scholarly journals Study on the Synthesis, Antioxidant Properties, and Self-Assembly of Carotenoid–Flavonoid Conjugates

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 636
Author(s):  
Ildikó Línzembold ◽  
Dalma Czett ◽  
Katalin Böddi ◽  
Tibor Kurtán ◽  
Sándor Balázs Király ◽  
...  

Flavonoids 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. The trolox-equivalent antioxidant capacity against ABTS•+ radical cation and self-assembly of the final products were examined. The 1:1 flavonoid–carotenoid hybrids generally showed higher antioxidant activity than their parent flavonoids but lower than that of the corresponding carotenoids. The diflavonoid hybrids of zeaxanthin and capsanthin, however, were found to exhibit a synergistic enhancement in antioxidant capacities. ECD (electronic circular dichroism) and UV-vis analysis of zeaxanthin–flavonoid conjugates revealed that they form different optically active J-aggregates in acetone/water and tetrahydrofuran/water mixtures depending on the solvent ratio and type of the applied aprotic polar solvent, while the capsanthin derivatives showed no self-assembly. The zeaxanthin bis-triazole conjugates with daidzein and with chrysin, differing only in the position of a phenolic hydroxyl group, showed significantly different aggregation profile upon the addition of water.

2007 ◽  
Vol 20 (3) ◽  
pp. 585-593 ◽  
Author(s):  
G. Cinnella ◽  
G. Vendemiale ◽  
M. Dambrosio ◽  
G. Serviddio ◽  
P.L. Pugliese ◽  
...  

We studied the effects of Propofol, Desflurane, and Sevoflurane on the systemic redox balance in patients undergoing laparohysterectomy. We measured blood concentration of glutathione (GSH), plasma antioxidant capacity (Trolox Equivalent Antioxidant Capacity-TEAC), and lipid peroxidation products (malondialdehyde (aMDA) and 4-hydroxynonenal (aHNE) protein adducts). Sixty patients were randomly placed into three groups of twenty people each. In Group P anesthesia was induced with Propofol 2 mg/kg and maintained with 12–10–8 mg/kg/min; in Groups S and D anesthesia was induced with 3 mg/kg Sodium Thiopental and maintained with 2% Sevoflurane and 6% Desflurane, respectively. Blood samples were collected prior to induction (T0bas), 60min and 24h postoperatively (T160' and T224 h). In Group P, GSH increased on T160' (p<0.02) and returned to baseline on T24h, while TEAC remained unmodified; in Groups S, GSH and TEAC decreased on T160' (p<0.01 vs. T0bas, p<0.03 vs. T0bas, respectively); in Group D, on T160' there was a slight decrease of GSH and TEAC. The levels of aMDA slightly decreased throughout the study periods in Group P, increased in Group D, and remained stable in Group S. Propofol showed antioxidant properties, while Sevoflurane and Desflurane seemed to shift the redox balance towards oxidation, yet without inducing overt oxidative damage.


2013 ◽  
Vol 67 (1) ◽  
pp. 77-88 ◽  
Author(s):  
Zoran Markovic ◽  
Nedeljko Manojlovic ◽  
Svetlana Jeremic ◽  
Miroslav Zivic

Purpurin (1,2,4-trihidroxyanthraquinone), a naurally occuring anthraquinone pigment present in the root of Rubia tinctorum (Mull. Arg.) Zahlbr. was isolated from the plant, purified and characterized by HPLC chromatography, UV-Vis and NMR spectroscopy. The geometries of the purpurin conformers were optimized using the B3LYP/6-311+G(d,p) level of theory. It was found that all conformations have similar energies and that the corresponding purpurin radicals are planar. In spite of their planarity, there is no significant electron delocalization over the A and C rings. The antioxidant properties of purpurin were investigated using the colorimetric assay as Trolox-equivalent antioxidant capacity, and theoretical BDE (Bond Dissociation Enthalpy). Both methods revealed that purpurin has strong antioxidant capacity.


