Effect of caffeic acid esters on antioxidant activity and oxidative stability of sunflower oil: Molecular simulation and experiments

Lu, Ling; Luo, Kaiqiang; Luan, Yajie; Zhao, Mi; Wang, Runguo; Zhao, Xiuying; Wu, Sizhu

doi:10.1016/j.foodres.2022.111760

Cited by 12 publications

(12 citation statements)

References 59 publications

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“…10,28,30,41 Thus, the first hydrogen dissociation energy (ΔG 1 ), second hydrogen dissociation energy (ΔG 2 ), and third hydrogen dissociation energy (ΔG 3 ) of O−H could be comprehensively used as a quantitative evaluation factor for AA. 13 The solubility parameter (δ) is another crucial factor in determining the compatibility between antioxidants and different matrices. 42 Incompatibility causes the agglomeration or migration of antioxidants, which usually hinders antiaging performance.…”

Section: Data Set Construction Of MLmentioning

confidence: 99%

“…In short, ΔG 1 , ΔG 2 , ΔG 3 , and δ could be quantitatively calculated as the important parameters to evaluate the comprehensive AA. 13 Therefore, the output data set for ML consisted of these four descriptors (ΔG 1 , ΔG 2 , ΔG 3 , and δ as outputs). The detailed simulation construction process was described in the following section.…”

Section: Data Set Construction Of MLmentioning

confidence: 99%

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Flavonoid as a Potent Antioxidant: Quantitative Structure–Activity Relationship Analysis, Mechanism Study, and Molecular Design by Synergizing Molecular Simulation and Machine Learning

Lu,

Luan,

Wang

et al. 2024

J. Phys. Chem. A

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In this work, a quantitative structure−antioxidant activity relationship of flavonoids was performed using a machine learning (ML) method. To achieve lipid-soluble, highly antioxidant flavonoids, 398 molecular structures with various substitute groups were designed based on the flavonoid skeleton. The hydrogen dissociation energies (ΔG 1 , ΔG 2 , and ΔG 3 ) related to multiple hydrogen atom transfer processes and the solubility parameter (δ) of flavonoids were calculated using molecular simulation. The group decomposition results and the calculated antioxidant parameters constituted the ML data set. The artificial neural network and random forest models were constructed to predict and analyze the contribution of the substitute groups and positions to the antioxidant activity. The results showed the hydroxyl group at positions B4′, B5′, and B6′ and the branched alkyl group at position C3 in the flavonoid skeleton were the optimal choice for improving antioxidant activity and compatibility with apolar organic materials. Compared to the pyrogallol group-grafted flavonoid, the designed potent flavonoid decreased ΔG 1 and δ by 2.2 and 15.1%, respectively, while ΔG 2 and ΔG 3 kept the favorable lower values. These findings suggest that an efficient flavonoid prefers multiple ortho-phenolic hydroxyl groups and suitable sites with hydrophobic groups. The combination of molecular simulation and the ML method may offer a new research approach for the molecular design of novel antioxidants.

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Section: Data Set Construction Of MLmentioning

confidence: 99%

Section: Data Set Construction Of MLmentioning

confidence: 99%

Flavonoid as a Potent Antioxidant: Quantitative Structure–Activity Relationship Analysis, Mechanism Study, and Molecular Design by Synergizing Molecular Simulation and Machine Learning

Lu,

Luan,

Wang

et al. 2024

J. Phys. Chem. A

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“…From a fundamental perspective, it is well established that various mechanisms associated with the antioxidant potential of polyphenols (such as hydrogen atom transfer (HAT), single electron transfer (SET), and other less common paths) can be explored through the use of electronic structure computations 6,7 and, thus, numerous computationally-based investigations on probing antioxidant-related mechanisms can be found in the recent literature. [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] Perhaps the main mechanism regarding antioxidant activity in polyphenols, the HAT mechanism, [23][24][25][26][27] can be written as ArOH + R -ArO + RH, (1) where an O-H bond is homolyticaly cleaved and an H atom is transferred from the polyphenol (ArOH) to the free radical (R ) to offset it (RH). Hence, bond dissociation enthalpies (BDEs) can be used to estimate the energy necessary for the O-H bonds to be broken.…”

Section: Introductionmentioning

confidence: 99%

A density functional theory benchmark on antioxidant-related properties of polyphenols

Mendes,

da Mata,

Brown

et al. 2024

Phys. Chem. Chem. Phys.

