scholarly journals Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural

Foods ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1391
Author(s):  
Shiqiang Yang ◽  
Zhongfei Zhang ◽  
Jiaoyong Li ◽  
Yuge Niu ◽  
Liangli Lucy Yu
Keyword(s):  
Maillard Reaction ◽  
Antioxidant Activities ◽  
Nutrient Utilization ◽  
In Vitro Assays ◽  
Raw 264.7 Cells ◽  
Inhibition Mechanism ◽  
Safety And Health ◽  
Processing And Storage ◽  
And Storage

The Maillard reaction (MR) can affect the color, flavor, organoleptic properties, and nutritional value of food. Sometimes, MR is undesirable due to lowering the nutrient utilization, producing harmful neo-formed compounds, etc. In this case, it is necessary to control MR. Some chemical substances, such as phenolic acid, vitamins, aminoguanidine, and thiols extracted from garlic or onion, can effectively prevent MR. In this study, L-cysteine (L-cys) was found to inhibit MR after screening 10 sulfhydryl compounds by comparing their ability to mitigate browning. The inhibition mechanism was speculated to be related to the removal of 5-hydroxymethylfurfural (HMF), a key mid-product of MR. The reaction product of HMF and L-cys was identified and named as 1-dicysteinethioacetal–5-hydroxymethylfurfural (DCH) according to the mass spectrum and nuclear magnetic resonance spectrum of the main product. Furthermore, DCH was detected in the glutamic–fructose mixture after L-cys was added. In addition, the production of DCH also increased with the addition of L-cys. It also was worth noting that DCH showed no cell toxicity to RAW 264.7 cells. Moreover, the in vitro assays indicated that DCH had anti-inflammatory and antioxidant activities. In conclusion, L-cys inhibits MR by converting HMF into another adduct DCH with higher safety and health benefits. L-cys has the potential to be applied as an inhibitor to prevent MR during food processing and storage.

scholarly journals Anti-Inflammatory Effects of Formononetin 7-O-phosphate, a Novel Biorenovation Product, on LPS-Stimulated RAW 264.7 Macrophage Cells

Molecules ◽  
2019 ◽  
Vol 24 (21) ◽  
pp. 3910 ◽  
Author(s):  
Min-Seon Kim ◽  
Jin-Soo Park ◽  
You Chul Chung ◽  
Sungchan Jang ◽  
Chang-Gu Hyun ◽  
...  
Keyword(s):  
Biological Properties ◽  
In Vitro Assays ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Raw 264.7 ◽  
Dependent Manner ◽  
Macrophage Cells ◽  
Anti Inflammatory ◽  
Reduced Toxicity

Biorenovation is a microbial enzyme-catalyzed structural modification of organic compounds with the potential benefits of reduced toxicity and improved biological properties relative to their precursor compounds. In this study, we synthesized a novel compound verified as formononetin 7-O-phosphate (FMP) from formononetin (FM) using microbial biotransformation. We further compared the anti-inflammatory properties of FMP to FM in lipopolysaccharide (LPS)-treated RAW264.7 macrophage cells. We observed that cell viabilities and inhibitory effects on LPS-induced nitric oxide (NO) production were greater in FMP-treated RAW 264.7 cells than in their FM-treated counterparts. In addition, FMP treatment suppressed the production of proinflammatory cytokines such as prostaglandin-E2 (PGE2), interleukin-6 (IL-6), and interleukin-1β (IL-1β) in a dose-dependent manner and concomitantly decreased the mRNA expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2). We also found that FMP exerted its anti-inflammatory effects through the downregulation of the extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK), and nuclear factor kappa B (NF-κB) signaling pathways. In conclusion, we generated a novel anti-inflammatory compound using biorenovation and demonstrated its efficacy in cell-based in vitro assays.

scholarly journals Behaviour of 9-Ethyl-9H-carbazole Hydrazone Derivatives Against Oxidant Systems

2019 ◽  
Vol 92 (1) ◽  
pp. 87-94 ◽  
Author(s):  
Cigdem Karaaslan ◽  
Hande Gurer-Orhan ◽  
Sibel Suzen ◽  
Luciano Saso ◽  
Omidreza Firuzi ◽  
...  
Keyword(s):  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Amyloid Β ◽  
In Vitro Assays ◽  
Cytotoxic Activities ◽  
Scavenging Activity ◽  
Neuroprotective Effects ◽  
Neuronal Pc12 Cells

