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

Abstract:

: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.

journal_name

Chirality

journal_title

Chirality

authors

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

doi

10.1002/chir.23206

subject

Has Abstract

pub_date

2020-05-01 00:00:00

pages

579-587

issue

5

eissn

0899-0042

issn

1520-636X

journal_volume

32

pub_type

杂志文章
  • Chiroptical studies on supramolecular chirality of molecular aggregates.

    abstract::The attempts of applying chiroptical spectroscopy to supramolecular chirality are reviewed with a focus on vibrational circular dichroism (VCD). Examples were taken from gels, solids, and monolayers formed by low-molecular mass weight chiral gelators. Particular attention was paid to a group of gelators with perfluoro...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22482

    authors: Sato H,Yajima T,Yamagishi A

    更新日期:2015-10-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:2<53::AID-CHIR1>3.

    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

  • Stereoselective Behavior of the Chiral Herbicides Diclofop-Methyl and Diclofop During the Soy Sauce Brewing Process.

    abstract::Chiral pesticides are now receiving more and more attention in the food-making process. This experiment studied the enantioselective behavior of diclofop-methyl (DM) and its main metabolite, diclofop (DC), during the soy sauce brewing process. Two kinds of commonly used strains, Aspergillus oryzae and Saccharomyces ro...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22545

    authors: Lu Y,Zhang D,Liao Y,Diao J,Chen X

    更新日期:2016-01-01 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, ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530070506

    authors: Dow J,Berg C

    更新日期:1995-01-01 00:00:00

  • Base-catalyzed epimerization of the butenolide in annonaceous acetogenins.

    abstract::The elusive epimerization process in the chiral butenolide moiety of Annonaceous acetogenins was examined under several sets of conditions commonly used for elimination leading to the alpha, beta-unsaturated lactone and the results provide practical guidance in choosing elimination conditions. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:3<127::AID-CHIR4>3

    authors: Yu Q,Wu Y,Wu YL,Xia LJ,Tang MH

    更新日期:2000-03-01 00:00:00

  • Enantioselectivity of inhibition of cytochrome P450 3A4 (CYP3A4) by ketoconazole: Testosterone and methadone as substrates.

    abstract::Racemic ketoconazole (KTZ) was the first orally active azole antifungal agent used in clinical practice and has become widely used in the treatment of mucosal fungal infections associated with AIDS immunosuppression and cancer chemotherapy. However, the use of KTZ has been limited because of adverse drug-drug interact...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10294

    authors: Dilmaghanian S,Gerber JG,Filler SG,Sanchez A,Gal J

    更新日期:2004-02-01 00:00:00

  • Chiral aggregates and asymmetric induction of the reduction of prochiral ketones.

    abstract::The aim of this work was to establish structure-reactivity relationships between chiral aggregates (micelles, vesicles, and "pseudo-micelles" of amphiphilic dendrimers) and asymmetric induction. In water, micelles or vesicles formed with sugar-headed surfactants gave less than 10% ee in the reduction of prochiral keto...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2001)13:1<24::AID-CHIR5>3.0.CO;2

    authors: Rico-Lattes I I,Schmitzer A,Perez E,Lattes A

    更新日期:2001-01-01 00:00:00

  • Determination of the absolute configuration and solution conformation of a novel disubstituted pyrrolidine acid A by vibrational circular dichroism.

    abstract::Compound A, a novel disubstituted pyrrolidine acid, is a member of a new class of agents that are potentially useful for the treatment of diabetes and dyslipidemia. The absolute configuration of this compound was determined by using vibrational circular dichroism (VCD). The results are in agreement with the assignment...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20316

    authors: Freedman TB,Cao X,Phillips LM,Cheng PT,Dalterio R,Shu YZ,Zhang H,Zhao N,Shukla RB,Tymiak A,Gozo SK,Nafie LA,Gougoutas JZ

    更新日期:2006-09-01 00:00:00

  • R2PI Study of intermolecular hydrogen bond in solvent-free chiral complexes.

    abstract::One- and two-color, mass selected R2PI spectra of the S(1)<--S(0) transitions in the bare (+)-(R)-1-phenyl-1-ethanol (E(R)) and its complexes with different solvent molecules (solv) (-)-(R)-2-butanol (B(R)) or (+)-(S)-2-butanol (B(S)) and (-)-(R)-2-butylamine (A(R)) or (+)-(S)-2-butylamine (A(S)), have been recorded a...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10010

    authors: Giardini Guidoni A,Piccirillo S,Scuderi D,Satta M,Di Palma TM,Speranza M,Filippi A,Paladini A

    更新日期:2001-01-01 00:00:00

  • Isothermal titration calorimetry for chiral chemistry.