Animals ◽  
2019 ◽  
Vol 9 (11) ◽  
pp. 992 ◽  
Author(s):  
Joanna Pokorska ◽  
Dominika Kułaj ◽  
Agata Piestrzyńska-Kajtoch ◽  
Anna Radko

In the recent years, antioxidant properties of food products have become an important aspect for consumers. Milk is a very good source of easily absorbable proteins and minerals, as well as a valuable source of antioxidants. Lipocalin-2 (LCN2), given that, inter alia, it is produced in large quantities by various types of cells in response to oxidative stress caused by physical or chemical factors, it can be considered a protein that determines the total antioxidant capacity of milk. The main objective of this study was to analyze polymorphisms within the lipocalin-2 gene and to determine their impact on antioxidant activity of milk from Holstein-Friesian cows. The genotyping was carried out by sequencing of PCR products. To determine the antioxidant activity of milk, the Trolox equivalent antioxidant capacity (TEAC) method was used. A total of four polymorphic sites were identified in the examined segment of the bovine lipocalin-2 gene. It was shown that cows of the CC genotype at the locus g.98793763G>C produced milk of significantly higher antioxidant capacity. The antioxidant capacity of milk also varied according to the age of cows, their daily milk yield, and SCC in milk.


2015 ◽  
Vol 11 (2) ◽  
pp. 207-219 ◽  
Author(s):  
Weiqi Chen ◽  
Yurong Guo ◽  
Juan Zhang ◽  
Xiaorui Zhang ◽  
Yonghong Meng

Abstract In China, there are about 1.6 million tons of thinned young apples (TYAs) every year after blossoming and fruit thinning. These resulting fruits, in reality, could be utilized as agricultural and food resource. This study was undertaken to evaluate the influence on physical properties, bioactive attributes of TYAs that were subjected to chosen drying techniques. In general, significant differences (p < 0.05) exist in physical appearance and polyphenol. Antioxidant capacity was also investigated on the basis of assay for Trolox equivalent antioxidant capacity (TEAC) by 2,2ʹ-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), reducing power and 2, 2-diphenyl-1-picrylhydrazyl (DPPH) scavenging ability. Judging from the results, it was concluded that hot air drying at 60℃ is appropriate for large-scale production; furthermore, vacuum freeze drying tends to manufacture high-value up-market TYA products that are available to give the best results for dehydrated fruits. It is suggested that TYA has great potential in the food industry as functional ingredient.


Author(s):  
Julian Alfke ◽  
Uta Kampermann ◽  
Svetlana Kalinina ◽  
Melanie Esselen

AbstractDietary polyphenols like epigallocatechin-3-gallate (EGCG)—which represents the most abundant flavan-3-ol in green tea—are subject of several studies regarding their bioactivity and health-related properties. On many occasions, cell culture or in vitro experiments form the basis of published data. Although the stability of these compounds is observed to be low, many reported effects are directly related to the parent compounds whereas the impact of EGCG degradation and autoxidation products is not yet understood and merely studied. EGCG autoxidation products like its dimers theasinensin A and D, “P2” and oolongtheanin are yet to be characterized in the same extent as their parental polyphenol. However, to investigate the bioactivity of autoxidation products—which would minimize the discrepancy between in vitro and in vivo data—isolation and structure elucidation techniques are urgently needed. In this study, a new protocol to acquire the dimers theasinensin A and D as well as oolongtheanin is depicted, including a variety of spectroscopic and quadrupole time-of-flight high-resolution mass spectrometric (qTOF-HRMS) data to characterize and assign these isolates. Through nuclear magnetic resonance (NMR) spectroscopy, polarimetry, and especially circular dichroism (CD) spectroscopy after enzymatic hydrolysis the complementary atropisomeric stereochemistry of the isolated theasinensins is illuminated and elucidated. Lastly, a direct comparison between the isolated EGCG autoxidation products and the monomer itself is carried out regarding their antioxidant properties featuring Trolox equivalent antioxidant capacity (TEAC) values. These findings help to characterize these products regarding their cellular effects and—which is of special interest in the flavonoid group—their redox properties.


Biomarkers ◽  
2002 ◽  
Vol 7 (4) ◽  
pp. 291-298 ◽  
Author(s):  
Jan W. Dallinga ◽  
Guido R. M. M. Haenen ◽  
Aalt Bast ◽  
Frederik-Jan Van Schooten

Reproduction ◽  
2014 ◽  
Vol 147 (6) ◽  
pp. 885-895 ◽  
Author(s):  
Maria Elena Manca ◽  
Maria Lucia Manunta ◽  
Antonio Spezzigu ◽  
Laura Torres-Rovira ◽  
Antonio Gonzalez-Bulnes ◽  
...  

