Isolation and identification of sapotexanthin 5,6-epoxide and 5,8-epoxide from red mamey (Pouteria sapota).


:Two new carotenoids, sapotexanthin 5,6-epoxide and sapotexanthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-performance liquid chromatography-electronic circular dichroism (HPLC-ECD) analysis. Spectroscopic data of the natural and semisynthetic derivatives obtained by acid-catalyzed rearrangement of cryptocapsin 5,8-epoxide stereoisomers were compared for structural elucidation.






Murillo E,Agócs A,Nagy V,Király SB,Kurtán T,Toribio EM,Lakey-Beitia J,Deli J




Has Abstract


2020-05-01 00:00:00












  • Photo-ionization spectroscopy and mass spectrometry of some molecular and supramolecular asymmetric systems in the isolated state.

    abstract::Asymmetric molecular and supramolecular systems are characterized by: i. the circular dicroism in the angular distribution of valence photoelectrons emitted from randomly oriented chiral molecules by their interaction with circularly polarized VUV light; ii. the different stability and reactivity of diastereomeric agg...


    pub_type: 杂志文章


    authors: Giardini A,Paladini A,Catone D,Piccirillo S,Rondino F,Satta M,Filippi A,Speranza M,Turchini S,Zema N

    更新日期:2006-08-01 00:00:00

  • Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives.

    abstract::The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled (31)P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:...


    pub_type: 杂志文章


    authors: Bui TT,Coles SJ,Davies DB,Drake AF,Eaton RJ,Hursthouse MB,Kiliç A,Shaw RA,Yeşilot S

    更新日期:2005-10-01 00:00:00

  • Stereochemical preference of 2'-deoxycytidine for chiral bis(diamido)-bridged basket resorcin[4]arenes.

    abstract::Bis(diamido)-bridged basket resorcin[4]arene (all-S)-1 and its (all-R)-1 enantiomer proved able to interact with 2'-deoxycytidine (2) and pyrimidine nucleoside analogs in dimethyl sulfoxide (DMSO) solution. In such a solvent, the resorcinarene hosts adopt a preferential 1,3-alternate-like conformation, with a larger c...


    pub_type: 杂志文章


    authors: D'Acquarica I,Calcaterra A,Sacco F,Balzano F,Aiello F,Tafi A,Pesci N,Uccello-Barretta G,Botta B

    更新日期:2013-12-01 00:00:00

  • Detection of the activity of ion channels and pores by circular dichroism spectroscopy: G-quartets as functional CD probes within chirogenic vesicles.

    abstract::We introduce a method to detect the activity of ion channels and pores with circular dichroism (CD) spectroscopy. G-quartets obtained by potassium templated self-assembly of 5'-guanosine monophosphate (GMP) are used as CD probes, the bee-toxin melittin as representative pore and gramicidin A as representative ion chan...


    pub_type: 杂志文章


    authors: Hennig A,Matile S

    更新日期:2008-09-01 00:00:00

  • Evaluation of the chiral recognition properties and the column performances of three chiral stationary phases based on cellulose for the enantioseparation of six dihydropyridines by high-performance liquid chromatography.

    abstract::Separations of six dihydropyridine enantiomers on three commercially available cellulose-based chiral stationary phases (Chiralcel OD-RH, Chiralpak IB, and Chiralpak IC) were evaluated with high-performance liquid chromatography (HPLC). The best enantioseparation of the six chiral drugs was obtained with a Chiralpak I...


    pub_type: 杂志文章


    authors: Yu J,Tang J,Yuan X,Guo X,Zhao L

    更新日期:2017-03-01 00:00:00

  • Substituent effects in the selective reductive opening of epoxides with borohydrides in the presence of beta-cyclodextrin

    abstract::The opening of ortho-substituted phenyl oxiranes by borohydrides is described both in aqueous and solid phases. Some remarkable differences in the regioselectivity and inversion of enantioselectivity of oxirane ring-opening are reported. The results obtained are compared with previous studies and have allowed some fac...


    pub_type: 杂志文章


    authors: Doussot J,Guy A,Siaugue JM,Ferroud C,Guieres AF

    更新日期:1999-01-01 00:00:00

  • Stereoselective determination of metoprolol and its metabolite α-hydroxymetoprolol in plasma by LC-MS/MS: application to pharmacokinetics during pregnancy.

    abstract::Metoprolol is available for clinical use as a racemic mixture. The S-(-)-metoprolol enantiomer is the one expressing higher activity in the blockade of the β(1)-adrenergic receptor. The α-hydroxymetoprolol metabolite also has activity in the blockade of the β(1)-adrenergic receptor. The present study describes the dev...


    pub_type: 杂志文章


    authors: Antunes Nde J,Cavalli RC,Marques MP,Lanchote VL

    更新日期:2013-01-01 00:00:00

  • Stereoselectivity of the carbonyl reduction of dolasetron in rats, dogs, and humans.

