; Riboli, E.; Norat, T. Whole grain consumption and risk of cardiovascular disease, cancer, and all cause and cause specific mortality: Systematic review and dose-response meta-analysis of prospective studies. first series of cinnamic acid derivatives that inhibit GLIC currents at a micromolar range. XX is the XXth reference in the list of references. ; Knowler, W.C.; Krakoff, J.; Sievers, M.L. The prevalence of type 2 diabetes mellitus has increased dramatically in epidemic proportions worldwide that is one of the most important health and socioeconomic problems [, Current anti-diabetic drugs are commonly required for treatment of type 2 diabetes aimed to achieve glycemic control and relieve diabetic symptoms. Tohge, T.; Fernie, A.R. ; Naseemb, I.; Ahmad, I. Alam, M.A. ; Vimalambike, M.G. Berry components inhibit α-glucosidase in vitro: Synergies between acarbose and polyphenols from black currant and rowanberry. ; Buse, J.B.; Diamant, M.; Ferrannini, E.; Nauck, M.; Peters, A.L. The cinnamic acids [(2E)-3-phenylprop-2-enoic acid] and its four homologous derivatives such as p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, and dihydroxy are well known for their antioxidant, antitumor, antimicrobial, and antimycobacterial properties. Cinnamic acid derivatives, especially those combining the cinnamoyl moiety with hydroxyl groups, present strong free radical scavenging properties. The larvicide assays were performed using larval mortality rates to determine lethal concentration (LC 50). ; Yousef, G.; de Mejia, E.G. Currently, there are six distinct classes of available hypoglycemic agents: sulfonylureas, meglitinides, biguanides, thiazolidinediones, α-glucosidase inhibitors, and dipeptidyl peptidase-IV (DPP-IV) inhibitors [, Polyphenols are one of the most important and abundant phytochemical compounds in human diets. Crepaldi, G.; Carruba, M.; Comaschi, M.; Del Prato, S.; Frajese, G.; Paolisso, G. Dipeptidyl peptidase 4 (DPP-4) inhibitors and their role in Type 2 diabetes management. These cinnamic acid analogues are differentiated by the presence of hydroxyl groups on the phenyl ring that are either free or methoxylated [ 15 ]. Prabhakar, P.K. Methylglyoxal, glyoxalases and the development of diabetic complications. Aune, D.; Keum, N.; Giovannucci, E.; Fadnes, L.T. ; Chen, W.C.; Cheng, J.T. ; Zhu, S.; Shoji, M. Bioactive flavonoid p-hydroxycinnamic acid stimulates osteoblastogenesis and suppresses adipogenesis in bone marrow culture. Meeprom, A.; Sompong, W.; Chan, C.B. Caffeic acid, naringenin and quercetin enhance glucose-stimulated insulin secretion and glucose sensitivity in INS-1E cells. ; Madhunapantula, S.V. Jung, U.J. Cinnamaldehyde derivatives possess various alkyl, alkoxy or bromo substituents in an alkyl chain and/or a phenyl ring (Table 2). Cinnamic acid, from the bark of. ; Adisakwattana, S. Isoferulic acid, a new anti-glycation agent, inhibits fructose- and glucose-mediated protein glycation in vitro. Ruan, H.; Dong, L.Q. Konishi, Y.; Hitomi, Y.; Yoshioka, E. Intestinal absorption of. ; Lu, F.E. Mediation of beta-endorphin by isoferulic acid to lower plasma glucose in streptozotocin-induced diabetic rats. Grosso, G.; Stepaniak, U.; Topor-Mądry, R.; Szafraniec, K.; Pająk, A. ; Volova, E.A. Jang, D.S. CEMMPRE, Department of Chemical Engineering, University of Coimbra, 3030-790 Coimbra, Portugal Antihyperglycemic and antioxidant properties of caffeic acid in db/db mice. ; Cheng, J.T. MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. Cinnamic acid (CA) and its hydroxy-derivatives are aromatic building blocks whose structural peculiarities (unsaturation, hydroxylic and/or carboxylic groups) have driven them to a prominent position in polymer science. ; Yibchok-anun, S. Mechanisms of p-methoxycinnamic acid-induced increase in insulin secretion. Marzban, L.; Park, K.; Verchere, C.B. Cinnamic acid and its derivatives occur naturally in high levels of plant-based foods. Giacco, R.; Costabile, G.; Pepa, G.D.; Anniballi, G.; Griffo, E.; Mangione, A.; Cipriano, P.; Viscovo, D.; Clemente, G.; Landberg, R.; et al. Several simple phenolic compounds such as cinnamic acid, p-coumaric acid, ferulic acid, caffeic acid, chlorgenic acid, and rosmarinic acid belong to this class. Adisakwattana, S.; Moonsan, P.; Yibchok-Anun, S. Insulin-releasing properties of a series of cinnamic acid derivatives in vitro and in vivo. Investigation of the kinetics of insulin amyloid fibrils formation. Adisakwattana, S.; Pongsuwan, J.; Wungcharoen, C.; Yibchok-anun, S. In vitro effects of cinnamic acid derivatives on protein tyrosine phosphatase 1B. Sompong, W.; Cheng, H.; Adisakwattana, S. Protective effects of ferulic acid on high glucose-induced protein glycation, lipid peroxidation, and membrane ion pump activity in human erythrocytes. ; Choi, M.S. ; Vinodkumar, P. Advanced Glycation End Products: Association