Enantiospecific analysis of 8-prenylnaringenin in biological fluids by liquid-chromatography-electrospray ionization mass spectrometry: application to preclinical pharmacokinetic investigations.


:8-Prenylnaringenin (8PN) is a naturally occurring bioactive chiral prenylflavonoid found most commonly in the female flowers of hops (Humulus lupulus L.). A stereospecific method of analysis for 8PN in biological fluids is necessary to study the pharmacokinetic disposition of each enantiomer. A novel and simple liquid chromatographic-electrospray ionization-mass spectrometry (LC-ESI-MS) method was developed for the simultaneous determination of R- and S-8PN in rat serum and urine. Carbamazepine was used as the internal standard (IS). Enantiomeric resolution of 8PN was achieved on a Chiralpak(®) AD-RH column with an isocratic mobile phase consisting of 2-propanol and 10 mM ammonium formate (pH 8.5) (40:60, v/v) and a flow rate of 0.7 mL/min. Detection was achieved using negative selective ion monitoring (SIM) of 8PN at m/z 339.15 for both enantiomers and positive SIM m/z at 237.15 for the IS. The calibration curves for urine were linear over a range of 0.01-75 µg/mL and 0.05-75 µg/mL for serum with a limit of quantification of 0.05 µg/mL in serum and 0.01 µg/mL in urine. The method was successfully validated showing that it was sensitive, reproducible, and accurate for enantiospecific quantification of 8PN in biological matrices. The assay was successfully applied to a preliminary study of 8PN enantiomers in rat.






Martinez SE,Lakowski TM,Davies NM




Has Abstract


2014-08-01 00:00:00












  • Chemoenzymatic and microbial dynamic kinetic resolutions.

    abstract::This review tracks a decade of dynamic kinetic resolution developments with a biocatalytic inclination using enzymatic/microbial means for the resolution part followed by the racemization reactions either by means of enzymatic or chemocatalyst. These fast developments are due to the ability of the biocatalysts to sign...


    pub_type: 杂志文章


    authors: Kamaruddin AH,Uzir MH,Aboul-Enein HY,Halim HN

    更新日期:2009-04-01 00:00:00

  • Enantioselectivity in the metabolism of mexiletine by conjugation in female patients with the arrhythmic form of chronic Chagas' heart disease.

    abstract::The phenomenon of enantioselectivity in the metabolism of mexiletine (MEX) conjugation was investigated in eight female patients with the arrhythmic form of chronic Chagas' heart disease treated with racemic mexiletine hydrochloride (two 100 mg capsules every 8 hr). Blood samples were collected up to 24 hr after the a...


    pub_type: 临床试验,杂志文章


    authors: Lanchote VL,Cesarino EJ,Santos VJ,Mere Júnior Y,Santos SR

    更新日期:1999-01-01 00:00:00

  • Enantioselective determination of isradipine in human serum using chiral stationary phase liquid chromatography and gas chromatography with nitrogen selective detection.

    abstract::rac-Isradipine is a dihydropyridine type calcium antagonist. Its calcium entry blocking effect is due primarily to the (+)-(S)-enantiomer. This study describes a sensitive enantioselective method for the determination of isradipine in human serum. Following alkaline extraction into hexane, the enantiomers of isradipin...


    pub_type: 杂志文章


    authors: Rask HS,Angelo HR,Christensen HR

    更新日期:1998-01-01 00:00:00

  • Detection and quantification of (R) and (S)-dechloroethylifosfamide metabolites in plasma from children by enantioselective LC/MS/MS.

    abstract::Ifosfamide (IF), a potent chemotherapeutic agent for solid tumors, is known to cause high rates of nephrotoxicity in children with cancer, which is most likely due to the renal production of the metabolite chloroacetaldehyde. Using plasma samples obtained from pediatric oncology patients, we developed a simple nonderi...


    pub_type: 杂志文章


    authors: Aleksa K,Nava-Ocampo A,Koren G

    更新日期:2009-07-01 00:00:00

  • Theoretical Modeling of Surface Confined Chiral Nanoporous Networks: Cruciform Molecules as Versatile Building Blocks.

    abstract::Patterning of solid surfaces with functional organic molecules has been a convenient route to fabricate two-dimensional materials with programmed architecture and activities. One example is the chiral nanoporous networks that can be created via controlled self-assembly of star-shaped molecules under 2D confinement. In...


    pub_type: 杂志文章


    authors: Kasperski A,Szabelski P

    更新日期:2015-07-01 00:00:00

  • Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush-type chiral stationary phases.

    abstract::The chiral discrimination ability of two recently prepared chiral stationary phases (CSP 1 and CSP 2), based on a leucine derived chiral selector, was tested for the enantiomers of dihydropyrimidone (DHPM) derivatives and compared with the commercially available Hyun-leucine CSP 3 and classical Pirkle-leucine CSP 4. B...


