Establishment of a Quantitative Structure-Activity Relationship Model for Evaluating and Predicting the Protective Potentials of Phenolic Antioxidants on Lipid Peroxidation

Cheng, Zhiyong; Ren, Jie; Li, Yuanzong; Chang, Wen‐Bao

doi:10.1002/jps.10301

Cited by 61 publications

(47 citation statements)

References 57 publications

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“…Therefore, it is more likely that all these isoflavones inhibited lipid oxidation in the lipid phase and presumably acted as chain terminating antioxidants by scavenging propagating radicals. The ability to partition into the lipid phase contributes to a significant degree in an antioxidant ability to inhibit lipid oxidation [59]. Our results indicated that G7G and D7G still retain significant radical scavenging and reducing ability for such antioxidant action as indicated by their significant TEAC and FRAP values, as these metabolites contain unmodified B-ring phenolic hydroxyl group.…”

Section: Effect Of Genistein-and Daidzein-7-o-b-dglucuronide On the Lmentioning

confidence: 83%

Genistein‐ and daidzein 7‐O‐β‐D‐glucuronic acid retain the ability to inhibit copper‐mediated lipid oxidation of low density lipoprotein

Kgomotso

Chiu

Ng³

2008

Molecular Nutrition Food Res

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Two isoflavones in vivo metabolites, genistein-7-O-beta-D-glucuronic acid (G7G) and daidzein-7-O-beta-D-glucuronic acid (D7G) were synthesised chemically. The ability of these metabolites to scavenge an organic radical was measured by the trolox equivalent antioxidant capacity (TEAC) assay, while their reducing ability was measured by the ferric reducing antioxidant power (FRAP) assay. The TEAC and FRAP values of G7G were 45 and 51% of that of genistein, while those of D7G were 52 and 77% of that of daidzein, respectively. A direct assessment of G7G and D7G antioxidant activity by their ability to delay copper(II)-mediated lipid oxidation of human LDL showed that these metabolites retained the ability to prevent oxidation in the lipid phase, but activity was diminished compared to their corresponding aglycones. However, G7G and D7G also decreased the rate of lipid oxidation to 53 and 86% of control without isoflavones, respectively, indicating a continuous exchange of antioxidants between the aqueous environment and the LDL lipid phase during the whole oxidation period.

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Section: Effect Of Genistein-and Daidzein-7-o-b-dglucuronide On the Lmentioning

confidence: 83%

Genistein‐ and daidzein 7‐O‐β‐D‐glucuronic acid retain the ability to inhibit copper‐mediated lipid oxidation of low density lipoprotein

Kgomotso

Chiu

Ng³

2008

Molecular Nutrition Food Res

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“…Lipid peroxidation of linoleic acid is thought to progress via radical-mediated withdrawal of hydrogen from methylene carbons (Ramarathnam et al 1988) which was effectively prevented by peptides molecules in OPHpap-3. Cheng et al (2003) reported that in a similar model system, phenolic compounds could perform antioxidative activity Percentage inhibition of hydroxyl radical Amount of oyster peptide hydrolysate per ml OPH 1, 2, 3: Ultrafiltration fractions obtained from papain-digested oyster protein hydrolysate using molecular weight cut off membranes namely 10, 3 and 1 respectively Fig. 1 Hydroxyl free radical scavenging activity of the UF fractions OPHpap-3 41 ± 0.24 a 0.4 ± 0.00 a 391 ± 18.8 a OPHpap 1, 2, 3: Ultrafiltration fractions obtained for papain-digested oyster protein hydrolysate using molecular weight cut off membranes namely 10, 3 and 1 respectively.…”

Section: Ultrafiltration (Uf) and Antioxidant Activity Of The Uf Fracmentioning

confidence: 97%

Sequence Determination of an Antioxidant Peptide Obtained by Enzymatic Hydrolysis of Oyster Crassostrea madrasensis (Preston)

