by comparison with known analogues. Antioxidant and cytotoxic activities were evaluated for these 10 compounds, but none showed positive activity.

Animals↗
PubMed2002

Iridoids with anti-inflammatory activity from Vitex peduncularis.

A new iridoid, pedunculariside, together with the known iridoid agnuside were isolated from the butanol extract of Vitex peduncularis stem bark. Both pedunculariside and agnuside showed preferential inhibition of COX-2, with IC50 values of 0.15 +/- 0.21 mg/ml and 0.026 +/- 0.015 mg/ml respectively, while having only small inhibitory effects on COX-1. Both compounds did not exhibit cytotoxicity against vero cells.

Animals↗
PubMed2002

Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia.

As part of our screening of antiviral agents from medicinal plants, 11 compounds from plant origin (Bupleurum rigidum and Scrophularia scorodonia), three saikosaponins, seven iridoids and one phenylpropanoid glycoside were tested in vitro against herpes simplex type I (HSV-1), vesicular stomatitis virus (VSV) and poliovirus type 1. Five of these compounds showed antiviral activity against VSV. The percentages of cellular viability at the non-toxic limit concentrations of the active compounds were: verbascoside 53.6 % at 500 microg/ml, 8-acetylharpagide 32.1 % at 500 microg/ml, harpagoside 43.3 % at 450 microg/ml, scorodioside 47.8 % at 500 microg/ml and buddlejasaponin IV 56.9 % at 25 microg/ml. Although none of the saikosaponins were active against HSV-1, the iridoid scorodioside showed moderate in vitro anti-HSV-1 activity (30.6 % at 500 microg/ml). However, none of the compounds tested in this survey had any effect against poliovirus.

Animals↗
PubMed2003

Iridoid glucosides from the flowers of Barleria lupulina.

A new iridoid diglucoside, lupulinoside, and eight known iridoid glucosides, acetylbarlerin, ipolamiidoside ( 3), 6-O-acetylshanzhiside methyl ester, barlerin, shanzhiside methyl ester, mussaenosidic acid, 8-O-acetylshanzhiside, and shanzhiside have been isolated from the flowers of Barleria lupulina. The structure of the new compound was established as 8-O-acetyl-2'- O-(beta-glucopyranosyl)mussaenoside by spectroscopic, especially 2D NMR, techniques. When tested for anti-herpes simplex type 1 activity, only compound 3 exhibited antiviral properties. None of the compounds showed cytotoxic effects to the vero cells and none of them inhibited cyclooxygenase-2 enzyme.

Acanthaceae↗
PubMed2005

Two new non-glycosidic iridoids from the leaves of Campsis grandiflora.

Two new non-glycosidic iridoids, which were named cachinol (1) and 1-O-methyl cachinol (2), were isolated from the methanol extract of the leaves of Campsis grandiflora together with a known iridoid cachineside I (3). The structures of compounds 1 and 2 were determined on the basis of spectroscopic methods including two dimensional NMR and high resolution mass spectrometry. All of the isolated compounds showed mild inhibitory activities on rat platelet aggregation. Compounds 1 and 3 (IC50 : 246 and 219 microM, respectively) showed about 2-fold higher inhibitory effects than acetylsalicylic acid (ASA, IC50: 412 microM) on collagen-induced aggregation. Compounds 1 and 2 (IC50: 43.2 and 38.4 microM, respectively) were about 2-fold more inhibitory than ASA (IC50: 75.2 microM), and about 4-fold more effective than their glycoside 3 (IC50: 189 microM) on AA-induced aggregation.

Animals↗
PubMedDate not supplied

Two new iridoid glucosides from Picrorhiza scrophulariiflora.

Two new iridoid glucosides with 3,4-dihydrocatalpol skeleton, piscrosides A (1) and B (2) together with nine known iridoid glucosides and three known cucurbitacin glucosides, were isolated from the stems of Picrorhiza scrophulariiflora. Their structures were established by MS, 1H NMR, 13C NMR and 2D NMR methods (including HSQC, HMBC and NOESY experiments).

Iridoids↗
PubMed2001

Iridoid and phenylethanoid glycosides from Phlomis longifolia var. longifolia.

From the aerial parts of Phlomis longifolia var. longifolia four iridoid glucosides, shanzhiside methyl ester (1), 5-deoxypulchelloside I (2), lamalbide (3), phlomiol (4) and three phenylethanoid glycosides, verbascoside (5), forsythoside B (6), leucosceptoside A (7) along with the caffeic acid ester, chlorogenic acid (8) were isolated. The structures of the isolated compounds were established by spectroscopic (UV, IR, 1D- and 2D-NMR, FABMS) and chemical evidence. The structure elucidation of the iridoid compounds 2 and 3 are discussed in detail.

Chromatography, Liquid↗
PubMed2004

Antioxidant iridoid glucosides from Wendlandia formosana.

