- CESTRIC ACID, A CAFFEIC ACID ESTER FROM CESTRUM EUANTHES
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Cestric acid, a new phenolic ester was isolated from leaves of Cestrum euanthes.By means of GC, HPLC, mass spectroscopy, GC/MS, and 13C NMR, it was shown to be an ester of caffeic acid with glucaric acid.The ester occurs as an equilibrium mixture of four isomers.Key Word Index - Cestrum euanthes; Solanaceae; caffeic acid; glucaric acid; phenolic esters; isomers.
- Nagels, Luc,Dongen, Walter van,Parmentier, Frits
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- Synthesis of 4-O-Methylcedrusin. Selective protection of catechols with diphenyl carbonate
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4-O-Methylcedrusin, a minor component in 'sangre de drago', has been synthesized using a strategy of successive protection and deprotection reactions under very mild conditions. The key step of this synthesis is a selective protection of a catechol group
- Van Dyck, Stefaan M. O.,Lemiere, Guy L. F.,Jonckers, Tim H. M.,Dommisse, Roger
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- β-Lactoglobulin Peptide Fragments Conjugated with Caffeic Acid Displaying Dual Activities for Tyrosinase Inhibition and Antioxidant Effect
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The regulation of tyrosinase activity and reactive oxygen species is of great importance for the prevention of dermatological disorders in the fields of medicine and cosmetics. Herein, we report a strategy based on solid-phase peptide chemistry for the sy
- Yang, Jin-Kyoung,Lee, Eunjin,Hwang, In-Jun,Yim, Dabin,Han, Juhee,Lee, Yoon-Sik,Kim, Jong-Ho
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- Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wines
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On the basis of observations from Vitis vinifera cv. Pinotage wines and experiments performed in model wine medium, a new chemical pathway responsible for the formation of anthocyanin-vinylphenol adducts in red wines is described. Until now, these pigments have been considered to be reaction products of anthocyanins and vinylphenols, the latter being generated during fermentation by enzymatic decarboxylation of the respective cinnamic acids. The mechanism of the novel pathway, involving intact hydroxycinnamic acid and anthocyanin, is explained. Only cinnamic acids with electrondonating substituents on the aromatic ring, such as coumaric acid, ferulic acid, caffeic acid, and sinapic acid, undergo this conversion, as they stabilize an intermediately formed carbenium ion. Decarboxylation and oxidation of the pyran moieties are the final steps in the generation of the corresponding 4-vinylphenol, 4-vinylguaiacol, 4-vinylcatechol, and 4-vinylsyringol adducts of anthocyanins in red wine.
- Schwarz, Michael,Wabnitz, Tobias C.,Winterhalter, Peter
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- Mushroom Tyrosinase-Based Enzyme Inhibition Assays Are Not Suitable for Bioactivity-Guided Fractionation of Extracts
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Tyrosinase (Tyr) catalyzes the rate-limiting step of melanogenesis in human skin and is thus the main target for treating pigmentation disorders today. This has led to an increased research interest in Tyr inhibitors during the last decades, with a frequent focus on polyphenols. In the early stages of drug discovery, it is typical to avoid the high costs of human Tyr by using the more economic mushroom tyrosinase (mh-Tyr). Since some polyphenols are accepted as substrates by mh-Tyr, the present study aimed to more generally investigate this enzyme's specificity toward polyphenols and to discuss its significance in the context of bioactivity-guided fractionation. Mh-Tyr substrates can change the sample color during an inhibition assay, leading to unreliable inhibition constants or to the discontinuation of a bioactivity-guided fractionation campaign. A data set of 56 natural products was investigated and classified into assay interferers (AIs) and noninterferers, using a spectrophotometric and an LC-ESIHRMS assay. Based on these experimental findings, structure-activity relationships defining AIs were deduced and implemented into an in silico tool that will allow for rapid prescreening in the future. We anticipate that these results will aid in the search for new Tyr inhibitors and contribute to the understanding of this enzyme, as well as its optimal use in pharmacological research.
- Mayr, Fabian,Sturm, Sonja,Ganzera, Markus,Waltenberger, Birgit,Martens, Stefan,Schwaiger, Stefan,Schuster, Daniela,Stuppner, Hermann
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- Ultrasound irradiation accelerates the lipase-catalyzed synthesis of methyl caffeate in an ionic liquid
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Methyl caffeate is a natural ingredient with several biological activities, but its preparation is generally limited to chemical synthesis. To set up a simple, high-yield and low-cost synthesis process for obtaining methyl caffeate, a novel synthesis meth
- Wang, Jun,Wang, Shasha,Li, Zhongjian,Gu, Shuangshuang,Wu, Xiangyang,Wu, Fuan
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- Development of a clickable designer monolignol for interrogation of lignification in plant cell walls
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Lignin is an abundant and essential polymer in land plants. It is a prime factor in the recalcitrance of lignocellulosic biomass to agricultural and industrial end-uses such as forage, pulp and papermaking, and biofuels. To better understand lignifi catio
- Bukowski, Natalie,Pandey, Jyotsna L.,Doyle, Lucas,Richard, Tom L.,Anderson, Charles T.,Zhu, Yimin
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- Three new hemiterpene glycosides from Ilex macropoda
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Phytochemical studies of Ilex macropoda led to the isolation of three new hemiterpene glycosides, 4-β- D-glucopyranosyloxy-5-hydroxyprenyl caffeate (aohada-glycoside A), 5-caffeoyloxy-4-β-D-glucopyranosyloxy-prenyl alcohol (aohada-glycoside B), 4-(6-O-caffeoyl-β-D-glucopyranosyloxy)-5- hydroxyprenyl caffeate (aohada-glycoside C), together with betulin, acetyl ursolic acid, ilexosides XVII and XVIII, and 3,4,5-trimethoxyphenol β-D-5- O-caffeoyl-apiofuranosyl-(1→6)-β-D-glucopyranoside from the bark. Rotundioic acid, ursolic acid, ilexosides II and XXX, ziyu-glycoside I and rutin were also isolated from fresh leaves, and 3,5-dicaffeoylquinic acid and 3,4-dicaffeoylquinic acid from the wood.
