Phenolamides: Plant specialized metabolites with a wide range of promising pharmacological and health-promoting interests

Roumani, Marwa; Duval, Raphaël E.; Ropars, Armelle; Risler, Arnaud; Robin, Christophe; Larbat, Romain

doi:10.1016/j.biopha.2020.110762

Cited by 48 publications

(26 citation statements)

References 169 publications

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“…Different protocols were tested for synthesis of feruloyltyramine (FerTrm) and feruloyltryptamine (FerTry). Tyramine and tryptamine were used as these two compounds are among the most studied amine subunits in natural phenol amides and represent two common types of amine subunits, the phenol and indole type, respectively [ 5 ]. For validation of the final protocol, the protocol was tested for ferulic acid in combination with six of the most common amines, which included representatives from each of the four different types of amines.…”

Section: Resultsmentioning

confidence: 99%

“… Overview of hydroxycinnamic acid and amine subunits present in naturally occurring phenol amides [ 4 , 5 ]. a Ahe, 2-amino-1-(4-hydroxyphenyl)ethanone; Ama, α-(aminomethyl)-4-methoxybenzyl alcohol b The n in Antn is replaced by the number of the corresponding acid.…”

Section: Figurementioning

confidence: 99%

“…Despite the fact that their bioactivity has been well established, it has recently been emphasized in three different reviews that further investigation of their possible beneficial effects on human health is needed [ 1 , 3 , 5 ].…”

Section: Introductionmentioning

confidence: 99%

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Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

2022

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Phenol amides are bioactive compounds naturally present in many plants. This class of compounds is known for antioxidant, anti-inflammatory, and anticancer activities. To better understand the reactivity and structure–bioactivity relationships of phenol amides, a large set of structurally diverse pure compounds are needed, however purification from plants is inefficient and laborious. Existing syntheses require multiple steps, including protection of functional groups and are generally overly complicated and only suitable for specific combinations of hydroxycinnamic acid and amine. Thus, to facilitate further studies on these promising compounds, we aimed to develop a facile general synthetic route to obtain phenol amides with a wide structural diversity. The result is a protocol for straightforward one-pot synthesis of phenol amides at room temperature within 25 h using equimolar amounts of N,N′-dicyclohexylcarbodiimide (DCC), amine, hydroxycinnamic acid, and sodium bicarbonate in aqueous acetone. Eight structurally diverse phenol amides were synthesized and fully chemically characterized. The facile synthetic route described in this work is suitable for a wide variety of biologically relevant phenol amides, consisting of different hydroxycinnamic acid subunits (coumaric acid, ferulic acid, and sinapic acid) and amine subunits (agmatine, anthranilic acid, putrescine, serotonin, tyramine, and tryptamine) with yields ranging between 14% and 24%.

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Section: Resultsmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

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Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

2022

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“…Therefore, hydroxycinnamic acid-amides can be considered the α-glucosidase-inhibitory active compounds present in the in vitro digested fried sample. Furthermore, there is strong evidence that hydroxycinnamic acid spermidine derivatives and, more in general, phenol amides exhibit a broad range of bioactivities including antioxidant, anti-microbial, and anti-cancer activities as well as protective effects against cardiovascular and metabolic syndrome-related diseases [ 45 ].…”

Section: Resultsmentioning

confidence: 99%

Cooking and In Vitro Digestion Modulate the Anti-Diabetic Properties of Red-Skinned Onion and Dark Purple Eggplant Phenolic Compounds

Cattivelli¹,

Conte²,

Martini³

et al. 2022

Foods

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The intake of phenolic-rich foods is an emerging preventive approach for the management of type 2 diabetes, thanks to the ability of these compounds to inhibit some key metabolic enzymes. In this study, the influence of cooking and in vitro digestion on the α-glucosidase, α-amylase, and dipeptidyl-peptidase IV (DPP-IV) inhibitory activity of red-skinned onion (RSO) and dark purple eggplant (DPE) phenolic fractions was assessed. The applied cooking procedures had different influences on the total and individual phenolic compounds gastrointestinal bioaccessibility. DPE in vitro digested phenolic fractions displayed no inhibitory activity versus α-amylase and DPP-IV, whereas the fried DPE sample exhibited moderate inhibitory activity against α-glucosidase. This sample mainly contained hydroxycinnamic acid amides that can be responsible for the observed effect. Contrariwise, raw and cooked in vitro digested RSO phenolic fractions inhibited all three enzymes but with different effectiveness. Fried and raw RSO samples were the most active against them. Statistical analysis pointed out that quercetin mono-hexosides (mainly quercetin-4′-O-hexoside) were responsible for the inhibition of α-glucosidase, whereas quercetin di-hexosides (mainly quercetin-3-O-hexoside-4′-O-hexoside) were responsible for the DPP-IV-inhibitory activity of RSO samples. An accurate design of the cooking methods could be essential to maximize the release of individual phenolic compounds and the related bioactivities.

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“…Anyway, the role of phenolamides in extracts with antibacterial activity is still unclear. Phenolamides are shown to also have anti-inflammatory activity in different cell cultures models, in molecular docking and in a murine itch model [ 57 ]. Several avenanthramides exhibited an inhibitory effect on TNF-α-induced NF-κB activation and NF-κB-mediated inflammatory response due to the downregulation of IKKβ activity in C2C12 skeletal muscle cell line [ 58 , 59 ].…”

Section: Medicinal Plants and Their Constituents With Antibacterial Activity Intended In The Treatment Of Skin Disorders According To Eurmentioning

confidence: 99%

Antibacterial Activity of Medicinal Plants and Their Constituents in the Context of Skin and Wound Infections, Considering European Legislation and Folk Medicine—A Review

Fialová

Rendeková

Mučaji

et al. 2021

IJMS

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Bacterial infections of skin and wounds may seriously decrease the quality of life and even cause death in some patients. One of the largest concerns in their treatment is the growing antimicrobial resistance of bacterial infectious agents and the spread of resistant strains not only in the hospitals but also in the community. This trend encourages researchers to seek for new effective and safe therapeutical agents. The pharmaceutical industry, focusing mainly on libraries of synthetic compounds as a drug discovery source, is often failing in the battle with bacteria. In contrast, many of the natural compounds, and/or the whole and complex plants extracts, are effective in this field, inactivating the resistant bacterial strains or decreasing their virulence. Natural products act comprehensively; many of them have not only antibacterial, but also anti-inflammatory effects and may support tissue regeneration and wound healing. The European legislative is in the field of natural products medicinal use formed by European Medicines Agency (EMA), based on the scientific work of its Committee on Herbal Medicinal Products (HMPC). HMPC establishes EU monographs covering the therapeutic uses and safe conditions for herbal substances and preparations, mostly based on folk medicine, but including data from scientific research. In this review, the medicinal plants and their active constituents recommended by EMA for skin disorders are discussed in terms of their antibacterial effect. The source of information about these plant products in the review is represented by research articles listed in scientific databases (Science Direct, PubMed, Scopus, Web of Science, etc.) published in recent years.

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Phenolamides: Plant specialized metabolites with a wide range of promising pharmacological and health-promoting interests

Cited by 48 publications

References 169 publications

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

Cooking and In Vitro Digestion Modulate the Anti-Diabetic Properties of Red-Skinned Onion and Dark Purple Eggplant Phenolic Compounds

Antibacterial Activity of Medicinal Plants and Their Constituents in the Context of Skin and Wound Infections, Considering European Legislation and Folk Medicine—A Review

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