Two new iridoid glucosides of 10-O-caffeoyl scandoside methyl ester (3), and 6-methoxy scandoside methyl ester (4) besides the known compounds of scandoside methyl ester (1), methyl deacetyl asperulosidate (2), 10-O-caffeoyl daphylloside (5), phytol (6), and ursolic acid (7) were isolated from the leaves of Wendlandia formosana. Structure elucidation of the new iridoid glucosides was based on interpretation of high-resolution 1D and 2D NMR spectral data and chemical conversions. Antioxidant activity of Compounds (1-5) against diphenylpicrylhydrazyl (DPPH) and hydroxyl radical, and peroxynitrite was reported.

Antioxidants↗
PubMed2006

Iridoid and lignan glycosides from Citharexylum spinosum L.

From the aerial parts of Citharexylum spinosum L., one new iridoid glucoside, the 7-ss-O-acetate (1) of lamiide, along with four known iridoid glucosides, lamiide (2), lamiidoside (3), duranterectoside C (4), 8-epiloganin (5) and one known lignan glucoside (+)-lyonirenisol-3a-O-ss-D-glucopyranoside (6) were isolated. The compound structures were established by one- and two-dimensional 1H- and 13C-NMR as well as by ESI-MS spectra.

Glycosides↗
PubMed2006

The inhibitory effect of phenylpropanoid glycosides and iridoid glucosides on free radical production and beta2 integrin expression in human leucocytes.

Rapid production of reactive oxygen species (ROS) and upregulation of beta2 integrin by leucocytes are two important inflammatory responses in human leucocytes. To evaluate whether three phenylpropanoid glycosides (acteoside, crenatoside, and rossicaside B) and two iridoid glucosides (boschnaloside and 8-epideoxyloganic acid) identified from two medicinal plants with similar indications (Orobanche caerulescens and Boschniakia rossica) exhibited anti-inflammatory activity, their effects on N-formyl-methionyl-leucyl-phenylalanine (fMLP) and phorbol-12-myristate-13-acetate (PMA)-activated peripheral human neutrophils (PMNs) and mononuclear cells were examined. Pretreatment with 1-50 microM phenylpropanoid glycoside concentration-dependently diminished PMA- and fMLP-induced ROS production with IC50 values of approximately 6.8-23.9 and 3.0-8.8 muM, respectively. Iridoid glucoside was less effective than phenylpropanoid glycoside with an IC50 value of approximately 8.9-28.4 microM in PMA-activated PMNs and 19.1-21.1 microM in fMLP-activated mononuclear cells. Phenylpropanoid glycosides also effectively inhibited NADPH oxidase (NOX) and displayed potent free radical-scavenging activity, but did not interfere with pan-protein kinase C (PKC) activity. Furthermore, all compounds, except rossicaside B, significantly inhibited PMA- and fMLP-induced Mac-1 (a beta2 integrin) upregulation at 50 microM but not that of fMLP-induced intracellular calcium mobilization. These drugs had no significant cytotoxicity as compared with the vehicle control. Our data suggested that inhibition of ROS production, possibly through modulation of NOX activity and/or the radical scavenging effect, and beta2 integrin expression in leucocytes indicated that these compounds had the potential to serve as anti-inflammatory agents during oxidative stress.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed2002

Iridoids and anthraquinones from the Malaysian medicinal plant, Saprosma scortechinii (Rubiaceae).

A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-beta-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-beta-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin.

Anthraquinones↗
PubMed2002

Iridoid glucosides from Veronica hederifolia.

A new iridoid glucoside, urphoside A, and six known iridoid glucosides, pikuroside, aucubin, veronicoside, catalposide, amphicoside, and verminoside, were isolated from Veronica hederifolia together with a known megastigmane glucoside, 3-hydroxy-5,6-epoxy-beta-ionol-9-O-beta-D-glucopyranoside, and a hexitol, dulcitol. The structures of the isolated compounds were established by the extensive 1D- and 2D-NMR spectroscopy.

Iridoids↗
PubMed2002

Studies on the constituents of Syringa species. X. Five new iridoid glycosides from the leaves of Syringa reticulata (Blume) Hara.

Five new iridoid glycosides, (8Z)-ligstroside (1), (8Z)-nüzhenide (3), 6'-O-alpha-D-glucopyranosylsyringopicroside (4), 3'-O-beta-D-glucopyranosylsyringopicroside (5) and 4'-O-beta-D-glucopyranosylsyringopicroside (6) were isolated, together with a known one, (8E)-nüzhenide (2), from the leaves of Syringa reticulata. Their structures were established on the basis of chemical and spectral data. Compounds 1 and 3 are the first findings of a (8Z)-oleoside-type secoiridoid. Compound 4 is the first naturally occurring iridoid di-glycoside having an isomaltose.

Iridoids↗
PubMed2004

Studies on the constituents of Catalpa species. IX. Iridoids from the fallen leaves of Catalpa ovata G. Don.

Two new iridoids, 6-O-trans-p-coumaroyl-7-deoxyrehmaglutin A (1) and 6-O-cis-p-coumaroyl-7-deoxyrehmaglutin A (2), were isolated from the fallen leaves of Catalpa ovata G. DON. together with six artifact iridoids (3-8). Their structures were established by spectral analysis. In addition, the scavenging effects of the principal compounds isolated from this plant on 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity were examined.

Bignoniaceae↗