- Fuchino, Hiroyuki,Tachibana, Hironori,Tanaka, Nobutoshi
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- PHENYLPROPANOID GLYCOSIDES OF PRUNUS SSIORI
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Two new bitter phenylpropanoid glucosides, 2-(3,4-methyllenedioxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside and 3-O-caffeoyl-β-D-fructofuranosyl, 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside, have been isolated together with the know compounds, 6-O-caffeoyl-D-glucopyranoside and 2-(3,4-dihydroxyphenyl)-ethyl-(6-O-caffeoyl)-β-D-glucopyranoside, from the bark of Prunus ssiori.The structures of the isolated compounds have been established by extensive spectroscopic studies. - Key words: Prunus ssiori; Rosaceae; bark; phenylpropanoid glucosides; caffeic acid esters.
- Abdallah, O. M.,Kamel, M. S.,Mohamed, M. H.
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- A study of the esterification of caffeic acid with methanol using p-toluenesulfonic acid as a catalyst
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Caffeic acid (CA) could be considered as an important natural antioxidant. However, the low solubility and stability of CA in various solvent systems is a major limiting factor governing its overall application in the lipid industry. However, the synthesi
- Wang, Jun,Gu, Shuangshuang,Pang, Na,Wang, Fangqin,Wu, Fuan
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- Electron-Transfer Reaction of Cinnamic Acids and Their Methyl Esters with the DPPH. Radical in Alcoholic Solutions
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The kinetic behavior of cinnamic acids, their methyl esters, and two catechols 1-10 (ArOH) in the reaction with DPPH. in methanol and ethanol is not compatible with a reaction mechanism that involves hydrogen atom abstraction from the hydroxyl
- Foti, Mario C.,Daquino, Carmelo,Geraci, Corrada
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- CARACTERISATION DE LA STICTICINE CHEZ LE LICHEN LOBARIA LAETEVIRENS
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Sticticin has been isolated from the thallus of Lobaria laetevirens.Its structure was determined by spectroscopic methods (NMR, MS) and comparison with a synthetic sample.It has been found in several spacies of the Stictaceae. - Key Word Index: Lobaria la
- Bernard, T.,Joucla, M.,Goas, G.,Hamelin, J.
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- Quinic acid derivatives from Pimpinella brachycarpa exert anti-neuroinflammatory activity in lipopolysaccharide-induced microglia
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Five new quinic acid derivatives (1-5), together with 10 known quinic acid derivatives (6-15), were isolated from the MeOH extract of Pimpinella brachycarpa (Umbelliferae). Their structures were established on the basis of spectroscopic analyses including extensive 2D NMR studies (COSY, HMQC and HMBC). Isolated compounds 1-15 were evaluated for their inhibitory activities on nitric oxide (NO) production in an activated murine microglial cell line. Compounds 2, 3, 8 and 11 significantly inhibited NO production without high cell toxicity in lipopolysaccharide (LPS)-activated BV-2 cells, a microglia cell line (IC50 = 4.66, 12.52, 9.04 and 12.11 μM, respectively).
- Lee, Seung Young,Moon, Eunjung,Kim, Sun Yeou,Lee, Kang Ro
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- Prenylated trans-cinnamic esters and ethers against clinical fusarium spp.: Repositioning of natural compounds in antimicrobial discovery
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Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 μM and 7.8–125 μM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.
- Balmas, Virgilio,Carta, Paola,Casalini, Stefano,Chtioui, Wiem,Delogu, Giovanna,Dettori, Maria A.,Fabbri, Davide,Migheli, Quirico,Oufensou, Safa
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- Phenyl glycosides from the leaves of Flacourtia indica (Burm. f.) Merr (Salicaceae)
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Thirteen phenolic glycosides, together with fourteen various known compounds, were isolated from the methanolic extract of leaves of Flacourtia indica. Twelve of these were composed of gentisyl or salicyl alcohols, glycosylated on the phenol and acylated on the primary alcohol with various more or less oxidized forms of pyrocatechuic acid. A number of positions on the glucose or on the acid were further acylated by benzoic or cinnamic acid. In addition to these, a glucoside of a phenyl propanoid was also isolated. The gross structures were elucidated by spectroscopic means including 1D and 2D NMR experiments and HR-ESI-MS analyses. Several of these structures, for example, xylosmin, were previously described but it proved extremely difficult to conclude on their exact identity with the absence of clear data on absolute configuration in the literature.
- Lavaud, Catherine,Massiot, Georges,Nguyen, Phuc-Dam,Sayagh, Charlotte
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- METHOD FOR PRODUCING CINNAMIC ACID ESTER COMPOUND
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A method for producing a cinnamic acid ester derivative includes reacting a cinnamic acid derivative compound represented by the formula (1), wherein the symbols are as defined in the description, with an alcohol compound represented by the formula: R6OH, wherein the symbol is as defined in the description, in the presence of a strong acid resin catalyst without using a solvent. As the cinnamic acid derivative compound, cinnamic acid, ferulic acid, and caffeic acid are preferred, and as the alcohol compound, methanol, ethanol, propanol, butanol, pentanol, hexanol, ethylene glycol, glycerol, phenethyl alcohol, and a monosaccharide are preferred.
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Paragraph 0066-0067; 0071; 0075
(2020/05/06)
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- Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
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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.
- Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
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- Crystal engineering construction of caffeic acid derivatives with potential applications in pharmaceuticals and degradable polymeric materials
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Natural products are precious feedstock in drug discovery and sustainable materials. This work using crystal engineering strategy, visible light, and solvent-free cycloaddition successfully constructed two caffeic acid derivatives, rel-(1R,2R,3S,4S)-2,4-b
- Flores, Quinton,Guo, Hongye,Trevizo, Raquel,Wang, Shihan,Wang, Zhihan,Zhang, Xiaochan
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p. 7847 - 7857
(2020/12/04)
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- Novel fluorozoone-like fluorinion probe based on flavonoids
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The invention discloses a preparation method of a novel fluorozoone-like visible fluorinion probe which is prepared from flavonoids of a formula I shown in the description and a 3-phenylacrylic acid type derivative. The preparation method comprises the fo
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Paragraph 0029; 0030
(2020/02/06)
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- Study on the formation of antihypertensive twin drugs by caffeic acid and ferulic acid with telmisartan
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Purpose: This study aimed to synthesize twin drugs from cinnamic acid compounds, caffeic acid (CFA) and ferulic acid (FLA), which can antagonize endothelin-1 (ET-1) with telmisartan through ester bonds. Moreover, the antihypertensive effect of telmisartan and its influence on blood pressure variability (BPV) were enhanced, and the bioavailability of caffeic acid and ferulic acid was improved. Methods: Six twin drugs, which were the target compounds, were synthesized. Hypertensive rats (SHR) and conscious sinoaortic-denervated (SAD) rats were spontaneously used as models for pharmacodynamic research to study the antihypertensive efficacy of these twin drugs. Wistar rats were employed as pharmacokinetic research models to investigate the pharmacokinetics of the target compounds via intragastric administration. Cellular pharmacodynamic research was also conducted on the antagonistic action on Ang II-AT1, ETA and ETB receptor. Results: Compound 1a was determined as the best antihypertensive twin drug and thus was further studied for its effect on BPV. Compared with that of telmisartan, the antihypertensive effect of compound 1a was improved (p50 of Lps-2 was still two orders of magnitude higher than that of the positive drug telmisartan. Hence, the twin drugs worked by metabolizing and regenerating telmisartan and caffeic acid or ferulic acid in the body. Conclusion: The synthesized twin drugs improved telmisartan’s antihypertensive effects, significantly decreased BPV in SAD rats and increased the bioavailability of caffeic acid and ferulic acid. This study serves as a basis for the development of new angiotensin receptor blocker (ARB) in the future and a reference for the development of new drugs to antagonize ET-1.
- Li, Pengshou,Li, Ziyong,Ma, Qixiang,Peng, Yingying,Zhang, Xiaohua
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p. 977 - 992
(2020/03/13)
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- Coumaric acid derivatives as tyrosinase inhibitors: Efficacy studies through in silico, in vitro and ex vivo approaches
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p-Coumaric acid is a known inhibitor of tyrosinase, an enzyme involved in the initial steps of the melanin synthesis in human and other species. However, its low lipophilicity impairs its penetration through skin and efficacy as antimelanogenic agent indeed. Accordingly, this paper reports the assessment of several coumaric acid derivatives as tyrosinase inhibitors and antimelanogenic agents in in vitro, in silico and ex vivo assays. The compounds were designed with modifications in the aromatic and acid moieties of p-coumaric acid, being the coumarate esters the most promising derivatives. The compounds showed higher tyrosinase inhibitory activity (pIC50 3.7–4.2) than the parent acid, being compounds 1d, 1e and 1f the most potent inhibitors. Docking analysis showed that these esters are competitive inhibitors per se, and act independently of a redox mechanism as suggested by DPPH assays. Moreover, the esters showed efficacy in reducing the melanin deposition in human skin fragments at 0.1% concentration, especially compound 1e. In summary, there is an important equilibria between tyrosinase affinity and lipophilicity that must be considered to get effective antimelanogenic agents with adequate permeability in the skin.
- Fernandes, Jo?o Paulo S.,Ferrarini, Márcio,Mercaldi, Vitória Gallo,Nazato, Lucas Idacir Sbrugnera,Padovani, Giovana,Sufi, Bianca da Silva,Varela, Marina Themoteo
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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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- Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal
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Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.
- Sang, Dayong,Yue, Huaxin,Zhao, Zhengdong,Yang, Pengtao,Tian, Juan
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p. 6429 - 6440
(2020/07/14)
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- Selective ether bond breaking method of aryl alkyl ether
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The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.
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Paragraph 0081-0091
(2020/09/16)
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- A New Series of Salicylic Acid Derivatives as Non-saccharide α-Glucosidase Inhibitors and Antioxidants
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In this study, a series of salicylic acid derivatives were designed and synthesized as novel non-saccharide α-glucosidase inhibitors. Biological evaluation indicated that when compared to acarbose, compounds T9, T10, and T32 exhibited a higher potency of α-glucosidase inhibitory activity with IC50 values of 0.15±0.01, 0.086±0.01 and 0.32±0.02mM, respectively. Evaluation of the inhibition kinetics indicated that T9, T10, T32, and acarbose interacted with α-glucosidase in a mixed non-competitive inhibitory manner. Moreover, T9, T10, and T32 statically quenched the fluorescence of α-glucosidase by formation of an inhibitor-α-glucosidase complex. The docking results showed that hydrogen bonds were generated between the test compounds and α-glucosidase. The antioxidant study revealed that compound T10 exhibited a higher antioxidant activity via scavenging 1,1-diphenyl-2-picrylhydrazyl free radical (DPPH), thereby inhibiting lipid peroxidation and the total reduction capacity. In brief, the salicylic acid derivatives identified in this study were promising candidates for development as novel non-saccharide α-glucosidase inhibitors.
