Derivatives of Ferulic Acid: Structure, Preparation and Biological Activities

Pei, Kehan; Ou, Juanying; Huang, Caihuan; Ou, Shiyi

doi:10.9734/arrb/2015/14104

Cited by 27 publications

(10 citation statements)

References 79 publications

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“…Many attempts have been made to develop the chemical and enzymatic methods of lipophilization of phenolic acids with fatty alcohols and acylglycerols [54,55] Currently, special attention is paid to production of conjugates of polyphenols with PLs where active molecule is attached to glycerol backbone of PC [19,20,56,57]. Phospholipid conjugates prepared according to this strategy can form liposomes or can enhance the incorporation of active molecule into PLs-based delivery systems [58].…”

Section: Discussionmentioning

confidence: 99%

Lysophosphatidylcholine Containing Anisic Acid Is Able to Stimulate Insulin Secretion Targeting G Protein Coupled Receptors

et al. 2020

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Diabetes mellitus is a worldwide health problem with high rates of mortality and morbidity. Management of diabetes mellitus by dietary components is achievable especially at the initial stage of the disease. Several studies confirmed the antidiabetic activities of simple phenolic acids and lysophosphatidylcholine (LPC). The main goal of this study was to identify new potential insulin secretion modulators obtained by combining the structures of two natural compounds, namely O-methyl derivatives of phenolic acids and phospholipids. LPC and phosphatidylcholine bearing methoxylated aromatic carboxylic acids were tested as potential agents able to improve glucose-stimulated insulin secretion (GSIS) and intracellular calcium mobilization in MIN6 β pancreatic cell line. Our results show that LPC with covalently bonded molecule of p-anisic acid at the sn-1 position was able to induce GSIS and intracellular calcium flux. Notably, 1-anisoyl-2-hydroxy-sn-glycero-3-phosphocholine did not affect the viability of MIN6 cells, suggesting its potential safe use. Furthermore, we have shown that three G protein coupled receptors, namely GPR40, GPR55, and GPR119, are targeted by this LPC derivative.

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Section: Discussionmentioning

confidence: 99%

Lysophosphatidylcholine Containing Anisic Acid Is Able to Stimulate Insulin Secretion Targeting G Protein Coupled Receptors

et al. 2020

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“…It is assumed that its main function in plants is to strengthen the cell walls and therefore prevent the entry of pathogens into suberizing tissue. The biosynthesis of hydroxycinnamoyl amides has been well studied, but a UGT capable of glucosylating phytoalexins has not been reported to date, although glucosides of the amides have been frequently found (Yahagi et al ., ; Bolleddula et al ., ; Nikolić et al ., , ; Yang et al ., ; Yim et al ., ; Zhang et al ., ; Pei et al ., ; Geng et al ., ; Oliveira de Silva and Batista, ; Wang et al ., ). The biological function of glucosides of hydroxycinnamoyl amides is unclear but they might play a similar role like monolignol glucosides in plant defence (Le Roy et al ., ).…”

Section: Discussionmentioning

confidence: 99%

Glucosylation of the phytoalexin N‐feruloyl tyramine modulates the levels of pathogen‐responsive metabolites in Nicotiana benthamiana

et al. 2019

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Summary Enzyme promiscuity, a common property of many uridine diphosphate sugar‐dependent glycosyltransferases (UGTs) that convert small molecules, significantly hinders the identification of natural substrates and therefore the characterization of the physiological role of enzymes. In this paper we present a simple but effective strategy to identify endogenous substrates of plant UGTs using LC‐MS‐guided targeted glycoside analysis of transgenic plants. We successfully identified natural substrates of two promiscuous Nicotiana benthamiana UGTs (NbUGT73A24 and NbUGT73A25), orthologues of pathogen‐induced tobacco UGT (TOGT) from Nicotiana tabacum, which is involved in the hypersensitive reaction. While in N. tabacum, TOGT glucosylated scopoletin after treatment with salicylate, fungal elicitors and the tobacco mosaic virus, NbUGT73A24 and NbUGT73A25 produced glucosides of phytoalexin N‐feruloyl tyramine, which may strengthen cell walls to prevent the intrusion of pathogens, and flavonols after agroinfiltration of the corresponding genes in N. benthamiana. Enzymatic glucosylation of fractions of a physiological aglycone library confirmed the biological substrates of UGTs. In addition, overexpression of both genes in N. benthamiana produced clear lesions on the leaves and led to a significantly reduced content of pathogen‐induced plant metabolites such as phenylalanine and tryptophan. Our results revealed some additional biological functions of TOGT enzymes and indicated a multifunctional role of UGTs in plant resistance.

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“…It has been reported that HCAAs exert interesting antioxidant, anti-inflammatory, and chemopreventive properties [ 8 , 9 , 13 , 14 , 15 , 16 ]. Similarly, most DFAs have shown higher radical-scavenging efficacies than free FA [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Hydroxycinnamic Acids and Their Derivatives in Broa, a Traditional Ethnic Maize Bread

Bento-Silva

Duarte

Mecha

et al. 2020

Foods

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Maize is one of the most interesting dietary sources of hydroxycinnamic acids, widely known for their beneficial health effects, namely antioxidant properties. This work aims to identify hydroxycinnamic acids and their derivatives in broa, a Portuguese traditional ethnic maize bread, and corresponding maize flours. Soluble and insoluble phenolic fractions of diverse maize flours and corresponding broas were prepared and analysed by HPLC-DAD-MS/MS (high-performance liquid chromatography coupled with diode array detector and tandem mass spectrometry). Besides free hydroxycinnamic acids, mainly ferulic and p-coumaric acids, several structural isomers and stereoisomers of insoluble ferulic acid dehydrodimers (n = 18) and trimers (n = 11), were also identified. Hydroxycinnamic acid amides consisting of coumaroyl and feruloyl conjugates (n = 22) were present in both soluble and insoluble fractions of maize flours and breads, in different isomeric forms. A new compound was putatively identified as bis-N,N′-diferuloyl putrescine. Additionally, more complex and insoluble hydroxycinnamic acid amides, derived from ferulic acid dehydrodimers (n = 47) and trimers (n = 18), were also putatively identified for the first time, suggesting that hydroxycinnamic acid amides are also linked to maize cell walls. Since hydroxycinnamic derivatives were not only identified in maize flours, but also in broas, they can contribute to the antioxidant properties and beneficial health effects of maize-based foods.

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Derivatives of Ferulic Acid: Structure, Preparation and Biological Activities

Cited by 27 publications

References 79 publications

Lysophosphatidylcholine Containing Anisic Acid Is Able to Stimulate Insulin Secretion Targeting G Protein Coupled Receptors

Lysophosphatidylcholine Containing Anisic Acid Is Able to Stimulate Insulin Secretion Targeting G Protein Coupled Receptors

Glucosylation of the phytoalexin N‐feruloyl tyramine modulates the levels of pathogen‐responsive metabolites in Nicotiana benthamiana

Hydroxycinnamic Acids and Their Derivatives in Broa, a Traditional Ethnic Maize Bread

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