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Food Bioscience · 2024 · IF 4.8

Folic acid-coupled phosphorylated Fe2+ chelating peptide: The properties of Fe2+ chelating capacity and mechanisms of anti-gastrointestinal enzyme degradation

Shanting Lin,Xiao Hu,Shengjun Chen,Hui Huang,Xiaoshan Long,Zhenxing Li

The aims of this study were to investigate the effect of precise phosphorylation of Ser in GL-Hyp-GPSGEEGKR on its Fe 2+ chelating capacity, and the effects and mechanisms of folic acid coupling to GL-Hyp-GPS (PO4) GEEGKR on its resistance against degradation by gastrointestinal enzymes. The results demonstrated that GL-Hyp-GPS (PO4) GEEGKR exhibited significantly enhanced Fe 2+ chelating capability compared to GL-Hyp-GPSGEEGKR. This was attributed to the phosphorylation of Ser introducing more Fe 2+ chelating sites. Furthermore, the results of UV–Vis, FTIR, and 1 H NMR showed that folic acid has successfully coupled with GL-Hyp-GPS (PO4) GEEGKR to generate folic acid-GL-Hyp-GPS (PO4) GEEGKR. Folic acid-GL-Hyp-GPS (PO4) GEEGKR demonstrated superior resistance against degradation by gastrointestinal enzymes. This may be attributed to the coupling of folic acid altering the original zeta potential of the peptide and the steric hindrance effect of folic acid hindering the interaction between enzymes and peptide. These findings can provide valuable insights for the production of high Fe 2+ chelating peptides that resist gastrointestinal enzyme degradation.

CAS / MDL: 59-30-3
研究领域: 生物化学 · 药学 · 营养科学
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JOURNAL OF THE CHINESE CHEMICAL SOCIETY · 2016 ·Vol. 63 ·期 11 ·924-929 · IF 0.879

Mechanistic Chemistry of Extraordinary Capacity of Salvianolic Acid B on Oxidatively-damaged Mesenchymal Stem Cells

Tingting Wang,Xican Li,Yunrong Li,Jianrun Wu,Yuyin Huang,Gang Wei,Dongfeng Chen

As the main bioactive component of Chinese herbal medicine Danshen, salvianolic acid B (Sal B, or lithospermic acid B) was observed to maintain the viability of mesenchymal stem cells (MSCs) treated by Fenton's reagent in the study. Interestingly, at a higher concentration, Sal B could even increase the viability rate to 175.1%. In mechanistic analysis experiments, Sal B was found to resist DNA destruction by •OH radical, scavenge various radicals in vitro , reduce Cu 2+ → Cu + , chelate Fe 2+ to yield an absorption maximum at 710 nm. Based on these results, we concluded that, (1) Sal B can not only protect MSCs against •OH-induced damages, but also promote their proliferation. This extraordinary capacity makes Sal B an ideal candidate in MSCs transplantation especially when MSCs are polluted by iron-overload or other oxidative stress factors and, can partly be responsible for the versatile properties of Sal B in pharmacology. The possible mechanisms of its protective effect are hypothesized to include Fe 2+ chelating, and direct radical scavenging which is involved in electron transfer (ET) or hydrogen atom transfer (HAT) from the catechol moieties. Its proliferation-promoting effect is presumed to be from its ester group, carboxylic group, or benzofuran ring.

研究领域: 药理学 · 干细胞生物学 · 化学 · 分子生物学
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BMC Complementary and Alternative Medicine · 2017 ·Vol. 17 ·期 1 ·1-11 · IF 2.288

Lyophilized aqueous extracts of Mori Fructus and Mori Ramulus protect Mesenchymal stem cells from •OH–treated damage: bioassay and antioxidant mechanism

Jiang Qian,Li Xican,Tian Yage,Lin Qiaoqi,Xie Hong,Lu Wenbiao,Chi Yuguang,Chen Dongfeng

