Inhibitory effects of the essential oil of chamomile (Matricaria recutita L.) and its major constituents on human cytochrome P450 enzymes.

Chamomile extracts and tea are widely used herbal preparations for the treatment of minor illnesses (e.g. indigestion, inflammation).

Differentiation of Cirsium japonicum and C. setosum by TLC and HPLC-MS.

The Chinese Pharmacopoeia indicates the use of field thistle (Cirsium setosum) and Japanese field thistle (C. japonicum) in the treatment of bleeding and inflammation. In the absence of an analytical method for the differentiation and analysis of these two species, TLC and HPLC-MS methods have been developed for this purpose.

Bibenzyls and dihydroisocoumarins from white salsify (Tragopogon porrifolius subsp. porrifolius).

A phytochemical investigation of three accessions of Tragopogon porrifolius L. subsp. porrifolius (Asteraceae, Lactuceae) yielded three new bibenzyl derivatives, 5,4'-dihydroxy-3-alpha-l-rhamnopyranosyl-(1-->3)-beta-d-xylopyranosyloxybibenzyl, 2-carboxyl-3,4'-dihydroxy-5-beta-d-xylopyranosyloxybibenzyl, tragopogonic acid (2'carboxyl-3',5',4''-trihydroxyphenylethanone) and three dihydroisocoumarin derivatives, including the new natural product 6-O-methylscorzocreticoside I.

Discovering COX-inhibiting constituents of Morus root bark: activity-guided versus computer-aided methods.

The aim of this study was to compare the efficiency of two well known approaches for the discovery of the bioactive principle/s in medicinal plants, namely the activity-guided isolation versus the computer-aided drug discovery by means of virtual screening (VS) techniques. Morus root bark of Morus sp. L.

Distribution of a new rosmarinic acid derivative in Eryngium alpinum L. and other Apiaceae.

The roots of Eryngium alpinum L. (Apiaceae) demonstrated radical scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in a TLC autographic assay. Isolation of the bioactive compounds allowed the identification of R-(+)-3'-O-beta-D-glucopyranosyl rosmarinic acid, a new rosmarinic acid derivative.

Urtica dioica agglutinin: separation, identification, and quantitation of individual isolectins by capillary electrophoresis and capillary electrophoresis-mass spectrometry.

With benign prostatic hyperplasia (BPH) being a major health problem in ageing men, alternative therapeutic approaches (e.g., with phytopharmaceuticals) are of great interest.

Polyacetylenes from the Apiaceae vegetables carrot, celery, fennel, parsley, and parsnip and their cytotoxic activities.

A dichloromethane extract of root celery yielded falcarinol, falcarindiol, panaxydiol, and the new polyacetylene 8-O-methylfalcarindiol. The structure of the new compound was established by one- and two-dimensional (1D and 2D) NMR, mass spectrometry, and optical rotation data. Nonpolar extracts of roots and bulbs of carrots, celery, fennel, parsley, and parsnip were investigated for their content of polyacetylenes by high-performance liquid chromatography with diode array detection (HPLC-DAD).

1H and 13C NMR signal assignment of cucurbitacin derivatives from Citrullus colocynthis (L.) Schrader and Ecballium elaterium L. (Cucurbitaceae).

2D NMR-derived 1H and 13C NMR signal assignments of six structurally closely related cucurbitacin derivatives are presented. The investigated 2-O-beta-D-glucopyranosylcucurbitacins I, J, K, and L were obtained from Citrullus colocynthis (L.) Schrader whereas the aglyca cucurbitacin E and I were isolated from Ecballium elaterium L.

Development of a sensitive high-performance liquid chromatography-diode array detection assay for the detection and quantification of the beauveria metabolite oosporein from submerged culture broth and bio-control formulations.

A sensitive high-performance liquid chromatography-diode array detection (HPLC-DAD) assay is described for the detection and quantification of the Beauveria metabolite oosporein from fungal culture broth and two biocontrol agent formulations. In all cases, analyte recovery was achieved with a Britton-Robinson buffer system at pH 5.5 diluted with methanol 3:7 (v/v) (BR5.

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.

Combination of a new sample preparation strategy with an accelerated high-performance liquid chromatography assay with photodiode array and mass spectrometric detection for the determination of destruxins from Metarhizium anisopliae culture broth.