- Chen, Jiangang,Lu, Wenfang,Chen, Hao,Bian, Xiaoli,Yang, Guangde
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p. 231 - 246
(2019/02/19)
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- The first total synthesis of (±)-methyl salvianolate A using a convergent strategy
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Herein, a convergent, practicable and first total synthesis of the natural product, (±)-methyl salvianolate A, is reported. The key features of the approach are the use of a Horner–Wadsworth–Emmons reaction and the protection of multiple hydroxyls using s
- Wang, Bo,Wang, Liping,Peng, Ying,Pang, Yiying,Xiao, Hesheng,Wang, Xiaoji,Huang, Shuangping
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- Colorimetric and ratiometric sensors derivated from natural building blocks for fluoride ion detection
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Three novel colorimetric and ratiometric probes (SH-1~3) for fluoride ion detection were designed and synthesized from nature small molecules. Obvious yellow-to-orange color change of these probes in the THF was achieved only in presence of F?
- Shi, Heng,Zhao, Fengfei,Chen, Xinghan,Yang, Shilong,Xing, Jieni,Chen, Hongjin,Zhang, Rui,Liu, Jian
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supporting information
(2019/11/03)
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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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- Antioxidant-Inspired Drug Discovery: Antitumor Metabolite Is Formed in Situ from a Hydroxycinnamic Acid Derivative upon Free-Radical Scavenging
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Cancer cells generally possess higher levels of reactive oxygen species than normal cells, and this can serve as a possible therapeutic target. In this proof-of-concept study, an antioxidant-inspired drug discovery strategy was evaluated using a hydroxycinnamic acid derivative. The processing of oxidized mixtures of p-coumaric acid methyl ester (pcm) revealed a new antitumor lead, graviquinone. Graviquinone bypassed ABCB1-mediated resistance, induced DNA damage in lung carcinoma cells but exerted DNA protective activity in normal keratinocytes, and modulated DNA damage response in MCF-7 cells. The cytotoxic effect of pcm in MCF-7 cells was potentiated under H2O2-induced oxidative stress, and the formation of graviquinone was confirmed by Fenton's reaction on pcm. In silico density functional theory calculations suggested graviquinone as a kinetic product of pcm-scavenging ?OH radicals. Our results demonstrate the pharmacological value of an in situ-formed, oxidative stress-related metabolite of an antioxidant. This might be of particular importance for designing new strategies for antioxidant-based drug discovery.
- Fási, Laura,Di Meo, Florent,Kuo, Ching-Ying,Stojkovic Buric, Sonja,Martins, Ana,Kúsz, Norbert,Béni, Zoltán,Dékány, Miklós,Balogh, Gy?rgy Tibor,Pesic, Milica,Wang, Hui-Chun,Trouillas, Patrick,Hunyadi, Attila
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p. 1657 - 1668
(2019/02/24)
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- Antifungal activity of cinnamic acid and benzoic acid esters against Candida albicans strains
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Candida albicans is an important opportunistic fungal pathogen capable of provoking infection in humans. In the present study, we evaluated the antifungal effect of 23 ester derivatives of the cinnamic and benzoic acids against 3 C. albicans strains (ATCC-76645, LM-106 and LM-23), as well as discuss their Structure–Activity Relationship (SAR). The antifungal assay results revealed that the screened compounds exhibited different levels of activity depending on structural variation. Among the ester analogues, methyl caffeate (5) and methyl 2-nitrocinnamate (10) were the analogues that presented the best antifungal effect against all C. albicans strains, presenting the same MIC values (MIC?=?128?μg/mL), followed by methyl biphenyl-2-carboxylate (21) (MIC?=?128, 128 and 256?μg/mL for C. albicans LM-106, LM-23, and ATCC-76645, respectively). Our results suggest that certain molecular characteristics are important for the antifungal action.
- Lima, Tamires C.,Ferreira, Alana R.,Silva, Daniele F.,Lima, Edeltrudes O.,de Sousa, Dami?o P.
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p. 572 - 575
(2017/09/30)
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- Enzymatic Synthesis and Antioxidant Activity of 1-Caffeoylglycerol Prepared from Alkyl Caffeates and Glycerol
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Caffeic acid (CA) as a strong antioxidant has lower solubility in nonpolar media, which limits its application in the food industry. To increase the lipophilicity of CA, 1-caffeoylglycerol (1-CG) was synthesized by lipase-catalyzed transesterification of
- Meng, Xiang-Yun,Xu, Yan,Wu, Jin-Xian,Zhu, Chang-Tong,Zhang, Dong-Yang,Wu, Guo-Hua,Wu, Fu-An,Wang, Jun
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p. 149 - 159
(2018/03/21)
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- In-vitro and in-vivo antimalarial activity of caffeic acid and some of its derivatives
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Objectives: To explore the in-vitro and in-vivo antimalarial potential of caffeic acid and derivatives. Methods: Two common phenolic acids (caffeic acid and chlorogenic acid) were evaluated for in-vitro and in-vivo antiplasmodial activity in comparison with some semi-synthetic derivatives that were synthesized. An in-vitro assay based on plasmodial lactate dehydrogenase activity, and the classical in-vivo 5-day suppressive test from Peters on an artemisinin-resistant Plasmodium berghei strain was used. Parasitic stage sensitivity to ethyl caffeate was determined in this work. Key findings: Phenolic acid esters derivatives showed better antiplasmodial activity than corresponding phenolic acids. The derivative with the highest in-vitro activity being caffeic acid ethyl ester, exhibiting an IC50?=?21.9?±?9.4?μm. Ethyl caffeate and methyl caffeate were then evaluated for antimalarial activity in?vivo and ethyl caffeate showed a growth inhibition of 55% at 100?mg/kg. Finally, it seems that ethyl caffeate blocks the growth of young parasitic forms. Conclusions: Our study provides evidence for an antimalarial potential of caffeic acid derivatives which are common in several medicinal plants traditionally used against malaria. It also demonstrates the possibility to use such derivatives in the treatment of malaria.