    abstract::One of the most powerful techniques that are currently available to measure thermodynamic parameters such as enthalpy (ΔH), Gibbs free energy (ΔG), entropy changes (ΔS), and binding affinity in chemical reactions is isothermal titration calorimetry (ITC). Recent advances in instrumentation have facilitated the develop...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22842

    authors: Werber L,Mastai Y

    更新日期:2018-05-01 00:00:00

  • Stereoselective effect of warfarin and bilirubin on the binding of 5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2- one enantiomers to human serum albumin.

    abstract::The binding of the title benzodiazepine enantiomers and its modulation by warfarin and bilirubin were studied by chromatography on human serum albumin (HSA) immobilized on Sepharose 4B, and also by a combination of ultrafiltration and circular dichroism (UF-CD) methods. In the absence of warfarin and bilirubin the bin...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530020307

    authors: Fitos I,Visy J,Magyar A,Kajtár J,Simonyi M

    更新日期:1990-01-01 00:00:00

  • Stereoselective pharmacokinetics and metabolism of flobufen in guinea pigs.

    abstract::Stereoselective aspects of pharmacokinetics and metabolism of a chiral nonsteroidal antiinflammatory drug, flobufen, 4-(2', 4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid, were studied in male guinea pigs after p.o. administration of racemic flobufen (rac-flobufen) at a dose of 10 mg/kg. Blood samples were coll...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10288

    authors: Trejtnar F,Král R,Pávek P,Wsól V

    更新日期:2003-10-01 00:00:00

  • Screening Approach for Chiral Separation of β-Aminoketones by HPLC on Various Polysaccharide-Based Chiral Stationary Phases.

    abstract::Nine β-aminoketones were synthesized via Mannich reaction when benzaldehyde was condensed with some primary amines and acetophenone. The purified compounds were identified by using spectroscopic methods. The enantiomeric separation of these derivatives was carried out by high-performance liquid chromatography (HPLC) u...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22434

    authors: Addadi K,Sekkoum K,Belboukhari N,Cheriti A,Aboul-Enein HY

    更新日期:2015-05-01 00:00:00

  • Alpha-aminophosphonates as novel organocatalysts for asymmetric Michael addition of carbonyl compounds to nitroolefins.

    abstract::A cyclic alpha-aminophosphonate was found to be a novel organocatalyst for Michael type addition reactions of carbonyl compounds to nitroolefins to afford the corresponding adducts in high enantio- and diastereoselectivities. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20552

    authors: Tao Q,Tang G,Lin K,Zhao YF

    更新日期:2008-07-01 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,...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.20872

    authors: Andrushchenko V,Bouř P

    更新日期:2010-01-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20703

    authors: Swarbrick JD,Ashton TD

    更新日期:2010-01-01 00:00:00

  • Trigonostemons G and H, dinorditerpenoid dimers with axially chiral biaryl linkage from Trigonostemon chinensis.

    abstract::Trigonostemons G and H, two novel dimeric dinorditerpenoids, were isolated from the stem barks of Trigonostemon chinensis. Their planar structures and relative configurations were established by extensive analysis of spectroscopic data. Trigonostemons G and H possess a homodimeric biaryl skeleton obtained from two rea...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23170

    authors: Zhu Q,Tang C,Mándi A,Kurtán T,Ye Y

    更新日期:2020-03-01 00:00:00

  • Structural Features and Asymmetric Environment of i-Pr-SPRIX Ligand.

    abstract::Novel chiral diisopropyl spiro bis(isoxazoline) ligands, anti-i-Pr-SPRIX and syn-i-Pr-SPRIX, were designed and synthesized. Their catalytic utility, X-ray crystallographic analyses, and complexation studies demonstrated the structural features of tetraisopropyl spiro bis(isoxazoline) ligand, i-Pr-SPRIX, which is a pro...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22467

    authors: Takenaka K,Lin X,Takizawa S,Sasai H

    更新日期:2015-08-01 00:00:00

  • Steady-state pharmacokinetics of indobufen enantiomers in patients with obliterative atherosclerosis.

    abstract::Steady-state pharmacokinetics of indobufen (INDB) enantiomers administered as racemic INDB (rac-INDB) tablets and bleeding time were studied in patients. Two-hundred mg INDB tablets (Ibustrin) were administered twice daily for 7 days to obliterative atherosclerosis patients. Enantiospecific reversed phase (RP) HPLC wi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1036

    authors: Glówka FK,Strzelecka D,Zapalski S

    更新日期:2001-06-01 00:00:00

  • Research into the oxidation of abietic acid-derived enone with atmospheric oxygen.

