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1.
AMB Express ; 10(1): 79, 2020 Apr 24.
Article in English | MEDLINE | ID: mdl-32333233

ABSTRACT

Hops is an almost unique source of the potent phytoestrogen 8-prenylnaringenin (8-PN). As hops contain only low levels of 8-PN, synthesis may be more attractive than extraction. A strain of the Gram-positive Eubacterium limosum was isolated previously for 8-PN production from more abundant precursor isoxanthohumol (IX) from hops. In this study, spent hops, an industrial side stream from the beer industry, was identified as interesting source of IX. Yet, hop-derived compounds are well-known antibacterial agents and the traces of a large variety of different compounds in spent hops interfered with growth and IX conversion. Critical factors to finally enable bacterial 8-PN production from spent hops, using a food and feed grade medium, were evaluated in this research. The use of bacterial resting cells and complex medium at a pH of 7.8-8 best fulfilled the requirements for 8-PN production and generated a solid basis for development of an economic process.

2.
J Nat Prod ; 80(5): 1505-1513, 2017 05 26.
Article in English | MEDLINE | ID: mdl-28489375

ABSTRACT

Species of the genus Laserpitium have been used traditionally to treat inflammation and infection. From the herb of Laserpitium zernyi, six new compounds were isolated and their structures elucidated (using IR, NMR, HRMS data) as derivatives of 8-daucene-2,4,10-triol (1, 2, and 4), 7-daucene-2,4,10-triol (3), a lapiferin derivative featuring a C-2 ester moiety (5), and a daucane featuring an exomethylene group at C-8 (6). Also isolated were the rare daucanes vaginatin (7) and laserpitin (8). In a search for selective glucocorticoid receptor (GR) modulators, the compounds were tested for their capacity to inhibit NF-κB and AP-1 pro-inflammatory factors and for a potential competitive effect on a dexamethasone (Dex)-induced GR-driven glucocorticoid response element (GRE) reporter gene. The new 2ß-angeloyloxy-10α-acetoxy-8-daucene-2,4,10-triol (2) significantly inhibited transactivation of both NF-κB and AP-1, while vaginatin (7) was the most active of the compounds tested in blocking AP-1. Both compounds competitively repressed Dex-induced GRE-driven promoter activities, indicative of a potential role for GR. In addition, a decreased potential to inhibit NF-κB was apparent in GR knockout A549 cells. In line with the transcriptional assays, compounds 2 and 7 also significantly lowered CCL-2 chemokine production, albeit to a lesser extent than Dex. The results suggest that daucanes may be interesting candidates in the search for compounds with GR-modulating activities.


Subject(s)
Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Apiaceae/chemistry , Bridged Bicyclo Compounds/isolation & purification , Bridged Bicyclo Compounds/pharmacology , Dexamethasone/antagonists & inhibitors , Dexamethasone/chemistry , NF-kappa B/antagonists & inhibitors , Receptors, Glucocorticoid/antagonists & inhibitors , Receptors, Glucocorticoid/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Anti-Inflammatory Agents/chemistry , Bridged Bicyclo Compounds/chemistry , Esters , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , NF-kappa B/chemistry , Sesquiterpenes/chemistry , Transcription Factor AP-1 , Transcriptional Activation
3.
Nanomaterials (Basel) ; 6(3)2016 Mar 09.
Article in English | MEDLINE | ID: mdl-28344301

ABSTRACT

We present the in situ synthesis of Pt nanoparticles within MIL-101-Cr (MIL = Materials Institute Lavoisier) by means of atomic layer deposition (ALD). The obtained Pt@MIL-101 materials were characterized by means of N2 adsorption and X-ray powder diffraction (XRPD) measurements, showing that the structure of the metal organic framework was well preserved during the ALD deposition. X-ray fluorescence (XRF) and transmission electron microscopy (TEM) analysis confirmed the deposition of highly dispersed Pt nanoparticles with sizes determined by the MIL-101-Cr pore sizes and with an increased Pt loading for an increasing number of ALD cycles. The Pt@MIL-101 material was examined as catalyst in the hydrogenation of different linear and cyclic olefins at room temperature, showing full conversion for each substrate. Moreover, even under solvent free conditions, full conversion of the substrate was observed. A high concentration test has been performed showing that the Pt@MIL-101 is stable for a long reaction time without loss of activity, crystallinity and with very low Pt leaching.

4.
Org Biomol Chem ; 10(42): 8539-50, 2012 Nov 14.
Article in English | MEDLINE | ID: mdl-23011476

ABSTRACT

A small library of chiral imidate-ferrocenylphosphane ligands was efficiently synthesized (8 examples) and evaluated in the iridium(I)-catalyzed hydrogenation of unfunctionalized and poorly functionalized olefins. These catalysts perform very well in a range of examples (yields and ee's up to 100%).


