- Effect of 1-ethyl-3-methylimidazolium acetate on the oxidation of caffeic acid benzyl ester: An electrochemical and theoretical study
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The effect of the ionic liquid (IL), 1-ethyl-3-methylimidazolium acetate ([emim][AcO]) on the oxidation of (E)-phenylmethyl-3-(3,4-dihydroxyphenyl)-2-propenoate (commonly known as caffeic acid benzyl ester [CABE]) was analyzed through experimental and theoretical methods, such as cyclic voltammetry (CV) and density functional theory (DFT) calculations. The obtained results demonstrated that the AcO? anion promotes the oxidation of the caffeic ester; this is because of the basic character of AcO?, which plays an important role to reduce the amount of energy required for the removal of one electron from the IL-CABE complex. This suggests that a strong hydrogen bond is formed between this anion and the phenolic H─O. Even the presence of water in the mixture of CABE-IL does not have a significant effect on the electrooxidation of the complex. Hence, it is possible to infer that CABE is more attached to [emim][AcO] than to the water molecules in the solvation sphere under the experimental conditions evaluated here. Other intermolecular interactions between CABE and IL also contribute to stabilize the resulting complex, e.g., van der Waals and cation-π interactions, which were evidenced through the theoretical noncovalent interactions (NCI) methodology. The relevant role of basic anions in the extraction of phenolic compounds, using ILs, has been documented in the literature; it should be considered that the strength of the hydrogen bond formed between the phenolic H─O and the IL should not contribute to the oxidation of target compounds.
- Pantoja-Hernández, Maurizio A.,Alemán-Vilis, Josué A.,Sánchez, Analilia,Salas-Reyes, Magali,López-Bonilla, Judith,Matus, Myrna H.,Domínguez, Zaira
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Read Online
- Bioinspired benzoxanthene lignans as a new class of antimycotic agents: synthesis and Candida spp. growth inhibition
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In this work we synthetized the bioinspired benzoxanthene lignans (BXLs) 3, 14–22, and the phenazine derivative 23 as potential antimycotic agents. MICs and MFCs against Candida strains were determined. In a preliminary screening, compounds 3, 15, 20, 21,
- Cardullo, Nunzio,Genovese, Carlo,Muccilli, Vera,Nicolosi, Daria,Pulvirenti, Luana,Tempera, Gianna,Tringali, Corrado
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p. 1653 - 1662
(2018/12/04)
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- Synthesis, DNA/RNA-interaction and biological activity of benzo[k,l]xanthene lignans
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Interactions of two newly synthesized and six previously reported benzoxanthene lignans (BXLs), analogues of rare natural products, with DNA/RNA, G-quadruplex and HSA were evaluated by a set of spectrophotometric methods. Presence/absence of methoxy and hydroxy groups on the benzoxanthene core and minor modifications at C-1/C-2 side pendants – presence/absence of phenyl ring and presence/absence of methoxy and hydroxy groups on phenyl ring – influenced the fluorescence changes and the binding strength to double-stranded (ds-) and G-quadruplex structures. In general, compounds without phenyl ring showed stronger fluorescence changes upon binding than phenyl-substituted BXLs. On the other hand, BXLs with an unsubstituted phenyl ring showed the best stabilization effects of G-quadruplex. Circular dichroism spectroscopy results suggest mixed binding mode, groove binding and partial intercalation, to ds-DNA/RNA and end-stacking to top or bottom G-tetrads as the main binding modes of BXLs to those targets. All compounds exhibited micromolar binding affinities toward HSA and an increased protein thermal stability. Moderate to strong antiradical scavenging activity was observed for all BXLs with hydroxy groups at C-6, C-9 and C-10 positions of the benzoxanthene core, except for derivative bearing methoxy groups at these positions. BXLs with unsubstituted or low-substituted phenyl ring and one derivative without phenyl ring showed strong growth inhibition of Gram-positive Staphylococcus aureus. All compounds showed moderate to strong tumor cell growth-inhibitory activity and cytotoxicity.