    abstract::This work presents results of methyl 7-oxoabiet-13(14)-en-18-oate (3) self-oxidation with air-oxygen in the presence of various bases such as triethylamine or sodium t-butoxide. While under aerobic conditions, the use of sodium t-butoxide as a base results in the formation of four isomeric alcohols, an addition of tri...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23176

    authors: Masnyk M,Kuśmirek D,Trzybiński D,Frelek J

    更新日期:2020-04-01 00:00:00

  • Enantiomeric separation of β-blockers and tryptophan using heparin as stationary and pseudostationary phases in capillary electrophoresis.

    abstract::The separation methods of the enantiomers of two β-blockers and tryptophan were studied using capillary electrochromatography with heparin covalently as well as non-covalently, bonded onto the capillary inner wall as stationary phase and electrokinetic chromatography with heparin as pseudostationary phase. In the case...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22972

    authors: Liu Y,Sombra LL,Stege PW

    更新日期:2018-06-25 00:00:00

  • Chiral 1,1'-binaphthyl-2,2'-dithiol-stabilized gold clusters: size separation and optical activity in the UV-vis.

    abstract::Gold particles covered with 1,1'-binaphthyl-2,2'-dithiol (BINAS) were prepared. Using size exclusion chromatography, it was possible for the first time to separate the sample into fractions with different sizes and colors. Transmission electron microscopy shows that the particles are very small, in the order of 1 nm o...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20488

    authors: Gautier C,Taras R,Gladiali S,Bürgi T

    更新日期:2008-03-01 00:00:00

  • Measurements of concentration dependence and enantiomeric purity of terpene solutions as a test of a new commercial VCD spectrometer

    abstract::Vibrational circular dichroism (VCD) spectra of (+)-alpha-pinene solutions in carbon tetrachloride have been measured in the range of volume fractions 5-100% (v/v) in the mid-infrared region. The concentration dependence measured was statistically analyzed with the aim of obtaining a reliable correlation between the V...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:4<199::AID-CHIR6>3

    authors: Urbanova M,Setnicka V V,Volka K

    更新日期:2000-05-01 00:00:00

  • Time-resolved circular dichroism in carbonmonoxy-myoglobin: the central role of the proximal histidine.

    abstract::A calculation of the circular dichroism (CD) spectra of carbonmonoxy- and deoxy-myoglobin is carried out in relation to a time-resolved CD experiment. This calculation allows us to assign a dominant role to the proximal histidine in the definition of the electronic normal modes and to interpret the transient CD struct...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20254

    authors: Dartigalongue T,Hache F

    更新日期:2006-05-05 00:00:00

  • Use of the exciton chirality method in the investigation of ligand-gated synthetic ion channels.

    abstract::The objective of this brief highlight is to point out the central role of the exciton chirality method to gain insights on the structural basis of the recently achieved ligand gating of synthetic ion channels. This unprecedented ligand gating was achieved with an equally unprecedented transmembrane rigid-rod pi-stack ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20221

    authors: Sakai N,Talukdar P,Matile S

    更新日期:2006-02-01 00:00:00

  • Polarization in France.

    abstract::The special relationship between France and the polarization of light from the beginning of the 19th century until the present day is reviewed in the lives and works of Étienne Louis Malus, François Arago, Jean-Baptiste Biot, Augustin Fresnel, Louis Pasteur, Frédéric Wallerant, Aimé Cotton, Francis Perrin, and Alain A...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22818

    authors: Kahr B

    更新日期:2018-04-01 00:00:00

  • A Solid Phase Vibrational Circular Dichroism Study of Polypeptide-Surfactant Interaction.

    abstract::We studied the interaction of poly-l-lysine (PLL) and poly-l-arginine (PLAG) with sodium dodecyl sulfate (SDS) surfactant and the interaction of poly-l-glutamic acid (PLGA) and poly-l-aspartic acid (PLAA) with tetradecyltrimethylammonium bromide (TTAB) surfactant using vibrational circular dichroism (VCD) spectroscopy...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22534

    authors: Novotná P,Urbanová M

    更新日期:2015-12-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22102

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

    更新日期:2013-01-01 00:00:00

  • Role of latent heat in chiral symmetry breaking transition in the crystallization of 1,1'-binaphthyl.

    abstract::The influence of latent heat dissipated by the crystallization of 1,1'-binaphthyl in its supercooled molten state on the chiral symmetry breaking transition was investigated. Temperature change in the crystallization system was monitored by infrared thermocamera. Temperature rise due to the dissipation of latent heat ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10187

    authors: Asakura K,Hayashi M,Osanai S

    更新日期:2003-03-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22386

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

    更新日期:2015-01-01 00:00:00