Subject(s)
Alkenes/chemistry , Ferrous Compounds/chemistry , Imidoesters/chemistry , Iridium/chemistry , Phosphines/chemistry , Catalysis , Ferrous Compounds/chemical synthesis , Hydrogenation , Imidoesters/chemical synthesis , Ligands , Metallocenes , Phosphines/chemical synthesis
5.
Nephrol Dial Transplant ; 27(6): 2388-96, 2012 Jun.
Article in English | MEDLINE | ID: mdl-22167586

ABSTRACT

BACKGROUND: The uraemic retention solutes p-cresylsulphate (pCS) and p-cresylglucuronide (pCG), two conjugates of p-cresol, were never determined simultaneously. In the present paper, a high-performance liquid chromatography (HPLC) method was developed and used to quantify both compounds in parallel in an in vivo observational study and their in vitro effect was evaluated by flow cytometry. METHODS: pCS and pCG were determined in serum. For the validation specificity, linearity, recovery, precision and the quantification limit were evaluated. In vivo, concentrations of both compounds were determined in 15 controls and 77 haemodialysis patients, as well as protein binding in the dialysed group and the reduction ratios during haemodiafiltration. In addition, the in vitro effect of the solutes on leucocyte free radical production at measured concentrations was assessed. RESULTS: A fast and accurate HPLC method was developed to simultaneously quantify pCS and pCG. Both conjugates are retained in uraemia with a substantially higher total serum pCS in comparison to pCG (31.4 ± 15.8 versus 7.3 ± 6.5 mg/L) but also a substantial difference in protein binding (92.4 ± 3.0 versus 8.3 ± 4.4%) and in reduction ratio during post-dilution haemodiafiltration (37.4 ± 7.1 versus 78.6 ± 6.4%). pCG per se has no effect on leucocyte oxidative burst activity, whereas in combination with pCS, a synergistic activating effect was observed. CONCLUSIONS: Serum concentrations of pCS and pCG are elevated in uraemia. Both conjugates show a different protein binding, resulting in a different dialytic behaviour. Biologically, both conjugates are synergistic in activating leucocytes.


Subject(s)
Biomarkers/blood , Cresols/blood , Glucuronides/blood , Sulfuric Acid Esters/blood , Uremia/blood , Uremia/physiopathology , Adult , Aged , Case-Control Studies , Chromatography, High Pressure Liquid , Female , Follow-Up Studies , Free Radicals/metabolism , Humans , Leukocytes/metabolism , Male , Middle Aged , Prognosis , Renal Dialysis , Respiratory Burst
6.
J Med Chem ; 49(8): 2656-60, 2006 Apr 20.
Article in English | MEDLINE | ID: mdl-16610809

ABSTRACT

A series of fosmidomycin analogues featuring restricted conformational mobility has been synthesized and evaluated as inhibitors of 1-deoxy-D-xylulose 5-phosphate (DOXP) reductoisomerase and as growth inhibitors of P. falciparum. The enantiomerically pure trans-cyclopropyl N-acetyl analogue 3b showed comparable inhibitory activity as fosmidomycin toward E. coli DOXP reductoisomerase and proved equally active when tested in vitro for P. falciparum growth inhibition. Conversely, the alpha-phenyl cis-cyclopropyl analogue 4 showed virtually no inhibition of the enzyme.


Subject(s)
Fosfomycin/analogs & derivatives , Plasmodium falciparum/drug effects , Plasmodium falciparum/growth & development , Aldose-Ketose Isomerases/antagonists & inhibitors , Animals , Escherichia coli/drug effects , Escherichia coli/enzymology , Fosfomycin/chemical synthesis , Fosfomycin/chemistry , Fosfomycin/pharmacology , In Vitro Techniques , Molecular Structure , Multienzyme Complexes/antagonists & inhibitors , Oxidoreductases/antagonists & inhibitors , Parasitic Sensitivity Tests , Plasmodium falciparum/cytology , Stereoisomerism , Structure-Activity Relationship
7.
Plant Physiol ; 136(4): 4023-36, 2004 Dec.
Article in English | MEDLINE | ID: mdl-15563622

ABSTRACT

Caffeic acid O-methyltransferase (COMT) catalyzes preferentially the methylation of 5-hydroxyconiferaldehyde to sinapaldehyde in monolignol biosynthesis. Here, we have compared HPLC profiles of the methanol-soluble phenolics fraction of xylem tissue from COMT-deficient and control poplars (Populus spp.), using statistical analysis of the peak heights. COMT down-regulation results in significant concentration differences for 25 of the 91 analyzed peaks. Eight peaks were exclusively detected in COMT-deficient poplar, of which four could be purified for further identification using mass spectrometry/mass spectrometry, nuclear magnetic resonance, and spiking of synthesized reference compounds. These new compounds were derived from 5-hydroxyconiferyl alcohol or 5-hydroxyconiferaldehyde and were characterized by benzodioxane moieties, a structural type that is also increased in the lignins of COMT-deficient plants. One of these four benzodioxanes amounted to the most abundant oligolignol in the HPLC profile. Furthermore, all of the differentially accumulating oligolignols involving sinapyl units were either reduced in abundance or undetectable. The concentration levels of all identified oligolignols were in agreement with the relative supply of monolignols and with their chemical coupling propensities, which supports the random coupling hypothesis. Chiral HPLC analysis of the most abundant benzodioxane dimer revealed the presence of both enantiomers in equal amounts, indicating that they were formed by radical coupling reactions under simple chemical control rather than guided by dirigent proteins.


Subject(s)
Lignin/biosynthesis , Methyltransferases/metabolism , Populus/metabolism , Alcohols/chemistry , Alcohols/metabolism , Chromatography, High Pressure Liquid , Cinnamates/metabolism , Down-Regulation , Gene Expression Profiling , Gene Expression Regulation, Plant , Lignans/chemistry , Lignans/metabolism , Mass Spectrometry , Methyltransferases/genetics , Molecular Structure , Phenols/metabolism , Plants, Genetically Modified , Populus/genetics
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