- Alson, Sylvain G.,Jansen, Olivia,Cieckiewicz, Ewa,Rakotoarimanana, Hajatiana,Rafatro, Herintsoa,Degotte, Gilles,Francotte, Pierre,Frederich, Michel
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p. 1349 - 1356
(2018/07/31)
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- Differential Partitioning of Bioantioxidants in Edible Oil-Water and Octanol-Water Systems: Linear Free Energy Relationships
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Partition coefficients, PWO, of antioxidants (AOs) between edible oils and water are scarce in the literature, despite that AOs are widely used to control lipid oxidation and the oxidative stress in cells. PWO values have a great importance to predict the efficiency and distribution of bioactives at different levels of biological organization from binary oil-water systems to living cells. Here, we determined the partition coefficients, PWO, of four series of potent, natural AOs of increasing lipophilicity between vegetable oils (olive, soybean, and corn) and water and, for the sake of comparison, between octanol-water, PWOCT. Results indicate that the contribution of the -CH2 groups to the overall lipophilicity of the AO is the same irrespective of the oil employed. The PWO values were compared with PWOCT values, and linear relationships were obtained for each series of AOs. Results indicate that, in general, PWO values cannot be predicted from the PWOCT values, making necessary to determine the PWO values for each oil and antioxidant.
- Freiría-Gándara,Losada-Barreiro,Paiva-Martins,Bravo-Díaz
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p. 2999 - 3007
(2018/08/31)
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- Method for synthesizing natural product salvianolic acid A methyl ester
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The invention relates to a novel method for synthesizing natural product salvianolic acid A methyl ester. A synthetic route is unique and novel in design; key strategies and steps comprise the step of using an easily-removed t-butyldimethylsilyl protectin
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Paragraph 0097; 0098; 0099; 0100
(2017/07/20)
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- Structure–activity relationship of caffeic acid phenethyl ester analogs as new 5-lipoxygenase inhibitors
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Leukotrienes (LTs) are a class of lipid mediators implicated in numerous inflammatory disorders. Caffeic acid phenethyl ester (CAPE) possesses potent anti-LTs activity through the inhibition of 5-lipoxygenase (5-LO), the key enzyme in the biosynthesis of LTs. In this study, we describe the design and synthesis of CAPE analogs as radical scavengers and 5-LO inhibitors. Caffeic esters bearing propargyl and allyl linkers between the caffeoyl and aryl moieties (4a–i and 5a–i, respectively) were synthesized by Sonogashira and Heck cross-coupling reactions to probe the effects of flexibility and aryl substitution on 5-LO inhibition. Caffeoyl alcohol and ethers (6, 7a–b) as well as caffeoyl aldehyde and ketones (8a–e) were synthesized to elucidate the importance of the ester linkage for inhibitory activity. All tested compounds proved to be good radical scavengers (IC50 of 10–30?μm). After preliminary anti-LTs activity screening in HEK293 cell models, 5-LO inhibition potential of selected compounds was determined in human polymorphonuclear leukocytes (PMNL). Most screened compounds outperformed CAPE 3 in concentration-dependent assays on PMNL, with ester dimers 4i and 5i along with caffeoyl ethers 7a–b being roughly eight-, seven-, and 16-fold more potent than Zileuton, with IC50 values of 0.36, 0.43, and 0.18?μm, respectively.
- Doiron, Jérémie A.,Leblanc, Luc M.,Hébert, Martin J. G.,Levesque, Natalie A.,Paré, Aurélie F.,Jean-Fran?ois, Jacques,Cormier, Marc,Surette, Marc E.,Touaibia, Mohamed
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p. 514 - 528
(2017/04/06)
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- New sulfurated derivatives of cinnamic acids and rosmaricine as inhibitors of STAT3 and NF-κB transcription factors
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A set of new sulfurated drug hybrids, mainly derived from caffeic and ferulic acids and rosmaricine, has been synthesized and their ability to inhibit both STAT3 and NF-κB transcription factors have been evaluated. Results showed that most of the new hybr
- Gabriele, Elena,Brambilla, Dario,Ricci, Chiara,Regazzoni, Luca,Taguchi, Kyoko,Ferri, Nicola,Asai, Akira,Sparatore, Anna
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p. 1012 - 1028
(2017/08/26)
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- Structure and urease inhibitory activity of copper(II) complex with (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylic acid
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A new caffeic acid derivative ((E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylic acid, HL1)) is synthesized from caffeic acid, followed by the preparation of a Cu(II) complex, [Cu2(L1)4DMSO2]·2DMSO.
- Chen,Wang,Kong,Li,Zhou,Zhang,Sheng,Zhu
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p. 797 - 803
(2017/09/25)
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- Structure–activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties
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Amyloid-β aggregation inhibitors are expected to be therapeutic or prophylactic agents for Alzheimer's disease. Rosmarinic acid, which is one of the main aggregation inhibitors derived from Lamiaceae, was employed as a lead compound and its 25 derivatives were synthesized. In this study, the structure–activity relations of rosmarinic acid derivatives for the amyloid-β aggregation inhibitory effect (MSHTS assay), antioxidant properties, and xanthine oxidase inhibition were evaluated. Among the tested compounds, compounds 16d and 19 were found to the most potent amyloid aggregation inhibitors. The SAR revealed that the necessity of the presence of the phenolic hydroxyl on one side of the molecule as well as the lipophilicity of the entire molecule. The importance of these structural properties was also supported by docking simulations.
