scholarly journals Uptake and metabolism of β-apo-8′-carotenal, β-apo-10′-carotenal, and β-apo-13-carotenone in Caco-2 cells

2019 ◽  
Vol 60 (6) ◽  
pp. 1121-1135 ◽  
Author(s):  
Boluwatiwi O. Durojaye ◽  
Kenneth M. Riedl ◽  
Robert W. Curley ◽  
Earl H. Harrison

β-Apocarotenoids are eccentric cleavage products of carotenoids formed by chemical and enzymatic oxidations. They occur in foods containing carotenoids and thus might be directly absorbed from the diet. However, there is limited information about their intestinal absorption. The present research examined the kinetics of uptake and metabolism of β-apocarotenoids. Caco-2 cells were grown on 6-well plastic plates until a differentiated cell monolayer was achieved. β-Apocarotenoids were prepared in Tween 40 micelles, delivered to differentiated cells in serum-free medium, and incubated at 37°C for up to 8 h. There was rapid uptake of β-apo-8′-carotenal into cells, and β-apo-8′-carotenal was largely converted to β-apo-8′-carotenoic acid and a minor metabolite that we identified as 5,6-epoxy-β-apo-8′-carotenol. There was also rapid uptake of β-apo-10′-carotenal into cells, and β-apo-10′-carotenal was converted into a major metabolite identified as 5,6-epoxy-β-apo-10′-carotenol and a minor metabolite that is likely a dihydro-β-apo-10′-carotenol. Finally, there was rapid cellular uptake of β-apo-13-carotenone, and this compound was extensively degraded. These results suggest that dietary β-apocarotenals are extensively metabolized in intestinal cells via pathways similar to the metabolism of retinal. Thus, they are likely not absorbed directly from the diet.

1997 ◽  
Vol 49 (2) ◽  
pp. 157-163 ◽  
Author(s):  
Muriel Raveton ◽  
Patrick Ravanel ◽  
Anne Marie Serre ◽  
Françoise Nurit ◽  
Michel Tissut

1987 ◽  
Vol 15 (2) ◽  
pp. 201-215 ◽  
Author(s):  
John H. Linehan ◽  
Thomas A. Bronikowski ◽  
Christopher A. Dawson

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Jarmila Králová ◽  
Michal Jurášek ◽  
Lucie Mikšátková ◽  
Anna Marešová ◽  
Jan Fähnrich ◽  
...  

AbstractFluorescent sterol probes, comprising a fluorophore connected to a sterol backbone by means of a linker, are promising tools for enabling high-resolution imaging of intracellular cholesterol. In this study, we evaluated how the size of the linker, site of its attachment and nature of the fluorophore, affect the localization and trafficking properties of fluorescent sterol probes. Varying lengths of linker using the same fluorophore affected cell penetration and retention in specific cell compartments. A C-4 linker was confirmed as optimal. Derivatives of heterocyclic sterol precursors attached with identical C-4 linker to different fluorophores at diverse positions also showed significant differences in their binding properties to various intracellular compartments and kinetics of trafficking. Two novel red-emitting probes with good cell permeability, fast intracellular labelling and slightly different distribution displayed very promising characteristics for sterol probes. These probes also strongly labelled endo/lysosomal compartment in cells with pharmacologically disrupted cholesterol transport, or with a genetic mutation of cholesterol transporting protein NPC1, that overlapped with filipin staining of cholesterol. Overall, the present study demonstrates that the physicochemical properties of the fluorophore/linker pairing determine the kinetics of uptake and distribution and subsequently influence the applicability of final probes.