- ?una, Kristina,Brkanac, Sandra Radi?,Cardullo, Nunzio,Crnolatac, Ivo,Durgo, Ksenija,Glava?-Obrovac, Ljubica,Hu?ek, Ana,Juki?, Marijana,Muccilli, Vera,Pulvirenti, Luana,Stojkovi?, Marijana Radi?,Tringali, Corrado,Tumir, Lidija-Marija,Zonji?, Iva
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- Synthesis and characterization of CAPE derivatives as xanthine oxidase inhibitors with radical scavenging properties
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Inhibitors of the enzyme xanthine oxidase (XO) with radical scavenging properties hold promise as novel agents against reperfusion injuries after ischemic events. By suppressing the formation of damaging reactive oxygen species (ROS) by XO or scavenging ROS from other sources, these compounds may prevent a buildup of ROS in the aftermath of a heart attack or stroke. To combine these two properties in a single molecule, we synthesized and characterized the non-purine XO inhibitor caffeic acid phenethylester (CAPE) and 19 derivatives using a convenient microwave-assisted Knoevenagel condensation protocol. Varying systematically the number and positions of the hydroxyl groups at the two phenyl rings, we derived structure-activity relationships based on experimentally determined XO inhibition data. Molecular docking suggested that critical enzyme/inhibitor interactions involved π-π interactions between the phenolic inhibitor ring and Tyr914, hydrogen bonds between inhibitor hydroxyl groups and Glu802, and hydrophobic interactions between the CAPE phenyl ring and non-polar residues located at the entrance of the binding site. To effectively scavenge the stable radical DPPH, two hydroxyl groups in 1,2- or 1,4-position at the phenyl ring were required. Among all compounds tested, E-phenyl 3-(3,4-dihydroxyphenyl)acrylate, a CAPE analog without the ethyl tether, showed the most promising properties.
- Choi, Wonbeen,Villegas, Valente,Istre, Hannah,Heppler, Ben,Gonzalez, Niki,Brusman, Nicole,Snider, Lindsey,Hogle, Emily,Tucker, Janelle,O?ate, Alma,O?ate, Sandra,Ma, Lili,Paula, Stefan
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p. 686 - 695
(2019/03/05)
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- Synthesis of Diverse Hydroxycinnamoyl Phenylethanoid Esters Using Escherichia coli
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Caffeic acid phenethyl ester (CAPE) is an ester of a hydroxycinnamic acid (phenylpropanoid) and a phenylethanoid (2-phenylethanol; 2-PE), which has long been used in traditional medicine. Here, we synthesized 54 hydroxycinnamic acid-phenylethanoid esters by feeding 64 combinations of hydroxycinnamic acids and phenylethanols to Escherichia coli harboring the rice genes OsPMT and Os4CL. The same approach was applied for ester synthesis with caffeic acid and eight different phenyl alcohols. Two hydroxycinnamoyl phenethyl esters, p-coumaroyl tyrosol and CAPE, were also synthesized from glucose using engineered E. coli by introducing genes for the synthesis of substrates. Consequently, we synthesized approximately 393.4 mg/L p-coumaroyl tyrosol and 23.8 mg/L CAPE with this approach. Overall, these findings demonstrate that the rice PMT and 4CL proteins can be used for the synthesis of diverse hydroxycinnamoyl phenylethanoid esters owing to their promiscuity and that further exploration of the biological activities of these compounds is warranted.