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“…), ⊎-carotene, squalene and phytosterols, retard lipid oxidation and thus improve the oxidative stability of vegetable oils. 4,5 For example, Tabee et al 6 found that the addition of ⊍-tocopherol (<1 g kg −1 ) in purified palm oil, sunflower oil, flaxseed oil and camellia seed oil significantly prolonged the oxidation stability index (OSI). According to Huang et al, 7 0.08% sesamol can significantly reduce the production of peroxides and had the longest OSI in high-oleic peanut oil.…”

Section: Introductionmentioning

confidence: 99%

“…Natural antioxidants derived from vegetable oils, including polyphenols (tocopherols, sesamol, canolol, ferulic acid, caffeic acid, etc. ), β ‐carotene, squalene and phytosterols, retard lipid oxidation and thus improve the oxidative stability of vegetable oils 4,5 . For example, Tabee et al 6 .…”

Section: Introductionmentioning

confidence: 99%

Natural antioxidants enhance the oxidation stability of blended oils enriched in unsaturated fatty acids

Wang,

Liu,

Peng

et al. 2023

J Sci Food Agric

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BACKGROUNDRancidity causes unpleasant tastes and smells, and the degradation of fatty acids and natural antioxidants, so that an oil is unfit to be consumed. Natural antioxidants, including tocopherols, polyphenols (sesamol, canolol, ferulic acid, caffeic acid, etc.), β‐carotene, squalene and phytosterols, contribute to delay the oxidation of vegetable oils. However, studies on the combination of natural antioxidants to lengthen the shelf life of unsaturated fatty acid‐rich blended oil have not been reported.RESULTSAll of the composite antioxidants had the potential to significantly improve the oxidation stability of blended oil. Blended oil G with 0.05 g kg−1 β‐carotene, 0.25 g kg−1 sesamol and 0.25 g kg−1 caffeic acid showed the best anti‐autooxidation. It is also effective in improving the oxidative stability of vegetable oils containing various fatty acids. The oxidation stability index of the blended oil containing the optimum composition of natural antioxidants was 2.17‐fold longer than that of the control sample. After the end of accelerated oxidation, the oil's peroxide value, p‐anisidine value and total oxidation value were 6.59 times, 12.26 times and 6.65 times lower than those of the control sample, respectively.CONCLUSION(1) The combination of natural antioxidants β‐carotene (0.05 g kg−1), sesamol (0.25 g kg−1) and caffeic acid (0.25 g kg−1) enhances the oxidative stability of unsaturated fatty acid‐rich blended oils. (2) β‐Carotene is the main antioxidant in the early stages of oxidation. (3) Sesamol and caffeic acid are the main antioxidants in the middle and late stages of oxidation. © 2023 Society of Chemical Industry.

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Effect of caffeic acid esters on antioxidant activity and oxidative stability of sunflower oil: Molecular simulation and experiments

Cited by 12 publications

References 59 publications

Flavonoid as a Potent Antioxidant: Quantitative Structure–Activity Relationship Analysis, Mechanism Study, and Molecular Design by Synergizing Molecular Simulation and Machine Learning

Flavonoid as a Potent Antioxidant: Quantitative Structure–Activity Relationship Analysis, Mechanism Study, and Molecular Design by Synergizing Molecular Simulation and Machine Learning

A density functional theory benchmark on antioxidant-related properties of polyphenols

Natural antioxidants enhance the oxidation stability of blended oils enriched in unsaturated fatty acids

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