Background Mori Fructus and Mori Ramulus are two traditional Chinese herbal medicines from mulberries. The present work explores their beneficial effects on •OH–treated mesenchymal stem cells (MSCs) and discusses possible mechanisms.Methods Lyophilized aqueous extracts of Mori Fructus (LAMF) and Mori Ramulus (LAMR) were prepared and analyzed using HPLC. LAMF and LAMR (along with morin) were further investigated for their effects on •OH-treated MSCs using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl (MTT) assay. The direct antioxidation mechanisms were studied using 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (PTIO•)-scavenging, 2,2′-azino-bis (3-ethylbenzo-thiazoline-6-sulfonic acid (ABTS+•)-scavenging and 1,1-diphenyl-2-picryl-hydrazl (DPPH•)-scavenging, as well as Cu2+-reducing and Fe3+-reducing antioxidant power. Finally, the indirect antioxidant mechanism was investigated based on the UV-vis spectra of Fe2+-chelation.Results In each LAMF and LAMR, seven phytophenols were successfully measured by HPLC, including five flavonoids (morin, rutin, astragalin, isoquercitrin and luteolin) and two non-flavonoids (chlorogenic acid and maclurin). MTT assays revealed that LAMF, LAMR and morin could effectively increase the survival of •OH-treated MSCs at 10–100 μg/mL, and could effectively scavenge PTIO• (IC 50 6609.7 ± 756.6, 4286.9 ± 84.9 and 103.4 ± 0.9 μg/mL, respectively), DPPH• (IC 50 208.7 ± 3.0, 97.3 ± 3.1 and 8.2 ± 0.7 μg/mL, respectively) and ABTS+• (IC 50 73.5 ± 5.8, 34.4 ± 0.1 and 4.2 ± 0.2 μg/mL, respectively), and reduce Cu2+ (IC 50 212.5 ± 7.0, 123.2 ± 0.9 and 14.1 ± 0.04 μg/mL, respectively) & Fe3+ (IC 50 277.0 ± 3.1, 191.9 ± 5.2 and 5.0 ± 0.2 μg/mL, respectively). In the Fe2+-chelating assay, the five flavonoids produced much stronger shoulder-peaks than the two non-flavonoids within 420–850 nm.Conclusion Mori Fructus and Mori Ramulus, can protect MSCs from •OH-induced damage. Such beneficial effects can mainly be attributed to the antioxidant action of phytophenols, which occurs via direct (ROS-scavenging) and indirect mechanism (Fe2+-chelating). The ROS-scavenging mechanism, however, include at least a H+-transfer and an electron-transfer (ET), and possibly includes a hydrogen-atom-transfer (HAT). In the Fe2+-chelating, flavonoids are more effective than non-flavonoids. This can be attributed to several adjacent planar chelating-sites between the 3-OH and 4-C = O, between the 4-C = O and 5-OH, or between the 3′-OH and 4′-OH in flavonoids. Such multiple-Fe2+-chelating reactions cause overlap in the UV-vis absorptions to deepen the complex color, enhance the peak strength, and form shoulder-peaks. By comparison, two non-flavonoids with catechol moiety produce only a weak single peak.

CAS / MDL: 153-18-4
研究领域: 药理学 · 细胞生物学 · 中药学 · 生物化学
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MOLECULES · 2016 ·Vol. 21 ·期 5 ·604 · IF 2.465

Protective Effects of Dihydromyricetin against •OH-Induced Mesenchymal Stem Cells Damage and Mechanistic Chemistry

Xican Li,Jingjing Liu,Jian Lin,Tingting Wang,Jieyuan Huang,Yongqiang Lin,Dongfeng Chen

As a natural flavonoid inAmpelopsis grossedentata, dihydromyricetin (DHM,2R,3R-3,5,7,3′,4′,5′-hexahydroxy-2,3-dihydroflavonol) was observed to increase the viability of •OH-treated mesenchymal stem cells using a MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl] assay and flow cytometry analysis. This protective effect indicates DHM may be a beneficial agent for cell transplantation therapy. Mechanistic chemistry studies indicated that compared with myricetin, DHM was less effective at ABTS+• (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid radical) scavenging and reducing Cu2+, and had higher •O2−and DPPH• (1,1-diphenyl-2-picrylhydrazyl radical) scavenging activities. Additionally, DHM could also chelate Fe2+to give an absorption maximum at 589 nm. Hence, such protective effect of DHM may arise from its antioxidant activities which are thought to occur via direct radical-scavenging and Fe2+-chelation. Direct radical-scavenging involves an electron transfer (ET) pathway. The hydrogenation of the 2,3-double bond is hypothesized to reduce the ET process by blocking the formation of a larger π-π conjugative system. The glycosidation of the 3–OH in myricitrin is assumed to sterically hinder atom transfer in the •O2−and DPPH• radical-scavenging processes. In DHM, the Fe2+-chelating effect can actually be attributed to the 5,3′,4′,5′–OH and 4–C=O groups, and the 3–OH group itself can neither scavenge radicals nor chelate metal.Keywords:dihydromyricetin;mesenchymal stem cells;antioxidant mechanisms;hydroxyl radical-induced;Fe2+-chelation;3–OH group;2,3-double bond;electron transfer (ET) pathway

研究领域: 药理学 · 细胞生物学 · 化学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2024 · IF 3.3

Anti-oxidant activity of 1-(1H-imidazo[4,5-c]pyridin-4-yl)ethenone, a Maillard reaction product derived from fructose and histidine

