Temporal profiling of human urine VOCs and its potential role under the ruins of collapsed buildings.

Context: The scent profile of human urine was investigated as potential source of chemical markers of human presence in collapsed buildings after natural or man-made disasters.

Objective: The main goals of this study were to build a library of potential biomarkers of human urine to be used for the detection of entrapped victims and to further examine their evolution profile in time.

Materials And Methods: Headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) was used to detect and identify the volatile organic compounds (VOCs) spontaneously released from urine of 20 healthy volunteers.

Phenolics from Rhagadiolus stellatus (Asteraceae, Cichorieae).

Rhagadiolus stellatus Gaertn., a Mediterranean member of the Cichorieae tribe of the Asteraceae family used as a food plant, was analyzed for its spectrum of phenolic compounds. Kaempferol 3-O-β-glucoside 1, kaempferol 3-O-β-rutinoside (nicotiflorin) 2, quercetin 3-O-β-glucoside 3, and luteolin 4 were isolated from the n-butanol layer of a methanolic extract of whole plants of Rh.

Analysis of iridoids, secoiridoids and xanthones in Centaurium erythraea, Frasera caroliniensis and Gentiana lutea using LC-MS and RP-HPLC.

This study presents a new and validated HPLC method for the simultaneous determination of bioactive compounds in Centaurium erythraea, Frasera caroliniensis and Gentiana lutea. The iridoid loganic acid, four secoiridoids and 29 xanthones were separated on a RP-18 column, using aqueous o-phosphoric acid (0.085%, v/v) and acetonitrile as mobile phase.

Natural products from Scorzonera aristata (Asteraceae).

The aerial parts of Scorzonera aristata Ramond ex DC., collected in the South Tyrolean Dolomites, yielded the flavonoids quercetin 3-O-glucoside, rutin, and isoorientin, and the caffeic acid derivatives chlorogenic acid, 4,5-dicaffeoyl quinic acid, and 3,5-dicaffeoyl quinic acid. Sub-aerial parts contained caffeic acid methyl ester, 3,5-dicaffeoyl quinic acid, and the triterpenes 3alpha-hydroxyolean-5-ene, lupeol, and magnificol.

A new bisabolane derivative of Leontopodium andersonii.

Phytochemical investigations of the roots of Leontopodium andersonii C. B. Clarke (Asteraceae) resulted in the isolation of a new bisabolane sesquiterpene derivative.

Computer-aided discovery, validation, and mechanistic characterization of novel neolignan activators of peroxisome proliferator-activated receptor gamma.

Peroxisome proliferator-activated receptor gamma (PPAR gamma) agonists are used for the treatment of type 2 diabetes and metabolic syndrome. However, the currently used PPAR gamma agonists display serious side effects, which has led to a great interest in the discovery of novel ligands with favorable properties. The aim of our study was to identify new PPARgamma agonists by a PPAR gamma pharmacophore-based virtual screening of 3D natural product libraries.

Development of a fast and convenient method for the isolation of triterpene saponins from Actaea racemosa by high-speed countercurrent chromatography coupled with evaporative light scattering detection.

In the present work, a fast and simple method for the separation and purification of triterpene saponins from Actaea racemosa was successfully established. Accelerated solvent extraction was used for defatting and extracting of the subaerial parts, giving a triterpene enriched crude extract. Size exclusion chromatography was used to separate actein and 23-epi-26-deoxyactein from other triterpenoids, which were collected in a third fraction.

Iridoid glycosides from the leaves of Sambucus ebulus.

Six new iridoid glycosides (1-6) of the "Valeriana type" were isolated from leaves of Sambucus ebulus. The structures were elucidated by 1D- and 2D-NMR spectroscopy, mass spectrometry, and chemical degradation methods as 10-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (1), 7-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (2), 10-O-acetylpatrinoside-aglycone-11-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (3), patrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-ribohexo-3-ulopyranoside] (4), 10-O-acetylpatrinoside-aglycone-11-O-[4''-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside] (5), and patrinoside-aglycone-11-O-2'-deoxy-beta-D-glucopyranoside (6). Compounds 1-4 represent the first examples of acylated iridoid diglycosides bearing the uncommon D-ribohexo-3-ulopyranosyl sugar moiety.

Synthesis and antimicrobial activity of some new pyrazole derivatives containing a ferrocene unit.

A series of new imines and amines have been synthesized by condensation of 1H-3-ferrocenyl-1-phenylpyrazole-4-carboxaldehyde with the corresponding amines, followed by reduction with sodium borohydride. The synthesized compounds have been screened for their in vitro antimicrobial activity against 11 bacteria and three fungal/yeast strains, using disc diffusion and broth microdilution susceptibility assays. They have shown a wide range of activities, from completely inactive to the highly active compounds.