- Song, Min Kyung,Cho, A Ra,Sim, Geunyoung,Ahn, Joong-Hoon
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p. 2028 - 2035
(2019/02/26)
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- A method for preparing coffee acid benzyl ester
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The invention discloses a coffee acid benzyl ester of preparation method, the overall steps are: a, the caffeic acid dissolved in organic solvent, the reaction is carried out by adding thionyl chloride, make intermediate A; b, alkali and the presence of o
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(2019/03/28)
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- Caffeic acid esters are effective bactericidal compounds against paenibacillus larvae by altering intracellular oxidant and antioxidant levels
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American Foulbrood (AFB) is a deadly bacterial disease affecting pupal and larval honey bees. AFB is caused by the endospore-forming bacterium Paenibacillus larvae (PL). Propolis, which contains a variety of organic compounds, is a product of bee foraging and is a resinous substance derived from botanical substances found primarily in trees. Several compounds from the class of caffeic acid esters, which are commonly found in propolis, have been shown to have antibacterial activity against PL. In this study, six different caffeic acid esters were synthesized, purified, spectroscopically analyzed, and tested for their activity against PL to determine the minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs). Caffeic acid isopropenyl ester (CAIE), caffeic acid benzyl ester (CABE), and caffeic acid phenethyl ester (CAPE) were the most effective in inhibiting PL growth and killing PL cell with MICs and MBCs of 125 μg/mL when used individually, and a MIC and MBC of 31.25 μg/mL for each compound alone when CAIE, CABE, and CAPE are used in combination against PL. These compounds inhibited bacterial growth through a bactericidal effect, which revealed cell killing but no lysis of PL cells after 18 h. Incubation with CAIE, CABE, and CAPE at their MICs significantly increased reactive oxygen species levels and significantly changed glutathione levels within PL cells. Caffeic acid esters are potent bactericidal compounds against PL and eliminate bacterial growth through an oxidative stress mechanism.
- Collins, William,Lowen, Noah,Blake, David J.
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- Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives
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The present study evaluates the antibacterial effects of a set of 16 synthesized caffeic acid ester derivatives against strains of Staphylococcus aureus and Escherichia coli, as well as discusses their structure-activity relationship (SAR). The antibacterial assays were performed using microdilution techniques in 96-well microplates to determine minimal inhibitory concentration (MIC). The results revealed that five of the compounds present strong to optimum antibacterial effect. Of the sixteen ester derivatives evaluated, the products with alkyl side chains, as propyl caffeate (3), butyl caffeate (6), and pentyl caffeate (7), presented the best antibacterial activity with MIC values of around 0.20 μM against Escherichia coli and only butyl caffeate (6) showing the same MIC against Staphylococcus aureus. For products with aryl substituents, the best MIC results against the tested strain of Escherichia coli were 0.23 μM for (di-(4-chlorobenzyl)) caffeate (13) and 0.29 μM for diphenylmethyl caffeate (10) and all were less active against the Staphylococcus aureus strain. Preliminary quantitative structure-activity relationship (QSAR) analyses confirmed that certain structural characteristics, such as a median linear carbon chain and the presence of electron withdrawal substituents at the para position of the aromatic ring, help potentiate antibacterial activity.
- Araújo, Marianna O.,Freire Pessoa, Hilzeth L.,Lira, Andressa B.,Castillo, Yunierkis P.,De Sousa, Dami?o P.
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- Synthesis and activity towards Alzheimer's disease in vitro: Tacrine, phenolic acid and ligustrazine hybrids
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A series of novel tacrine-phenolic acid dihybrids and tacrine-phenolic acid-ligustrazine trihybrids were synthesized, characterized and screened as novel potential anti-Alzheimer drug candidates. These compounds showed potent inhibition activity towards cholinesterases (ChEs), among of them, 9i was the most potent one towards acetylcholinesterase (eeAChE, IC50 = 3.9 nM; hAChE, IC50 = 65.2 nM). 9i could also effectively block β-amyloid (Aβ) self-aggregation with an inhibition ratio of 47% at 20 μM. In addition, its strong anti-oxidation activity could protect PC12 cells from CoCl2-damage in the experimental condition while no neurotoxicity. Furthermore, its hepatotoxicity was lower than tacrine in vitro and in vivo. Kinetic and molecular modeling studies revealed that 9i worked in a mixed-type way, could interact simultaneously with catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. Therefore, 9i was a promising multifunctional candidate for the treatment of AD.