Kangyu Zhao,Xin Long,Junle Li,Ying Wang,Ping Lan,Yong Wang

BACKGROUND The Maillard reaction involves the interaction of various amino acids and reducing sugars, resulting in food browning. It often produces appealing aromas and flavors. The complexities of the reaction are such that it can be challenging to identify the often numerous and frequently volatile products formed by it. In the present study, we sought to identify and evaluate an unusual product with anti-oxidant activity arising from a fructose-histidine Maillard reaction model. The anti-oxidant profile of this product was assessed by computational means. RESULTS The fructose-histidine Maillard reaction products (FH-MRPs) were generated by heating a 2:1 mixture of the sugar and the amino acid at 140 °C for 2 h. Chromatographically separable fractions, labelled DM-1 to DM-8, were obtained using silica gel as the stationary phase and dichloromethane/methanol (DCM/MeOH) mixtures as the mobile one. Fraction DM-5 exhibited the highest 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, and further bio-assay guided fractionation led to isolation and identification of 1-(1 H -imidazo[4,5- c ]pyridin-4-yl)ethenone (IMPE) as the active principal, the structure of which was established by nuclear magnetic resonance (NMR) spectroscopic and mass spectral techniques. A mechanism for the formation of IMPE from its precursors is proposed. Density functional theory (DFT) calculations suggest this novel heterocyclic compound exerts its anti-oxidant effects by interacting with DPPH and 2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radicals. Essentially, IMPE was non-toxic below 300 ug mL −1 , showing a concentration-dependent free radical clearance capacity and reducing power within the 100–1000 μg mL −1 range, and moreover, exhibiting significant Fe 2+ chelating abilities wihin the 50-200 μg mL −1 range. CONCLUSION This study identified the unique FH-MRP, IMPE, and found that it acts as food antioxidant through the chelation of metal ions. © 2024 Society of Chemical Industry.

研究领域: 食品化学 · 分析化学 · 计算化学
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Antioxidants · 2024 ·Vol. 13 ·期 6 ·665 · IF 6

Studies on the Increasing Saltiness and Antioxidant Effects of Peanut Protein Maillard Reaction Products

Wenjing Xing,Chunmin Ma,Yang Yu,Fenglian Chen,Chunhua Yang,Na Zhang

The salt taste-enhancing and antioxidant effect of the Maillard reaction on peanut protein hydrolysates (PPH) was explored. The multi-spectroscopic and sensory analysis results showed that the Maillard reaction products (MRPs) of hexose (glucose and galactose) had slower reaction rates than those of pentose (xylose and arabinose), but stronger umami and increasing saltiness effects. The Maillard reaction can improve the flavor of PPH, and the galactose-Maillard reaction product (Ga-MRP) has the best umami and salinity-enhancing effects. The measured molecular weight of Ga-MRP were all below 3000 Da, among which the molecular weights between 500–3000 Da accounted for 46.7%. The products produced during the Maillard reaction process resulted in a decrease in brightness and an increase in red value of Ga-MRP. The amino acid analysis results revealed that compared with PPH, the content of salty and umami amino acids in Ga-MRPs decreased, but their proportion in total free amino acids increased, and the content of bitter amino acids decreased. In addition, the Maillard reaction enhances the reducing ability, DPPH radical scavenging ability, and Fe2+chelating ability of PPH. Therefore, the Maillard reaction product of peanut protein can be expected to be used as a substitute for salt seasoning, with excellent antioxidant properties.

CAS / MDL: 95-50-1 66-71-7
研究领域: 食品科学 · 营养学 · 化学 · 感官分析
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Antioxidants · 2023 ·Vol. 12 ·期 3 ·606 · IF 7

Insight into Antioxidant Activity and Peptide Profile of Jinhua Ham Broth Peptides at Different Cooking Times

Ziyi Yang,Jiaming Cai,Evans Frimpong Boateng,Lujuan Xing,Wangang Zhang

This present study aimed to investigate the effects of various cooking times (1 h, 1.5 h, 2 h, 2.5 h, named as JHBP-1, JHBP-1.5, JHBP-2, JHBP-2.5) on the antioxidant activity and peptide profile of Jinhua ham broth peptides (JHBP). The peptides extracted from uncooked ham were used as an uncooked group with the name of JHBP-0. The results revealed that the antioxidant efficacy in the four cooked groups changed dramatically compared to JHBP-0. After cooking, the DPPH radical scavenging activity, hydroxyl radical scavenging activity and superoxide anion radical scavenging activity decreased, except for the Fe2+chelation and ABTS+scavenging capacity which increased significantly. However, the cooked groups still showed a strong antioxidant capacity. In particular, the superoxide anion radical scavenging ability and the Fe2+chelation action were significantly stronger compared to glutathione (GSH) and butylated hydroxytoluene (BHT) (p< 0.05). JHBP-1.5 also displayed stronger antioxidant capacity than the other three cooked groups, and its secondary structure and mass distribution changed significantly after cooking, specifically with an increased proportion of helix and <1 kDa peptides. Moreover, the constitution of free amino acids (FAAs) and the types of peptides released in the broth increased significantly with a longer cooking time. In total, 1306 (JHBP-0), 1352 (JHBP-1), 1431 (JHBP-1.5), 1500 (JHBP-2), and 1556 (JHBP-2.5) peptide sequences were detected using LC-MC/MC. The proportion of <1 kDa peptides also gradually increased as the cooking time extended, which is consistent with the molecular weight distribution measurements.Keywords:Jinhua ham;broth;bioactive peptides;antioxidant activity;peptide profile

研究领域: 食品科学 · 生物化学 · 营养学
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