    pub_type: 杂志文章


    authors: Forjan DM,Gazić I,Vinković V

    更新日期:2007-06-01 00:00:00

  • Experimental methods for measuring optical rotatory dispersion: survey and outlook.

    abstract::The measurement of optical rotation (OR) and optical rotatory dispersion has been finding renewed interest for some years, because of advancement in computational methods and in the performance of new experiments. Here, we shortly review the traditional and most-used experimental methods. We define and discuss the two...


    pub_type: 杂志文章,评审


    authors: Castiglioni E,Abbate S,Longhi G

    更新日期:2011-10-01 00:00:00

  • Chiral discrimination by albumin: a mechanistic study of liquid chromatographic optical resolution of nonaromatic carboxylic acids.

    abstract::In order to get further insight into the mechanism by which bovine serum albumin (BSA) discriminates between enantiomers of organic acids, some radioisotopically labeled, nonaromatic carboxylic acids were studied under varying mobile phase conditions. It was found for a series of N-alkanoyl-DL-[3H]leucines that the D-...


    pub_type: 杂志文章


    authors: Allenmark S

    更新日期:1993-01-01 00:00:00

  • NMR studies of dextromethorphan in both isotropic and anisotropic states.

    abstract::Herein, we present the solution-state NMR studies on dextromethorphan (1) under both isotropic and anisotropic conditions. From the measurement of 22 residual dipolar couplings using a stretched polystyrene gel (PS), we show that accurate and detailed structural information is readily determined including the relative...


    pub_type: 杂志文章


    authors: Swarbrick JD,Ashton TD

    更新日期:2010-01-01 00:00:00

  • Improved synthesis and pharmacologic activity of the enantiomers of a new benzofurane type antiarrhythmic compound.

    abstract::An improved synthesis of the enantiomers of the new benzofurane-type antiarrhythmic compound 1 is described, which makes use of the enantiomerically pure mbe-lactol. Thus, acylation of the benzofurane 4 with acetic anhydride and subsequent bromination gave the bromoacetyl-derivative 6, which, after reduction with LiAl...


    pub_type: 杂志文章


    authors: Ecker G,Fleischhacker W,Helml T,Noe CR,Scasny S,Lemmens-Gruber R,Studenik C,Marei H,Heistracher P

    更新日期:1994-01-01 00:00:00

  • Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and Aldol reactions.

    abstract::Spontaneous symmetry breaking in reactive systems, known as a rare physical phenomenon and for the Soai autocatalytic irreversible reaction, might in principle also occur in other, more common asymmetric reactions when the chiral product is capable to promote its formation and an element of "nonlinearity" is involved ...


    pub_type: 杂志文章


    authors: Mauksch M,Tsogoeva SB,Wei S,Martynova IM

    更新日期:2007-11-01 00:00:00

  • C3-symmetrical self-assembled structures investigated by vibrational circular dichroism.

    abstract::We demonstrate by using vibrational circular dichroism (VCD) spectroscopy that it is possible to investigate the chirality of a supramolecular polymeric system in relatively dilute solutions. Chiral C(3)-symmetrical discotic molecules, based on a trialkylbenzene-1,3,5-carboxamide, form supramolecular columnar stacks w...


    pub_type: 杂志文章


    authors: Smulders MM,Buffeteau T,Cavagnat D,Wolffs M,Schenning AP,Meijer EW

    更新日期:2008-09-01 00:00:00

  • Asymmetric aldol reactions catalyzed by efficient and recyclable silica-supported proline-based peptides.

    abstract::A series of silica-supported proline-based peptides were synthesized and applied as catalysts for direct asymmetric intermolecular aldol reactions. Among these, a peptide with two L-proline units was found to be the most efficient one for the asymmetric aldol reactions between acetone and aromatic aldehydes. The react...


    pub_type: 杂志文章


    authors: Yan J,Wang L

    更新日期:2009-04-01 00:00:00

  • Derivatization, complexation, and absolute configurational assignment of chiral primary amines: application of exciton-coupled circular dichroism.

    abstract::We report here a sensitive method for the determination of the absolute configurations of primary amines using exciton-coupled circular dichroism (ECCD). The method works on a microgram scale by derivatization of chiral amines with quinoline chromophores. Complexation of the chiral ligands with metal ion fixes the geo...


    pub_type: 杂志文章


    authors: Zhang J,Holmes AE,Sharma A,Brooks NR,Rarig RS,Zubieta J,Canary JW

    更新日期:2003-02-01 00:00:00

  • Chiral memory: induction, amplification, and switching in porphyrin assemblies.

