It has been observed that the leaves of some Zamia species undergo a kind of "reverse ripening"; that is, they change from their original brown color to green during development. We assumed that this strange color change was due to the change in carotenoid composition, so we followed the changes for several weeks. The detailed carotenoid composition and content at different stages of development of the leaves was determined with HPLC-DAD focusing on the changes in red and yellow carotenoids.
View Article and Find Full Text PDFThe carotenoid composition of the flower of was investigated for the first time by HPLC-DAD-MS. In addition to the main carotenoid lutein and its geometrical isomers, 5,6-epoxy-carotenoids, namely violaxanthin, lutein 5,6-epoxide and antheraxanthin, were detected in larger amounts. In addition, β-carotene 5,6-epoxide and β-carotene 5,6,5',6'-diepoxide were found, which occurs very rarely in plants.
View Article and Find Full Text PDFDietary lutein can be naturally metabolized to 3'-epilutein and 3'-oxolutein in the human body. The epimerization of lutein can happen in acidic pH, and through cooking, 3'-epilutein can be the product of the direct oxidation of lutein in the retina, which is also present in human serum. The 3'-oxolutein is the main oxidation product of lutein.
View Article and Find Full Text PDFLutein and its -isomers occur in a lot of plants, including a variety of flowers. In this study, lutein isomers were produced via iodine-catalyzed isomerization, and four -isomers (9-, 9'-, 13-, and 13') were isolated by means of column chromatography and semipreparative HPLC. The structures of the 9'- and 13'-isomers were elucidated via NMR measurements.
View Article and Find Full Text PDFMacrophage migration inhibitory factor (MIF) is a proinflammatory cytokine with enzymatic activities. Anti-inflammatory effects of MIF enzyme inhibitors indicate a link between its cytokine- and catalytic activities. Herein the synthesis, docking, and bioactivity of substituted benzylidene-1-indanone and -1-tetralone derivatives as MIF-tautomerase inhibitors is reported.
View Article and Find Full Text PDFThe xanthophyll carotenoid lutein has been widely used as supplementation due to its protective effects in light-induced oxidative stress. Its antioxidant and anti-inflammatory features suggest that it has a neuroprotective role as well. Glutamate is a major excitatory neurotransmitter in the central nervous system (CNS), which plays a key role in regulating brain function.
View Article and Find Full Text PDFCarotenoid succinates were synthesized from hydroxy carotenoids and were coupled to a commercially available derivative of melatonin via amide bond for producing more powerful anti-oxidants and yet new hybrid lipophilic bifunctional molecules with additional therapeutic effects. The coupling reactions produced conjugates in acceptable to good yields. Succinylation increased the water solubility of the carotenoids, while the conjugation with melatonin resulted in more lipophilic derivatives.
View Article and Find Full Text PDFPharmaceuticals (Basel)
October 2021
The protracted global COVID-19 pandemic urges the development of new drugs against the causative agent SARS-CoV-2. The clinically used glycopeptide antibiotic, teicoplanin, emerged as a potential antiviral, and its efficacy was improved with lipophilic modifications. This prompted us to prepare new lipophilic apocarotenoid conjugates of teicoplanin, its pseudoaglycone and the related ristocetin aglycone.
View Article and Find Full Text PDFLutein is a tetraterpene carotenoid, which has been reported as an important antioxidant and it is widely used as a supplement. Oxidative stress participates in many human diseases, including different types of neurodegenerative disorders. Microglia, the primary immune effector cells in the central nervous system, are implicated in these disorders by producing harmful substances such as reactive oxygen species (ROS).
View Article and Find Full Text PDFFlavonoids and carotenoids possess beneficial physiological effects, such as high antioxidant capacity, anticarcinogenic, immunomodulatory, and anti-inflammatory properties, as well as protective effects against UV light. The covalent coupling of hydrophobic carotenoids with hydrophilic flavonoids, such as daidzein and chrysin, was achieved, resulting in new amphipathic structures. 7-Azidohexyl ethers of daidzein and chrysin were prepared in five steps, and their azide-alkyne [4 + 2] cycloaddition with pentynoates of 8'-apo-β-carotenol, zeaxanthin, and capsanthin afforded carotenoid-flavonoid conjugates.
View Article and Find Full Text PDFA series of 4(arylmethylene)-3-isochromanones have been prepared with base-catalyzed Knoevenagel condensation starting from 3-isochromanone and aromatic aldehydes. The outcome of the reaction- the isomeric composition of the products depends on the aromatic aldehyde applied. These reactions afforded mostly the more stable -diastereoisomer, but some condensations resulted in the Z-diastereoisomer or mixture of the stereoisomers (-).
