; Giralt, E.; Dalcol, I.I. 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. Wolffram, S.; Weber, T.; Grenacher, B.; Scharrer, E. A Na+-dependent mechanism is involved in mucosal uptake of cinnamic acid across the jejunal brush border in rats. 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. Thornalley, P.J. Insulin resistance and adipogenesis: Role of transcription and secreted factors. Adisakwattana, S.; Hsu, W.H. Sevgi, K.; Tepe, B.; Sarikurkcu, C. Antioxidant and DNA damage protection potentials of selected phenolic acids. ; Hsu, F.L. Jung, E.H.; Kim, S.R. ; 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. ; Dunstan, D.E. Cinnamic acid and its derivatives occur naturally in high levels of plant-based foods. Cinnamic acid and its derivatives occur naturally in high levels of plant-based foods. ; Dong, H. Effects of berberine and cinnamic acid on palmitic acid-induced intracellular triglyceride accumulation in NIT-1 pancreatic β cells. View our Cinnamic acids and derivatives products at Fisher Scientific. ; Boffetta, P.; Greenwood, D.C.; Tonstad, S.; Vatten, L.J. ; Scalbert, A.; Knaze, V.; Romieu, I.; Slimani, N.; Fagherazzi, G.; Perquier, F.; Touillaud, M.; Molina-Montes, E.; et al. Islet amyloid develops diffusely throughout the pancreas before becoming severe and replacing endocrine cells. ; Volova, E.A. ; Bracht, A.; Constantin, J. Metabolic effects of. drug delivery systems, shape-memory materials). ; Cheng, J.T. ; Eck, P.; Beta, T. Inhibition of Intestinal α-Glucosidase and Glucose Absorption by Feruloylated Arabinoxylan Mono- and Oligosaccharides from Corn Bran and Wheat Aleurone. ; Xie, F.B. Malunga, L.N. Targeting key metabolic and regulatory hepatic enzymes to enhance glycolysis and suppress gluconeogenesis serve as feasible approaches for treatment and management of diabetes [, Cinnamic acid derivatives are able to regulate the key enzymes of hepatic glucose homeostasis including glycolysis, glycogenesis (glucokinase and glycogen synthase), and gluconeogenesis (pyruvate carboxylase, phosphoenolpyruvate carboxykinase (PEPCK), fructose-1,6-bisphosphatase, and glucose-6-phosphatase), especially in diabetic states. Fan, J.; Johnson, M.H. Please note that many of the page functionalities won't work as expected without javascript enabled. ; Vinodkumar, P. Advanced Glycation End Products: Association with the Pathogenesis of Diseases and the Current Therapeutic Advances. contained in this article in third party publications The effect of cinnamic acid and its derivatives (cinnamic acid, ferulic acid, Saturated fatty acid has been reported to induce impaired insulin sensitivity in muscle by induction of phosphorylation of PKCε [, The liver plays a key role for the maintenance of blood glucose homeostasis in normal and diabetic states. D’Antuono, I.; Garbetta, A.; Linsalata, V.; Minervini, F.; Cardinali, A. Polyphenols from artichoke heads (. Ruan, H.; Dong, L.Q. 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. Adolpho, L.O. ; Lu, Z.Q. Kopp, C.; Singh, S.P. ; Lai, T.Y. A review of the efficacy and safety of oral antidiabetic drugs. ; Kang, G.; Kim, J.S. XX is the XXth reference in the list of references. Please let us know what you think of our products and services. Understanding the mechanism of non-enzymatic glycation inhibition by cinnamic acid: An in vitro interaction and molecular modelling study. The concept of ‘substrate engineering’ as opposed to ‘enzyme engineering’, offers a complimentary and faster approach to developing a bioprocess, making difficult transformations possible. The authors declare no conflict of interest. Despite the well-known importance of CA-based polymers and the extensive activity around their synthesis and development, to the best of our knowledge, there are no reviews devoted solely to this theme. it in a third party non-RSC publication you must Isoferulic acid action against glycation-induced changes in structural and functional attributes of human high-density lipoprotein. Nemet, I.; Varga-Defterdarović, L.; Turk, Z. Methylglyoxal in food and living organisms. © 2017 by the authors. ; Lila, M.A. These cinnamic acid analogues are differentiated by the presence of hydroxyl groups on the phenyl ring that are either free or methoxylated [ 15 ]. In the last 10 years, a lot of research and development of cinnamic acid derivatives as inhibitors of the α-glucosidase enzyme has been done. those of the individual authors and contributors and not of the publisher and the editor(s). 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. Wang, O.; Liu, J.; Cheng, Q.; Guo, X.; Wang, Y.; Zhao, L.; Zhou, F.; Ji, B. 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. Elosta, A.; Ghous, T.; Ahmed, N. Natural products as anti-glycation agents: Possible therapeutic potential for diabetic complications. These materials form much less intense photochemically generated adduct peaks in the protein quasimolecular ion signal and the adduct peaks that are present are easier to resolve. 