    abstract::The initial step in the metabolism of dolasetron or MDL 73,147EF [(2 alpha, 6 alpha, 8 alpha, 9a beta)-octahydro-3-oxo-2,6-methano-2H- quinolizin-8-yl 1H-indol-3-carboxylate, monomethanesulfonate] is the reduction of the prochiral carbonyl group to give a chiral secondary alcohol "reduced dolasetron." An HPLC method, ...


    pub_type: 杂志文章


    authors: Dow J,Berg C

    更新日期:1995-01-01 00:00:00

  • Applications of the Cartesian coordinate tensor transfer technique in the simulations of vibrational circular dichroism spectra of oligonucleotides.

    abstract::The application of the Cartesian coordinate tensor transfer (CCT) technique for simulations of the IR absorption and vibrational circular dichroism (VCD) spectra of relatively large nucleic acid fragments is demonstrated on several case studies. The approach is based on direct ab initio calculations of atomic tensors,...


    pub_type: 杂志文章,评审


    authors: Andrushchenko V,Bouř P

    更新日期:2010-01-01 00:00:00

  • Unexpected rearrangement of enantiomerically pure 3-aminoquinuclidine as a simple way of preparing diastereomeric octahydropyrrolo[2,3-c]pyridine derivatives.

    abstract::Reaction of (S)- or (R)-3-aminoquinuclidine with 2-chloropyrimidine or 2-bromopyrimidine led to an unexpected formation of both cis- and trans-octahydropyrrolo [2,3]pyridine derivatives. A single-step synthesis of two of the four stereoisomers of these octahydropyrrolo[2,3]pyridine derivatives provides a convenient wa...


    pub_type: 杂志文章


    authors: Goljer I,Molinari A,He Y,Nogle L,Sun W,Campbell B,McConnell O

    更新日期:2009-07-01 00:00:00

  • Headspace gas chromatography-mass spectrometry analysis of isoflurane enantiomers in blood samples after anesthesia with the racemic mixture.

    abstract::Several in vivo and in vitro studies on the stereoselective potency of isoflurane enantiomers suggest beneficial effects of the (+)-(S)-enantiomer. In order to detect possible differences in the pharmacokinetics of isoflurane enantiomers, a clinical study of 41 patients undergoing general anesthesia maintained with ra...


    pub_type: 临床试验,杂志文章


    authors: Schmidt R,Wahl HG,Häberle H,Dieterich HJ,Schurig V

    更新日期:1999-01-01 00:00:00

  • Pharmacologic implications of alpha-adrenoreceptor interactive parameters for epinephrine enantiomers in the rat vas deferens.

    abstract::After alkylation of a fraction of the total alpha-adrenoreceptors by phenoxybenzamine in rat vas deferens, the dissociation constants of (-)- and (+)-epinephrine in functional studies were 7 X 10(-7) M and 2 X 10(-5) M, respectively. In the adrenoreceptor-containing tissue fraction, when 3H-labeled WB4101 was used as ...


    pub_type: 杂志文章


    authors: Rice PJ,Miller DD,Sokoloski TD,Patil PN

    更新日期:1989-01-01 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

  • Preparative and analytical separation of the zopiclone enantiomers and determination of their affinity to the benzodiazepine receptor binding site.

    abstract::We report the preparative separation of rac-zopiclone using malic acid as the resolving agent. Furthermore, two different methods for the analytical determination of zopiclone enantiomers by HPLC on chiral stationary phases are described. The benzodiazepine receptor binding of the isolated enantiomers was investigated...


    pub_type: 杂志文章


    authors: Blaschke G,Hempel G,Müller WE

    更新日期:1993-01-01 00:00:00

  • Effect of the mobile phase on the retention behavior of optical isomers of the mandelic acid derivative methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate by chiral HPLC.

    abstract::Conditions for separation of enantiomers of a mandelic acid derivative, methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate (the analyte) were studied. Because of the presence of two chiral carbons, the analyte consists of four stereoisomers stable at ambient temperature. Chiral HPLC of the analyte resulted in four peaks...


    pub_type: 杂志文章


    authors: Shen B,Xu X,Chen J,Zhang X,Xu B

    更新日期:2006-09-01 00:00:00

  • HPLC enantioseparation and absolute configuration of novel anti-inflammatory pyrrole derivatives.

    abstract::The assignment of the absolute configuration of novel anti-inflammatory pyrrole derivatives has been accomplished by a combined strategy based on independent physical methods. The key step of our stereochemical characterization approach is the production at mg-scale of enantiomerically pure forms by HPLC on Chiralpak ...


    pub_type: 杂志文章


    authors: Biava M,Cirilli R,Fares V,Ferretti R,Gallinella B,La Torre F,Poce G,Porretta GC,Supino S,Villani C

    更新日期:2008-06-01 00:00:00

  • Synthesis of novel camphor-derived bifunctional thiourea organocatalysts.

    abstract::Synthesis and catalyst performance of 2,3- (types and ) and 2,8-disubstituted (type ) thiourea bifunctional organocatalysts was attempted. The synthesis of catalyst of type has, so far, not been realized, while catalysts of type , i.e., the 2,3-exo- and the 2-endo-3-exo-thiourea catalysts, were prepared in six steps s...