- Li, Guoliang,Hong, Ge,Li, Xinyu,Zhang, Yan,Xu, Zengping,Mao, Lina,Feng, Xizeng,Liu, Tianjun
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p. 238 - 254
(2018/02/20)
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- Protective effect of caffeic acid derivatives on tert-butyl hydroperoxide-induced oxidative hepato-toxicity and mitochondrial dysfunction in HepG2 cells
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Oxidative stress results in structural and functional abnormalities in the liver and is thought to be a crucial factor in liver diseases. The aim of this study was to investigate the cytoprotective and antioxidant effects of caffeic acid (CA) derivatives
- Tsai, Tzung-Hsun,Yu, Chun-Hsien,Chang, Yu-Ping,Lin, Yu-Ting,Huang, Ching-Jang,Kuo, Yueh-Hsiung,Tsai, Po-Jung
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- Development of blood-brain barrier permeable nitrocatechol-based catechol O-methyltransferase inhibitors with reduced potential for hepatotoxicity
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Recent efforts have been focused on the development of centrally active COMT inhibitors, which can be valuable assets for neurological disorders such as Parkinson's disease, due to the severe hepatotoxicity risk associated with tolcapone. New nitrocatechol COMT inhibitors based on naturally occurring caffeic acid and caffeic acid phenethyl ester were developed. All nitrocatechol derivatives displayed potent inhibition of peripheral and cerebral COMT within the nanomolar range. Druglike derivatives 13, 15, and 16 were predicted to cross the blood-brain barrier in vitro and were significantly less toxic than tolcapone and entacapone when incubated at 50 μM with rat primary hepatocytes. Moreover, their unique acidity and electrochemical properties decreased the chances of formation of reactive quinone-imines and, as such, the potential for hepatotoxicity. The binding mode of 16 confirmed that the major interactions with COMT were established via the nitrocatechol ring, allowing derivatization of the side chain for future lead optimization efforts.
- Silva, Tiago,Mohamed, Tarek,Shakeri, Arash,Rao, Praveen P.N.,Martínez-Gonzalez, Loreto,Pérez, Daniel I.,Martínez, Ana,Valente, Maria Jo?o,Garrido, Jorge,Uriarte, Eugenio,Serr?o, Paula,Soares-Da-silva, Patrício,Remi?o, Fernando,Borges, Fernanda
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p. 7584 - 7597
(2016/09/04)
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- Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students
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We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.
- Chen, Hui-Zhen,Chen, You-Bao,Lv, Ya-Ping,Zeng, Fang,Zhang, Juan,Zhou, Yong-Lie,Li, Han-Bing,Chen, Li-Fei,Zhou, Bin-Jie,Gao, Jian-Rong,Xia, Chun-Nian
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p. 4367 - 4371
(2015/02/06)
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- Synthesis of caffeic acid phenethyl ester derivatives, and their cytoprotective and neuritogenic activities in PC12 cells
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Twenty-one caffeic acid phenethyl ester (CAPE) derivatives were synthesized, and characterized by IR, HR-MS, 1H and 13C NMR analyses. All compounds were evaluated for their cytoprotective effects against H2O2-induced cytotoxicity and neuritogenic activities in the neurite outgrowth in PC12 cells. Compounds 1 and 20 exhibited stronger cytoprotective activities than their parent compound CAPE at 4 nM. Compounds 1, 4, 12 and 13 showed potential neuritogenic activities at 0.5 nM, while compounds 19 and 20 induced neurite outgrowth at 10 nM. The results from this study suggested that CAPE and its derivatives may be potential functional food ingredients for the prevention of neurodegenerative diseases.
