N-Hydroxycinnamoyl amides of fluorinated amino acids: Synthesis, anti-tyrosinase and DPPH scavenging activities

Chochkova, Maya; Stoykova, Boyka; Ivanova, Galya; Ranz, Andreas; Guo, Xiaomei; Lankmayr, Ernst; Milkova, Tsenka

doi:10.1016/j.jfluchem.2013.09.013

Cited by 13 publications

(6 citation statements)

References 41 publications

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“…Clearly, the RSA(1) values are slightly lower for t-FEF77. This result is consistent with previous studies, where it has been shown that FA was more effective than the urethane amide derivative [9] or a tyrosine-amide derivative [18] in scavenging DPPH radicals. Since the lower antioxidant efficiency of monophenol rings has been well established in literature [19,20], we decided to carry out the experiments for a longer time, in order to evaluate the contribution of the additional monophenolic groups present in FEF77.…”

Section: Antioxidant Activity Of Fa T-fef77 and C-fef77 241 Dpphsupporting

confidence: 93%

Synthesis, Photoisomerization, Antioxidant Activity, and Lipid-Lowering Effect of Ferulic Acid and Feruloyl Amides

et al. 2020

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The Ugi four-component reaction employing naturally occurred ferulic acid (FA) is proposed as a convenient method to synthesize feruloyl tertiary amides. Applying this strategy, a peptoid-like derivative of ferulic acid (FEF77) containing 2 additional hydroxy-substituted aryl groups, has been synthesized. The influence of the configuration of the double bond of ferulic acid and feruloyl amide on the antioxidant activity has been investigated thanks to light-mediated isomerization studies. At the cellular level, both FA, trans and cis isomers of FEF77 were able to protect human endothelial cord vein (HECV) cells from the oxidative damage induced by exposure to hydrogen peroxide, as measured by cell viability and ROS production assays. Moreover, in steatotic FaO rat hepatoma cells, an in vitro model resembling non-alcoholic fatty liver disease (NAFLD), the molecules exhibited a lipid-lowering effect, which, along with the antioxidant properties, points to consider feruloyl amides for further investigations in a therapeutic perspective.

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Section: Antioxidant Activity Of Fa T-fef77 and C-fef77 241 Dpphsupporting

confidence: 93%

Synthesis, Photoisomerization, Antioxidant Activity, and Lipid-Lowering Effect of Ferulic Acid and Feruloyl Amides

et al. 2020

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“…The DPPH assay is based on measuring the scavenging ability of antioxidants towards the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) [7]. The free radical DPPH is reduced to the corresponding hydrazine when it reacts with hydrogen donors [8].…”

Section: Resultsmentioning

confidence: 99%

Chemical Composition and Biological Activities of Gerbera anandria

Wang

Gao

et al. 2014

Molecules

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Gerbera anandria (Compositae) was extracted with 75% ethanol and the residue was fractionated using light petroleum, chloroform and ethyl acetate. The constituents of the extracts were separated by column chromatography employing solvents of different polarity. Column chromatography of the light petroleum fraction resulted in the isolation of methyl hexadecanoate, while the chloroform fraction afforded xanthotoxin, 2-hydroxy-6-methylbenzoic acid, 7-hydroxy-1(3H)-isobenzofuranone, a mixture of β-sitosterol and stigmasterol, and 8-methoxysmyrindiol and the ethyl acetate fraction gave gerberinside, apigenin-7-O-β-D-glucopyranoside and quercetin. A new coumarin, 8-methoxysmyrindiol, was found. The chemical structures of the isolated compounds were established by MS and NMR (HSQC, HMBC). Free radical scavenging and cytotoxic activities of crude extracts and 8-methoxysmyrindiol were further investigated. The ethyl acetate phase exerted the strongest DPPH free radical scavenging activity in comparison to the other fractions. The coumarin 8-methoxysmyrindiol demonstrated cytotoxicity against multiple human cancer cell lines, with the highest potency in HepG2 cells.

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“…After that, the effect of the isosteric exchange of hydrogen with fluorine in amino acids against inhibitor capability was investigated by Chockova et al ( 2013) [31] in a series of N-hydroxycinnamoyl amides. The amides that react with derivatives of hydroxycinnamoyl are phenylalanine and tryptophan.…”

Section: Derivatives Of Ferulic Acid and Their Activity As Anti-tyros...mentioning

confidence: 99%

Exploration of Ferulic Acid and Its Derivatives as Potent Anti-Tyrosinase: A Systematic Review

Alifah,

Jatmika,

Hayun

2023

Egypt. J. Chem.

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Tyrosinase is an enzyme that catalyzes melanin biosynthesis. Recently, it has become a popular target for developing cosmetics as a skin lightening or skin whitening agent, an anti-aging agent, an anti-wrinkle agent, and other therapeutics for skin disorders. Based on the previous reports, many compounds have been developed and designed to be tyrosinase inhibitors, including ferulic acid and cinnamic acid derivatives. However, until now, the use of these compounds in commercial cosmetic products has been limited. It may be due to chemical instability, lipophilicity, and poor efficacy. In this review, we assessed research studies to discuss the structure-activity of ferulic acid and its derivatives, which can contribute to their better efficacy as anti-tyrosinases. Either ferulic acid as a single compound or its hybridization with other cinnamic acid derivatives proved beneficial in designing tyrosinase inhibitors as active functional groups. The structure-activity of the phenyl ring's substituent improved inhibitory effects on monophenolase activity, especially the halogen substituent. In addition, the alkyl chain length and other functional groups linked, such as amide and acetyl groups, could alter the inhibitory properties, including hydrophobicity, to produce a more stable complex ligand-receptor.

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N-Hydroxycinnamoyl amides of fluorinated amino acids: Synthesis, anti-tyrosinase and DPPH scavenging activities

Cited by 13 publications

References 41 publications

Synthesis, Photoisomerization, Antioxidant Activity, and Lipid-Lowering Effect of Ferulic Acid and Feruloyl Amides

Synthesis, Photoisomerization, Antioxidant Activity, and Lipid-Lowering Effect of Ferulic Acid and Feruloyl Amides

Chemical Composition and Biological Activities of Gerbera anandria

Exploration of Ferulic Acid and Its Derivatives as Potent Anti-Tyrosinase: A Systematic Review

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