    pub_type: 杂志文章


    authors: Ričko S,Golobič A,Svete J,Stanovnik B,Grošelj U

    更新日期:2015-01-01 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

  • Highly enantiomeric reduction of acetophenone and its derivatives by locally isolated Rhodotorula glutinis.

    abstract::Ninety isolates of microorganisms belonging to different taxonomical groups (30 bacteria, 20 yeast, and 40 fungi) were previously isolated from various samples. These isolates were screened as reducing agents for acetophenone 1a to phenylethanol 2a. It was found that the isolate EBK-10 was the most effective biocataly...


    pub_type: 杂志文章


    authors: Zilbeyaz K,Kurbanoglu EB

    更新日期:2010-10-01 00:00:00

  • A new definition of life.

    abstract::Chirality is often glossed over in theoretical or experimental discussions concerning the origin of life, but the ubiquity of homochiral building blocks in known biological systems demands explanation. Information theory can provide a quantitative framework for understanding the role of chirality in biology. Here I sh...


    pub_type: 杂志文章


    authors: Carroll JD

    更新日期:2009-03-01 00:00:00

  • Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism.

    abstract::Advances in the measurement, calculation, and application of vibrational circular dichroism (VCD) for the determination of absolute configuration are described. The purpose of the review is to provide an up-to-date perspective on the capability of VCD to solve problems of absolute stereochemistry for chiral molecules ...


    pub_type: 杂志文章


    authors: Freedman TB,Cao X,Dukor RK,Nafie LA

    更新日期:2003-11-01 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

  • Unprecedented crystallization and X-ray crystal structure of racemic N(alpha)-(t-butyloxycarbonyl)-L-L-phenylalanine N-methoxy-N-methylamide.

    abstract::Weinreb amide 3 was synthesized using isobutyl chloroformate, carbonyldiimidazole, or ethylcarbodiimide as the coupling agent in the reaction of Boc-phenylalanine with O,N-dimethylhydroxylamine hydrochloride. An optically active oil was isolated along with an optically inactive solid irrespective of the type of coupli...


    pub_type: 杂志文章


    authors: Zheng X,Donkor IO,Miller DD,Ross CR 2nd

    更新日期:2000-01-01 00:00:00

  • Parallel kinetic resolution of an oxazolidinone using a quasi-enantiomeric combination of [D,13C]-isotopomers of pentafluorophenyl 2-phenyl propionate.

    abstract::Parallel kinetic resolution of Evans' phenylglycine derived oxazolidinone using an equimolar combination of quasi-enantiomeric active esters (derived from [D,13C]-labeled 2-phenylpropionic acid) was achieved. The levels of stereocontrol were high, leading to products with predictable configurations. ...


    pub_type: 杂志文章


    authors: Coumbarides GS,Dingjan M,Eames J,Flinn A,Northen J

    更新日期:2007-05-05 00:00:00

  • Chiroptical properties of diamino carboxylic acids.

    abstract::Diamino carboxylic acids have recently come to the attention of scientists working in the field of early life and its development. These are the monomers of a hypothetic early form of genetic material, the so-called Peptide Nucleic Acid (PNA) (Nielson et al., Proc Natl Acad Sci USA 2000;97:3868-3871). Since all biopol...


    pub_type: 杂志文章


    authors: Bredehöft JH,Breme K,Meierhenrich UJ,Hoffmann SV,Thiemann WH

    更新日期:2007-07-01 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

  • 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

  • Cyclodextrin-Functionalized Monolithic Capillary Columns: Preparation and Chiral Applications.

    abstract::In this review, the recently reported approaches for the preparation of cyclodextrin-functionalized capillary monolithic columns are highlighted, with few applications in chiral separations using capillary liquid chromatography (CLC) and capillary electrochromatography (CEC). Chirality 28:97-109, 2016. © 2015 Wiley Pe...


    pub_type: 杂志文章,评审


    authors: Adly FG,Antwi NY,Ghanem A

    更新日期:2016-02-01 00:00:00

  • Modulatory effect of chiral nonsteroidal anti-inflammatory drugs on apoptosis of human neutrophils.

    abstract::Polymorphonuclear neutrophils (PMNs) are short-lived leukocytes that die by apoptosis. Although PMNs are crucial in the defense against infection, they have been implicated in the pathogenesis of tissue injury observed in inflammatory diseases. The induction or prevention of PMN apoptosis is currently discussed as a k...


    pub_type: 杂志文章


    authors: Zielińska-Przyjemska M,Główka FK,Klaczyńska J

    更新日期:2008-02-01 00:00:00

  • High-performance liquid chromatographic enantioseparation of Betti base analogs on a newly developed isopropyl carbamate-cyclofructan6-based chiral stationary phase.

    abstract::The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1-naphthol analogs, and 2-(1-amino-2-methylpropyl)-1-naphthol) was performed on a newly developed chiral stationary phase containing isopropyl carbamate-cyclofructan6 as chiral selector, wit...


    pub_type: 杂志文章


    authors: Aranyi A,Ilisz I,Pataj Z,Szatmári I,Fülöp F,Armstrong DW,Péter A

    更新日期:2011-08-01 00:00:00