4657-33-4Relevant academic research and scientific papers
Studies on temperature dependent kinetics of Aspergillus awamori feruloyl esterase in water solutions
Fazary,Ismadji,Ju
, p. 31 - 37 (2010)
The initial reaction rate (V 0) for the esterification reaction of feruloyl esterase (FAE-II) at different temperatures (288, 298, 308, 318, 328, 338, 348, and 358 K) and various ethyl ferulate concentrations [(2, 4, 6, 8, 10, 12, 14, and 16) ×
Immobilization of feruloyl esterases in mesoporous materials leads to improved transesterification yield
Thoern, Christian,Gustafsson, Hanna,Olsson, Lisbeth
, p. 57 - 64 (2011)
Feruloyl esterases are used in biocatalysis for refinement of hydroxycinnamic acids, a group of compounds with antioxidant and antibacterial properties where modification of solubility is necessary for the compounds to be of interest in different commercial products. In industrially feasible and efficient processes, immobilization of enzymes is often required for sufficient enzyme stability and to enable recovery. In recent years, mesoporous materials have become popular as immobilization support due to advantages such as high protein loading capacity and enhanced enzyme activity because of confinement into pores. We used mesoporous silica, for the first time, as immobilization support for feruloyl esterases. The crude enzyme preparation Depol 740L was adsorbed into two SBA-15 mesoporous silica materials of different pore size and the effects of the immobilization on transesterification of methyl ferulate with 1-butanol into butyl ferulate were studied, tested in a reaction system based on 92.5% 1-butanol and 7.5% MOPS buffer (pH 6.0). Immobilization in mesoporous silica with larger pore size (9 nm) showed higher protein loading and higher specific activity compared to immobilization with smaller pore size (5 nm). Importantly, adsorption into mesoporous silica changed the product specificity of the enzymes to favor transesterification and decrease the rate of hydrolysis compared to free enzymes. The immobilized enzyme had a butyl ferulate yield of up to 90%, significantly higher compared to free enzymes. Additionally, the immobilized enzymes showed an excellent operational stability and reusability, retaining ≥70% of the initial activity after 6 sequential runs, each lasting 6 days. Consequently, we show that mesoporous silica is a robust immobilization support for feruloyl esterases to be used in the development of biocatalysts for customization of the antioxidant properties of hydroxycinnamic acids.
Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
, p. 68 - 78 (2019/11/22)
Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.
Alkyl Ferulate Esters as Multifunctional Food Additives: Antibacterial Activity and Mode of Action against Escherichia coli in Vitro
Shi, Yu-Gang,Zhu, Yun-Jie,Shao, Shi-Yin,Zhang, Run-Run,Wu, Yu,Zhu, Chen-Min,Liang, Xian-Rui,Cai, Wen-Qiang
, p. 12088 - 12101 (2018/11/23)
This work aims to prepare ferulic acid alkyl esters (FAEs) through the lipase-catalyzed reaction between methyl ferulate and various fatty alcohols in deep eutectic solvents and ascertain their antibacterial activities and mechanisms. Screens of antibacterial effects of FAEs against Escherichia coli ATCC 25922 (E. coli) and Listeria monocytogenes ATCC 19115 (L. monocytogenes) revealed that hexyl ferulate (FAC6) exerted excellent bacteriostatic and bactericidal effects on E. coli and L. monocytogenes (minimum inhibitory concentration (MIC): 1.6 and 0.1 mM, minimum bactericidal concentration (MBC): 25.6 and 0.2 mM, respectively). The antibacterial mechanism of FAC6 against E. coli was systematically studied to facilitate its practical use as a food additive with multifunctionalities. The growth and time-kill curves implied the partial cell lysis and inhibition of the growth of E. coli caused by FAC6. The result related to propidium iodide uptake and cell constituents' leakage (K+, proteins, nucleotides, and β-galactosidase) implied that bacterial cytomembranes were substantially compromised by FAC6. Variations on morphology and cardiolipin microdomains and membrane hyperpolarization of cells visually verified that FAC6 induced cell elongation and destructed the cell membrane with cell wall perforation. SDS-PAGE analysis and alterations of fluorescence spectra of bacterial membrane proteins manifested that FAC6 caused significant changes in constitutions and conformation of membrane proteins. Furthermore, it also could bind to minor grooves of E. coli DNA to form complexes. Meanwhile, FAC6 exhibited antibiofilm formation activity. These findings indicated that that FAC6 has promising potential to be developed as a multifunctional food additive.
