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1.
Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria 总被引:2,自引:0,他引:2
Xie LH Ahn EM Akao T Abdel-Hafez AA Nakamura N Hattori M 《Chemical & pharmaceutical bulletin》2003,51(4):378-384
After anaerobic incubation of arctiin (1) from the seeds of Arctium lappa with a human fecal suspension, six metabolites were formed, and their structures were identified as (-)-arctigenin (2), (2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3",4"-dimethoxybenzyl)butyrolactone (3), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3",4"-dimethoxybenzyl)butyrolactone (4), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3"-hydroxy-4"-methoxybenzyl)butyrolactone (5), (2R,3R)-2-(3'-hydroxybenzyl)-3-(3",4"-dihydroxybenzyl)butyrolactone (6), and (-)-enterolactone (7) by various spectroscopic means including two dimensional (2D)-NMR, mass spectrometry, and circular dichroism. A possible metabolic pathway was proposed on the basis of their structures and the time course of the transformation. Enterolactones obtained from the biotransformation of arctiin and secoisolariciresinol diglucoside (SDG, from the seeds of Linum usitatissium) by human intestinal bacteria were proved to be enantiomers, with the (-)-(2R,3R) and (+)-(2S,3S) configurations, respectively. Compound 6 showed the most potent proliferative effect on the growth of MCF-7 human breast cancer cells in culture among 1 and six metabolites, while it showed inhibitory activity on estradiol-mediated proliferation of MCF-7 cells at a concentration of 10 microM. These results indicate that the transformation of 1 by intestinal flora might be essential for the manifestation of the estrogenic and antiestrogenic activity of 1. 相似文献
2.
Summary. The regioselectivity of 1,3-dipolar cycloaddition reactions of 1-aza-2-azoniaallene salts with ,-unsaturated nitriles such as acrylonitrile or cyclohexylidene acetonitrile afforded only 1,2,4-triazolium salts via addition to the nitrile group, while the other expected pyrazolium salts were not observed. Moreover, 1-aza-2-azonia-allene salts reacted with other competitive systems such as -iminonitrile derivatives yielding only triazolium salts via addition to the nitrile and not to the imino group. Treatment of cumulene with 3-pyridylnitrile afforded the pyridinium salt. However, 2,3-dimethyl-5-(2,6-dimethoxyphenyl)-[1,2,4]triazole could be prepared from cumulene and 2,6-dimethoxybenzonitrile. Some reactions of nitriles with 1-aza-2-azonia-allene salts prepared from 1,2,3-indantrione and 9-acetylphenanthrene are discussed. 相似文献
3.
Acid dissociation constants of acetoacetanilide abbreviated (AAA); Orthocarboxy-phenylhydrazoacetoacetanilide (o-CPHAAA); and orthocarboxy-phenylhydrazo-parachloro-acetoacetanilide (o-CPH-p-Cl-AAA) and chelate stability constants of the corresponding anions with Cu+2, Ni+2, CO+2, Zn+2, Mn+2, and Cd+2 ions are reported. The infra-red spectra of o-CPHAAA and o-CPH-p-Cl-AAA ligands and their chelates for copper and nickel are discussed. 相似文献
4.
Banoub J Cohen A Mansour A Thibault P 《European journal of mass spectrometry (Chichester, England)》2004,10(1):121-134
Vitellogenin (VTG) is a protein produced by the liver of oviparous animals in response to circulating estrogens. In the plasma of males and immature females, VTG is undetectable. VTG has been used as a biomarker for exposure to endocrine disruptors in many species. In the present study, characterization of intact Atlantic salmon VTG was effected using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI ToF MS). Tryptic digest peptides were analyzed by MALDI ToF MS to obtain a peptide mass fingerprint. De novo sequencing of the tryptic peptides used low-energy collisionally-induced dissociation (CID) in an electrospray ionization quadrupole-ToF orthogonal hybrid mass spectrometer (ESI Q-ToF MS/MS). The interpretation of the product-ion spectra obtained from the ESI Q-ToF MS/MS was done by Lutefisk, a computer-based software algorithm. The molecular mass of the intact protein was found to be 187335 Da. A total of 14 tryptic peptides were sequenced and compared with the complete rainbow trout VTG and the partial Atlantic salmon VTG sequences found in the Swiss-Prot database. De novo sequencing by CID MS/MS of 11 Atlantic salmon tryptic digest peptides with selected precursor ions at m/z 788.24, 700.20, 794.75, 834.31, 889.28, 819.79, 865.27, 843.81, 572.20, 573.66 and 561.68 showed high homology with the known sequence of rainbow trout VTG. The last two precursor peptide ions, found at m/z 573.66 and m/z 561.68, also specifically matched the known portion of the Atlantic salmon VTG sequence. Finally, three tryptic precursor peptide ions found at m/z 795.18, 893.28 and 791.05, provided product-ion spectra, which were exclusive to the unsequenced portion of the Atlantic salmon VTG. 相似文献
5.
Chlorocarbenium salts
-
of the Vilsmeier-Arnold type react with the silylated isocyanuric acid
to give 1-oxa-3-azabutatrienium salts
under mild conditions. From reactions of diarylchloromethenium salts
-
with
and ketones or tertiary carboxamides high yields of 2-azaallenium salts
were obtained. A few chloro substituted 2-azaallenium salts
were prepared from
and carbonyl compounds. The mechanisms of the new reactions are discussed. 相似文献
6.
