Synthesis of phenolic amides and evaluation of their antioxidant and anti-inflammatory activity in vitro and in vivo

Lee, Ya Ting; Hsieh, You Liang; Yeh, Yen Hung; Huang, Chih Yang

doi:10.1039/c5ra14137k

Cited by 16 publications

(10 citation statements)

References 43 publications

(45 reference statements)

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“…The results are summarized in Table 1. DPPH Free Radical Scavenging Activity Caffeic acid derivatives (1-4, 13-15) containing catechol moiety showed a significant activity, followed by ferulic acid derivatives (5-8, 16, 17) containing o-methoxyphenol moiety. p-Coumaric acid derivatives (9, 10) containing 5-hydroxyindole or catechol moiety, respectively, also showed a significant activity, but the other p-coumaric acid derivatives (11,19,20) except for compound 12 showed almost no activity similar to cinnamic acid derivatives (21,22). From the view of amines or alcohols, serotonin amide derivatives (1, 5, 9) showed significant activities, followed by dopamine amide derivatives (2, 6, 10), 3,4-dihydroxyphenethylalcohol ester derivatives ( 22) also reported that MAO-B inhibitory activities of the ester derivatives, (E)-3-…”

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confidence: 99%

“…1), and the structureactivity relationships (SARs) of the cinnamic acid derivatives with respect to antioxidant capacity and MAO and ChE inhibitory activities were investigated. feic acid, ferulic acid and p-coumaric acid were reacted with biogenic amines (i.e., serotonin, dopamine, tyramine, vanillylamine) to get amide compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), and with alcohols (i.e., 3,4-dihydroxyphenethylalcohol, 4-hydroxyphenethylalcohol, phenethylalcohol) to get ester compounds (13, 14, 16-22) (Chart 1). Their yields were satisfactory.…”

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confidence: 99%

“…Because of their potential neuroprotective effects, MAO-B inhibitors may be useful for the treatment of Alzheimer's disease. [6][7][8] Several natural and synthetic cinnamic acid amides and their esters were found to possess various biological properties such as antioxidant, 9,10) anti-inflammatory, 11) anti-tumor, 12) cytoprotective, 13,14) protection of β-amyloid protein aggregation, 15) tyrosinase inhibitory, 16,17) α-glucosidase inhibitory, 18,19) cholinesterase inhibitory, 20) and MAO inhibitory [21][22][23] activities. However, no systematically evaluated data are available on the antioxidant and MAO and ChE inhibitory activities of cinnamic acid derivatives.…”

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confidence: 99%

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Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities

Takao

Toda

Saito

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of cinnamic acid derivatives, amides (1-12) and esters (13-22), were synthesized, and structureactivity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1-10, 12-18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxyindole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9-11, 15, 17-22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer's disease.Key words cinnamic acid amide; cinnamic acid ester; monoamine oxidase; cholinesterase; antioxidant; Alzheimer's disease Plant secondary metabolites are important sources of bioactive constituents that promote health. Natural products have long played a significant role in the development of new therapeutic leads. For example, phenolic compounds have been shown to prevent oxidative stress, a condition known to cause cell injury and death and to exacerbate the development of several age-related chronic pathologies like cancer, and neurodegenerative diseases such as Alzheimer's and Parkinson's diseases.

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities

Takao

Toda

Saito

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In the same way, several studies have reported amides as naturally occurring anti-inflammatory compounds [ 226 , 227 , 228 ]. Nonetheless, anti-inflammatory amides exhibiting antioxidant activity have also been reported [ 229 , 230 ], which supports the chance to find compounds having dual antioxidant and anti-inflammatory activities. This fact, in addition to the diversified gene arrays involved in the synthesis of specialized metabolites in Streptomyces [ 220 , 221 ], makes these microbes a suitable source to find new and efficient photoprotective molecules.…”

Section: Discussionmentioning

confidence: 89%

Streptomyces-Derived Metabolites with Potential Photoprotective Properties—A Systematic Literature Review and Meta-Analysis on the Reported Chemodiversity

et al. 2020

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Sun overexposure is associated with the development of diseases that primarily affect the skin, which can lead to skin cancer. Among the main measures of photoprotection is the use of sunscreens. However, there is currently concern about the reported harmful effects to both humans and the environment due to several of the sunscreen ingredients available on the market. For this reason, the search for and development of new agents with photoprotective properties is required. In searching for these metabolites, researchers have turned their attention to microbial sources, especially the microbiota in unusual hostile environments. Among the diverse microorganisms available in nature, Actinobacteria and specifically Streptomyces, have been shown to be a source of metabolites with various biological activities of interest, such as antimicrobial, antitumor and immunomodulator activities. Herein, we present the results of a systematic review of the literature in which Streptomyces isolates were studied as a source of compounds with photoprotective properties. A meta-analysis of the structure-property and structure-activity relationships of those metabolites identified in the qualitative analysis phase was also carried out. These findings indicate that Streptomyces are a source of metabolites with potential applications in the development of new, safe and more eco-friendly sunscreens.

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“…A number of amides were prepared from ferulic acid and other phenolic acids ( Scheme 30 ), with the aim to evaluate their antioxidant activity [ 314 ]. The results of four different in vitro tests indicated a very high antioxidant activity, especially when –OH or –OMe groups were present in the amide.…”

Section: Phenolic Acidsmentioning

confidence: 99%

Tailored Functionalization of Natural Phenols to Improve Biological Activity

et al. 2021

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Phenols are widespread in nature, being the major components of several plants and essential oils. Natural phenols’ anti-microbial, anti-bacterial, anti-oxidant, pharmacological and nutritional properties are, nowadays, well established. Hence, given their peculiar biological role, numerous studies are currently ongoing to overcome their limitations, as well as to enhance their activity. In this review, the functionalization of selected natural phenols is critically examined, mainly highlighting their improved bioactivity after the proper chemical transformations. In particular, functionalization of the most abundant naturally occurring monophenols, diphenols, lipidic phenols, phenolic acids, polyphenols and curcumin derivatives is explored.

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Synthesis of phenolic amides and evaluation of their antioxidant and anti-inflammatory activity in vitro and in vivo

Abstract: 15 phenolic amides (PAs) have been synthesized and examinedin vitrousing four tests: (1) prevention of Cu2+-induced human low-density lipoprotein oxidation, (2) scavenging of stable radicals, (3) anti-inflammatory activity, and (4) scavenging of superoxide radicals.

Cited by 16 publications

References 43 publications

Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities

Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities

Streptomyces-Derived Metabolites with Potential Photoprotective Properties—A Systematic Literature Review and Meta-Analysis on the Reported Chemodiversity

Tailored Functionalization of Natural Phenols to Improve Biological Activity

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