- Taguchi, Riho,Hatayama, Koki,Takahashi, Tomohito,Hayashi, Takafumi,Sato, Yuki,Sato, Daisuke,Ohta, Kiminori,Nakano, Hiroto,Seki, Chigusa,Endo, Yasuyuki,Tokuraku, Kiyotaka,Uwai, Koji
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supporting information
p. 1066 - 1075
(2017/08/02)
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- New Hydroxycinnamic Acid Esters as Novel 5-Lipoxygenase Inhibitors That Affect Leukotriene Biosynthesis
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Leukotrienes are inflammatory mediators that actively participate in the inflammatory response and host defense against pathogens. However, leukotrienes also participate in chronic inflammatory diseases. 5-lipoxygenase is a key enzyme in the biosynthesis
- Boudreau, Luc H.,Lassalle-Claux, Grégoire,Cormier, Marc,Blanchard, Sébastien,Doucet, Marco S.,Surette, Marc E.,Touaibia, Mohamed
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- Ethyl acetate as a co-solvent and sacrificial ester in the aluminum triiodide promoted chemoselective demethylation of methyl vanillate
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A synthetic approach towards methyl protocatechuate via chemoselective ether cleavage of methyl vanillate without affecting the carboxylate group is disclosed utilizing a ternary reagent system consisting of aluminum triiodide, 1,3-diisopropylcarbodiimide and ethyl acetate. Ethyl acetate serves as a co-solvent and sacrificial ester. Methyl isovanillate, ethyl vanillate and methyl feruate were analogously demethylated to give methyl protocatechuate, ethyl protocatechuate and methyl caffeate, respectively, in fair to excellent yields.
- Tian, Juan,Yi, Cuicui,Fang, Huasheng,Sang, Dayong,He, Zhoujun,Wang, Jiahui,Gan, Yongjiang,An, Qing
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supporting information
p. 3522 - 3524
(2017/10/06)
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- Palladium nanoparticles immobilized on amphiphilic and hyperbranched polymer-functionalized magnetic nanoparticles: An efficient semi-heterogeneous catalyst for Heck reaction
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To address the obstacles facing the use of palladium-based homogeneous and heterogeneous catalysts in C─C cross-coupling reactions, a novel semi-heterogeneous support was developed based on hyperbranched poly(ethylene glycol)-block-poly(citric acid)-functionalized Fe3O4 magnetic nanoparticles (Fe3O4@PCA-b-PEG). Because of the surface modification of the Fe3O4 nanoparticles with amphiphilic and hyperbranched polymers (PCA-b-PEG), these hybrid materials are not only soluble in a wide range of solvents (e.g. water, ethanol and dimethylformamide) but also are able to trap Pd2+ ions via complex formation of free carboxyl groups of the PCA dendrimer with metal ions. The reduction of trapped palladium ions in the dendritic shell of Fe3O4@PCA-b-PEG leads to immobilized palladium nanoparticles. The morphology and structural features of the catalyst were characterized using various microscopic and spectroscopic techniques. The catalyst was effectively used in the palladium-catalysed Mizoroki–Heck coupling reaction in water as a green solvent. In addition, the catalyst can be easily recovered from the reaction mixture by applying an external magnetic field and reused for more than ten consecutive cycles without much loss in activity, exhibiting an example of a sustainable and green methodology.
- Tabatabaei Rezaei, Seyed Jamal,Shamseddin, Azin,Ramazani, Ali,Mashhadi Malekzadeh, Asemeh,Azimzadeh Asiabi, Pegah
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- Stereoselective synthesis of peracetylated (?)-gloeosporiol via acid catalysed intramolecular etherification
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A simple and an efficient strategy have been developed for the stereoselective synthesis of peracetylated (?)-gloeosporiol by acid catalysed cyclisation from the commercially available starting materials.
- Dorigundla, Aravind Reddy,Gurrapu, Raju,Batchu, Venkateswara Rao
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supporting information
p. 563 - 565
(2017/01/16)
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- Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol
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Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.
- Konrádová, Daniela,Kozubíková, Hana,Dole?al, Karel,Pospí?il, Ji?í
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supporting information
p. 5204 - 5213
(2017/09/29)
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- Synthesis, antifungal activity of caffeic acid derivative esters, and their synergism with fluconazole and nystatin against Candida spp.
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We tested the antifungal potential of caffeic acid and 8 of its derivative esters against Candidaalbicans ATCC 90028 and 9 clinical isolatesand carried out a synergism assay with fluconazole and nystatin. Propyl caffeate (C3) showed the best antifungal ac
- Sardi, Janaína de Cássia Orlandi,Gullo, Fernanda Patrícia,Freires, Irlan Almeida,Pitangui, Nayla de Souza,Segalla, Maicon Petr?nio,Fusco-Almeida, Ana Marisa,Rosalen, Pedro Luiz,Regasini, Luís Octávio,Mendes-Giannini, Maria José Soares
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p. 387 - 391
(2016/11/13)
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- Optimizing the efficiency of antioxidants in emulsions by lipophilization: Tuning interfacial concentrations
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Optimization of the efficiency of antioxidants, AOs, in lipid-based emulsions via chemical modifications of their reactive moieties is not always possible because of the inherent experimental difficulties and because of the regulatory status of AOs. Esterification of hydrophilic AOs may be a practical, convenient, alternative approach. Here we employed a series of caffeic acid derivatives bearing the same reactive moiety but of different hydrophobicity (alkyl chain lengths of 1 to 16 carbon atoms) to investigate the effects of hydrophobicity on the oxidative stability of stripped corn oil-in-water emulsions. AO efficiency was determined by monitoring the production of primary oxidation products (conjugated dienes) with time and a non-linear, parabolic-like, variation of their efficiency with the number of C atoms in their alkyl chain, with a maximum at the C8 derivative, found. To rationalize the results, we also determined the distribution of the AOs between the oil, interfacial and aqueous regions of the same emulsions by employing a recently developed kinetic method that provides the partition constants of the AO between the oil-interfacial, PIO, and water-interfacial, PIW, regions of the intact emulsions. Values of both PIO and PIW range between 180-2000, suggesting that the transfer of the AOs to the interfacial region is spontaneous. The results indicate that the variations of both the percentage of AO in the interfacial region, % AOI, of the emulsions and the AO efficiency with the number of C atoms in the AO alkyl chain parallel each other with a maxima at the C8 derivative. The results illustrate an effective and convenient way to control lipid oxidation by modulation of the hydrophobicity (HLB) of the AOs. An increase in the alkyl chain length of the AOs promote their incorporation into the interfacial region of emulsions but only up to a critical chain length, after which a further increase makes their efficiency decrease as a consequence of the decrease in their % AOI.