Ines ELouedi Régis Fournier Amine Naït-Ali Atef Hamouda 《Signal, Image and Video Processing》2015,9(1):145-154
This paper presents a new approach called polynomial discrete Radon transform (PDRT), regarded as a generalization of the classical finite discrete Radon transform. Specifically, the PDRT transforms an image into Radon space by summing the pixels according to polynomial curves. The PDRT can be applied on square \(p \times p\) images where \(p\) is assumed to be a prime number. It is based on a simple arithmetic operations and requires no data interpolation. An interesting property of the PDRT is its exact inversion. This means that an image can be transformed and then perfectly reconstructed. Through this study, we show that the new approach can be applied for some pattern recognition applications. 相似文献
7.
Ahmed M. Metwaly Frank R. Fronczek Guoyi Ma Hazem A. Kadry Atef A. El-Hela Abd-Elsalam I. Mohammad Stephen J. Cutler Samir A. Ross 《Tetrahedron letters》2014
Four new (1–4) and two known (5 and 6) α-pyrone derivatives have been isolated from Alternaria phragmospora, an endophytic fungus from Vinca rosea, leaves. The isolated compounds were chemically identified to be 5-butyl-4-methoxy-6-methyl-2H-pyran-2-one (1), 5-butyl-6-(hydroxymethyl)-4-methoxy-2H-pyran-2-one (2), 5-(1-hydroxybutyl)-4-methoxy-6-methyl-2H-pyran-2-one (3), 4-methoxy-6-methyl-5-(3-oxobutyl)-2H-pyran-2-one (4), 5-(2-hydroxyethyl)-4-methoxy-6-methyl-2H-pyran-2-one (5), and 5-[(2E)-but-2-en-1-yl]-4-methoxy-6-methyl-2H-pyran-2-one (6). Compounds 2 and 4 showed moderate antileukemic activities against HL60 cells with IC50 values of 2.2 and 0.9 μM and against K562 cells with IC50 values of 4.5 and 1.5 μM, respectively. 相似文献
8.
Mohammed?M?Hefnawy Atef?M?Homoda Mohammed?A?Abounassif Amer?M?Alanazi Abdulrahaman?Al-Majed Gamal?A?MostafaEmail author 《Chemistry Central journal》2014,8(1):59
Background
The construction and electrochemical response characteristics of Poly (vinyl chloride) membrane sensors for moxifloxacin HCl (MOX) are described. The sensing membranes incorporate ion association complexes of moxifloxacin cation and sodium tetraphenyl borate (NaTPB) (sensor 1), phosphomolybdic acid (PMA) (sensor 2) or phosphotungstic acid (PTA) (sensor 3) as electroactive materials.Results
The sensors display a fast, stable and near-Nernstian response over a relative wide moxifloxacin concentration range (1 × 10-2 - 4.0 × 10-6, 1 × 10-2 - 5.0 × 10-6, 1 × 10-2 - 5.0 × 10-6 M), with detection limits of 3 × 10-6, 4 × 10-6 and 4.0 × 10-6 M for sensor 1, 2 and 3, respectively over a pH range of 6.0 - 9.0. The sensors show good discrimination of moxifloxacin from several inorganic and organic compounds. The direct determination of 400 μg/ml of moxifloxacin show an average recovery of 98.5, 99.1 and 98.6% and a mean relative standard deviation of 1.8, 1.6 and 1.8% for sensors 1, 2 and 3 respectively.Conclusions
The proposed sensors have been applied for direct determination of moxifloxacin in some pharmaceutical preparations. The results obtained by determination of moxifloxacin in tablets using the proposed sensors are comparable favorably with those obtained using the US Pharmacopeia method. The sensors have been used as indicator electrodes for potentiometric titration of moxifloxacin.9.
The consecutive stepwise formation constants of 1:1 and 1:2 chelate species formed by the interaction of DC-2-CPHD and DC-3-CPHD anions with tripositive lanthanon and divalent copper, nickel, cobalt, zinc, manganese, and cadmium cations were determined potentiometrically at ionic strengh of 0.1 (KNO3) and 30°C. The results indicate that two different coordination modes, one tridentate (DC-2-CPHD), and one bidentate (DC-3-CPHD), are in evidence. 相似文献
10.
Saoussen Turki Atef Ayed Néjib Chalghoumi Frederic Weekers Philippe Thonart Héla Kallel 《Applied biochemistry and biotechnology》2010,160(5):1371-1385
Yarrowia lipolytica LgX64.81 is a non-genetically modified mutant that was previously identified as a promising microorganism for extracellular
lipase production. In this work, the development of a fed-batch process for the production of this enzyme in this strain was
described. A lipolytic activity of 2,145 U/mL was obtained after 32 h of batch culture in a defined medium supplemented with
10 g/L of tryptone, an enhancer of lipase expression. To maximize the volumetric productivity, two different fed-batch strategies
had been investigated. In comparison to batch process, the intermittent fed-batch strategy had not improved the volumetric
lipase productivity. In contrast, the stepwise feeding strategy combined with uncoupled cell growth and lipase production
phases resulted in a 2-fold increase in the volumetric lipase productivity, namely, the lipase activity reached 10,000 U/mL
after 80 h of culture. Furthermore, this lipase was purified to homogeneity by anion exchange chromatography on MonoQ resin
followed by gel filtration on Sephacryl S-100. This process resulted in an overall yield of 72% and a 3.5-fold increase of
the specific lipase activity. The developed process offers a great potential for an economic production of Lip2 at large scale
in Y. lipolytica LgX64.81. 相似文献