- Shi, Haiming,Xie, Dongsheng,Yang, Ruoling,Cheng, Yaqian
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p. 5046 - 5053
(2015/04/22)
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- Antiproliferative, antiandrogenic and cytotoxic effects of novel caffeic acid derivatives in LNCaP human androgen-dependent prostate cancer cells
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Caffeic acid and its naturally occurring derivative caffeic acid phenethyl ester (CAPE) have antiproliferative and cytotoxic properties in a variety of cancer cell lines without displaying significant toxicity toward healthy cells, and are considered to be potential anticancer agents. However, little is known about their effects on prostate cancer cells. We synthesized and evaluated the effects of caffeic acid, CAPE (2) and 18 synthetic derivatives on cell viability and androgen-dependent cell proliferation, subcellular localisation and expression of androgen receptor (AR) and secretion of prostate-specific antigen (PSA) in LNCaP human hormone-dependent prostate cancer cells. Several synthetic derivatives of CAPE were strong, concentration-dependent cytotoxic agents in LNCaP cells with IC50 values in the 6.8-26.6 μM range, potencies that were up to five-fold greater than that of CAPE (33.7 ± 4.0 μM). A number of caffeic acid derivatives were inhibitors of androgen-stimulated LNCaP cell proliferation with concomitant inhibition of DHT-stimulated PSA secretion. Compound 24 was the most cytotoxic and antiproliferative caffeic acid derivative (IC50 values of 6.8 ± 0.3 and 2.4 ± 0.8 μM, respectively) inhibiting DHT-stimulated cell proliferation and PSA secretion statistically significantly at concentrations as low as 0.3 μM. Exposure to DHT increased cytoplasmic and nuclear AR levels and co-treatment with increasing concentrations of compound 24 or CAPE (2), notably, further increased these levels. In conclusion, a number of synthetic derivatives of caffeic acid are potent inhibitors of androgen-dependent prostate cancer cell proliferation and viability, acting, at least in part, via an antiandrogenic mechanism that involves increased nuclear accumulation of (presumably inactive) AR.
- Sanderson, J. Thomas,Clabault, Hélène,Patton, Cody,Lassalle-Claux, Grégoire,Jean-Fran?ois, Jacques,Paré, Aurélie F.,Hébert, Martin J.G.,Surette, Marc E.,Touaibia, Mohamed
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p. 7182 - 7193
(2013/11/06)
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- DRUG DERIVATIVES
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The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.
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Paragraph 0252; 0259
(2013/09/12)
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- CAFFEIC ACID DERIVATIVES AND THEIR USE IN IMPROVING NEURONAL CELL VIABILITY
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This invention relates to caffeic acid derivatives and improving viability of neuronal cells by contacting neuronal cells by caffeic acid derivatives as shown in the specification.
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Page/Page column 3
(2012/06/01)
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- DRUG DERIVATIVES
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The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.
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Page/Page column 82
(2012/05/31)
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- Inhibitory effects of caffeic acid ester analogues on free radicals and human liver microsome CYP1A2 activities
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Ethyl caffeate (EC), octyl caffeate(OC), benzyl caffeate(BC) and phenethyl caffeate(PC) were synthesized and evaluated for scavenging of superoxide anion, nitric oxide radical and 1,1-diphenyl-1-picrylhydrazyl radical(DPPH). Antioxidant activity was inves
- Jaikang, Churdsak,Chaiyasut, Chaiyavat,Narongchai, Paitoon,Niwatananun, Kanokporn,Narongchai, Siripun,Kusirisin, Winthana
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- Evaluation of allergens in propolis by ultra-performance liquid chromatography/tandem mass spectrometry
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The purified extract of propolis is used as a traditional remedy for the treatment of several diseases. Its beneficial activities are mainly attributed to the polyphenolic fraction. Nevertheless, propolis can cause allergic dermatitis and the sensitization rate in humans is increasing significantly mainly in younger subjects. The aim of this study was to develop and validate a selective and sensitive ultra-performance liquid chromatography tandem mass spectrometry analysis (UPLC/MS/MS) for the evaluation of the amount of caffeic acid and its esters with allergenic action in raw propolis samples and commercial formulations. The separation was carried out on a 1.7 μm C 18 BEH Shield column and the detection performed by means of electrospray ionization in negative ion mode with multiple reaction monitoring. The confirmation of formulae of the precursor and product ions was accomplished by injection into a high-resolution system (FTICR-MS) using accurate mass measurements. The error was below 1.4 ppm.The range of the standard curves was 0.5-10 μg/mL and dihydrocaffeic acid was used as internal standard (IS). The lower limit of detection (LLOD) for 3-methyl-2-butenyl- (3M2B), 3-methyl-3-butenyl- (3M3B), 2-methyl-2-butenyl- (2M2B), benzyl- (CABE), phenylethylcaffeic acid (CAPE) and for caffeic acid (CA) and the IS was 0.1 and 0.3 μg/mL, respectively. The recoveries were in the range 96-104% and the intra- and inter-day precisions were within 6.2%. In the European (n = 8) and Asiatic (n = 3) propolis the most abundant allergens were CABE>3M2B> CAPE>3M3B>CA>2M2B. These compounds were not found in the red (n = 1) and green (n = 1) Brazilian propolis. Hydroalcoholic extracts (n = 6) and tablets (n = 6) were analyzed by the proposed UPLC/MS/MS method. The results showed that in the commercial products CABE, 3M2B, CAPE and 3M3B were also the most abundant.
