Biomedical subjects

Matthias Hamburger

Publications and source records attributed to Matthias Hamburger.

29 records · Page 2Linked to original sources

PubMed2003

A simple method for preparation of D-rhamnose.

A rapid procedure for the preparation of D-rhamnose from bacterial lipopolysaccharide (LPS) has been developed. It involves purification of LPS from Pseudomonas syringae pv. phaseolicola by phenol extraction and hydrophobic interaction chromatography (HIC), followed by mild hydrolysis and cleavage of the O-antigen into D-fucose and D-rhamnose. The monosaccharides were separated by column chromatography, and D-rhamnose recovered after filtration over Sephadex-LH 20.

Chromatography↗

PubMed2003

Novel tetramic acids and pyridone alkaloids, militarinones B, C, and D, from the insect pathogenic fungus Paecilomyces militaris.

Three yellow pigments were isolated from a mycelial extract of the entomopathogenic fungus Paecilomyces militaris. With the aid of spectroscopic means, one compound was identified as a new pyridone alkaloid, militarinone D (1). The two other metabolites were characterized as two novel 3-acyl tetramic acids, militarinones B (2) and C (3). In contrast to the structurally related pyridone militarinone A (4), compounds 1-3 showed only negliable neuritogenic activity in PC-12 cells, whereas militarinone D (1) exhibited cytotoxicity. On the basis of a co-occurrence of 3-acyl tetramic acids and biogenetically related pyridone alkaloids in P. militaris, a revised biosynthetic pathway for pyridone alkaloids is proposed.

Alkaloids↗

PubMed2003

Ultraviolet a induces generation of squalene monohydroperoxide isomers in human sebum and skin surface lipids in vitro and in vivo.

At the outermost surface of human skin, skin surface lipids are first-line targets of solar ultraviolet radiation. Therefore, we hypothesized that ultraviolet A and ultraviolet B irradiation induce photo-oxidation of skin surface lipids. To test this, sebum samples were collected from facial skin of 17 healthy volunteers, weighed, and immediately irradiated with either ultraviolet B or ultraviolet A. Squalene, the major sebum lipid, as well as photo-oxidation products were identified in sebum lipid extracts by high-performance liquid chromatography analysis. Upon ultraviolet A exposures squalene was depleted in a concentration-dependent manner, whereas an unidentified sebum lipid photo-oxidation product was detected. Using high-performance thin layer chromatography, high-performance liquid chromatography, atmospheric pressure chemical ionization mass spectrometry, and nuclear magnetic resonance, unidentified sebum lipid photo-oxidation product was identified as a mixture of squalene monohydroperoxide isomers. Squalene monohydroperoxide isomers purified from sebum were identical with squalene monohydroperoxide isomers synthesized by preparative photo-oxidation of squalene. Squalene monohydroperoxide isomers were formed even after small suberythematogenic doses of ultraviolet A (5 J per cm2). Whereas physiologic baseline levels of squalene monohydroperoxide isomers in human skin were only slightly above detection limits, squalene monohydroperoxide isomer levels were strongly increased by suberythematogenic doses of ultraviolet A both in vitro and in vivo. High-performance liquid chromatography results could be complemented by a straightforward thin layer chromatography method for rapid screening of lipid peroxide formation in human sebum/skin surface lipids. In conclusion, specific squalene monohydroperoxide isomers were identified as highly ultraviolet A sensitive skin surface lipid breakdown products that may serve as a marker for photo-oxidative stress in vitro and in vivo.

Adult↗

PubMed2003

A comparative study on the skin penetration of pure tryptanthrin and tryptanthrin in Isatis tinctoria extract by dermal microdialysis coupled with isotope dilution ESI-LC-MS.

The indolo[2,1- b]quinazoline alkaloid tryptanthrin has recently been identified as a pharmacologically active compound in Isatis tinctoria, with potent dual inhibitory activity on prostaglandin and leukotriene synthesis. To investigate the skin penetration of tryptanthrin from solutions of pure compound and Isatis extracts, we developed and validated a cutaneous microdialysis model using ex vivo pig foreleg. Microdialysis was performed by placing linear probes in the dermis of the skin in situ, and tryptanthrin concentrations in the dialysates were determined by isotope dilution electrospray ionization LC-MS in the selected ion mode. Measurable concentrations of tryptanthrin were detected 30 min after application. A dose-dependent increase in tryptanthrin concentrations in the dialysate was observed for the Isatis extracts, but not for pure tryptanthrin. Microscopic analysis showed that the pure compound crystallized from the solution but remained in an amorphous state in the extracts.

Animals↗

PubMed2002

Constituents in evening primrose oil with radical scavenging, cyclooxygenase, and neutrophil elastase inhibitory activities.

Cold-pressed, non-raffinated evening primrose oil was found to contain lipophilic radical scavengers. A highly enriched fraction of these compounds could be obtained from the oil by extraction with aqueous ethanol and subsequent liquid-liquid partitioning with petroleum. LC-DAD-MS analysis revealed that the fraction contained three aromatic compounds with identical UV and ESI-MS spectra. The compounds were isolated by RP-HPLC and their structures established by chemical and spectroscopic means as 3-O-trans-caffeoyl derivatives of betulinic, morolic, and oleanolic acid. The morolic acid derivative was a new compound. The three esters exhibited pronounced radical scavenging activity against the stable 2,2-diphenyl-1-picrylhydrazyl radical and were potent inhibitors of neutrophil elastase and cyclooxygenase-1 and -2 in vitro. Commercial samples of evening primrose oils contained only traces of these lipophilic antioxidants.

Antioxidants↗

PubMed2002

Occurrence of stable foam in the upper Rhine River caused by plant-derived surfactants.