Asha

Kumari

Kumar

et al. 2016

Int J Pept Res Ther

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Soft tissue from cultured farm fresh oysters (Crassostrea madrasensis) was subjected to two standard enzymatic peptide extraction procedures using pepsin and papain. The crude extracts obtained were partially purified by column chromatography and were freeze-dried. The hydrolysates obtained were compared with respect to their degree of hydrolysis (DH), antioxidant potential (AP) and total phenolic content (TPC). The hydrolysate showing better antioxidant property was further subjected to purification by high performance liquid chromatography and characterized by LC-MS/MS. Papain-digested oyster protein (OPHpap) hydrolysate showed higher DH, AP and TPC. OPHpap was further subjected to ultrafiltration and fractionated into 3 sizes namely, above 10, 3-10 and 1-3 kDa according to the molecular size. Antioxidant capacity of\3 kDa fraction OPHpap-3 evaluated by DPPH free radical scavenging assay, metal chelating activity, linoleic acid autoxidation assay showed maximum effectiveness. Of the seven fractions collected by purification of OPH-pap-3 on semi-preparative RP-HPLC, fraction 7 that showed the highest antioxidant activity was further characterized by LC-ESI-MS/MS and its sequence determined. An antioxidant peptide molecule with thirteen amino acids was identified in oyster protein hydrolysate obtained by papain digestion that may find application as a nutraceutical or may be utilized in food industry for prevention of rancidity in foods.

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“…6, the control (without antioxidant) had-as expected-the highest absorbance value in the Osawa and Namiki (1985) test, indicating the highest degree of oxidation among the samples after a 7-day incubation, whereas the peptide from croaker skin protein hydrolysate had the lowest absorbance followed by a-tocopherol and by the peptide from horse mackerel skin protein hydrolysate. Cheng et al (2003) reported that phenolic compounds afford their protective actions in lipid peroxidation by scavenging the lipid-derived radicals (R Á , RO Á or ROO Á ) in a heterogeneous lipid phase. According to this model, the presence of hydrophobic properties is very important for a compound to inhibit lipid peroxidation.…”

Section: Identification Of Peptides By Esi-ms/msmentioning

confidence: 99%

Purification and identification of antioxidant peptides from the skin protein hydrolysate of two marine fishes, horse mackerel (Magalaspis cordyla) and croaker (Otolithes ruber)

2011

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In the current study, two peptides with antioxidant properties were purified from skin protein hydrolysates of horse mackerel (Magalaspis cordyla) and croaker (Otolithes ruber) by consecutive chromatographic fractionations including ion exchange chromatography and gel filtration chromatography. By electron spray ionization double mass spectrometry (ESI-MS/MS), the sequence of the peptide from the skin protein hydrolysate of horse mackerel was identified to be Asn-His-Arg-Tyr-Asp-Arg (856 Da) and that of croaker to be Gly-Asn-Arg-Gly-Phe-Ala-Cys-Arg-His-Ala (1101.5 Da). The antioxidant activity of these peptides was tested by electron spin resonance (ESR) spectrometry using 1-diphenyl-2-picryl hydrazyl (DPPH·) and hydroxyl (OH·) radical scavenging assays. Both peptides exhibited higher activity against polyunsaturated fatty acid (PUFA) peroxidation than the natural antioxidant α-tocopherol. These results suggest that the two peptides isolated from the skin protein hydrolysates of horse mackerel and croaker are potent antioxidants and may be effectively used as food additives and as pharmaceutical agents.

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Establishment of a Quantitative Structure-Activity Relationship Model for Evaluating and Predicting the Protective Potentials of Phenolic Antioxidants on Lipid Peroxidation

Cited by 61 publications

References 57 publications

Genistein‐ and daidzein 7‐O‐β‐D‐glucuronic acid retain the ability to inhibit copper‐mediated lipid oxidation of low density lipoprotein

Genistein‐ and daidzein 7‐O‐β‐D‐glucuronic acid retain the ability to inhibit copper‐mediated lipid oxidation of low density lipoprotein

Sequence Determination of an Antioxidant Peptide Obtained by Enzymatic Hydrolysis of Oyster Crassostrea madrasensis (Preston)

Purification and identification of antioxidant peptides from the skin protein hydrolysate of two marine fishes, horse mackerel (Magalaspis cordyla) and croaker (Otolithes ruber)

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