- Costa, Marlene,Losada-Barreiro, Sonia,Paiva-Martins, Fátima,Bravo-Díaz, Carlos
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p. 91483 - 91493
(2016/10/09)
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- Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold
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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.
- 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
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p. 926 - 937
(2016/11/11)
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- Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD
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A new strategy for treating Pseudomonas aeruginosa infections could be disrupting the Pseudomonas Quinolone Signal (PQS) quorum sensing (QS) system. The goal is to impair communication among the cells and, hence, reduce the expression of virulence factors and the formation of biofilms. PqsD is an essential enzyme for the synthesis of PQS and shares some features with chalcone synthase (CHS2), an enzyme expressed in Medicago sativa. Both proteins are quite similar concerning the size of the active site, the catalytic residues and the electrostatic surface potential at the entrance of the substrate tunnel. Hence, we evaluated selected substrates of the vegetable enzyme as potential inhibitors of the bacterial protein. This similarity-guided approach led to the identification of a new class of PqsD inhibitors having a catechol structure as an essential feature for activity, a saturated linker with two or more carbons and an ester moiety bearing bulky substituents. The developed compounds showed PqsD inhibition with IC50 values in the single-digit micromolar range. The binding mode of these compounds was investigated by Surface Plasmon Resonance (SPR) experiments revealing that their interaction with the protein is not influenced by the presence of the anthranilic acid bound to active site cysteine. Importantly, some compounds reduced the signal molecule production in cellulo.
- Allegretta, Giuseppe,Weidel, Elisabeth,Empting, Martin,Hartmann, Rolf W.
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p. 351 - 359
(2015/02/19)
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- Efficient and versatile synthesis of 5-O-acylquinic acids with a direct esterification using a p-methoxybenzyl quinate as a key intermediate
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An efficient and versatile synthesis of 5-O-acylquinic acids from commercially available (-)-quinic acid was accomplished. We designed p-methoxybenzyl quinate as a key intermediate, and two problems, the esterification of the sterically hindered 5-OH group for the concise divergent synthesis and the low yield of the final deprotection step, were solved. For the first problem, we improved Tanabe's method, TsCl/NMI-mediated esterification using free carboxylic acids, by the addition of i-Pr2NEt. For the second problem, we established a TFA- or BCl3/C6HMe5-catalyzed deprotection reaction for the final deprotection step. 5-O-Acylquinic acids were synthesized in seven steps with 45-60% overall yield.
- Oyama, Kin-Ichi,Watanabe, Noriyuki,Yamada, Tomomi,Suzuki, Masako,Sekiguchi, Yukiko,Kondo, Tadao,Yoshida, Kumi
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p. 3120 - 3130
(2015/05/04)
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- Design and synthesis of novel aspirin-caffeic acid ester hybrids for cardioprotection with reduced risk of hemorrhagic stroke
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A series of novel aspirin-caffeic acid ester hybrids for cardioprotection with reduced risk of hemorrhagic stroke were designed and synthesized by coupling aspirin and caffeic acid esters inspired by NCX-4016. The synthesized compounds were evaluated for
- Shi, Zhi-Hao,Li, Nian-Guang,Tang, Yu-Ping,Shi, Qian-Ping,Zhang, Wei,Zhang, Peng-Xuan,Dong, Ze-Xi,Li, Wei,Duan, Jin-Ao
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p. 1342 - 1346
(2016/06/13)
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- Chemo and regioselective serendipitous electrochemically initiated spirocyclization of caffeic acid esters with barbituric acid derivatives
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An interesting sequence of oxidation/Michael addition/oxidation/spirocyclization is observed in the electrolysis of caffeic acid esters in the presence of barbituric acid derivatives leading to the synthesis of a series of novel spirocycles. In an experim
- Alizadeh, Abdolhamid,Khodaei, Mohammad Mehdi,Fakhari, Mitra,Abdi, Gisya,Ghouzivand, Sohrab
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p. 533 - 540
(2015/09/01)
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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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- A highly efficient transformation of cis- to trans-cinnamic acid derivatives by iodine
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Cinnamic acid derivatives (CAs), which have proven to be versatile components, are present in abundance in biologically active natural products, and are widely used as intermediates in the manufacture of pharmaceuticals, and chemicals. The presence of cis- and trans-CAs created difficulties for natural product and organic synthetic studies. A highly efficient method that utilized iodine to entirely convert cis- CAs into their trans-forms was developed to solve this problem. The mechanism of study revealed this conversion occurred via an anti-diiodo intermediate.
- Li, Zhen-Jie,Cai, Le,Mei, Rui-Feng,Dong, Jian-Wei,Li, Shu-Quan,Yang, Xue-Qiong,Zhou, Hao,Yin, Tian-Peng,Ding, Zhong-Tao
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supporting information
p. 7197 - 7200
(2015/12/12)
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- Efficient and magnetically recoverable "click" PEGylated γ-Fe2O3-Pd nanoparticle catalysts for Suzuki-Miyaura, Sonogashira, and Heck reactions with positive dendritic effects
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The engineering of novel catalytic nanomaterials that are highly active for crucial carbon-carbon bond formations, easily recoverable many times, and biocompatible is highly desirable in terms of sustainable and green chemistry. To this end, catalysts comprising dendritic "click" ligands that are immobilized on a magnetic nanoparticle (MNP) core, terminated by triethylene glycol (TEG) groups, and incorporate Pd nanoparticles (PdNPs) have been prepared. These nanomaterials are characterized by transmission electron microscopy (TEM), high-resolution TEM, inductively coupled plasma analysis, Fourier transform infrared spectroscopy, X-ray photoelectron spectra and energy-dispersive X-ray spectroscopy. They are shown to be highly active, dispersible, and magnetically recoverable many times in Suzuki, Sonogashira, and Heck reactions. In addition, a series of pharmacologically relevant or natural products were successfully synthesized using these magnetic PdNPs as catalyst. For comparison, related PdNP catalysts deposited on MNPs bearing linear "click" PEGylated ligands are also prepared. Strong positive dendritic effects concerning ligand loading, catalyst loading, catalytic activity, and recyclability are observed, that is, the dendritic catalysts are much more efficient than nondendritic analogues.