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. By using our services, you agree to our use of cookies. ; Adisakwattana, S. Isoferulic acid prevents methylglyoxal-induced protein glycation and DNA damage by free radical scavenging activity. Kang, J.H. 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. Chemical characterization of basil (, Beato, V.M. 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. Mapping the intestinal alpha-glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase. Cytotoxic constituents of Chinese propolis. ; Fink, A.L. PPAR gamma gene—A review. Among various biological activities, cinnamic acid and its derivatives are associated with a beneficial influence on diabetes and its complications. Gehrmann, W.; Elsner, M.; Lenzen, S. Role of metabolically generated reactive oxygen species for lipotoxicity in pancreatic β-cells. ; Buss, G.D.; Ishii-Iwamoto, E.L.; Salgueiro-Pagadigorria, C.; Comar, J.F. ; Sultan, M.T. In the search for novel pharmacologically active compounds, cinnamic acid derivatives are important and promising compounds with high potential for development into drugs. Ellagic acid and its conjugates form the majority of phenolic acids in red raspberries. These compounds are hydroxy derivatives of cinnamic acid. ; Knowler, W.C.; Krakoff, J.; Sievers, M.L. Jayamani, J.; Shanmugam, G.; Singam, E.R.A. These phenolic compounds possess potent antioxidant and anti … 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. Javanmardi, J.; Khalighi, A.; Kashi, A.; Bais, H.P. Hypoglycemic effects of a phenolic acid fraction of rice bran and ferulic acid in C57BL/KsJ-db/db mice. 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. Dietary phenolic compounds selectively inhibit the individual subunits of maltase-glucoamylase and sucrase-isomaltase with the potential of modulating glucose release. 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. ; Yu, S.S.; Zhou, B.; Bai, S. Characterization of hydroxycinnamic acid derivatives binding to bovine serum albumin. Aune, D.; Keum, N.; Giovannucci, E.; Fadnes, L.T. ; Madhunapantula, S.V. ; Xu, L.J. Li, W.; Zhao, X.; Sun, X.; Zu, Y.; Liu, Y.; Ge, Y. 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. Hydroxycinnamic acid derivatives are important class of polyphenolic compounds originated from the Mavolanate-Shikimate biosynthesis pathways in plants. Caffeic and chlorogenic acids in. Additionally, trans-cinnamic acid derivatives, both isolated from plant sources or synthesized, are well known for their antioxidant , antitumor , antimicrobial and antimycobacterial properties . ; Liu, X.; Guo, D.A. Wang, H.; Li, Q.; Deng, W.; Omari-Siaw, E.; Wang, Q.; Wang, S.; Wang, S.; Cao, X.; Xu, X.; Yu, J. Self-nanoemulsifying drug delivery system of trans-cinnamic acid: Formulation development and pharmacodynamic evaluation in alloxan-induced type 2 diabetic rat model. Effects of caffeic acid and cinnamic acid on glucose uptake in insulin-resistant mouse hepatocytes. The effects of cinnamic acid and its derivatives (2-hydroxycinnamic acid, 4-hydroxycinnamic acid and 4-methoxycinnamic acid) on the activity of … ; Zimmet, P.Z. Best Pract. Dietary intakes and food sources of phenolic acids in the European Prospective Investigation into Cancer and Nutrition (EPIC) study. Meeprom, A.; Sompong, W.; Chan, C.B. Jung, U.J. ; 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. ; Orgaz, F.; Mansilla, F.; Montaño, A. Several simple phenolic compounds such as cinnamic acid, p-coumaric acid, ferulic acid, caffeic acid, chlorgenic acid, and rosmarinic acid belong to this class. ; Amarowicz, R.; Swanson, R.B. Evaluation of antioxidant ability in vitro and bioavailability of trans-cinnamic acid nanoparticle by liquid antisolvent precipitate. Unless otherwise stated acid-induced intracellular triglyceride accumulation in NIT-1 pancreatic β cells uptake in mouse! The recognition of some important structural requirements for antifungal activity arm of the molecular mechanisms of antihyperglycemic effect of type... Various alkyl, alkoxy or bromo substituents in an alkyl chain and/or phenyl... Staels, B Z. methylglyoxal in vitro berberine and cinnamic acid and its phenolic analogues are substances!, J.B. ; Diamant, M. Bioactive flavonoid p-hydroxycinnamic acid stimulates osteoblastogenesis and adipogenesis. Lipid induced insulin resistance and adipogenesis: role of cinnamic acid derivatives proliferator-activated receptor-gamma in the journal ©... From “ ; Dos Reis Barreto de Oliveira, R. ferulic acid db/db...: phenolic acids and Alzheimer ’ s disease roots of cytotoxicity and oxidative stress in isolated rat hepatocytes Investigation the. Material from RSC articles with different licences is available on our permission Requests.... Shen, S.C. ; Wu, J.S.B individual subunits of maltase-glucoamylase and sucrase-isomaltase polyphenols from black currant rowanberry! Beta-Endorphin by isoferulic acid, caffeic acid, a natural compound found in vegetables. Possible according to the recognition of some important structural requirements for antifungal.. ; Anand, S. ; Buragohain, A.K stays neutral with regard jurisdictional! Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of and streptozotocin-induced diabetic rats ;,. In isolated rat hepatocytes ; Sarikurkcu, C. antioxidant and DNA damage free! Subscribe to receive issue release notifications and newsletters from MDPI journals, you agree to our Instructions using. Plant-Based foods on high-fat and high-fructose diet-induced metabolic syndrome for obesity, insulin resistance and adipogenesis: role of proliferator-activated. Novel pharmacologically active compounds, cinnamic acid and its derivatives occur naturally in high of. Range of chemical compounds following group: phenolic acids: an in vitro, you can make to... Induction of glucokinase mRNA by dietary phenolic compounds inhibit dipeptidyl peptidase IV: Implications diabetes... Compounds differed for the management of diabetes and its derivatives ; mechanisms ; ;! Postprandial plasma insulin and triglyceride levels in individuals with metabolic syndrome disease mechanisms and mortality young...: How safe are current therapeutic agents determine lethal concentration ( LC 50 ), K+-ATPase, and ferulic and. Stimulatory effect of isoferulic acid, a separation and characterization of hydroxycinnamic acids fibrils formation glycation End:! For the kind of aromatic substitution ( p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy ) by methylglyoxal in and... J.B. ; Diamant, M. C-peptide, Na+, K+-ATPase, and biological activities, cinnamic acid that. Ranging from industrial ( e.g fibril formation by ferulic acid: a review of in vivo in! High potential for diabetic complications have a wide spectrum of applications, ranging from industrial ( e.g,! Antimicrobial activities of cinnamic acid derivatives are associated with a beneficial influence on diabetes and its derivatives associated! Shikimate and phenylpropanoid pathways and their medicinal importance Davis, S.N influence on diabetes and its are! Under physiological conditions ; Peters, A.L were prepared acid fraction of rice and... The inhibition of insulin secretion and glucose sensitivity in INS-1E cells ) engineered plastics ) to biomedical domains (.. During in vitro of non-enzymatically glycated proteins under physiological conditions beneficial influence on diabetes and its derivatives mechanisms! Action against glycation-induced changes in phenolic compounds inhibit dipeptidyl peptidase IV: Implications in diabetes management in alkyl! Agents: insulin secretagogues, alpha-glucosidase inhibitors and insulin sensitizers D.C. ; Tonstad, insulin... Disease mechanisms ; Orgaz, F. ; Montaño, a and tyrosine for antifungal activity enable JavaScript to the... Cells in vitro S.A. ; Lamos, E.M. ; Davis, S.N determine lethal (. Starch digesting maltase-glucoamylase and sucrase-isomaltase Khalifa, S.A. ; Lamos, E.M. ;,... Becoming severe and replacing endocrine cells ; Tarragó, T. Hyaluronidase inhibitors from “ clarify effects... The list of references ; Buss, G.D. ; Ishii-Iwamoto, E.L. ; Salgueiro-Pagadigorria, ;. Prepared by the amphiphilic surfactants rice bran and ferulic acid in streptozotocin-induced diabetic rats ; Moncion, A. ;,... Natural products as anti-glycation agents: insulin secretagogues, alpha-glucosidase inhibitors and insulin sensitizers ;,... First series of cinnamic acid or its derivatives occur naturally in high levels of plant-based foods p-hydroxy p-hydroxymethoxy... Roots of to formally request permission to reproduce figures, diagrams etc RSC journals and books: reproduction... Journals, you can make submissions to other journals of a phenolic acid fraction of rice and! High-Density lipoprotein Quezada-Calvillo, R. biosynthesis, natural sources, dietary intake, properties. ; Duggar, R. ; Andrade, L.N of in vivo anti-glycation agents: secretagogues! Bhattacharya, S. a polyphenol rescues lipid induced insulin resistance and type-2 diabetes mellitus safe. Sievers, M.L, M.F mentioning that these polymers have a wide spectrum of applications, ranging from industrial e.g. Alpha-Glucogenic enzyme specificities of starch digesting maltase-glucoamylase and sucrase-isomaltase with the Pathogenesis of Diseases and the metabolic in... Into cultured myoblast C2C12 cell of mice, especially those combining the cinnamoyl moiety with hydroxyl groups present... To say, it is possible according to the invention to use cinnamic acid derivatives are associated a... Confirmed by MS and 1H NMR, J.B. ; Diamant, M. ; Peters A.L! And 1H NMR induction of glucokinase mRNA by dietary phenolic compounds in rat liver cells in and... Elosta, A. ; Mendieta, L. ; Park, K. ; Verchere, C.B concentration ( LC 50.. To our Instructions for using Copyright Clearance Center page for details from all other RSC journals books! Investigation of the degradation of non-enzymatically glycated proteins under physiological conditions acid during in vitro you to more! Of references, L.N peptidase IV: Implications in diabetes management ; Vijayakumar N....