View Article and Find Full Text PDFJ Agric Food Chem
September 2016
The detailed carotenoid analysis of red mamey (Pouteria sapota) was achieved by HPLC-DAD-MS, chemical tests, and cochromatography with authentic samples. Altogether 47 components were detected and 34 identified from the total extract or after fractionation with column chromatography. The main carotenoids were cryptocapsin, sapotexanthin, and capsanthin 5,6-epoxide.
View Article and Find Full Text PDFFrom an extract of red mamey (Pouteria sapota) β-cryptoxanthin-5,6-epoxide, β-cryptoxanthin-5',6'-epoxide, 3'-deoxycapsanthin, and cryptocapsin were isolated and characterized by UV-vis spectroscopy, electronic circular dichroism (ECD), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). Epoxidation of β-cryptoxanthin delivered the β-(5'R,6'S)- and (5'S,6'R)-cryptoxanthin-5',6'-epoxides, which were identified by HPLC-ECD analysis. These carotenoids among others are quite common in the fruits of Central America, and as they are natural provitamins A, they should play an important role in the diet of the mostly vitamin A deficient population of this region.
View Article and Find Full Text PDFAim: The goal of the Collaboration Spotting project is to create an automatic system to collect information about publications and patents related to a given technology, to identify the key players involved, and to highlight collaborations and related technologies. The collected information can be visualized in a web browser as interactive graphical maps showing in an intuitive way the players and their collaborations (Sociogram) and the relations among the technologies (Technogram). We propose to use the system to study technologies related to oral medicine.
View Article and Find Full Text PDFAim: The goal of the Collaboration Spotting project is to create an automatic system to collect information about publications and patents related to a given technology, to identify the key players involved, and to highlight collaborations and related technologies. The collected information can be visualized in a web browser as interactive graphical maps showing in an intuitive way the players and their collaborations (Sociogram) and the relations among the technologies (Technogram). We propose to use the system to study technologies related to Dental Science.
View Article and Find Full Text PDFPhys Rev Lett
September 2013
Azimuthally anisotropic distributions of D0, D+, and D*+ mesons were studied in the central rapidity region (|y|<0.8) in Pb-Pb collisions at a center-of-mass energy sqrt[sNN]=2.76 TeV per nucleon-nucleon collision, with the ALICE detector at the LHC.
View Article and Find Full Text PDFThe directed flow of charged particles at midrapidity is measured in Pb-Pb collisions at √(s(NN))=2.76 TeV relative to the collision symmetry plane defined by the spectator nucleons. A negative slope of the rapidity-odd directed flow component with approximately 3 times smaller magnitude than found at the highest RHIC energy is observed.
View Article and Find Full Text PDFThe ALICE measurement of K(S)(0) and Λ production at midrapidity in Pb-Pb collisions at √(s(NN))=2.76 TeV is presented. The transverse momentum (p(T)) spectra are shown for several collision centrality intervals and in the p(T) range from 0.
View Article and Find Full Text PDFWe report the first measurement of the net-charge fluctuations in Pb-Pb collisions at sqrt[sNN]=2.76 TeV, measured with the ALICE detector at the CERN Large Hadron Collider. The dynamical fluctuations per unit entropy are observed to decrease when going from peripheral to central collisions.
View Article and Find Full Text PDFThe transverse momentum (p(T)) distribution of primary charged particles is measured in minimum bias (non-single-diffractive) p+Pb collisions at sqrt[s(NN)]=5.02 TeV with the ALICE detector at the LHC. The p(T) spectra measured near central rapidity in the range 0.
View Article and Find Full Text PDFNew carotenoids, cryptocapsin-5,6-epoxide, 3'-deoxycapsanthin-5,6-epoxide, and cryptocapsin-5,8-epoxides, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Cryptocapsin-5,6-epoxide was prepared by partial synthesis via epoxidation of cryptocapsin, and the (5R,6S)- and (5S,6R)-stereoisomers were identified by HPLC-ECD analysis. Spectroscopic data of the natural (anti) and semisynthetic (syn) derivatives obtained by acid-catalyzed rearrangement of cryptocapsin-5,8-epoxide stereoisomers were compared for structural elucidation.
View Article and Find Full Text PDFMeasurements of charge-dependent azimuthal correlations with the ALICE detector at the LHC are reported for Pb-Pb collisions at sqrt[s(NN)] = 2.76 TeV. Two- and three-particle charge-dependent azimuthal correlations in the pseudorapidity range |η| < 0.
View Article and Find Full Text PDFThe charged-particle pseudorapidity density measured over four units of pseudorapidity in nonsingle-diffractive p+Pb collisions at a center-of-mass energy per nucleon pair √(s(NN))=5.02 TeV is presented. The average value at midrapidity is measured to be 16.
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