- Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions
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To develop novel antiviral agents, some novel conjugates between ferulic acid and eugenol or isoeugenol were designed and synthesized by the link reaction. The antiviral activities of compounds were evaluated using the half leaf dead spot method. Bioassay results showed acceptable antiviral activities of some conjugates against the tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Compounds A9, A10, E1, and E4 showed remarkable curative, protective, and inactivating effects on TMV and CMV at 500 μg mL-1. Notably, these compounds exhibited excellent protective effects on TMV and CMV. The EC50 values of compounds A9, A10, E1, and E4 against TMV were 180.5, 169.5, 211.4, and 135.5 μg mL-1, respectively, and those against CMV were 210.5, 239.1, 218.4, and 178.6 μg mL-1, respectively, which were superior to those of ferulic acid (471.5 and 489.2 μg mL-1), eugenol (456.3 and 463.2 μg mL-1), isoeugenol (478.4 and 487.5 μg mL-1), and ningnanmycin (246.5 and 286.6 μg mL-1). Then, the antiviral mechanisms of compound E4 were investigated by determining defensive enzyme activities and multi-omics analysis. The results indicated that compound E4 resisted the virus infection by enhancing defensive responses via inducing the accumulation of secondary metabolites from the phenylpropanoid biosynthesis pathway in tobacco.
- Gan, Xiuhai,Wang, Zhengxing,Hu, Deyu
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p. 13724 - 13733
(2021/11/23)
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- Br?nsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio-Catechol
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An efficient conversion of biorenewable ferulic acid into bio-catechol has been developed. The transformation comprises two consecutive defunctionalizations of the substrate, that is, C?O (demethylation) and C?C (de-2-carboxyvinylation) bond cleavage, occurring in one step. The process only requires heating of ferulic acid with HCl (or H2SO4) as catalyst in pressurized hot water (250 °C, 50 bar N2). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.
- Bal, Mathias,Bomon, Jeroen,Liao, Yuhe,Maes, Bert U. W.,Sels, Bert F.,Sergeyev, Sergey,Van Den Broeck, Elias,Van Speybroeck, Veronique
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supporting information
p. 3063 - 3068
(2020/02/05)
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- Novel trans-Ferulic Acid Derivatives Containing a Chalcone Moiety as Potential Activator for Plant Resistance Induction
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A series of novel trans-ferulic acid derivatives containing a chalcone moiety were designed and synthesized to induce plant resistance. Antiviral activities of the compounds were evaluated. Bioassay results demonstrated that compounds F3, F6, F17, and F27 showed remarkable curative, protective, and inactivating activities against tobacco mosaic virus (TMV). With a 50% effective concentration (EC50) value of 98.78 μg mL-1, compound F27 exhibited the best protective activity compared with trans-ferulic acid (328.6 μg mL-1), dufulin (385.6 μg mL-1), and ningnanmycin (241.3 μg mL-1). This protective ability was associated with potentiation of defense-related enzyme activity and activation of photosynthesis of tobacco at an early stage. This notion was confirmed by up-regulated expression of stress responses and photosynthesis regulating proteins. This work revealed that F27 can induce resistance and enhance plant tolerance to TMV infection. Hence, F27 can be considered as a novel activator for inducing plant resistance.
- Gan, Xiuhai,Hu, Deyu,Wang, Yanjiao,Yu, Lu,Song, Baoan
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p. 4367 - 4377
(2017/06/13)
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- Ferulic acid ester derivative containing quinazoline, as well as preparation method and purpose of ferulic acid ester derivative
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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.
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Paragraph 0013; 0021
(2016/10/09)
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- COMPOUNDS AND METHODS FOR THE TREATMENT OF MICROBIAL INFECTION(S)
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The present invention relates to compounds useful in methods of treating at least one microbial infection, such methods and uses of said compounds, pharmaceutical formulations comprising said compounds, and/or synthetic processes. The compounds have the general formula (I) wherein R1 is H, N02, Br, I, NHC2H4OH, NHC(=NH)NH2; NH2; R2 is H, CH(CH3)2) S02-4-C6H4F or SO2-4-C6H4-OCH3; R3 is H or NO2; and R4 is CHO or CH=CHC(0)OR5, wherein R5 is CH2CH2CH2CH3, or more preferably H, CH3, CH2CH3 or CH2CH2CH3.
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Page/Page column 30; 31;32
(2016/02/29)
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- Dependence of Mesomorphism on Molecular Rigidity with Reference to Lateral Substitution and Central Bridge
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A novel mesogenic ester homologous series is synthesized and studied with a view to understanding and establishing the effect of laterally substituted-OCH3 on mesomorphic behavior. The series consists of twelve members. C1 to C4 members are nonmesogenic, C6 to C12 are smectogenic in addition to nematogenic, and C14 to C16 are only smectogenic. The textures of smectic and nematic phases are A or C type and threaded or Schlieren, respectively. The transition curves in a phase diagram exhibit an odd-even effect and behave in normal manner except for the C14 and C16 derivatives in Sm-I transitions. Thermometric data were determined by an optical polarizing microscope equippedwith a heating stage. Average thermal stability for smectic and nematic are 107.7°C and 121.0°C, respectively. Smectogenic and nematogenicmesophase length ranges from 11.0 to 44.0°C and 12.0°C to 39.0°C, respectively. The mesomorphic properties of present series are comparedwith structurally similar other known series. Thus, present series is predominantly smectogenic and partly nematogenic ofmiddle ordered melting type.
