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PubMed2006

Five new iridoids from Patrinia rupestris.

Five new iridoids, namely rupesin A-E (1-5, resp.), together with six known iridoids, 6-11, were isolated from the roots of Patrinia rupestris. Their structures were elucidated by spectroscopic methods including IR, UV, MS, and 1D- and 2D-NMR experiments, and comparison with data of known analogues. Compounds 4 and 11, compounds 1, 2, 5, 6, 8, 9, and 10, and compounds 3, 4, and 8 showed significant antibacterial activities against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus, respectively.

Anti-Bacterial Agents↗
PubMed2006

Iridoid glucosides and flavones from the aerial parts of Avicennia marina.

Two new iridoid glucosides, namely, 2'-O-[(2E,4E)-5-phenylpenta-2,4-dienoyl]mussaenosidic acid (1; mussaenosidic acid = [1S-(1alpha,4aalpha,7alpha,7aalpha)]-1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid) and 2'-O-(4-methoxycinnamoyl)mussaenosidic acid (2), were isolated from the aerial parts of the mangrove plant Avicennia marina. Beside that, one known iridoid glucoside, 2'-O-coumaroylmussaenosidic acid (3) and four known flavones (flavone = 2-phenyl-4H-1-benzopyran-4-one) including 4',5-dihydroxy-3',7-dimethoxyflavone (4), 4',5-dihydroxy-3',5',7-trimethoxyflavone (5), 4',5,7-trihydroxyflavone (6), and 3',4',5-trihydroxy-7-methoxyflavone (7) were also isolated and identified. The structures of these compounds were elucidated by NMR spectroscopy and by low- and high-resolution mass spectrometry. The chemotaxonomic significance of these findings was discussed. In addition, each isolated compound was evaluated for the ability of alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical-scavenging activity.

Avicennia↗
PubMedDate not supplied

On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR.

HPLC-UV-MS analysis of the methanol extract of Jamesbrittenia fodina (Wild) O. M. Hilliard (Scrophulariaceae) revealed the presence of different iridoid cinnamic esters; however, isolation of these constituents was prevented by instability problems. HPLC-UV-MS and HPLC-NMR analysis of the mixtures obtained after a tentative isolation indicated that, in the first instance, instability was due to a light-induced cis/trans isomerisation of the cinnamic moieties. Further investigation of related compounds showed an additional instability problem linked to other chemical transformations. A detailed HPLC-NMR-MS study of these fractions demonstrated that the modifications occurred on the rhamnose moiety of these iridoids. It could be concluded that the second type of instability was attributable to transesterification of the cinnamic moiety on the rhamnose unit. The recording of stop-flow HPLC-NMR spectra for specific HPLC peaks permitted the direct monitoring of these transformations. Based on these on-line data, six new unstable aucubin derivatives were efficiently characterised.

Chromatography, High Pressure Liquid↗
PubMed2003

Benzoxazinoids and iridoid glucosides from four Lamium species.

A new class of compounds for the plant family Lamiaceae, benzoxazinoids, was found in Lamium galeobdolon. From the aerial parts of the species were isolated the new 2-O-beta-D-glucopyranosyl-6-hydroxy-2H-1,4-benzoxazin-3(4H)-one (6-hydroxy blepharin) together with four known benzoxazinoids, DHBOA-Glc, blepharin, DIBOA, DIBOA-Glc, as well as harpagide, 8-O-acetyl-harpagide and salidroside. Eight known iridoid glucosides, 24-epi-pterosterone and verbascoside were isolated from Lamium amplexicaule, L. purpureum and L. garganicum. The iridoids, 5-deoxylamiol and sesamoside, as well as the phytoecdysone, 24-epi-pterosterone, were found for the first time for the genus Lamium. The phytochemical data are discussed from a systematic and evolutionary point of view.

Ecdysone↗
PubMed2004

Iridoids from the aerial parts of Verbena littoralis (Verbenaceae).

The iridoids, 6S-hydroxy-8S-methyl-4-methylene-hexahydro-cyclopenta[c]pyran-3-one and 6S,9S-dihydroxy-8S-methyl-4-methylene-hexahydro-cyclopenta[c]pyran-3-one, were isolated from the aerial parts of Verbena littoralis. Their structures and stereochemistry were elucidated by means of NMR spectral data analysis. Both compounds showed moderate in vitro activity against gram positive and negative bacteria as well as moderate in vivo intestinal peristaltic action in mouse. The iridoids also showed moderate free radical scavenging activity against l,l-diphenyl-2-picrylhydrazyl (DPPH) as well as antioxidant activity, the latter being evidenced by redox properties measured using E1CD-HPLC.