Antioxidants are helpful in prevention of several diseases related with oxidative stress including neurodegenerative disorders. In recent studies, carbazoles were given proof of promising antioxidant activities. In this article, 9-ethyl-9H-carbazole hydrazone derivatives were synthesized, characterized and their in vitro antioxidant activity and possible cytotoxic effects were investigated. Furthermore, protective effect of the synthesized derivatives against amyloid β-induced damage in PC12 neuronal cells was examined by using MTT assay. The newly synthesized carbazoles were found to have radical scavenging activity with a varying potency both in cell-free and cell-based in vitro assays. Several compounds, especially such as 3d and 3e, 3m and 3n bearing two halogen groups on the phenyl ring, were found to have cytotoxic activity. However, their cytotoxic activities were not higher than that of melatonin. Several compounds also significantly protected neuronal PC12 cells against amyloid β-induced damage, which can be defined as neuroprotective agents. (4-(2-((9-Ethyl-9H-carbazol-3-yl)methylene)hydrazinyl)benzonitrile) 3r was found as the most active compound with both radical scavenging activity and neuroprotective effects against amyloid β-induced damage. These findings might provide an alternative strategy for developing novel carbazole derivatives for management of neurodegenerative diseases, such as Alzheimer's disease.

Chemical synthesis and characterization of a new quinazolinedione competitive antagonist for strigolactone receptors with an unexpected binding mode

2019 ◽  
Vol 476 (12) ◽  
pp. 1843-1856 ◽  
Author(s):  
Cyril Hamiaux ◽  
Lesley Larsen ◽  
Hui Wen Lee ◽  
Zhiwei Luo ◽  
Prachi Sharma ◽  
...  
Keyword(s):  
In Silico ◽  
Binding Mode ◽  
Crystal Structure Analysis ◽  
Tolfenamic Acid ◽  
In Vitro Assays ◽  
Inhibition Mechanism ◽  
In Planta ◽  
Competitive Antagonist ◽  
In Silico Docking

Abstract Strigolactones (SLs) are multifunctional plant hormones regulating essential physiological processes affecting growth and development. In vascular plants, SLs are recognized by α/β hydrolase-fold proteins from the D14/DAD2 (Dwarf14/Decreased Apical Dominance 2) family in the initial step of the signaling pathway. We have previously discovered that N-phenylanthranilic acid derivatives (e.g. tolfenamic acid) are potent antagonists of SL receptors, prompting us to design quinazolinone and quinazolinedione derivatives (QADs and QADDs, respectively) as second-generation antagonists. Initial in silico docking studies suggested that these compounds would bind to DAD2, the petunia SL receptor, with higher affinity than the first-generation compounds. However, only one of the QADs/QADDs tested in in vitro assays acted as a competitive antagonist of SL receptors, with reduced affinity and potency compared with its N-phenylanthranilic acid ‘parent’. X-ray crystal structure analysis revealed that the binding mode of the active QADD inside DAD2's cavity was not that predicted in silico, highlighting a novel inhibition mechanism for SL receptors. Despite a ∼10-fold difference in potency in vitro, the QADD and tolfenamic acid had comparable activity in planta, suggesting that the QADD compensates for lower potency with increased bioavailability. Altogether, our results establish this QADD as a novel lead compound towards the development of potent and bioavailable antagonists of SL receptors.

scholarly journals On the Molecular Pharmacology of Resveratrol on Oxidative Burst Inhibition in Professional Phagocytes

2014 ◽  
Vol 2014 ◽  
pp. 1-9 ◽  
Author(s):  
Radomír Nosáľ ◽  
Katarína Drábiková ◽  
Viera Jančinová ◽  
Tomáš Perečko ◽  
Gabriela Ambrožová ◽  
...  
Keyword(s):  
Oxidative Burst ◽  
Antioxidant Activities ◽  
Raw 264.7 Cells ◽  
Human Neutrophils ◽  
Nitrite Production ◽  
Inos Protein Expression ◽  
Dependent Inhibition ◽  
Dose Dependent Inhibition ◽  
Dose Dependent