- Gardana, Claudio,Simonetti, Paolo
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experimental part
p. 1675 - 1682
(2012/03/12)
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- CATECHOL-BASED DERIVATIVES FOR TREATING OR PREVENTING DIABETICS
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The present invention provides a catechol-based derivative and a pharmaceutical acceptable salt therefrom and a solvate therefrom. A pharmaceutical composition for preventing or treating diabetics and ischemics, comprising a catechol-based derivative of formula (I) and at least one selected from the group consisting of a pharmaceutical excipient, a diluent and a carrier.
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Page/Page column 3; 5
(2009/06/27)
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- Antinociceptive properties of caffeic acid derivatives in mice
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Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID50 value of 15.1 (11.9-19.1) μmol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental models, such as formalin, capsaicin and glutamate-induced pain tests, but was inactive in the hot-plate test. Although the mechanism of action has still not been elucidated, these results appear to support its therapeutic potential against painful diseases.
- de Campos Buzzi, Fatima,Franzoi, Caroline Liandra,Antonini, Graziele,Fracasso, Mauricio,Filho, Valdir Cechinel,Yunes, Rosendo Augusto,Niero, Rivaldo
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experimental part
p. 4596 - 4602
(2009/12/26)
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- Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
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Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 μM, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 μM for CAPE against BEL-7404.
- Xia, Chun-nian,Li, Hai-bo,liu, Feng,Hu, Wei-xiao
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supporting information; experimental part
p. 6553 - 6557
(2009/09/06)
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- Inhibitory effect of the alkyl side chain of caffeic acid analogues on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages
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Caffeic acid esters, one of the components of propolis, are known to show a variety of biological effects such as anti-tumor, anti-oxidant, and anti-inflammatory activities. Although, the anti-inflammatory activities of caffeic acid esters have been studi
- Uwai, Koji,Osanai, Yuu,Imaizumi, Takuma,Kanno, Syu-ichi,Takeshita, Mitsuhiro,Ishikawa, Masaaki
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p. 7795 - 7803
(2008/12/23)
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- Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L.
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Two new furanoflavonoids (1, 2), one new chalcone dimer (3) along with six known compounds, chrysophanol, 5-O-methyl squarrosin, 5-methoxy furano[4″,5″,6,7]flavone, calodenone, lophirone A and lophirone H were isolated from the ethyl acetate-soluble fraction of methanol extract of root bark of Ochna squarrosa. Chrysophanol, calodenone, lophirone A and lophirone H were isolated from this plant for the first time. The structures of all the isolated compounds were confirmed by 1D and 2D spectroscopic data. These compounds were tested for analgesic and anti-inflammatory activity. All the new compounds showed good analgesic and anti-inflammatory activity. A simple and facile method for the cleavage of benzyl ethers using I2 in trigol is also reported.