- Travadi,Vadodaria,Ladva,Doshi
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- Design, synthesis, and in vitro antiplatelet aggregation activities of ferulic acid derivatives
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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.
- 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
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- Antiallergic activity of rosmarinic acid esters is modulated by hydrophobicity, and bulkiness of alkyl side chain
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Methyl, propyl and hexyl esters of rosmarinic, caffeic and p-coumaric acids were tested for antiallergic activity, and rosmarinic acid propyl ester exhibited the greatest β-hexosaminidase release suppression (IC50, 23.7 μM). Quadratic correlations between pIC50 and cLogP (r2 = 0.94, 0.98, and 1.00, respectively) were observed in each acid ester series. The antiallergic activity is modulated by hydrophobicity, and alkyl chain bulkiness.
- Zhu, Fengxian,Xu, Zhongming,Yonekura, Lina,Yang, Ronghua,Tamura, Hirotoshi
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p. 1178 - 1182
(2015/10/05)
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- Laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives
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The laccase-catalyzed oxidative phenolic coupling of vanillidene derivatives using aerial oxygen as the oxidant has been developed. Depending on the substitution pattern of the vanillidene double bond of the substrate, either dilactones, dihydrobenzo[b]furans or biphenyls are formed.
- Constantin, Mihaela-Anca,Conrad, Juergen,Beifuss, Uwe
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p. 2375 - 2379
(2013/02/21)
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- Alkyl esters of hydroxycinnamic acids with improved antioxidant activity and lipophilicity protect PC12 cells against oxidative stress
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Hydroxycinnamic acids (HCAs) are phenolic compounds present in dietary plants, which possess considerable antioxidant activity. In order to increase the lipophilicity of HCAs, with the aim of improving their cellular absorption and expansion of their use in lipophilic media, methyl, ethyl, propyl and butyl esters of caffeic acid and ferulic acid have been synthesized. All caffeate esters had a slightly lower DPPH IC50 (13.5-14.5 μM) and higher ferric reducing antioxidant power (FRAP) values (1490-1588 mM quercetin/mole [mMQ/mole]) compared to caffeic acid (16.6 μM and 1398 mMQ/mole, respectively) in antioxidant assays. In contrast, ferulate esters were less active in DPPH (56.3-74.7 μM) and FRAP assays (193-262 mMQ/mole) compared to ferulic acid (44.6 μM and 324 mMQ/mole, respectively). Redox properties of HCAs were in line with their antioxidant capacities, so that compounds with higher antioxidant activities had lower oxidation potentials. Measurement of partition coefficients disclosed the higher lipophilicity of the esters compared to parent compounds. All esters of caffeic acid significantly inhibited hydrogen peroxide-induced neuronal PC12 cell death assessed by MTT assay at 5 and 25 μM. However, caffeic acid, ferulic acid and ferulate esters were not able to protect the cells. In conclusion, these findings suggest that alkyl esterification of some HCAs augments their antioxidant properties as well as their lipophilicity and as a consequence, improves their cell protective activity against oxidative stress. These compounds could have useful applications in conditions where oxidative stress plays a pathogenic role.
- Garrido, Jorge,Gaspar, Alexandra,Garrido, E. Manuela,Miri, Ramin,Tavakkoli, Marjan,Pourali, Samaneh,Saso, Luciano,Borges, Fernanda,Firuzi, Omidreza
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experimental part
p. 961 - 967
(2012/07/17)
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- Biological activity evaluation and structure-activity relationships analysis of ferulic acid and caffeic acid derivatives for anticancer
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The anticancer activities of alkyl esters and NO-donors of ferulic acid (FA) and caffeic acid (CA) were assessed by a high-throughout screening (HTS) method, and the structure-activity relationships were described. CA alkyl esters had better anticancer activities than FA alkyl esters with the same alkyl substituent. Mono-nitrates and phenylfuroxan nitrates were more potent than the dual nitrates. Phenylsulfonylfuroxan nitrates of FA, especially compounds 8b-8d, exhibited more potent activities in anticancer.
- Li, Weixia,Li, Nianguang,Tang, Yuping,Li, Baoquan,Liu, Li,Zhang, Xu,Fu, Haian,Duan, Jin-Ao
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p. 6085 - 6088
(2012/10/29)
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- Highly efficient esterification of ferulic acid under microwave irradiation
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A highly efficient synthesis of alkyl ferulates under microwave irradiation is described. The time of these reactions ranged from 3 to 5 minutes, which was much shorter than the traditional synthetic methods, and the alkyl ferulates were obtained in higher yields.