- Wang, Dong,Deraedt, Christophe,Salmon, Lionel,Labrugre, Christine,Etienne, Laetitia,Ruiz, Jaime,Astruc, Didier
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supporting information
p. 1508 - 1519
(2015/01/30)
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- (-)-Tarchonanthuslactone: Design of New Analogues, Evaluation of their Antiproliferative Activity on Cancer Cell Lines, and Preliminary Mechanistic Studies
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Natural products containing the α,β-unsaturated δ-lactone skeleton have been shown to possess a variety of biological activities. The natural product (-)-tarchonanthuslactone (1) possessing this privileged scaffold is a popular synthetic target, but its biological activity remains underexplored. Herein, the total syntheses of dihydropyran-2-ones modeled on the structure of 1 were undertaken. These compounds were obtained in overall yields of 17-21 % based on the Keck asymmetric allylation reaction and were evaluated in vitro against eight different cultured human tumor cell lines. We further conducted initial investigation into the mechanism of action of selected analogues. Dihydropyran-2-one 8 [(S,E)-(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl 3-(3,4-dihydroxyphenyl)acrylate], a simplified analogue of (-)-tarchonanthuslactone (1) bearing an additional electrophilic site and a catechol system, was the most cytotoxic and selective compound against six of the eight cancer cell lines analyzed, including the pancreatic cancer cell line. Preliminary studies on the mechanism of action of compound 8 on pancreatic cancer demonstrated that apoptotic cell death takes place mediated by an increase in the level of reactive oxygen species. It appears as though compound 8, possessing two Michael acceptors and a catechol system, may be a promising scaffold for the selective killing of cancer cells, and thus, it deserves further investigation to determine its potential for cancer therapy. Fighting the big C: We describe the synthesis of a new family of analogues based on the scaffold of the natural product (-)-tarchonanthuslactone; these compounds were evaluated in vitro against tumor cell lines. We further conducted an initial investigation into the mechanism of action, including the inhibition of phosphatases and glutathione-S-transferase and the production of reactive oxygen species.
- Toneto Novaes, Luiz Fernando,Martins Avila, Carolina,Pelizzaro-Rocha, Karin Juliane,Vendramini-Costa, Débora Barbosa,Pereira Dias, Marina,Barbosa Trivella, Daniela Barreto,Ernesto De Carvalho, Jo?o,Ferreira-Halder, Carmen Veríssima,Pilli, Ronaldo Aloise
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supporting information
p. 1687 - 1699
(2015/10/06)
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- A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism
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Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.
- Sirasani, Gopal,Tong, Liuchuan,Balskus, Emily P.
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supporting information
p. 7785 - 7788
(2014/08/05)
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- Activity of caffeic acid derivatives against Candida albicans biofilm
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The aim of this study was to evaluate the caffeic acid (1) and ester derivatives (2-10) against Candida albicans biofilm and to investigate whether these compounds are able to inhibit the biofilm formation or destroy pre-formed biofilm. Caffeic acid ester 7, cinnamic acid ester 8 and 3,4-dihydroxybenzoic acid ester 10 are more active than fluconazole, used as reference drug, both on biofilm in formation with MIC50 values of 32, 32 and 16 μg/mL, respectively, and in the early stage of biofilm formation (4 h) with MIC 50 values of 64, 32 and 64 μg/mL, respectively. These esters result also more active than fluconazole on mature biofilm (24 h), especially 8 and 10 with MIC50 values of 64 μg/mL.
- De Vita, Daniela,Friggeri, Laura,D'Auria, Felicia Diodata,Pandolfi, Fabiana,Piccoli, Francesco,Panella, Simona,Palamara, Anna Teresa,Simonetti, Giovanna,Scipione, Luigi,Di Santo, Roberto,Costi, Roberta,Tortorella, Silvano
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p. 1502 - 1505
(2014/03/21)
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- Antihypertensive effect of caffeic acid and its analogs through dual renin-angiotensin-aldosterone system inhibition
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Hypertension is a crucial risk factor for cardiovascular diseases and contributes to one third of global mortality. In addition to conventional antihypertensive drugs such as captopril, naturally occurring phytochemicals and their analogs are used for red
- Bhullar, Khushwant S.,Lassalle-Claux, Grégoire,Touaibia, Mohamed,Vasantha Rupasinghe
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p. 125 - 132
(2014/04/17)
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- Direct electrosynthesis of a series of novel caffeic acid analogues through a clean and serendipitous domino oxidation/thia-Michael reaction
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A series of novel caffeic acid analogues have been synthesized in an experimentally simple electrochemical procedure employing electrons as the only reagents in aqueous solution without introducing any catalyst or oxidant. It has been shown that the react
- Alizadeh,Khodaei,Fakhari,Shamsuddin
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p. 20781 - 20788
(2014/06/09)
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- Antioxidant properties and efficacies of synthesized alkyl caffeates, ferulates, and coumarates
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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.
- Sorensen, Ann-Dorit Moltke,Jacobsen, Charlotte,Durand, Erwann,Laguerre, Mickal,Bayrasy, Christelle,Lecomte, Jrme,Villeneuve, Pierre
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p. 12553 - 12562
(2015/04/21)
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