1952 ◽  
Vol 25 (1) ◽  
pp. 21-32 ◽  
Author(s):  
W. C. Warner ◽  
J. Reid Shelton

Abstract Three olefins were oxidized in the liquid phase with molecular oxygen to determine the kinetics of the oxidation reactions and the relationship to oxidation of rubber. The instantaneous rate of oxidation was found to be related to the analytically determined olefin and peroxide concentrations by the equation : Rate=k (unreacted olefin)(peroxide), where rate equals moles of oxygen per mole of original olefin per hour and the parentheses represent molarities. Presence of a phenyl group was found to affect k, but only in a minor way, indicating that the same fundamental kinetic mechanism applies in both aromatic and aliphatic olefins. The data are consistent with the general kinetic mechanism of Bolland involving oxygen attack at the alpha-methylenic group. However, it appears probable that initial oxygen attack can also occur at the double bond, resulting in the formation of a peroxide biradical, which may then react with other olefin molecules, initiating the usual chain reaction mechanism.


2012 ◽  
Vol 142 (12) ◽  
pp. 2091-2096 ◽  
Author(s):  
Lisa Scheid ◽  
Sabine Ellinger ◽  
Birgit Alteheld ◽  
Hannes Herholz ◽  
Jörg Ellinger ◽  
...  

2014 ◽  
Vol 14 (8) ◽  
pp. 12121-12165 ◽  
Author(s):  
M. I. Jacobs ◽  
W. J. Burke ◽  
M. J. Elrod

Abstract. Isoprene, the most abundant non-methane volatile organic compound (VOC) emitted into the atmosphere, is known to undergo gas phase oxidation to form eight different hydroxynitrate isomers in "high NOx" environments. These hydroxynitrates are known to affect the global and regional formation of ozone and secondary organic aerosol (SOA), as well as affect the distribution of nitrogen. In the present study, we have synthesized three of the eight possible hydroxynitrates: 4-hydroxy-3-nitroxy isoprene (4,3-HNI) and E/Z-1-hydroxy-4-nitroxy isoprene (1,4-HNI). Oxidation of the 4,3-HNI isomer by the OH radical was monitored using a flow tube chemical ionization mass spectrometer (FT-CIMS), and its OH rate constant was determined to be (3.64 ± 0.41) × 10−11 cm3 molecule−1 s−1. The products of 4,3-HNI oxidation were monitored, and a mechanism to explain the products was developed. An isoprene epoxide (IEPOX) – a species important in SOA chemistry and thought to originate only from "low NOx" isoprene oxidation – was found as a minor, but significant product. Additionally, hydrolysis kinetics of the three synthesized isomers were monitored with NMR. The bulk, neutral solution hydrolysis rate constants for 4,3-HNI and the 1,4-HNI isomers were (1.59±0.03 × 10−5 s−1 and (6.76 ± 0.09) × 10−3 s−1, respectively. The hydrolysis reactions of each isomer were found to be general acid-catalyzed. The reaction pathways, product yields and atmospheric implications for both the gas phase and aerosol-phase reactions are discussed.


2007 ◽  
Vol 39 (9) ◽  
pp. 1698-1706 ◽  
Author(s):  
Julia E. Raftos ◽  
Stephney Whillier ◽  
Bogdan E. Chapman ◽  
Philip W. Kuchel

Weed Science ◽  
1971 ◽  
Vol 19 (1) ◽  
pp. 113-117 ◽  
Author(s):  
F. Y. Chang ◽  
W. H. Vanden Born

Greenhouse studies indicated that 3,6-dichloro-o-anisic acid (dicamba) or its metabolic derivative was strongly accumulated in meristematic tissues of Tartary buckwheat (Fagopyrum tataricum(L.) Gaertn.) and wild mustard (Sinapis arvensisL.) following both foliar and root uptake. In barley (Hordeum vulgareL.) and wheat (Triticum vulgareL.), it was distributed throughout the plants. Detoxification of dicamba occurred in all four species though not at equal rates, and a common major metabolite was identified chromatographically as 5-hydroxy-3,6-dichloro-o-anisic acid. A minor metabolite, 3,6-dichlorosalicylic acid, was found in barley and wheat but not in Tartary buckwheat or wild mustard. The four species tolerated dicamba treatment in the order of wheat, barley, wild mustard, and Tartary buckwheat. This ranking corresponds with the ability of the plants to detoxify dicamba and is inversely related to the extent of dicamba absorption and translocation in them.


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