    abstract::The interaction between the tetra-anionic porphyrin H2TPPS and its copper derivative, CuTPPS, with the tetra-cationic porphyrin H2T4 and its copper derivative, CuT4, leads, in aqueous solution, to the formation of remarkably stable and kinetically inert heteroaggregates. The aggregation process is under hierarchic con...


    pub_type: 杂志文章


    authors: Rosaria L,D'urso A,Mammana A,Purrello R

    更新日期:2008-03-01 00:00:00

  • Enantioselective separation and degradation of the herbicide dichlorprop methyl in sediment.

    abstract::Chiral pesticides currently constitute about 50% of all pesticides dosage used in China, and this ratio is increasing as more complex structures are introduced. Dichlorprop methyl (DCPPM) is a chiral herbicide consisting of a pair of enantiomers. In this study, the enantiomeric separation of DCPPM was investigated by ...


    pub_type: 杂志文章


    authors: Ma Y,Xu C,Wen Y,Liu W

    更新日期:2009-04-01 00:00:00

  • Resolution of 1-n-butyl-3-methyl-3-phospholene 1-oxide with TADDOL derivatives and calcium salts of O,O'-Dibenzoyl-(2R,3R)- or O,O'-di-p-toluoyl-(2R,3R)-tartaric acid.

    abstract::The resolution methods applying (-)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ("TADDOL"), (-)-(2R,3R)-α,α,α',α'-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol ("spiro-TADDOL"), as well as the acidic and neutral Ca(2+) salts of (-)-O,O'-dibenzoyl- and (-)-O,O'-di-p-toluoyl-(2R,3R)-tartaric acid ...


    pub_type: 杂志文章


    authors: Bagi P,Fekete A,Kállay M,Hessz D,Kubinyi M,Holczbauer T,Czugler M,Fogassy E,Keglevich G

    更新日期:2014-03-01 00:00:00

  • From cosmic chirality to protein structure: Lord Kelvin's legacy.

    abstract::A selection of my work on chirality is sketched in two distinct parts of this lecture. Symmetry and Chirality explains how the discrete symmetries of parity P, time reversal T, and charge conjugation C may be used to characterize the properties of chiral systems. The concepts of true chirality (time-invariant enantiom...


    pub_type: 杂志文章,评审


    authors: Barron LD

    更新日期:2012-11-01 00:00:00

  • Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase.

    abstract::The macrocyclic glycopeptide, ristocetin A, was covalently bonded to a silica gel support and evaluated as a liquid chromatographic (LC) chiral stationary phase (CSP). Over 230 racemates were resolved in either the reversed-phase mode, the normal-phase mode, or the polar-organic mode. The retention behavior and select...


    pub_type: 杂志文章


    authors: Ekborg-Ott KH,Liu Y,Armstrong DW

    更新日期:1998-01-01 00:00:00

  • Synthesis and characterization of conformationally rigid chiral pyridine-N-heterocyclic carbene-based palladacycles with an unexpected Pd-N bond cleavage.

    abstract::The versatility of a previously developed method for the synthesis of chiral carbene-based palladacycles is demonstrated through the synthesis of two new chiral pyridine-functionalized N-heterocyclic carbene palladacycles with different wingtip groups. The efficiency in their resolution with different counter anions a...


    pub_type: 杂志文章


    authors: Ng KH,Li Y,Tan WX,Chiang M,Pullarkat SA

    更新日期:2013-03-01 00:00:00

  • High-Performance Liquid Chromatographic Enantioseparation of Cyclic β-Amino Acids on Zwitterionic Chiral Stationary Phases Based on Cinchona Alkaloids.

    abstract::Stereoselective high-performance liquid chromatographic separations of eight sterically constrained cyclic β-amino acid enantiomer pairs were carried out using the newly developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+) and ZWIX(-). The effects of the mobile phase composition, t...


    pub_type: 杂志文章


    authors: Ilisz I,Gecse Z,Lajkó G,Forró E,Fülöp F,Lindner W,Péter A

    更新日期:2015-09-01 00:00:00

  • In vitro stereoselective degradation of carprofen glucuronide by human serum albumin. Characterization of sites and reactive amino acids.

    abstract::Acyl glucuronides formed from carboxylic acids can undergo hydrolysis, acyl migration, and covalent binding to proteins. In buffers at physiological pH, the degradation of acylglucuronide of a chiral NSAID, carprofen, consisted mainly of acyl migration. Acidic pH reduced hydrolysis and acyl migration, thus stabilizing...


    pub_type: 杂志文章


    authors: Georges H,Presle N,Buronfosse T,Fournel-Gigleux S,Netter P,Magdalou J,Lapicque F

    更新日期:2000-02-01 00:00:00

  • Rationalization of the multireceptorial character of chiral solvating agents based on quinine and its derivatives: overview of selected NMR investigations.