Structure-based virtual screening for the discovery of natural inhibitors for human rhinovirus coat protein.

Inhibitors of the human rhinovirus (HRV) coat protein are promising candidates to treat and prevent a number of upper respiratory diseases. The aim of this study was to find antiviral compounds from nature, focusing on the HRV coat protein. Through computational structure-based screening of an in-house 3D database containing 9676 individual plant metabolites from ancient herbal medicines, combined with knowledge from traditional use, we selected sesquiterpene coumarins from the gum resin asafetida as promising natural products.

Eudesmane derivatives from Hieracium intybaceum.

Two new eudesmanolides, 4beta-H,3beta-(beta-D-glucopyranosyloxy)eudesma-1,11(13)-dien-12,6-olide (5a) and 3beta-D-glucopyranosyloxyeudesma-1,4(15),11(13)-trien-12,6-olide (5b), as well as two related, known compounds, tuberiferin (7a) and dehydrobrachylaenolide (7b), were isolated from the CH2Cl2 extract of subaerial parts of Hieracium intybaceum All. Compounds 6a, 6b, 8a, and 8b, the Me esters of the corresponding sesquiterpenic acids related to 5a, 5b, 7a, and 7b, respectively, were obtained as artifacts during the isolation process. Additionally, linoleic acid (1), linolenic acid (2), the lignane syringaresinol 4'-O-beta-D-glucopyranoside (3), and the guaianolide dehydrocostus lactone (4) were also isolated from H.

Venturia inaequalis-inhibiting Diels-Alder adducts from Morus root bark.

In organic apple orcharding there is a continuous need for natural fungicides effective against Venturia inaequalis (Cooke) Winter, the causal agent of apple scab. In this study an in vitro assay is presented for determining the germination inhibitory potential of extracts and pure compounds. From a screening of plant extracts, the methanol extract of Morus root bark revealed distinct V.

Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents.

The analytical assessment of edelweiss (Leontopodium alpinum) herb extracts, used in traditional alpine medicine, has resulted in the development of a HPLC-PAD-MS method that allows baseline separation of almost all constituents. Peak assignment of 14 analytes was achieved by comparison of retention times, UV and mass spectra with those of reference compounds either commercially available (luteolin, apigenin and chlorogenic acid) or isolated from edelweiss plants by column chromatography. Ten of the isolated analytes were identified as the known natural products: quercetin-3-O-beta-D-glucoside, luteolin-7-O-beta-D-glucoside, luteolin-3'-O-beta-D-glucoside, luteolin-4'-O-beta-D-glucoside, apigenin-7-O-beta-D-glucoside, 6-hydroxy-luteolin-7-O-beta-D-glucoside, luteolin-7,4'-di-O-beta-D-glucoside, chrysoeriol-7-O-beta-D-glucoside, leontopodic acid and 3,5-dicaffeolyquinic acid.

Taspine: bioactivity-guided isolation and molecular ligand-target insight of a potent acetylcholinesterase inhibitor from Magnolia x soulangiana.

A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE, EC 3.1.1.

Stilbenoids from Tragopogon orientalis.

A phytochemical investigation of Tragopogon orientalis L. (Asteraceae, Cichorieae) yielded the natural products 6''-O-(7,8-dihydrocaffeoyl)-alpha,beta-dihydrorhaponticin, 3'-O-methyl-alpha,beta-dihydrorhaponticin, and (S)-3-(4-beta-glucopyranosyloxybenzyl)-7-hydroxy-5-methoxyphtalide as well as known compounds alpha,beta-dihydrorhaponticin, 3-(4-methoxybenzyl)-5,7-dimethoxyphthalide, p-dihydrocoumaric acid methyl ester, and 1-hydroxypinoresinol-1-O-beta-glucopyranoside. The structures were established by HR mass spectrometry, extensive 1D and 2D NMR spectroscopy, and CD spectroscopy.

Altitudinal variation of secondary metabolite profiles in flowering heads of Arnica montana cv. ARBO.

The altitudinal variation on the contents of secondary metabolites in flowering heads of Arnica montana was assessed. Plants of A. montana cultivar ARBO were grown in nine experimental plots at altitudes between 590 and 2230m at Mount Patscherkofel near Innsbruck/Austria.

New insights into the acetylcholinesterase inhibitory activity of Lycopodium clavatum.

Looking for acetylcholinesterase (AChE) inhibiting compounds within the plant kingdom, we came across the triterpene alpha-onocerin, which has recently been described as the active principle (IC(50) of 5.2 microM) of Lycopodium clavatum L. In order to discover related terpenoid structures with similar AChE inhibitory activity, we investigated the roots of Ononis spinosa L.

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.

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.

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.

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.