For 30 yr, a persistent foam cover has been observed during the summer months in the Rhine River beneath the Rhine Fall, a waterfall near Schaffhausen, Switzerland. This phenomenon has been a matter of public concern ever since its first appearance, but all previous attempts to clarify the origin of this foam had remained inconclusive. With the aid of electrospray LC-MS,triterpene saponins and mono- and digalactosyldiacylglycerolipids (MGDAG and DGDAG), two classes of tensioactive metabolites occurring in the aquatic plant Ranunculus fluitans Lamk. (Ranunculaceae), were detected in river water and foam samples. Saponin concentrations in water and foam samples were monitored at regular intervals during the years 1998 and 2000. Other compound classes with surfactant properties such as proteins, humic acids, and synthetic detergents were also analyzed. Foam occurrence paralleled with saponin concentration and with the amounts of detached Ranunculus biomass accumulating at the dam of the hydroelectric power plant of Schaffhausen located just above the Rhine Fall but not with the concentration of synthetic detergents. The ecotoxicological potential of Ranunculus constituents, water, and foam samples was checked with a representative range of aquatic indicator organisms. No acute toxicity was observed at concentrations that were at least 50-fold higher than those found in the environmental samples.

Biomass↗

PubMed2002

Militarinone A, a neurotrophic pyridone alkaloid from Paecilomyces militaris.

[structure: see text] A new pyridone alkaloid, militarinone A (1), was isolated by bioassay-guided fractionation from the mycelium of the entomogenous fungus Paecilomyces militaris. Its structure was established by extensive spectroscopic analysis. The compound features an unprecedented side chain and a 1,4-substituted cyclohexyl moiety not previously encountered in microbial metabolites. Militarinone A had a pronounced neurotrophic effect in PC-12 cells at 10 microM concentrations.

Alkaloids↗

PubMed2002

Radical scavengers from the entomogenous deuteromycete Beauveria amorpha.

The culture medium of Beauveria amorpha Hohn. exhibited strong radical scavenging properties. Activity-directed fractionation assisted by a radical scavenging assay on TLC afforded two active compounds which were identified as 6-methyl-2,4-dihydroxyphenyl 4-O-methyl-beta-D-glucopyranoside (1) and (-)-terredionol (2). Compound 1 displays radical scavenging and lipid peroxidation inhibitory activity comparable to those of TroloxC, ascorbic acid or quercetin.

Animals↗

PubMed2002

Quantitative determination of the dual COX-2/5-LOX inhibitor tryptanthrin in Isatis tinctoria by ESI-LC-MS.

Isatis tinctoria L. is an old European and Chinese dye plant and anti-inflammatory herb from which the potent cyclooxygenase-2 and 5-lipoxygenase inhibitor tryptanthrin (1) (indolo-[2,1-b]-quinazoline-6,12-dione) was recently isolated as one of the active principles. An HPLC method for the quantitative analysis of the compound in plant material was developed. Reproducible extraction was achieved by accelerated solvent extraction (ASE). Detection by UV at 254 and 387 nm and by electrospray-MS were compared. The low tryptanthrin content in the herb and possible interferences required isocratic high-performance liquid chromatography coupled with electrospray-MS in single ion mode. More than 70 Isatis samples of different origin were analyzed. The tryptanthrin content in leaf samples varied from 0.56 to 16.74 x 10(-3) %.

Arachidonate 5-Lipoxygenase↗

PubMed2002

Inhibitory activity of tryptanthrin on prostaglandin and leukotriene synthesis.

The indolo[2,1- b]quinazoline alkaloid tryptanthrin has previously been identified as the cyclooxygenase-2 (COX-2) inhibitory principle in the extract ZE550 prepared from the medicinal plant Isatis tinctoria (Brassicaceae). We here investigated the potential inhibitory activity of tryptanthrin and ZE550 on COX-2, COX-1 in cellular and cell-free systems. A certain degree of selectivity towards COX-2 was observed when COX-1-dependent formation of thromboxane B(2) (TxB(2)) in HEL cells and COX-2-dependent formation of 6-ketoprostaglandin F(1alpha) (6-keto-PGF(1alpha)) in Mono Mac 6 and RAW 264.7 cells were compared. Preferential inhibition of COX-2 by two orders of magnitude was found in phorbol myristate acetate (PMA) activated bovine aortic coronary endothelial cells (BAECs). Assays with purified COX isoenzymes from sheep confirmed the high selectivity towards COX-2. The leukotriene B(4) (LTB(4)) release from calcium ionophore-stimulated human granulocytes (neutrophils) was used as a model to determine 5-lipoxygenase (5-LOX) activity. Tryptanthrin and the extract ZE550 inhibited LTB(4) release in a dose dependent manner and with a potency comparable to that of the clinically used 5-LOX inhibitor zileuton.

Animals↗

PubMedDate not supplied

Supercritical carbon dioxide extraction of marigold at high pressures: comparison of analytical and pilot-scale extraction.

The effects of pressure and co-solvent on the extraction of anti-inflammatory faradiol esters in marigold (Calendula officinalis L.) were investigated by supercritical fluid extraction at laboratory and pilot scales. Pressures higher than 300 bar and modifier (ethanol) concentrations ranging from 0 to 20% (v/v) were used at an extraction temperature of 50 degrees C. With an analytical extractor, exhaustive extraction of the drug and highest concentrations in the extracts were achieved with 0.5% ethanol at the maximum pressure of 689 bar. Increased modifier concentrations improved the extractability at lower pressure, but the higher amount of total extractables led to a lower concentration of faradiol esters in the extracts. The HPLC fingerprints of the extracts, the yields of total extract and the concentration of faradiol esters obtained with analytical and pilot scale extractors under the same conditions were comparable.

Anti-Inflammatory Agents↗