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Christoph Seger

Publications and source records attributed to Christoph Seger.

24 records · Page 2Linked to original sources

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. Known compounds, reported here for the first time for the genus Leontopodium, were identified as ent-kaur-16-en-19-oic acid and T-cadinol. The obtained compounds were tested together with 15 previously described compounds of L. alpinum in an ex vivo leukotriene biosynthesis inhibition assay. The highest activities were determined for the bisabolane derivates (IC50: 7.7 to 11.4 microM), one lignan (IC50: 10.7 microM) and the ent-kaurenoate (IC50: 10.4 microM).

Asteraceae↗

Donor exposure to the plasticizer di(2-ethylhexyl)phthalate during plateletpheresis.

BACKGROUND: Di(2-ethylhexyl)phthalate (DEHP) is a plasticizer that is contained in most PVC devices, including apheresis disposables. Because DEHP can be extracted from apheresis disposables as the blood passes through the apheresis device, DEHP exposure was determined in healthy donors undergoing plateletpheresis performed with commercially available apheresis systems. STUDY DESIGN AND METHODS: The study population consisted of 36 healthy PLT donors undergoing plateletpheresis with either continuous or discontinuous apheresis devices. Serum concentrations of DEHP were determined from peripheral blood obtained before and after plateletpheresis, with gas chromatography-mass spectroscopy. RESULTS: Plateletpheresis performed with standard collection disposables resulted in a median increase of 232 percent of serum DEHP compared to levels before apheresis, corresponding to a total amount of DEHP exposed during a single apheresis of a median of 6.46 (range, 1.8-20.3) microg per kg of body weight. Endogenous levels of triglycerides showed a positive correlation with the amount of DEHP released. Increase in serum DEHP was short-term as serum DEHP rapidly returned to levels obtained before apheresis within 3 hours after completion of the apheresis course. Donor exposure to DEHP led to no variation in liver cell function within 48 hours after plateletpheresis. CONCLUSION: Commercial plateletpheresis disposables release considerable amounts of DEHP during the apheresis procedure, but the total dose of DEHP retained by the donor is within the normal range of DEHP exposure of the general population.

Blood Donors↗

Feeding deterrence and contact toxicity of Stemona alkaloids-a source of potent natural insecticides.

On the basis of chronic feeding bioassays with neonate larvae of Spodoptera littoralis reared on an artificial diet, the methanolic leaf and root extracts from Stemona collinsae displayed very high insect toxicity compared to those of two Aglaia species, a commercial Pyrethrum extract, and azadirachtin, whereas S. tuberosa extracts demonstrated low activity in roots and no activity in leaves. Beyond that, in leaf disk choice tests against fifth instar larvae, S. collinsae showed strong antifeedant activity, whereas S. tuberosa was characterized by remarkable repellency. The anti-insect properties of both species were based on pyrrolo[1,2-a]azepine alkaloids, from which didehydrostemofoline (asparagamine A) was the major compound of the roots of S. collinsae, exhibiting the highest toxicity in feeding assays. Saturation and hydroxylation of the side chain in the co-occurring stemofoline and 2'-hydroxystemofoline, respectively, led to an increasing loss of activity. Contact toxicity tests with stemofoline and didehydrostemofoline exhibited even higher activities than those of Pyrethrum extract. Tuberostemonine was the dominating alkaloid in the roots of S. tuberosa, showing outstanding repellency but no toxic effects.

Aglaia↗

A new pyrrole alkaloid from seeds of Castanea sativa.

A new pyrrole alkaloid, methyl-(5-formyl-1H-pyrrole-2-yl)-4-hydroxybutyrate (1), was isolated from sweet chestnut seeds and its structure elucidated on the basis of data from NMR spectroscopy and by comparison with synthetic analogues.

Alkaloids↗

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. One analyte, 3,4,5-tri-(E)-caffeoly-D-glucaric acid proved to be a new natural product and was named leontopodic acid B. Structure elucidation was carried out by means of MS and NMR spectroscopy in all cases. The aerial plant parts of L. alpinum (capitula, inflorescence leaves, stems, stem leaves and leaves of the basal rosette) showed variable amounts of the above-mentioned constituents, although qualitative differences were not observable.

Asteraceae↗

A novel, high-affinity, fluorescent progesterone receptor antagonist. Synthesis and in vitro studies.

The present paper describes the chemical synthesis and in vitro characterization of a novel, high-affinity, fluorescent progesterone receptor (PR) antagonist. The three-step synthesis was carried out starting from mifepristone. After demethylation with calcium oxide, the methylamino group was alkylated with 6-bromohexanol, and the resulting compound was reacted with fluorescein 5-isothiocyanate, yielding the fluorescein-mifepristone conjugate. Interaction of the conjugate as well as of its precursors with PR was determined in cell culture (alkaline phosphatase assay and transactivation assay). Antiprogestagenic activity of the intermediates were comparable to that of the parent compound. Even after attachment of the bulky fluorescein moiety, considerable antiprogestagenic activity was maintained. Microscopic studies revealed that fluorescence of the conjugate was almost confined to the nuclei of steroid hormone receptor-positive cells, whereas the nuclei of steroid hormone receptor-negative cells remained unstained. To our knowledge, this is the first report on a fluorescent ligand for PR suitable for studies in living cells. It is proposed that the present fluorescent PR antagonist might serve as a lead compound for the development of contrast agents for PR imaging, e.g., by near-infrared optical imaging.

Cell Line, Tumor↗