Long Chain Alkyl Esters of Hydroxycinnamic Acids as Promising Anticancer Agents: Selective Induction of Apoptosis in Cancer Cells
Menezes, José C. J. M. D. S.,Edraki, Najmeh,Kamat, Shrivallabh P.,Khoshneviszadeh, Mahsima,Kayani, Zahra,Mirzaei, Hossein Hadavand,Miri, Ramin,Erfani, Nasrollah,Nejati, Maryam,Cavaleiro, José A. S.,Silva, Tiago,Saso, Luciano,Borges, Fernanda,Firuzi, Omidreza
, p. 7228 - 7239 (2017/08/30)
Cancer is the major cause of morbidity and mortality worldwide. Hydroxycinnamic acids (HCAs) are naturally occurring compounds and their alkyl esters may possess enhanced biological activities. We evaluated C4, C14, C16, and C18 alkyl esters of p-coumaric, ferulic, sinapic, and caffeic acids (19 compounds) for their cytotoxic activity against four human cancer cells and also examined their effect on cell cycle alteration and apoptosis induction. The tetradecyl (1c) and hexadecyl (1d) esters of p-coumaric acid and tetradecyl ester of caffeic acid (4c), but not the parental HCAs, were selectively effective against MOLT-4 (human lymphoblastic leukemia) cells with IC50 values of 0.123 ± 0.012, 0.301 ± 0.069 and 1.0 ± 0.1 μM, respectively. Compounds 1c, 1d, and 4c significantly increased apoptotic cells in sub-G1 phase and activated the caspase-3 enzyme in MOLT-4 cells. Compound 1c was 15.4 and 23.6 times more potent than doxorubicin and cisplatin, respectively, against the drug resistant MES-SA-DX5 uterine sarcoma cells. These p-coumarate esters were several times less effective against NIH/3T3 fibroblast cells. Docking studies showed that 1c may cause cytotoxicity by interaction with carbonic anhydrase IX. In conclusion, long chain alkyl esters of p-coumaric acid are promising scaffolds for selective apoptosis induction in cancer cells.
Study of the Effect of Lateral Substitution on Mesogenic Behavior with Reference to -CH=CH- Unit
Travadi,Vadodaria,Ladva,Doshi
, p. 90 - 99 (2016/04/05)
A novel cinnamate ester homologous series has been synthesized and studied with a view to understanding and establishing the effects of molecular structure on liquid crystal (LC) properties with a focus on the highly polar methoxy group as a lateral substituent. The series consists of twelve homologs; of which C1-C5 are nonmesogenic, and the rest of the homologs are enantiotropically smectogenic or and nematogenic. The texture of nematic phases is threaded or Schlieren and that of the smectic is either smectic A or C, as recognized and determined through an optical polarizing microscope equipped with a heating stage. The Sm-N I and N-I transition curves exhibit odd-even effects and behave in normalmanner. The Cr-IMbehaves in normalmanner. Analytical and spectral data confirm the molecular structures of homologs. The average thermal stabilities for smectic and nematic are 125.3 C and 129.8 C, respectively, whose total mesophase length varies from 13 C to 51 C. Some LC properties of present series are compared with the structurally similar known series.
Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold
Hosseini, Razieh,Moosavi, Fatemeh,Rajaian, Hamid,Silva, Tiago,Magalh?es e Silva, Diogo,Soares, Pedro,Saso, Luciano,Edraki, Najmeh,Miri, Ramin,Borges, Fernanda,Firuzi, Omidreza
, p. 926 - 937 (2016/11/11)
The number of people affected by neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease is rapidly increasing owing to the global increase in life expectancy. Small molecules with neurotrophic effects have great potential for management of these neurological disorders. In this study, different (C1–C12) alkyl ester derivatives of hydroxycinnamic acids (HCAs) were synthesized (a total of 30 compounds). The neurotrophic capacity of the test compounds was examined by measuring promotion of survival in serum-deprived conditions and enhancement of nerve growth factor (NGF)-induced neurite outgrowth in PC12 neuronal cells. p-Coumaric, ferulic, and sinapic acids and their esters did not alter cell survival, while caffeic acid and all its alkyl esters, especially decyl and dodecyl caffeate, significantly promoted neuronal survival at 25?μm. Methyl, ethyl, propyl, and butyl caffeate esters also significantly enhanced NGF-induced neurite outgrowth, among which the most effective ones were propyl and butyl esters, which at 5?μm led to 25- and 22-fold increases in the number of neurites, respectively. The findings of the docking study suggested phosphatidylinositol 3-kinase (PI3K) as the potential molecular target. In conclusion, our findings demonstrate that alkyl esters of caffeic acid can be useful as scaffolds for the discovery of therapeutic agents for neurodegenerative diseases.
Ferulic acid ester derivative containing quinazoline, as well as preparation method and purpose of ferulic acid ester derivative
-
Paragraph 0013; 0028, (2016/10/09)
The invention discloses a ferulic acid ester derivative containing quinazoline, as well as a preparation method and a purpose of the ferulic acid ester. A structural general formula (I) of the ferulic acid ester derivative containing the quinazoline is as follows: R1 is methyl, ethyl, n-propyl, isopropyl and normal-butyl; R2 is hydrogen, 6,7-dimethoxy and 6,7-bis-methoxyethoxy. The ferulic acid ester derivative containing the quinazoline can resist the cucumber mosaic virus, the tobacco mosaic virus, the southern rice black-streaked dwarf virus and the rice stripe virus.The structural general formula (I) is shown in the specification.
Design, synthesis, and in vitro antiplatelet aggregation activities of ferulic acid derivatives
Zhang, Peng-Xuan,Lin, Hang,Qu, Cheng,Tang, Yu-Ping,Li, Nian-Guang,Kai, Jun,Shang, Guanxiong,Li, Baoquan,Zhang, Li,Yan, Hui,Liu, Pei,Duan, Jin-Ao
, (2015/05/05)
In order to discover new compounds with antiplatelet aggregation activities, some ferulic acid (FA) derivatives were designed and synthesized. The in vitro antiplatelet aggregation activities of these compounds were assessed by turbidimetric test. The results showed that the target compound 7f had potent antiplatelet aggregation activity with its IC50 27.6 μmol/L, and 7f can be regarded as a novel potent antiplatelet aggregation candidate.
Antioxidant properties and efficacies of synthesized alkyl caffeates, ferulates, and coumarates
Sorensen, Ann-Dorit Moltke,Jacobsen, Charlotte,Durand, Erwann,Laguerre, Mickal,Bayrasy, Christelle,Lecomte, Jrme,Villeneuve, Pierre
, p. 12553 - 12562 (2015/04/21)
Caffeic, ferulic, and coumaric acids were lipophilized with saturated fatty alcohols (C1-C20). The antioxidant properties of these hydroxycinnamic acids and their alkyl esters were evaluated in various assays. Furthermore, the antioxidant efficiency of the compounds was evaluated in a simple o/w microemulsion using the conjugated autoxidizable triene (CAT) assay. All evaluated phenolipids had radical scavenging, reducing power, and metal chelating properties. Only caffeic acid and caffeates were able to form a complex with iron via their catechol group in the phenolic ring. In the o/w emulsion, the medium chain phenolipids of the three homologues series were most efficient. The antioxidant properties and efficacies were dependent upon functional groups substituted to the ring structure and were in the following order: caffeic acid and caffeates > ferulic acid and ferulates > coumaric acid and coumarates. Moreover, the results demonstrated that the test system has an impact on the antioxidative properties measured.