- Anuradha,Srinivas, Pullela V.,Ranga Rao,Manjulatha,Purohit, Muralidhar G.,Madhusudana Rao
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p. 6820 - 6826
(2007/10/03)
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- One-pot preparation of caffeic acid esters from 3,4-dihydroxybenzaldehyde
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A convenient one-pot process for preparing various esters of caffeic acid from 3,4-dihydroxybenzaldehyde has been developed. The alcohols or phenols react with Meldrum's acid to form malonic acid mono-esters, which, without separating, immediately react with 3,4-dihydroxybenzaldehyde to afford the desired esters in good yield. The 1H NMR data and X-ray diffraction analyses indicate that these α,β-unsaturated esters are in trans (E) form in accord with natural esters.
- Hu, Wei-Xiao,Xia, Chun-Nian,Wang, Guo-Hong,Zhou, Wei
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p. 586 - 588
(2007/10/03)
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- Synthesis of caffeic acid esters
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A new method for the preparation of caffeic acid esters was investigated. Ten caffeic acid esters were prepared by condensation of protocatechualdehyde with malonic acid mono-esters in moderate yield. Malonic acid mono-esters were prepared from the corresponding malonate di-esters. The conformations of compounds are trans (E) form.
- Xia, Chun-Nian,Hu, Wei-Xiao
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p. 332 - 334
(2007/10/03)
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- Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line
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Caffeic acid phenethyl ester (CAPE, 2) and its 20 analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02μM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10μg/mL towards murine colon 26-L5 carcinoma cells. Copyright
- Nagaoka, Takema,Banskota, Arjun H,Tezuka, Yasuhiro,Saiki, Ikuo,Kadota, Shigetoshi
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p. 3351 - 3359
(2007/10/03)
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- Mechanism of toxicity of esters of caffeic and dihydrocaffeic acids
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Ten esters each of caffeic acid and dihydrocaffeic acid have recently been synthesized. Cytotoxicity evaluations of these esters versus L1210 leukemia and MCF-7 breast cancer cells in culture have led to the delineation of substantially different QSAR for each series. The L1210 QSAR for dihydrocaffeic acid esters resembles the QSAR obtained for simple phenols and estrogenic phenols. However, the QSAR pertaining to the caffeic acid esters differs considerably from its sister QSAR. This difference may be attributed to the presence of the olefinic linkage in the side chain. The octyl ester of caffeic acid is nearly ten times as toxic to the leukemia cells than the widely studied phenethyl ester, CAPE.
- Etzenhouser, Beth,Hansch, Corwin,Kapur, Sanjay,Selassie
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p. 199 - 209
(2007/10/03)
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- Hydroxylated aromatic inhibitors of HIV-1 integrase
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Efficient replication of HIV-1 requires integration of a DNA copy of the viral genome into a chromosome of the host cell. Integration is catalyzed by the viral integrase, and we have previously reported that phenolic moieties in compounds such as flavones, caffeic acid phenethyl ester (CAPE, 2), and curcumin confer inhibitory activity against HIV-1 integrase. We now extend these findings by performing a comprehensive structure-activity relationship using CAPE analogues. Approximately 30 compounds have been prepared as HIV integrase inhibitors based on the structural lead provided by CAPE, which has previously been shown to exhibit an IC50 value of 7 μM in our integration assay. These analogues were designed to examine specific features of the parent CAPE structure which may be important for activity. Among the features examined for their effects on inhibitory potency were ring substitution, side chain length and composition, and phenyl ring conformational orientation. In an assay which measured the combined effect of two sequential steps, dinucleotide cleavage and strand transfer, several analogues have IC50 values for 3'-processing and strand transfer lower than those of CAPE. Inhibition of strand transfer was assayed using both blunt-ended and 'precleaved' DNA substrates. Disintegration using an integrase mutant lacking the N-terminal zinc finger and C-terminal DNA-binding domains was also inhibited by these analogues, suggesting that the binding site for these compounds resides in the central catalytic core. Several CAPE analogues were also tested for selective activity against transformed cells. Taken together, these results suggest that the development of novel antiviral agents for the treatment of acquired immune deficiency syndrome can be based upon inhibition of HIV-1 integrase.
- Burke Jr.,Fesen,Mazumder,Wang,Carothers,Grunberger,Driscoll,Kohn,Pommier
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p. 4171 - 4178
(2007/10/03)
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