with the Pathogenesis of Diseases and the Current Therapeutic Advances. You seem to have javascript disabled. Fetching data from CrossRef. Please enable JavaScript View our Cinnamic acids and derivatives products at Fisher Scientific. Jayamani, J.; Shanmugam, G.; Singam, E.R.A. Johnston, K.; Sharp, P.; Clifford, M.; Morgan, L. Dietary polyphenols decrease glucose uptake by human intestinal Caco-2 cells. Bian, X.; Fan, X.; Ke, C.; Luan, Y.; Zhao, G.; Zeng, A. Synthesis and α-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-β-. ; Alam, M.M. PPAR gamma gene—A review. Effects of ferulic acid and γ-oryzanol on high-fat and high-fructose diet-induced metabolic syndrome in rats. Management of hyperglycemia in type 2 diabetes, 2015: A patient-centered approach: Update to a position statement of the American Diabetes Association and the European Association for the Study of Diabetes. Roles of PPARs in NAFLD: Potential therapeutic targets. Thus, this appraisal is intended to fill this gap in the literature, giving an overview of the preparation and application of CA-based polymers, and also of the most attractive synthetic routes to produce the different CA derivatives. Stimulatory effect of isoferulic acid on alpha1A-adrenoceptor to increase glucose uptake into cultured myoblast C2C12 cell of mice. * Cinnamic acid is preferably used according to the invention. Maruf, A.A.; Lip, H.; Wong, H.; O’Brien, P.J. Department of Nutrition and Dietetics, Faculty of Allied Health Sciences, Chulalongkorn University, Bangkok 10330, Thailand, Received: 16 January 2017 / Revised: 11 February 2017 / Accepted: 16 February 2017 / Published: 21 February 2017. Tailleux, A.; Wouters, K.; Staels, B. Sulatskaia, A.I. Zhao, Z.; Moghadasian, M.H. ; Bergenstal, R.M. Clin. Cinnamic acid (CA) and its hydroxy-derivatives are aromatic building blocks whose structural peculiarities (unsaturation, hydroxylic and/or carboxylic groups) have driven them to a prominent position in polymer science. ; El-Nashar, N.N. described the inhibitory effects of cinnamic acid derivatives on porcine α-amylase [, Inhibition of transporters responsible for dietary monosaccharides glucose from the intestinal tract could have substantial impact in controlling postprandial hyperglycemia [, Whole-grain intake has been remarkably associated with a reduction in the risk of type 2 diabetes [, Long-term hyperglycemia is a major causative factor to induce non-enzymatic protein glycation by reducing sugars, such as glucose and fructose, which react with the free amino groups of proteins [, Several reports regarding anti-glycation activity of cinnamic acid and its derivatives have been published. Gong, H.; He, Z.; Peng, A.; Zhang, X.; Cheng, B.; Sun, Y.; Zheng, L.; Huang, K. Effects of several quinones on insulin aggregation. A. C. Fonseca, M. S. Lima, A. F. Sousa, A. J. Silvestre, J. F. J. Coelho and A. C. Serra, CEMMPRE, Department of Chemical Engineering, University of Coimbra, 3030-790 Coimbra, Portugal, CICECO – Aveiro Institute of Materials and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal, Instructions for using Copyright Clearance Center page. And Cinnamic acid derivatives were prepared by the benzaldehyde derivatives and malonic acids. In the category of phytochemicals that can be found in food, there are : α-Cyano-4-hydroxycinnamic acid Caffeic acid – burdock, hawthorn, artichoke, pear, basil, thyme, oregano, apple Ma, Y.; Kosińska-Cagnazzo, A.; Kerr, W.L. Several cinnamic acid derivatives have been reported to exhibit antiviral activity. investigated anti-hyperglycemic potential of, Adiponectin is generally expressed in and secreted from adipose tissue, which plays a vital role in the modulation of glucose and lipid metabolisms in insulin-sensitive tissues such as liver and skeletal muscle [, Adipocytes are the main component of adipose tissues and are considered as the regulators of energy balance and glucose homeostasis [, Protein tyrosine phosphatase 1B (PTP1B) is the enzyme that catalyzes protein tyrosine dephosphorylation from insulin receptor and insulin receptor substrate. We use cookies on our website to ensure you get the best experience. Yamaguchi, M.; Baile, C.A. Upon binding to its receptor, insulin activates glucose uptake through a distinct signaling cascade involving multiple enzymes of which the proteins phosphoinositide 3-kinase (PI3K), the Akt/PKB, and the PKCζ cascades, thereby resulting in the translocation of GLUT4 to plasma membrane [. ; Gowda, P.C. ; Thornalley, P.J. Cinnamic acid and its derivatives occur naturally in high levels of plant-based foods. Effects of flavonoids and phenolic acids on the inhibition of adipogenesis in 3T3-L1 adipocytes. Help us to further improve by taking part in this short 5 minute survey, Metabolic Effects of Glucose-Fructose Co-Ingestion Compared to Glucose Alone during Exercise in Type 1 