This study assessed the effect of melatonin deprival on ovarian status and function in sheep. Experimental procedures were carried out within two consecutive breeding seasons. Animals were divided into two groups: pinealectomised (n=6) and sham-operated (n=6). The completeness of the pineal gland removal was confirmed by the plasma concentration of melatonin. Ovarian status was monitored by ovarian ultrasonography for 1 year to study reproductive seasonality. Follicular and corpus luteal growth dynamics were assessed during an induced oestrous cycle. As the effects of melatonin on the ovary may also be mediated by its antioxidant properties, plasma Trolox equivalent antioxidant capacity (TEAC) was determined monthly for 1 year. Pinealectomy significantly extended the breeding season (310±24.7 vs 217.5±24.7 days in controls;P<0.05). Both pinealectomised and sham-operated ewes showed a well-defined wave-like pattern of follicle dynamics; however, melatonin deficiency caused fewer waves during the oestrous cycle (4.3±0.2 vs 5.2±0.2;P<0.05), because waves were 1 day longer when compared with the controls (7.2±0.3 vs 6.1±0.3;P<0.05). The mean area of the corpora lutea (105.4±5.9 vs 65.4±5.9 mm2;P<0.05) and plasma progesterone levels (7.1±0.7 vs 4.9±0.6 ng/ml;P<0.05) were significantly higher in sham-operated ewes compared with pinealectomised ewes. In addition, TEAC values were significantly lower in pinealectomised ewes compared with control ones. These data suggest that melatonin, besides exerting its well-known role in the synchronisation of seasonal reproductive fluctuations, influences the growth pattern of the follicles and the steroidogenic capacity of the corpus luteum.Free Italian abstractAn Italian translation of this abstract is freely available athttp://www.reproduction-online.org/content/147/6/885/suppl/DC1.


2014 ◽  
Vol 2014 ◽  
pp. 1-6 ◽  
Author(s):  
Martina Horvathova ◽  
Zuzana Orszaghova ◽  
Lucia Laubertova ◽  
Magdalena Vavakova ◽  
Peter Sabaka ◽  
...  

We examinedin vitroantioxidant capacity of polyphenolic extract obtained from the wood of oakQuercus robur(QR), Robuvit, using TEAC (Trolox equivalent antioxidant capacity) method and the effect of its intake on markers of oxidative stress, activity of antioxidant enzymes, and total antioxidant capacity in plasma of 20 healthy volunteers. Markers of oxidative damage to proteins, DNA, and lipids and activities of Cu/Zn-superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPx) were determined in the erythrocytes. We have found anin vitroantioxidant capacity of Robuvit of 6.37 micromole Trolox equivalent/mg of Robuvit. One month intake of Robuvit in daily dose of 300 mg has significantly decreased the serum level of advanced oxidation protein products (AOPP) and lipid peroxides (LP). Significantly increased activities of SOD and CAT as well as total antioxidant capacity of plasma after one month intake of Robuvit have been shown. In conclusion, we have demonstrated for the first time that the intake of Robuvit is associated with decrease of markers of oxidative stress and increase of activity of antioxidant enzymes and total antioxidant capacity of plasmain vivo.


Author(s):  
José María Giménez-Egido ◽  
Raquel Hernández-García ◽  
Damián Escribano ◽  
Silvia Martínez-Subiela ◽  
Gema Torres-Luque ◽  
...  

The purpose of this paper was to analyze the changes caused by a one-day tennis tournament in biomarkers of oxidative stress and α-amylase in saliva in children. The sample was 20 male active children with the following characteristics: (a) age of players = 9.46 ± 0.66 years; (b) weight = 34.8 ± 6.5 kg; (c) height = 136.0 ± 7.9 cm; (d) mean weekly training tennis = 2.9 ± 1.0 h. The tennis competition ran for one day, with four matches for each player. Data were taken from the average duration per match and the rating of perceived exertion (RPE). Four biomarkers of antioxidant status: uric acid (AU), Trolox equivalent antioxidant capacity (TEAC), ferric reducing ability of saliva (FRAS, cupric reducing antioxidant capacity (CUPRAC) and salivary alpha-amylase (sAA) as a biomarker of psychological stress were measured in saliva. The time points were baseline (at home before the tournament), pre-competition (immediately before the first match) and post-match (after each match) measurements. The four biomarkers of antioxidant status showed a similar dynamic with lower values at baseline and a progressive increase during the four matches. Overall one-day tennis competition in children showed a tendency to increase antioxidant biomarkers in saliva. In addition, there was an increase in pre-competition sAA possibly associated with psychological stress. Further studies about the possible physiological implications of these findings should be performed in the future.


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