- Li, Nian-Guang,Shi, Zhi-Hao,Tang, Yu-Ping,Li, Bao-Quan,Duan, Jin-Ao
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experimental part
p. 2118 - 2126
(2009/10/10)
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- Nitrification inhibitors from the root tissues of Brachiaria humidicola, a tropical grass
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Nitrification inhibitory activity was found in root tissue extracts of Brachiaria humidicola, a tropical pasture grass. Two active inhibitory compounds were isolated by activity-guided fractionation, using recombinant Nitrosomonas europaea containing luxAB genes derived from the bioluminescent marine gram-negative bacterium Vibrio harveyi. The compounds were identified as methyl-p-coumarate and methyl ferulate, respectively. Their nitrification inhibitory properties were confirmed in chemically synthesized preparations of each. The IC50 values of chemically synthesized preparations were 19.5 and 4.4 μM, respectively. The ethyl, propyl, and butyl esters of p-coumaric and ferulic acids inhibited nitrification, whereas the free acid forms did not show inhibitory activity.
- Gopalakrishnan, Subramaniam,Subbarao, Guntur V.,Nakahara, Kazuhiko,Yoshihashi, Tadashi,Ito, Osamu,Maeda, Ikuko,Ono, Hiroshi,Yoshida, Mitsuru
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experimental part
p. 1385 - 1388
(2009/10/01)
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- Impact of alkyl esters of caffeic and ferulic acids on tumor cell proliferation, cyclooxygenase enzyme, and lipid peroxidation
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The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C12-caffeate), 11 (C16-caffeate), 21 (C 8-ferulate), and 23 (C12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 μg/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 μg/ mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 μg/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 μg/ mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C4-C 12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C3-C8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 μg/mL. Long-chain caffeates 11-14 (C 16-C22) and short-chain ferulates 15-20 (C 3-C5) were the most active in lipid peroxidation inhibition and showed 60-70% activity at 5 μg/mL concentration.
- Jayaprakasam, Bolleddula,Vanisree, Mulabagal,Zhang, Yanjun,Dewitt, David L.,Nair, Muraleedharan G.
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p. 5375 - 5381
(2008/04/03)
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- Mapping the hydrolytic and synthetic selectivity of a type C feruloyl esterase (StFaeC) from Sporotrichum thermophile using alkyl ferulates
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The active site of Sporotrichum thermophile type C feruloyl esterase (StFaeC) was probed using a series of C1-C4 alkyl ferulates. The affinities for straight and branched alkyl ferulates were demonstrated by the Km values of 1.64-0.51 and 0.19-0.1, respectively. Comparison of kcat and kcat/Km values shows that the enzyme hydrolyzed n-propyl ferulate faster and iso-propyl ferulate more efficiently. Alkyl ferulates were applied also for substrate selectivity mapping of feruloyl esterase to catalyze feruloyl group transfer to l-arabinose, using as a reaction system a ternary water-organic mixture consisting of n-hexane, t-butanol and water. Lengthening the aliphatic side chain was the most significant factor causing lower synthetic activity of the enzyme. The reaction parameters affecting the feruloylation rate and the conversion of the enzymatic process, such as the temperature and substrate concentration have been investigated. Under identical reaction conditions, the enzyme feruloylated other monosaccharides such as d-arabinose, d-glucose, d-xylose, d-mannose, d-fructose, d-galactose, d-ribose and model substrates such as 4-nitrophenyl α-l-arabinofuranoside and 4-nitrophenyl α-l-arabinopyranoside.
- Vafiadi, Christina,Topakas, Evangelos,Wong, Ken K.Y.,Suckling, Ian D.,Christakopoulos, Paul
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p. 373 - 379
(2007/10/03)
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- Chondroprotective agents
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A chondroprotective agent comprising a carboxylic acid compound of the general formula (I): STR1 wherein R1 and R2 are, independently, a hydrogen atom or an alkyl group of 1 to 6 carbon atoms, or a cis- or trans-isomer thereof, or a pharmaceutically acceptable salt or ester thereof, and a pharmaceutically acceptable carrier is disclosed. The above compound strongly inhibits proteoglycan depletion from the chondrocyte matrix and exhibits a function to protect cartilage, and thus, is extremely effective for the treatment of arthropathy.
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- Synthesis and antifungal activity of cinnamic acid esters
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Cinnamic, p-coumaric and ferulic acids were isolated from pineapple stems (Ananas comosus var. Cayenne). Twenty-four kinds of esters were prepared from these acids, alcohols and the components of Alpinia. Isopropyl 4-hydroxycinnamate (11) and butyl 4-hydroxycinnamate (12) were found to have almost the same effectiveness in antifungal activity against Pythium sp. at l0 ppm as that of the commercial fungicide iprobenfos (Kitazin P).
- Tawata,Taira,Kobamoto,Zhu,Ishihara,Toyama
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p. 909 - 910
(2007/10/03)
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