Resveratrol—3,5,4′-trihydroxystilbene—possesses antioxidant activitiesin vitro. It dose-dependently inhibited the generation of peroxyl, hydroxyl, peroxides, and lipid peroxidation products in cell free systems. Oxidative burst of whole human blood stimulated with PMA, fMLP, OpZ, and A23187 was inhibited in a concentration-dependent way, indicating suppression of both receptor and nonreceptor activated chemiluminescence by resveratrol. Results from isolated human neutrophils revealed that resveratrol was active extracellularly as well as intracellularly in inhibiting the generation of reactive oxygen species. Liberation of ATP and analysis of apoptosis showed that in the concentration of 100 μM, resveratrol did not change the viability and integrity of isolated neutrophils. Western blot analysis documented that resveratrol in concentrations of 10 and 100 μM significantly decreased PMA-induced phosphorylation of PKCα/βII. Dose-dependent inhibition of nitrite production and iNOS protein expression in RAW 264.7 cells indicated possible interference of resveratrol with reactive nitrogen radical generation in professional phagocytes. The results suggest that resveratrol represents an effective naturally occurring substance with potent pharmacological effect on oxidative burst of human neutrophils and nitric oxide production by macrophages. It should be further investigated for its pharmacological activity against oxidative stress in ischaemia reperfusion, inflammation, and other pathological conditions, particularly neoplasia.

scholarly journals Identification of phenolic secondary metabolites from Schotia brachypetala Sond. (Fabaceae) and demonstration of their antioxidant activities in Caenorhabditis elegans

2016 ◽  
Author(s):  
Mansour Sobeh ◽  
Esraa A ElHawary ◽  
Herbenya Peixoto ◽  
Rola M Labib ◽  
Heba Handoussa ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Caenorhabditis Elegans ◽  
Nuclear Translocation ◽  
Antioxidant Activities ◽  
In Vitro Assays ◽  
Flavonoid Glycosides ◽  
Alcoholic Extract ◽  
C Elegans

Background: Schotia brachypetala Sond. (Fabaceae) is an endemic tree of Southern Africa whose phytochemistry and pharmacology were slightly studied.The present work aimed at profiling the major phenolics compounds present in the hydro-alcoholic extract from S. brachypetala leaves (SBE) using LC/HRESI/MS/MS and NMR and prove their antioxidant capabilities using novel methods. Methods: In vitro assays; DPPH, TEAC persulfate decolorizing kinetic and FRAP assays, and in vivo assays: Caenorhabditis elegans strains maintenance, Intracellular ROS in C. elegans, Survival assay, GFP expression and Subcellular DAF-16 localization were employed to evaluate the antioxidant activity. Results: More than forty polyphenols ,including flavonoid glycosides, galloylated flavonoid glycosides, isoflavones, dihydrochalcones, procyanidins, anthocyanins, hydroxybenzoic acid derivatives, hydrolysable tannins, and traces of methylated and acetylated flavonoid derivatives were identified. Three compounds were isolated and identified from the genus Schotia for the first time, namely gallic acid, myricetin-3-O-α-L-1C4-rhamnoside and quercetin-3-O-L-1C4-rhamnoside.The tested extract was able to protect the worms against juglone induced oxidative stress and attenuate the reactive oxygen species (ROS) accumulation. SBE was also able to attenuate the levels of heat shock protein (HSP) expression. Discussion: A pronounced antioxidant activity in vivo, which can be attributed to its ability to promote the nuclear translocation of DAF-16/FOXO, the main transcription factor regulating the expression of stress response genes. The remarkable antioxidant activity in vitro and in vivo correlates to SBE rich phenolic profile.

scholarly journals Antioxidant Activities of the Leaf Extract and Fractions of Dryopteris filix-mas (L.) Schott could be Attributed to The Abundance of Polyphenol Compounds

2020 ◽  
Vol 9 (1) ◽  
pp. 1-6
Author(s):  
Earnest Oghenesuvwe Erhirhie ◽  
Emmanuel Emeka Ilodigwe ◽  
Daniel Lotanna Ajaghaku ◽  
Blessing Ogechukwu Umeokoli ◽  
Peter Maduabuchi Eze ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Leaf Extract ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Bioactive Compound ◽  
Ethyl Acetate Fraction ◽  
In Vitro Assays ◽  
Anti Oxidant