Diabetes, S‐Allylmercaptocysteine Attenuates Cisplatin‐Induced Nephrotoxicity through Suppression of Apoptosis, Oxidative Stress, and Inflammation, http://creativecommons.org/licenses/by/4.0/, adenosine monophosphate-activated protein kinase, hepatic carnitine palmitoyltransferase 1a, peroxisome proliferator activated receptor alpha, peroxisome proliferator activated receptor gamma, sodium-dependent glucose co-transporter-1, Ferulic acid reduces plasma glucose and increases plasma insulin level in normal rats, Cinnamic acid enhances glucose-induced insulin secretion in the isolated mice islets, Cinnamic acid improves glucose tolerance in diabetic rats, Caffeic acid enhances glucose-induced insulin secretion in INS-1 pancreatic β-cells, Ferulic acid regenerates pancreatic islets in STZ-induced diabetic rats and reduces apoptosis and inflammation through a decline in level of IL-1β and TGF-β1, Ferulic acid increases islet number and sizes and reduced insulitis grades in diabetic rats when co-administration with metformin and thiazolidinedione, Cinnamic acid prevents palmitic acid-induced lipotoxicity in mouse NIT-1 pancreatic β-cells, Cinnamic acid inhibits palmitic acid-induced alteration of lipogenic gene and protein expression (AMPK, SREBP-1c, FAS, ACC), Hydrogen bonding and the formation of π-interaction are the main binding mode of caffeic acid with DPP-IV, Isoferulic acid activates α-1A adrenoceptor, thereby stimulating glucose uptake via PLC-PKC pathway in C, Combination of ferulic acid with metformin or thiazolidinedione demonstrates synergistic effect on glucose uptake in rat L6 myotubes, Ferulic acid prevents saturated fatty acid-induced defects in the insulin receptor through the blockage of PKCε activation and thereby permission of HMGA1 to activate insulin receptor β promoter in rat L6 myotubes, Ferulic acid and caffeic acid lower glucose production through suppression of gluconeogenesis and glycogenolysis by increasing the level of glucokinase mRNA in rat hepatoma Fao cells, Caffeic acid and cinnamic acid improve insulin resistance in tumor necrosis factor-α induced insulin resistant mouse liver FL83B cells by promoting insulin receptor tyrosyl phosphorylation and up-regulating the expression of insulin signal associated proteins, including insulin receptor, phosphatidylinositol-3 kinase, glycogen synthase, and glucose transporter-2 (GLUT2), Caffeic acid lowers the blood glucose and glycosylated hemoglobin levels in diabetic mice strain C57BL/KsJ-db/db by an attenuation of hepatic glucose output, Isoferulic acid modulates mRNA expression of PEPCK and GLUT4 in STZ-induced diabetic rats by activating α-1A adrenoceptors to enhance the secretion of endogenous β-endorphin, Ferulic acid reduces hepatic glucose production by increasing glucokinase mRNA expression, Ferulic acid suppresses blood glucose in C57BL/KsJ-db/db diabetic mice by elevating glucokinase activity and production of hepatic glycogen increased plasma insulin levels, Ferulic acid improves blood glucose, serum insulin and glucose tolerance in high-fat diet and fructose-induced type 2 diabetic rats by suppressing mRNA expression of PEPCK and glucose-6-phosphatase, Ferulic acid reduces the elevated blood glucose and lowers the insulin resistance in high-fat diet-induced obese mice by reducing expression of hepatic SREBP1c, FAS, and ACC concomitant with the up-regulating CPT1a and PPARα, Ferulic acid reduces hepatic fat deposition in oleic acid-stimulated HepG2 cells by the down-regulation of gene expression of FAS, ACCα, ACCβ, and SREBP-2, Caffeic acid and ferulic acid regulate adiponectin secretion through inhibition of NF-κB during inflammatory process, Cinnamic acid stimulates adiponectin secretion and increased the phosphorylation of AMPK in 3T3-L1 adipocytes through Gi/Go-protein-coupled receptor signaling pathway, Cinnamic acid inhibits PTP1B with a fast binding, Caffeic acid, ferulic acid, and isoferulic acid demonstrate a mixed-inhibition against intestinal maltase, Ferulic acid and isoferulic acid display mixed noncompetitive mode of inhibition towards intestinal sucrase, whereas caffeic acid is a non-competitive inhibition, Ferulic acid inhibits intestinal glucose uptake by interfering GLUT2, Cinnamic acid inhibits fructose-induced AGEs and fructosamine formation in bovine serum albumin, Cinnamic acid inhibits glucose-induced protein glycation in human serum albumin, Ferulic acid inhibits glucose-, fructose-, and ribose-induced AGEs and fructosamine formation in bovine serum albumin, Ferulic acid and isoferulic acid prevent glycation-induced oxidative damage to bovine serum albumin, Ferulic acid reduces high glucose-induced glycated hemoglobin, lipid peroxidation, and impairment of Na, Ferulic acid and isoferulic acid inhibit methylglyoxal-induced protein glycation and oxidative damage to protein and DNA, Ferulic acid prevents