    abstract::A summary of selected NMR studies of enantiodiscrimination phenomena regarding the use of quinine-based chiral solvating agents (CSAs) for the determination of the enantiomeric compositions in solution is reported, with explanations of their multireceptorial character offered. ...


    pub_type: 杂志文章


    authors: Uccello-Barretta G,Balzano F,Salvadori P

    更新日期:2005-01-01 00:00:00

  • Spontaneous resolution of 2,3-bis-fluoren-9-ylidenesuccinic acid induced by achiral guest inclusion.

    abstract::The racemic title host compound (1) formed homochiral inclusion crystals (conglomerate) of 1 with acetone, while heterochiral inclusion crystals (racemate) were obtained when complexed with ethyl acetate. Upon treatment of the homochiral inclusion crystals of 1 with gaseous acetyl chloride in the solid state, opticall...


    pub_type: 杂志文章


    authors: Tanaka K,Iwamoto T,Wada S,Frelek J,Caira MR

    更新日期:2006-08-01 00:00:00

  • Configuration of heptopyranoside and heptofuranoside side chains: 2-anthroate, a powerful chromophore for exciton coupled CD.

    abstract::The absolute configuration of the acyclic side chain of heptopyranosides and heptofuranosides was determined by exciton coupled CD, employing the strongly fluorescent 2-anthroate chromophore. The usage of this chromophore offers significant improvements over previous chemical and spectroscopic procedures since its int...


    pub_type: 杂志文章


    authors: Akritopoulou-Zanze I,Nakanishi K,Stepowska H,Grzeszczyk B,Zamojski A,Berova N

    更新日期:1997-01-01 00:00:00

  • Asymmetric catalytic ene-cyclization approach to 2-fluoro-19-nor-1,25-dihydroxyvitamin D(3) A-ring analog with significant transactivation activity.

    abstract::1alpha,25-Dihydroxyvitamin D(3) (1alpha,25(OH)2D3) has been shown to modulate not only proliferation and differentiation, but also apoptosis in malignant cells, indicating that it could be useful for the treatment of cancer and psoriasis. However, little information has been available on the binding conformation of th...


    pub_type: 杂志文章


    authors: Mikami K,Ohba S,Ohmura H,Kubodera N,Nakagawa K,Okano T

    更新日期:2001-07-01 00:00:00

  • Circular dichroism eigenspectra of polyproline II and β-strand conformers of trialanine in water: Singular value decomposition analysis.

    abstract::Despite that a number of experimental and theoretical investigations have been carried out to determine the structure of trialanine in water, the reported populations of polyproline II (PPII) and β-strand conformers vary and were found to be dependent on which spectroscopic method was used. Such discrepancies are due ...


    pub_type: 杂志文章


    authors: Oh KI,Lee KK,Park EK,Yoo DG,Hwang GS,Cho M

    更新日期:2010-01-01 00:00:00

  • Discrimination in resolving systems: ephedrine-mandelic acid.

    abstract::Resolution of mandelic acid with (-)-(1R,2S)-ephedrine in water and ethanol produces intermediate diastereomeric salts with greatly disparate solubilities and melting points. Single crystal X-ray analysis of the less (L) and more (M) soluble (-)-ephedrinium mandelates (I, II) shows crystal structures which are isoster...


    pub_type: 杂志文章


    authors: Valente EJ,Zubkowski J,Eggleston DS

    更新日期:1992-01-01 00:00:00

  • Gas chromatographic separation of saturated aliphatic hydrocarbon enantiomers on permethylated beta-cyclodextrin.

    abstract::Enantiomers of chiral aliphatic hydrocarbons are generally difficult to separate because they lack functional groups to be derivatized in order to generate diastereomers. The systematic and quantitative separation of a series of branched hydrocarbon enantiomers using a chiral cyclodextrin stationary phase and a cryost...


    pub_type: 杂志文章


    authors: Meierhenrich UJ,Nguyen MJ,Barbier B,Brack A,Thiemann WH

    更新日期:2003-01-01 00:00:00

  • Absolute configuration of oplopanone derivatives from Serphidium stenocephalum: ECD spectra of acyclic ketones with front-octant contributions.

    abstract::The electronic circular dichroism (ECD) spectra of two sesquiterpenoids (1 and 2) related to oplopanone, obtained from a methanolic extract of the plant Serphidium stenocephalum (Artemisia stenocephala), were measured and reproduced by means of time-dependent density functional theory (TDDFT) calculations, establishin...


    pub_type: 杂志文章


    authors: Shafiq N,Saleem M,Riaz N,Tousif MI,Jabbar A,Tareen RB,Pescitelli G

    更新日期:2014-01-01 00:00:00