A method is presented allowing the qualitative and quantitative analysis of destruxins (dtxs) in fungal culture broth. Sample preparation was carried out by ultrafiltration over a commercially available acetylated cellulose (CTA) membrane with a Mr 10000 cut-off. The developed high-performance liquid chromatography assay with diode array detection (HPLC-DAD) cuts down the analysis time by 50% compared to most of the currently applied methods (retention times: dtx A = 8.

Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products.

For the targeting selection of acetylcholinesterase (AChE) inhibitors from natural sources we generated a structure-based pharmacophore model utilizing an in silico filtering experiment for the discovery of promising candidates out of a 3D multiconformational database consisting of more than 110,000 natural products. In our study, scopoletin (1) and its glucoside scopolin (2) emerged as potential AChE inhibitors by the virtual screening procedure. They were isolated by different chromatographic methods from the medicinal plant Scopolia carniolica Jaqc.

Simultaneous determination of saponins and isoflavones in soybean (Glycine max L.) by reversed-phase liquid chromatography with evaporative light-scattering and ultraviolet detection.

The first validated analytical method permitting the simultaneous qualitative and quantitative determination of isoflavones and saponins in soy has been developed. It combines liquid chromatography with an ultraviolet and evaporative light-scattering detector (ELSD). Within less than 30 min, 6 isoflavones (detected at 254 nm) and 4 triterpene saponins (monitored with the ELSD) were baseline separated, using a reversed-phase C18 column and a mobile phase consisting of water and acetonitrile, both containing 0.

New constituents of Leontopodium alpinum and their in vitro leukotriene biosynthesis inhibitory activity.

Phytochemical investigations of the roots of Leontopodium alpinum Cass. resulted in the isolation and structure elucidation of six novel compounds and two known compounds. Novel constituents could be identified as the polyacetylenes 1-acetoxy-3-angeloyloxy-(4 E,6 E)-tetradeca-4,6-diene-8,10,12-triyne and its (6 Z)-isomer, the kaurenic acid derivative methyl ent-7alpha,9alpha-dihydroxy-15beta-[(2 Z)-2-methyl-but-2-enoyloxy]kaur-16-en-19-oate, the bisabolane derivative (1 R*,3 S*,4 R*,6 S*)-9-(acetoxy)-4-hydroxy-1-[(2Z)-2-methylbut-2-enoyloxy]bisabol-10(11)-ene and the lignans [(2 S,3 R,4 R)-4-(3,4-dimethoxybenzyl)-2-(3,4,5-trimethoxyphenyl)-tetrahydrofuran-3-yl]-methyl-(2 Z)-2-methylbut-2-enoate and its 3,4,5-trimethoxybenzyl derivative.

1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae).

The NMR signal assignments of a series of structurally divergent benzylisoquinolines isolated from Fumaria officinalis L. (Fumariaceae, Papaverales), namely adlumine, corlumine, corydamine, cryptopine, fumarophycine, O-methylfumarophycine, hydrastine, parfumine, protopine and sinactine, are presented.

Wulfenia carinthiaca Jacq., antioxidant and pharmacological activities.

Relative antioxidant activities of a methanolic extract of three phenylpropanoid glycosides and three iridoid glycosides from Wulfenia carinthiaca were evaluated using the Briggs-Rauscher (BR) reaction method. This method is based on the inhibitory effects by antioxidants on oscillations of the BR reaction. The total extract showed a certain antioxidant activity with respect to resorcinol chosen as standard.

Anti-inflammatory activity of Leontopodium alpinum and its constituents.

The aerial parts and roots of Leontopodium alpinum Cass. (Asteraceae) were investigated for their in vivo topical anti-inflammatory activity using the inhibition of Croton oil-induced ear dermatitis in mice. For both of the plant parts, the dichloromethane extract induced a dose-dependent oedema reduction, being more active than the methanol and 70% aqueous methanol ex-tracts.

Combining ethnopharmacology and virtual screening for lead structure discovery: COX-inhibitors as application example.

Virtual screening of large libraries of organic compounds combined with pharmacological high throughput screening is widely used for drug discovery in the pharmaceutical industry. Our aim was to explore the efficiency of using a biased 3D database comprising secondary metabolites from antiinflammatory medicinal plants as a source for the virtual screening. For this study pharmacophore models of cyclooxygenase I and II (COX-1, COX-2), key enzymes in the inflammation process, were generated with structure-based as well as common feature based modeling, resulting in three COX hypotheses.