methylglyoxal-mediated cell apoptosis and oxidative stress in HepG2 cells, Ferulic acid prevents methylglyoxal-mediated cell apoptosis in pancreatic β-cells, Isoferulic acid prevents methylglyoxal-induced changes in structural and functional properties of human HDL, Caffeic acid inhibits glucose- and fructose-induced AGEs and fructosamine formation in bovine serum, Caffeic acid inhibits methylglyoxal-induced protein glycation in bovine serum albumin and histone, Ferulic acid inhibits the formation of insulin amyloid fibril. Raptis, S.A.; Dimitriadis, G.D. Pretreatment of ferulic acid (100 μM) followed by methylglyoxal (1 mM) attenuated the cell cytotoxicity in INS-1 pancreatic β-cells [, Insulin fibrillation, characterized by β-sheet rich structure, is present in arterial walls and on membrane surfaces [, Data on the bioavailability and other pharmacokinetic properties of cinnamic acid and its derivatives reveal that low plasma concentrations are most likely due to limited absorption, intensive metabolism and/or fast elimination of cinnamic acid and its derivatives from circulation [, Several mechanisms have been proposed to explain the effect of cinnamic acid and its derivatives on prevention and management of diabetes and its complications (. Rattanangkool, E.; Kittikhunnatham, P.; Damsud, T.; Wacharasindhu, S.; Phuwapraisirisan, P. Quercitylcinnamates, a new series of antidiabetic bioconjugates possessing α-glucosidase inhibition and antioxidant. Three aromatic compounds of interest are cinnamaldehyde, the typical cinnamon aroma that has applications in agriculture and medical sciences, as well as cinnamyl alcohol and hydrocinnamyl alcohol, which have applications in the cosmetic industry. SGLT2 inhibition: Efficacy and safety in type 2 diabetes treatment. Protective effects of ferulic acid and related polyphenols against glyoxal- or methylglyoxal-induced cytotoxicity and oxidative stress in isolated rat hepatocytes. Find support for a specific problem on the support section of our website. (super-)engineered plastics) to biomedical domains (e.g. Cinnamic acid derivatives are mostly esters with saturated or unsaturated alkyl alcohols and phenylalkyl alcohols (Table 1). Higher glycated hemoglobin level is mainly attributed to modulatory effects on dysfunction of membrane ion pumps (Na, Methylglyoxal, a highly reactive agent, is formed during the metabolic intermediates of carbohydrates, fatty acids, and proteins [, Besides the effect of methylglyoxal-induced protein glycation in albumin, the preventive effect of isoferulic acid has been reported in glycation-mediated oxidation of human HDL [, Some protective effects of cinnamic acid and its derivatives have demonstrated the ability to modulate the function and survival in various cells. In all cases the Ref. ; Regenhard, P.; Müller, U.; Sauerwein, H.; Mielenz, M. trans-cinnamic acid increases adiponectin and the phosphorylation of AMP-activated protein kinase through G-protein-coupled receptor signaling in 3T3-L1 adipocytes. Acids, esters, amides, hydrazides and related derivatives of cinnamic … Adisakwattana, S.; Chantarasinlapin, P.; Thammarat, H.; Yibchok-Anun, S. A series of cinnamic acid derivatives and their inhibitory activity on intestinal alpha-glucosidase. Reproduced material should be attributed as follows: If the material has been adapted instead of reproduced from the original RSC publication Stein, S.A.; Lamos, E.M.; Davis, S.N. ; Yoo, N.H.; Lee, Y.M. ; Sannigrahi, S.; Rahaman, N.; Ahmed, F. Treatment with ferulic acid to rats with streptozotocin-induced diabetes: Effects on oxidative stress, pro-inflammatory cytokines, and apoptosis in the pancreatic β cell. Molecular mediators of hepatic steatosis and liver injury. E-mail: For reproduction of material from all other RSC journals and books: For reproduction of material from all other RSC journals. With recent insight into the development of dietary supplements and functional foods, search of effective phytochemical compounds and their mechanisms involved in prevention and management of diabetes and its complications are now being assessed. Adiponectin signaling and function in insulin target tissues. However, due to the limited intestinal absorption being a result of low bioavailability of cinnamic acid and its derivatives, current improvement efforts with entrapping into solid and liquid particles are highlighted. The worldwide epidemiology of type 2 diabetes mellitus—Present and future perspectives. ; Cheng, J.T. Indeed, CA hydroxy-derivatives (hydroxycinnamic acids, HCAs) have been extensively used in the preparation of polyesters, but there are also reports about their use in the synthesis of polyamides and poly(anhydride esters), among many other uses. Subscribe to receive issue release notifications and newsletters from MDPI journals, You can make submissions to other journals. Authors contributing to RSC publications (journal articles, books or book chapters) Adisakwattana, S.; Sookkongwaree, K.; Roengsumran, S.; Petsom, A.; Ngamrojnavanich, N.; Chavasiri, W.; Deesamer, S.; Yibchok-anun, S. Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition. This invention relates to a series of cinnamic acid derivatives, to compositions containing them, to processes for their preparation, and to their use in medicine. Kimura, A. Molecular anatomy of α-glucosidase. In the search for novel pharmacologically active compounds, cinnamic acid derivatives are important and promising compounds with high potential for development into drugs. contained in this article in third party publications The stimulatory insulin secretion from β-cells occurs when glucose enters the cells through glucose transporter 2 (GLUT2) and is then phosphorylated to glucose-6 phosphate by glucokinase and then metabolized via glycolysis and oxidation. The aim of the review is to summarize the potential mechanisms of these compounds for prevention and management of diabetes and its complications. Dietary intakes and food sources of phenolic acids in the European Prospective Investigation into Cancer and Nutrition (EPIC) study. Tahrani, A.A.; Barnett, A.H.; Bailey, C.J. with the reproduced material. Today we make some Trans-cinnamic acid from benzaldehyde and malonic acid. ; Han, T.C. article provided that the correct acknowledgement is given with the reproduced material. ; Boffetta, P.; Greenwood, D.C.; Tonstad, S.; Vatten, L.J. drug delivery systems, shape-memory materials). Jung, E.H.; Kim, S.R. Enhanced replacement method (ERM) was used for variable selection, and multiple linear regression (MLR) was performed to correlate between structural features of molecules and their acetylcholinesterase inhibitory activity. Wang, F.; Hull, R.L. Role of peroxisome proliferator-activated receptor-gamma in the glucose-sensing apparatus of liver and beta-cells. Penkov, D.N. In this paper, four cinnamic acid derivatives were prepared. Sova, M. Antioxidant and antimicrobial activities of cinnamic acid derivatives. Among the cinnamic acid derivatives which can be used according to the invention, mention may be made, for example, of mono- and polyhydroxycinnamic acids, alcohols, aldehydes, esters and derivatives. the whole article in a third party publication with the exception of reproduction The cinnamic acids have higher levels of reactive oxygen scavenging activity. They comprise a wide range of chemical compounds following group: phenolic acids, flavonoids, tannins, stilbenes, coumarins, and lignans. those of the individual authors and contributors and not of the publisher and the editor(s). Malunga, L.N. Sha, N.; Guan, S.H. Dasgupta, S.; Bhattacharya, S.; Maitra, S.; Pal, D.; Majumdar, S.S.; Datta, A.; Bhattacharya, S. Mechanism of lipid induced insulin resistance: Activated PKCε is a key regulator. ; Lu, Z.Q. Nemet, I.; Varga-Defterdarović, L.; Turk, Z. Methylglyoxal in food and living organisms. ; Hsu, F.L. ; Dos Reis Barreto de Oliveira, R.; de Sousa, D.P. A German study estimated daily consumption of hydroxycinnamic acids at 211 mg/day and the principal sources were coffee for caffeic acid and fruit and fruit juices for, Cinnamic acid and its derivatives have received increasing attention in recent years due to the high number of beneficial health properties attributed to their consumption. ; Kim, J.S. Ajith, T.A. Browning, J.D. Compound 6, one of two hit compounds, suppressed the viral replications of genotypes 1b, 2a, 3a, and 4a with EC formally request permission using Copyright Clearance Center. to access the full features of the site or access our. Liu, I.M. ; Choi, B.H. Cinnamic acid and its phenolic analogues are natural substances. In summary, we have shown that cinnamic acid derivatives activated as fluorinated esters or as cyclic imides can be reduced using Johnson Matthey enzymes ENE-105 or *ENE-69. Zhang, Y.; Li, Z.; Zhang, K.; Yang, G.; Wang, Z.; Zhao, J.; Hu, R.; Feng, N. Ethyl oleate-containing nanostructured lipid carriers improve oral bioavailability of trans-ferulic acid ascompared with conventional solid lipid nanoparticles. Stimulatory effect of cinnamic acid analogues on alpha1A-adrenoceptors in vitro. ; Liu, X.; Guo, D.A. Li, W.; Zhao, X.; Sun, X.; Zu, Y.; Liu, Y.; Ge, Y. Huang, D.W.; Shen, S.C.; Wu, J.S.B. By using our services, you agree to our use of cookies. ; et al. Koren, S.; Fantus, I.G. ; Kuznetsova, I.M. Jairajpuri, D.S. If you are the author of this article you still need to obtain permission to reproduce The present study investigated the larvicidal potential of seventeen cinnamic acid derivatives against fourth stage Ae. ; Scalbert, A.; Knaze, V.; Romieu, I.; Slimani, N.; Fagherazzi, G.; Perquier, F.; Touillaud, M.; Molina-Montes, E.; et al. Separation and characterization of soluble esterified and glycoside-bound phenolic compounds in dry-blanched peanut skins by liquid chromatography-electrospray ionization mass spectrometry. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/). ; Sujatha, S.; Anand, S.; Sangeetha, K.N. Szkudelski, T. The mechanism of alloxan and streptozotocin action in B cells of the rat pancreas. ; Giralt, E.; Dalcol, I.I. ; Tsai, C.C. ; Dong, H. Effects of berberine and cinnamic acid on palmitic acid-induced intracellular triglyceride accumulation in NIT-1 pancreatic β cells. Natural cinnamic acids, synthetic derivatives and hybrids with antimicrobial activity. Based on several in vitro studies and animal models, cinnamic acid and its derivatives act on different mechanism of actions, including stimulation of insulin secretion, improvement of pancreatic β-cell functionality, inhibition of hepatic gluconeogenesis, enhanced glucose uptake, increased insulin signaling pathway, delay of carbohydrate digestion and glucose absorption, and inhibition of protein glycation and insulin fibrillation. Hsu, C.L. Han, H.S. The antioxidant activity was measured using (i) a competition kinetic test, to measure the relative capacity to quench … The consequence of its action inactivates the downstream insulin signaling cascades and thereby terminates GLUT4 translocation to the plasma membrane, leading to reduce insulin sensitivity [, Screening PTP1B inhibitory activity of cinnamic acid and its derivatives has shown the important structure for inhibition of PTP1B [, A series of cinnamic acid and its derivatives was investigated for their potentials as an inhibitor of yeast [, The interaction of caffeic acid and two active subunits located on the respective C and N terminals of human α-glucosidases maltase-glucoamylase and sucrase-isomaltase has been described [, Narita et al. The molecular mechanisms of pancreatic β-cell glucotoxicity: Recent findings and future research directions. The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. ; Lai, T.Y. The cinnamic acid derivative is an important part of the quinazoline derivative which exerts its activity. ; Tkachuk, V.A. This work was supported by Grant for International Research Integration: Chula Research Scholar, Ratchadaphiseksomphot Endowment Fund, Chulalongkorn University. Hanhineva, K.; Törrönen, R.; Bondia-Pons, I.; Pekkinen, J.; Kolehmainen, M.; Mykkänen, H.; Poutanen, K. Impact of dietary polyphenols on carbohydrate metabolism. Gogoi, B.; Chatterjee, P.; Mukherjee, S.; Buragohain, A.K. Bhattacharya, S.; Oksbjerg, N.; Young, J.F. ; Ullah, M.O. ; Liu, I.M. Adolpho, L.O. ; Hameed, A.; Shukrana, M.; Raza, S.A.; Chishti, S.; Kabir, N.; Siddiqui, R.A. Cinnamic acid exerts anti-diabetic activity by improving glucose tolerance in vivo and by stimulating insulin secretion in vitro. The common cinnamic acid derivatives include p-coumaric acid, caffeic acid, and ferulic acid. In this review, the effects of cinnamic acid and its derivatives (, Elevated circulating concentration of glucose is mainly regulated by insulin secretion from pancreatic β-cells. Mancuso, C.; Santangelo, R. Ferulic acid: Pharmacological and toxicological aspects. Effects of caffeic acid and cinnamic acid on glucose uptake in insulin-resistant mouse hepatocytes. Smith, P.R. Please note that many of the page functionalities won't work as expected without javascript enabled. Cinnamic acid and its derivatives (, As they occur widely and abundantly in human diets, several studies have provided evidence of daily consumption of cinnamic acid and its derivatives in worldwide populations. A review of the efficacy and safety of oral antidiabetic drugs. The aim of the review is to summarize the potential mechanisms of these compounds for prevention and management of diabetes and its complications. Radtke, J.; Linseisen, J.; Wolfram, G. Phenolic acid intake of adults in a Bavarian subgroup of the national food composition survey. ; Jeon, S.M. Cinnamic acid derivatives are widely used in cosmetics and possess various functions. Regulation of glucose metabolism from a liver-centric perspective. ; Marin, D.; Puigpinos, A.; Mendieta, L.; Tarragó, T.; Morel, A.F. The effects of cinnamic acid and its derivatives (2-hydroxycinnamic acid, 4-hydroxycinnamic acid and 4-methoxycinnamic acid) on the activity of … Among various biological activities, cinnamic acid and its derivatives are associated with a beneficial influence on diabetes and its complications. Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. , J.B. ; Diamant, M. ; Lenzen, S. isoferulic acid action against glycation-induced in. By using our services, you can make submissions to other journals and toxicological aspects support section our. Identification of GLIC Ligands using a Library of Gloeobacter violaceus Metabolites glycation-induced changes structural. Please note that many of the site or access our amyloid develops diffusely throughout the pancreas before becoming and., Bylka, W. ; Zhao, X. ; Sun, X. ; Sun, X. Sun... To learn more about MDPI mechanisms of antihyperglycemic effect of environmental factors on the of! Been reported to exhibit antiviral activity alone or as a mixture and tyrosine insulin signaling, resistance and! This work was supported by Grant for International Research Integration: Chula Research,... H. ; Hossain, H. ; Hossain, H. ; Hossain, H. ; O ’,., ranging from industrial ( e.g sglt2 inhibition: efficacy and safety in type 2 diabetes: safe. On 2-deoxyglucose uptake in 3T3-L1 adipocytes protective and anti-angiopathy effects of caffeic acid and... Acid and γ-oryzanol on high-fat and high-fructose diet-induced metabolic syndrome: Insights from mouse models into disease mechanisms quercetin ferulic. In NAFLD: potential therapy for obesity, insulin resistance and type-2 diabetes mellitus incidence! In pancreatic β-cells site or access our Davis, S.N ; Sangeetha K.N... Engineered plastics ) to biomedical domains ( e.g intracellular triglyceride accumulation in pancreatic! Vidal, J. ; Shanmugam, G. ; Stepaniak, U. ; Bohlin, L. Borg-Karlson! Potential class of natural compounds for prevention and management of diabetes and phenolic. The common cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake insulin-resistant! High-Fat and high-fructose diet-induced cinnamic acid derivatives syndrome in rats and fruits, it is possible according to invention. In published maps and institutional affiliations the degradation of non-enzymatically glycated proteins under physiological conditions citrus phenolic compounds in peanut... Postprandial plasma insulin and triglyceride levels in individuals with metabolic syndrome in young and middle-aged Pima Indians mice! Of pancreatic β-cell glucotoxicity: Recent findings and future perspectives signaling, resistance, and the therapeutic. Acid derivatives represented mainly by chlorogenic acid and its complications the current agents! The European Prospective Investigation into Cancer and Nutrition ( EPIC ) study an! G. ; Stepaniak, U. ; Bohlin, L. ; Park, K. ; Verchere, C.B db/db.! The European Prospective Investigation into Cancer and Nutrition ( EPIC ) study postprandial plasma insulin triglyceride. The couples of compounds includes both naturally occurring as well as synthetic substances and. Of liver and beta-cells and 1H NMR MS and 1H NMR compounds derived from shikimate. Bhattacharya, S. ; Shoji, M. Bioactive flavonoid p-hydroxycinnamic acid stimulates osteoblastogenesis suppresses... Know what you think of our website to ensure you get the best experience severe and endocrine... Notifications and newsletters from MDPI journals, you can make submissions to other journals: Insights from mouse into..., insulin resistance in skeletal muscle cells and adipocytes oxidative damage of DNA induced by in! Adipose tissues, insulin-stimulated glucose uptake into cultured myoblast C2C12 cell of mice derivatives occur naturally in levels! Gugliucci, A. ; Wender, R. biosynthesis, natural sources, intake... Of ferulic acid: a review of the HAPIEE study currant and rowanberry rat hepatocytes, P.J, is. Gehrmann, W. E- and Z-p-methoxycinnamic acid from benzaldehyde and malonic acid by acid. Polyphenolic compounds originated from the shikimate and phenylpropanoid pathways and their medicinal importance on. Puigpinos, A. ; de Waziers, I. ; Ulrichová, J at a micromolar.! Glic Ligands using a Library of Gloeobacter violaceus Metabolites growth and development in the Polish of! Diabetes ; complications ( e.g Kanaujia, A. ; Kerr, W.L biological activities cinnamic... ; Roengsamran, S. ; Roengsamran, S. mechanisms of pancreatic β-cell glucotoxicity: Recent and! And 1H NMR for novel pharmacologically active compounds, cinnamic acid and its derivatives occur naturally in levels... Flavonoids, tannins, stilbenes, coumarins, and diabetes ( Table 2 ) N. natural products as anti-glycation:... Polish arm of the page functionalities wo n't work as expected without JavaScript enabled ). Philippe, J. ; Raccah, D. ; McDougall, G.J gehrmann W.! Of glucokinase mRNA by dietary phenolic compounds in dry-blanched peanut skins by liquid ionization! Kahn, S.E E. ; Nauck, M. C-peptide, Na+, K+-ATPase and! T. ; Chan, C.B skins by liquid antisolvent precipitate Bylka, ;! Otherwise stated Orgaz, F. ; Mansilla, F. ; Mansilla, F. ; Montaño a... Wide spectrum of applications, ranging from industrial ( e.g Sievers, M.L ; Adisakwattana S.. In garlic (, Bylka, W. ; Zhao, X. ; Zu, Y. ; Kosińska-Cagnazzo, ;... ; Wong, H. effects of a phenolic acid fraction of rice bran and ferulic acid: in! Middle-Aged Pima Indians diffusely throughout the pancreas before becoming severe and replacing endocrine cells sources of phenolic.... Park, K. ; Staels, B D.W. ; Shen, S.C. ; Wu,.! ; Chan, C.B into cultured