Animals↗
PubMed2006

Iridoid glycosides from Harpagophytum procumbens D.C. (devil's claw).

Iridoid glycosides, harprocumbide A (6''-O-alpha-D-galactopyranosylharpagoside, 1) and harprocumbide B (6''-O-(cis-p-coumaroyl)-procumbide, 2) were isolated from the tubers of Harpagophytum prucumbens D.C., along with nine known iridoid glycosides 6-O-alpha-D-galactopyranosylharpagoside (3), and harpagoside (4), harpagide (5), 8-cinnamoylmyoporoside (6), 8-O-feruloylhapagide (7), procumbide (8), 6''-O-(p-coumaroyl)-procumbide (9), 8-O-(p-coumaroyl)-harpagide (10) and 8-O-(cis-p-coumaroyl)-harpagide (11). Compound 10 showed marginal inhibition activity against macrophages respiratory burst.

Animals↗
PubMed2006

Iridoid glycosides and cucurbitacin glycoside from Neopicrorhiza scrophulariiflora.

Three iridoid glycosides, picrorosides A (1), B (2) and C (3), and a cucurbitacin glycoside, scrophoside A (4), were isolated from the rhizomes of Neopicrorhiza scrophulariiflora (Scrophulariaceae), along with two known iridoid glycosides, picrosides I (5) and II (6), and three known cucurbitacin glycosides (7-9). Their structures were elucidated on the basis of both chemical and spectroscopic data.

Cucurbitacins↗
PubMed2002

Coelobillardin, an iridoid glucoside dimer from Coelospermum billardieri.

A new iridoid glucoside dimer, coelobillardin (1), was isolated from the aerial parts of Coelospermum billardieri. Its structure has been elucidated on the basis of MS and NMR data. From a biogenetic point of view, this compound, which includes a cyclobutane basic core, should be considered as a [2+2] dimerization product of (E)-10-(4-hydroxycinnamoyloxy)loganin, which is the major iridoid isolated from the plant.

Acylation↗
PubMed2002

4'-deoxy iridoid glycosides from Centranthus longiflorus.

The new iridoid glycosides, 4'-deoxykanokoside A and 4'-deoxykanokoside C, were isolated from the methanolic root extract of Centranthus longiflorus ssp. longiflorus. They were accompanied by the three known iridoid glycosides, kanokoside A, kanokoside C and valerosidatum, and two known phenylpropanoid glycosides, coniferin and isoconiferinoside. The structures were elucidated mainly by spectroscopic methods. The presence of 4-deoxy glucose as a part of plant glycosides is rather unusual. Cytotoxic effects of the isolated compounds were also investigated.

Iridoids↗
PubMed2003

Iridoid glucosides from Randia spinosa (Rubiaceae).

An iridoid glucoside: randinoside, along with five known iridoids: galioside, deacetylasperulosidic acid methyl ester, scandoside methyl ester, geniposide and gardenoside, were isolated from the stems of Randia spinosa. The structures were determined by spectroscopic analysis, including 2D NMR techniques.

Iridoids↗
PubMed2003

Iridoids from Kigelia pinnata DC. fruits.

From the fruits of Kigelia pinnata DC., a new furanone derivative formulated as 3-(2'-hydroxyethyl)-5-(2"-hydroxypropyl)-dihydrofuran-2(3H)-one (1), and four new iridoids named; 7-hydroxy viteoid II (2), 7-hydroxy eucommic acid (3), 7-hydroxy-10-deoxyeucommiol (4) and 10-deoxyeucommiol (5) have been isolated together with seven known iridoids, jiofuran (6), jioglutolide (7), 1-dehydroxy-3,4-dihydroaucubigenin (8), des-p-hydroxybenzoyl kisasagenol B (9), ajugol (10), verminoside (11) and 6-trans-caffeoyl ajugol (12). The structures of the isolated compounds were characterized by different spectroscopic methods.

4-Butyrolactone↗
PubMed2003

Iridoid glucosides from Strychnos nux-vomica.

From seeds of Strychnos nux-vomica three iridoids, 6'-O-acetylloganic acid, 4'-O-acetylloganic acid and 3'-O-acetylloganic acid were isolated together with two known iridoid glucosides, loganic acid and 7-O-acetylloganic acid. The structures of the compounds were established by ESI-MS and by 1D and 2D NMR spectroscopic methods.

Iridoids↗
PubMed2000

Phlorigidosides A-C, iridoid glucosides from Phlomis rigida.