Dryopteris filix mas (D filix-mas) is wildly used in ethnomedicine for the management of rheumatoid arthritis, wounds and other diseases. We investigated the anti-oxidant activities of its leaf extract, and chromatographic fractions. The ethanol leaf extract was partitioned into four fractions; n-hexane, ethyl acetate, n-butanol and water. Ferric reducing anti-oxidant power (FRAP), 1, 1-diphenyl-2-picrylhydrazil (DPPH) and nitric oxide (NO) scavenging in vitro assays were carried out on the extract and fractions at 6.25, 12.5, 25, 50, 100, 200, 400 and 800 µg/mL. The most active fraction (ethyl acetate fraction) was further purified using chromatographic techniques to isolate its major compound whose structure was elucidated using ID nuclear magnetic resonance (NMR) and mass spectrometry. The ethyl acetate fraction produced the highest free radical scavenging activity among the other fractions. The fraction (VLC-E7) from which the bioactive compound, quercetin-3-O-αL-rhamnopyranoside, was isolated had the best FRAP and DPPH scavenging activities with EC50 and IC50 values of 88.81 ± 3.41 and 26.87 ± 0.24 respectively more than the ethyl acetate fraction. This study revealed that the polyphenol flavonoid, quercetin-3-O-αL-rhamnopyranoside could be responsible for antioxidant activity of ethno-medicinal property of D filix-mas leaf.

scholarly journals INHIBITION OF NITRIC OXIDE PRODUCTION IN LPS-STIMULATED RAW 264.7 CELLS BY DOLICHANDRONE ATROVIRENS BARK

2019 ◽  
Vol 6 (1) ◽  
pp. 67-72
Author(s):  
Ponnuvel Deepa ◽  
Kandhasamy Sowndhararajan ◽  
Minju Kim ◽  
Songmun Kim
Keyword(s):  
Nitric Oxide ◽  
Methanol Extract ◽  
Antioxidant Activities ◽  
Raw 264.7 Cells ◽  
Total Phenolic ◽  
No Production ◽  
Raw 264.7 ◽  
Phenolic Components ◽  
Inflammatory Effect

In traditional systems of medicine, the bark of Dolichandroneatrovirens has been used to treat various disorders. The main aim of this study was to determine the anti-inflammatory effect of D. atrovirens bark through the inhibition of nitric oxide (NO) production in lipopolysaccharide-stimulated RAW 264.7 cells.For this purpose, preliminary phytochemical composition and in vitro antioxidant activities of various solvent extracts of D. atrovirens bark were evaluated to select the most effective extract.The methanol extract of D.atrovirens registered the highest amount of total phenolics (476.2 mg GAE/g) and flavonoid (129.0 mg RE/g)contents witha strong antioxidant activity as measured in DPPH (IC50 of 19.52 μg/mL) and ABTS (IC50of 10.82 μg/mL) scavenging activities.Hence, the methanol extract was selected for cell line study. Further, the methanol extract of D. atrovirens effectively inhibited the production of NO in RAW 264.7 cells induced by LPS (13.1 μM at the concentration of 80 μg/mL). It could be concluded that the presence of higher level of total phenolic components in the methanol extract of D. atrovirens bark might be responsible for reducing the NO level in cells.

scholarly journals Purification and Partial Characterization of Melanoidins Fractions from Toasted Oak Heartwood, Comparison with Melanoidins from Roasted Coffee

2018 ◽  
Vol 7 (6) ◽  
pp. 37 ◽  
Author(s):  
M. F. Nonier ◽  
N. Vivas ◽  
N. Vivas de Gaulejac ◽  
C. Mouche ◽  
C. Rossy Huguet ◽  
...  
Keyword(s):  
Antioxidant Activities ◽  
Degradation Products ◽  
Partial Characterization ◽  
Maillard Reaction Products ◽  
Reaction Products ◽  
Roasted Coffee ◽  
Oak Wood ◽  
Processing And Storage ◽  
And Storage

During the cooking, processing, and storage of food products, a whole range of browning reactions occurs, initiated by the reaction of a carbohydrate with a compound possessing a free amino group. Melanoidins formed, influence food quality, mainly their colour, their flavour, and their antioxidant activities. Melanoidins are complex Maillard reaction products. We developed a method to isolate coffee melanoidins and melanoidins from toasted oak wood. We noted that coffee is richer in melanoidin compounds than oak wood. We presented a partial characterization of melanoidins fractions from toasted oak heartwood, and a comparison with melanoidins from roasted coffee. Mass spectra of the fractions isolated from toasted oak wood indicate the presence of pentose and hexose-based oligosaccharides with different degrees of polymerisation. The presence of the oligosaccharide moieties, as well as their degradation products found in the oak wood melanoidins, supports the postulated carbohydrate-based origin of melanoidins.

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