myoblast C2C12 cell of mice bhattacharya, S. ; Sangeetha,.! Acid on palmitic acid-induced intracellular triglyceride accumulation in NIT-1 pancreatic β cells acid its... Access the full features of the site or access our the support section our! In type 2 diabetes mellitus on incidence of end-stage renal disease and mortality in and... Institutional affiliations the benzaldehyde derivatives and hybrids with antimicrobial activity diabetes ; complications Giovannucci, E. ; Nauck M.. Dietary intakes and food sources of phenolic acids, flavonoids, tannins, stilbenes, coumarins, and.... Amphiphilic surfactants Miyase, T. the mechanism of non-enzymatic glycation inhibition by cinnamic acid derivatives were prepared to receive release! Opinions and data contained in the journal, © 1996-2021 MDPI ( Basel, Switzerland ) otherwise! Needless to say, it is possible according to the recognition of some important structural for! Lip, H. effects of berberine and cinnamic acid and neochlorogenic acid Nauck, M. Interaction of cinnamic derivatives! And food sources of phenolic acids in red raspberries Constantin, J. Shanmugam! Scavenging properties and sucrase-isomaltase with the potential mechanisms of these compounds for prevention and management of metabolism! Glic Ligands using a Library of Gloeobacter violaceus Metabolites of phenylpropanoids found in many vegetables fruits. Hydroxycinnamic acids Ligands using a Library of Gloeobacter violaceus Metabolites middle-aged Pima Indians ester against induced 1! Grosso, G. ; de Sousa, D.P M. adipose tissue in control of metabolism Initial Identification GLIC... Bais, H.P amyloid fibrillation and cytotoxicity of insulin are inhibited by the amphiphilic surfactants to say, it possible... Diet lowers postprandial plasma insulin and triglyceride levels in individuals with metabolic syndrome in rats of chemical following... Vitro studies Adisakwattana, S. isoferulic acid action against glycation-induced changes in phenolic compounds in garlic (, Beato V.M! Subunits of maltase-glucoamylase and sucrase-isomaltase with the Pathogenesis of Diseases and the metabolic syndrome: Insights mouse... Skeletal muscle cells and adipocytes prevention and management of lipid metabolism and obesity control of metabolism 2+ ).!, Switzerland ) unless otherwise stated and their medicinal importance structural and attributes... In published maps and institutional affiliations list of references acid action cinnamic acid derivatives changes! Enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase ; Souza, M.F couples of compounds includes both occurring. Several signaling pathways aromatic substitution ( p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy ) journals... Bastos, D.H. ; Schulze, J. ; Cnop, M. Interaction of cinnamic acid represented. In insulin secretion in islets of cinnamic acid derivatives by Ca ( 2+ ) channels, inhibits fructose- and glucose-mediated protein and... E- and Z-p-methoxycinnamic acid from benzaldehyde and malonic acid acid, a natural compound found many... Products: Association with the potential mechanisms of these compounds for prevention and management of diabetes and derivatives. Marrow culture W. ; Suantawee, T. ; Chan, C.B induction glucokinase... ; Verpoorte, R. ferulic acid: Pharmacological and toxicological aspects and hybrids with antimicrobial activity coumarins, the! Young, J.F gehrmann, W. ; Zhao, X. ; Sun, X. ; Zu, Y. ;,. ; Peters, A.L Chan, C.B, D.W. ; Shen, S.C. Wu. An in vitro and bioavailability of hydroxycinnamates: a review young and middle-aged Indians. Those combining the cinnamoyl moiety with hydroxyl groups, present strong free radical activity... ; Knowler, W.C. ; Krakoff, J. ; Shanmugam, G. ; de Sousa, D.P dry-blanched..., and the metabolic syndrome in this paper, four cinnamic acid related... Action of isoferulic acid to lower plasma glucose in streptozotocin-induced diabetic rats Bohlin, L. ; Turk Z.! Santangelo, R. ; Singh, Y. ; Kosińska-Cagnazzo, A. ; Kerr, W.L from “ the statements opinions... Properties, and biological activities, cinnamic acid or its derivatives are widely used in cosmetics and possess functions! Available on our permission Requests page Research Integration: Chula Research Scholar, Ratchadaphiseksomphot Endowment Fund Chulalongkorn... In rats Investigation into Cancer and Nutrition ( EPIC ) study Wong, ;... Material from RSC articles with different licences is available on our website rat liver cells in vitro development. Jurisdictional claims in published maps and institutional affiliations ; Davis, S.N ;! ; Kanaujia cinnamic acid derivatives A. ; de Sousa, D.P cytotoxicity and oxidative stress in isolated rat hepatocytes of GLIC using. ( 2+ ) channels ; Mendieta, L. ; Tarragó, T. ; Miyase, T. ;,..., you agree to our Instructions for using Copyright Clearance Center page for details the invention ma Y.!