A new cucurbitacin D related 16,23-epoxy derivative and its isomerization products.

[reaction: see text] A new (23S,24Z)-16,23-epoxy cucurbitacin derivative was isolated from Ecballium elaterium L. (Cucurbitaceae) fruit juice along with known cucurbitacin derivatives. Structure elucidation of these derivatives was accomplished by NMR spectroscopy and mass spectrometry from HPLC-MS data.

Antibacterial activity of Leontopodium alpinum (Edelweiss).

Extracts and individual constituents of Leontopodium alpinum Cass. (Asteraceae) were tested for their antimicrobial activity in two different assays. Extracts were screened in agar diffusion assays, whereas the minimum inhibitory concentrations (MIC) of single compounds were determined by the microbroth dilution method according to NCCLS criteria.

Lignans, phenylpropanoids and polyacetylenes from Chaerophyllum aureum L. (Apiaceae).

Sub-aerial parts of Chaerophyllum aureum L. yielded two polyacetylenes, falcarinol (1), falcarindiol (2), three lignans, namely nemerosin (3), deoxypodorhizone (4), deoxypodo-phyllotoxin (5), two phenylpropanoids, 1'-hydroxymyristicin (6) and its angeloyl ester (7). Compounds 6 and 7 were isolated for the first time from plant material and their structures were elucidated by means of extensive 1- and 2-dimensional NMR spectroscopy and high resolution mass spectrometry.

Tyrolobibenzyls E and F from Scorzonera humilis and distribution of caffeic acid derivatives, lignans and tyrolobibenzyls in European taxa of the subtribe Scorzonerinae (Lactuceae, Asteraceae).

A chemosystematic study of the subtribe Scorzonerinae, a subtribe of the Lactuceae tribe of the Asteraceae family was performed, using the recently discovered tyrolobibenzyls as well as lignans and caffeic acid derivatives as diagnostic characters. In addition to the known compounds two new tyrolobibenzyls (E and F) were isolated and their structures were established by mass spectrometry and 1D and 2D NMR spectroscopy. Twenty four samples from rootstocks of seventeen different Scorzonerinae taxa, comprising members of three genera (Podospermum, Scorzonera, and Tragopogon), were analyzed.

Iridoid and phenolic glycosides from Wulfenia carinthiaca.

Two new phenylpropanoid glycosides (2'-O-acetylplantamajoside and 2'-O, 6"-O-diacetylplantamajoside), a new iridoid glycoside (10-O-(cinnamoyl)-6'-O-(desacetylalpinosidyl)-catalpol), the two known iridoid glycosides globularin and isoscrophularioside, and the known phenylpropanoid glycoside platamajoside were isolated from the methanolic extract of the underground parts of Wulfenia carinthiaca. Structure elucidations were based on high-resolution mass spectrometry and extensive 1-D and 2-D NMR spectroscopy.

Structure of tyrolobibenzyl D and biological activity of tyrolobibenzyls from Scorzonera humilis.

A novel tyrolobibenzyl derivative, 1-->beta-D-apiosyl-beta-D-glucopyranosyl 4-[2-(4-hydroxyphenyl)ethyl]benzofuran-2-carboxylate 3 (tyrolobibenzyl D) was isolated from Scorzonera humilis L. and its structure established by mass spectrometry and 1D- and 2D-NMR spectroscopy. The biological activities of the new compound and related tyrolobibenzyls A-C (1-2, 4) and the semi-synthetic peracetyl derivatives of tyrolobibenzyls B (2a) and C (4a) were assessed.

Chemosystematic investigations of irregular diterpenes in Anisotome and related New Zealand Apiaceae.

A chemosystematic HPLC-UV and HPLC-MS investigation of New Zealand members of the Apiaceae was performed. Diterpenes were identified and quantified in methanolic extracts from subaerial parts of 28 taxa and 54 samples of Aciphylla, Anisotome, Apium, Gingidia, Lignocarpa, Oreomyrrhis, and Scandia. Six diterpenes (1-2, 4-7) and four polyacetylenes (8-11) were identified.