From the aerial parts of Phlomis rigida, three iridoid glucosides, phlorigidoside A (2-O-acetyllamiridoside), B (8-O-acetyl-6-beta-hydroxyipolamide) and C (5-deoxysesamoside), were isolated together with the known iridoid glucosides, shanzhiside methyl ester, 8-O-acetylshanzhiside methyl ester, deoxypulcheloside I, lamiridoside, and 6-beta-hydroxyipolamide. The structures of the new compounds were elucidated based on spectral and chemical evidence.

Glucosides↗
PubMed2000

An iridoid glucoside from Euphrasia pectinata.

A new iridoid glucoside, 5beta,6beta-dihydroxyboschnaloside (1), was isolated from the aerial parts of Euphrasia pectinata. Five known iridoid glucosides, 6beta-hydroxyboschnaloside (2), aucubin, euphroside, plantarenaloside, and geniposidic acid, and two known phenylethanoid glycosides, verbascoside (= acteoside) and leucosceptoside A, were also obtained and characterized. The structure of compound 1 was established by spectroscopic evidence.

Glucosides↗
PubMed2001

Iridoid glycosides from the leaves of Morinda citrifolia.

A new iridoid glucoside (1), named citrifolinoside A, was isolated from the leaves of Morinda citrifolia along with the known iridoids asperuloside and asperulosidic acid. The structure of 1 was established by interpretation and full assignments of NMR spectroscopic data.

Glucosides↗
PubMed2003

Complement-inhibiting iridoids from Morinda morindoides.

Morinda morindoides (Baker) Milne-Redhead (syn. Gaertnera morindoides Bak.) is one of the most popular medicinal plants in the Democratic Republic of Congo. In relation to its traditional use against rheumatic pains, fractionation of both the EtOAc- and the n-BuOH-soluble fraction of the 80% MeOH extract of the leaves, guided by the anticomplementary activity on the classical activation pathway, yielded eight novel iridoids (1-8), all containing a spirolactone functionality. Their structure was elucidated using spectroscopic methods. Gaertneroside 1, acetylgaertneroside 2, and gaertneric acid 5 were found to inhibit the activation of the classical pathway of the complement system, with IC(50) values between 58 and 69 microM. In addition to the biologically active flavonoids reported before from the same plant, these complement-inhibiting iridoids may contribute at least in part to the traditional use against rheumatic pains.

Complement Inactivator Proteins↗
PubMed2003

A novel antibacterial iridoid and triterpene from Caiophora coronata.

Bioassay-guided fractionation of the antibacterial CH(2)Cl(2)-MeOH extract obtained from the aerial parts of the Argentinean plant Caiophora coronata led to the isolation of a new triterpene, 1beta,3beta-dihydroxyurs-12-en-27-oic acid, 1, and a new iridoid, 1alpha-methoxy-6alpha,10-dihydroxyisoepiiridomyrmecin (caiophoraenin), 2, along with the known iridoid isoboonein 3. Their structures were established by spectroscopic techniques (1D and 2D NMR, HRFABMS, FTIR). The MIC values of isolated compounds were determined against methicillin-sensitive (MSSA) and -resistant (MRSA) strains of Staphylococcus aureus, Bacillus subtilis (BS), vancomycin-resistant Enterococcus faecium (VREF), Escherichia coli (EC), E. coli imp (ECimp), and Candida albicans (CA). Compound 1 was found active against BS, MSSA, MRSA, VREF, and ECimp with MIC values of 2, 4, 4, 4, and 16 microg/mL, respectively.

Anti-Bacterial Agents↗
PubMed2004

New acylated iridoid glucosides from Vitex altissima.

Six new iridoid glucosides, 6'-O-trans-feruloylnegundoside (1), 6'-O-trans-caffeoylnegundoside (2), 2'-O-p-hydroxybenzoyl-6'-O-trans-caffeoylgardoside (3), 2'-O-p-hydroxybenzoyl-6'-O-trans-caffeoyl-8-epiloganic acid (4), 2'-O-p-hydroxybenzoyl gardoside (5), and 2'-O-p-hydroxybenzoyl-8-epiloganic acid (6), along with two known iridoids, agnuside and negundoside, have been isolated from the ethyl acetate extractive of the leaves of Vitex altissima. The structures of these compounds were elucidated on the basis of spectral data interpretation. These isolates did not exhibit significant 5-lipoxygenase enzyme inhibitory activity, but compounds 2-4 showed potent antioxidant activity by both the superoxide (NBT riboflavin photoreduction) free-radical-scavenging and DPPH-radical-scavenging methods. Compounds 1, 2, and negundoside were evaluated in a rat paw edema assay.

Animals↗