64190-80-3Relevant academic research and scientific papers
Natural product-inspired esters and amides of ferulic and caffeic acid as dual inhibitors of HIV-1 reverse transcriptase
Sonar, Vijay P.,Corona, Angela,Distinto, Simona,Maccioni, Elias,Meleddu, Rita,Fois, Benedetta,Floris, Costantino,Malpure, Nilesh V.,Alcaro, Stefano,Tramontano, Enzo,Cottiglia, Filippo
, p. 248 - 260 (2017/03/09)
Using an HIV-1 Reverse Transcriptase (RT)-associated RNase H inhibition assay as lead, bioguided fractionation of the dichloromethane extract of the Ocimum sanctum leaves led to the isolation of five triterpenes (1–5) along with three 3-methoxy-4-hydroxy phenyl derivatives (6–8). The structure of this isolates were determined by 1D and 2D NMR experiments as well as ESI-MS. Tetradecyl ferulate (8) showed an interesting RNase H IC50value of 12.4?μM and due to the synthetic accessibility of this secondary metabolite, a structure-activity relationship study was carried out. A series of esters and amides of ferulic and caffeic acids were synthesized and, among all, the most active was N-oleylcaffeamide displaying a strong inhibitory activity towards both RT-associated functions, ribonuclease H and DNA polymerase. Molecular modeling studies together with Yonetani-Theorell analysis, demonstrated that N-oleylcaffeamide is able to bind both two allosteric site located one close to the NNRTI binding pocket and the other close to RNase H catalytic site.
Long Chain Alkyl Esters of Hydroxycinnamic Acids as Promising Anticancer Agents: Selective Induction of Apoptosis in Cancer Cells
Menezes, José C. J. M. D. S.,Edraki, Najmeh,Kamat, Shrivallabh P.,Khoshneviszadeh, Mahsima,Kayani, Zahra,Mirzaei, Hossein Hadavand,Miri, Ramin,Erfani, Nasrollah,Nejati, Maryam,Cavaleiro, José A. S.,Silva, Tiago,Saso, Luciano,Borges, Fernanda,Firuzi, Omidreza
, p. 7228 - 7239 (2017/08/30)
Cancer is the major cause of morbidity and mortality worldwide. Hydroxycinnamic acids (HCAs) are naturally occurring compounds and their alkyl esters may possess enhanced biological activities. We evaluated C4, C14, C16, and C18 alkyl esters of p-coumaric, ferulic, sinapic, and caffeic acids (19 compounds) for their cytotoxic activity against four human cancer cells and also examined their effect on cell cycle alteration and apoptosis induction. The tetradecyl (1c) and hexadecyl (1d) esters of p-coumaric acid and tetradecyl ester of caffeic acid (4c), but not the parental HCAs, were selectively effective against MOLT-4 (human lymphoblastic leukemia) cells with IC50 values of 0.123 ± 0.012, 0.301 ± 0.069 and 1.0 ± 0.1 μM, respectively. Compounds 1c, 1d, and 4c significantly increased apoptotic cells in sub-G1 phase and activated the caspase-3 enzyme in MOLT-4 cells. Compound 1c was 15.4 and 23.6 times more potent than doxorubicin and cisplatin, respectively, against the drug resistant MES-SA-DX5 uterine sarcoma cells. These p-coumarate esters were several times less effective against NIH/3T3 fibroblast cells. Docking studies showed that 1c may cause cytotoxicity by interaction with carbonic anhydrase IX. In conclusion, long chain alkyl esters of p-coumaric acid are promising scaffolds for selective apoptosis induction in cancer cells.
Zn(OTf)2-promoted chemoselective esterification of hydroxyl group bearing carboxylic acids
Mamidi, Narsimha,Manna, Debasis
, p. 2386 - 2396 (2013/05/21)
Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I2, and a catalytic amount of Zn(OTf)2. Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from transesterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.
Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates
Menezes, Jose C.J.M.D.S.,Kamat, Shrivallabh P.,Cavaleiro, Jose A.S.,Gaspar, Alexandra,Garrido, Jorge,Borges, Fernanda
experimental part, p. 773 - 777 (2011/03/19)
Long chain alkyl hydroxycinnamates (8-21) were synthesized from the corresponding half esters of malonic acid (5-7) and benzaldehyde derivatives by Knoevenagel condensation. The total antioxidant capacity of these hydroxycinnamyl esters was evaluated usin
Impact of alkyl esters of caffeic and ferulic acids on tumor cell proliferation, cyclooxygenase enzyme, and lipid peroxidation
Jayaprakasam, Bolleddula,Vanisree, Mulabagal,Zhang, Yanjun,Dewitt, David L.,Nair, Muraleedharan G.
, p. 5375 - 5381 (2008/04/03)
The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C12-caffeate), 11 (C16-caffeate), 21 (C 8-ferulate), and 23 (C12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 μg/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 μg/ mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 μg/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 μg/ mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C4-C 12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C3-C8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 μg/mL. Long-chain caffeates 11-14 (C 16-C22) and short-chain ferulates 15-20 (C 3-C5) were the most active in lipid peroxidation inhibition and showed 60-70% activity at 5 μg/mL concentration.
Highly efficient preparation of lipophilic hydroxycinnamates by solvent-free lipase-catalyzed transesterification
Weitkamp, Petra,Vosmann, Klaus,Weber, Nikolaus
, p. 7062 - 7068 (2008/02/08)
Various medium- or long-chain alkyl cinnamates and hydroxycinnamates, including oleyl p-coumarate as well as palmityl and oleyl ferulates, were prepared in high yield by lipase-catalyzed transesterification of an equimolar mixture of a short-chain alkyl cinnamate and a fatty alcohol such as lauryl, palmityl, and oleyl alcohol under partial vacuum at moderate temperature in the absence of solvents and drying agents in direct contact with the reaction mixture. Immobilized lipase B from Candida antarctica was the most effective biocatalyst for the various transesterification reactions. Transesterification activity of this enzyme was up to 56-fold higher than esterification activity for the preparation of medium-and long-chain alkyl ferulates. The relative transesterification activities found for C. antarctica lipase were of the following order: hydrocinnamate > cinnamate > 4-hydroxyhydrocinnamate > 3-methoxycinnamate > 2-methoxycinnamate ≈ 4-methoxycinnamate ≈ 3-hydroxycinnamate > hydrocaffeate ≈ 4-hydroxycinnamate > ferulate > 2-hydroxycinnamate > caffeate ≈ sinapate. With respect to the position of the hydroxy substituents at the phenyl moiety, the transesterification activity of C. antarctica lipase B increased in the order meta > para > ortho. The immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus demonstrated moderate and low transesterification activity, respectively. Compounds with inverse chemical structure, that is, 3-phenylpropyl alkanoates such as 3-(4-hydroxyphenyl)propyl oleate and 3-(3,4-dimethoxyphenyl)propyl oleate, were obtained by C. antarctica lipase-catalyzed transesterification of fatty acid methyl esters with the corresponding 3-phenylpropan-1-ols in high yield, as well.
Characterization and Quantitation of Hexadecyl, Octadecyl, and Eicosyl Esters of p-Coumaric Acid in the Vine and Root Latex of Sweetpotato
Snook, Maurice E.,Data, Emma S.,Kays, Stanley J.
, p. 2589 - 2595 (2007/10/02)
Methanol extracts of vine latex of four cultivars of sweetpotato were analyzed for their chemical phenolic composition by reversed-phase HPLC.Major components were identified as hexadecyl, octadecyl, and eicosyl p-coumarates by
Alkyl ferulates in wound healing potato tubers.
Bernards,Lewis
, p. 3409 - 3412 (2007/10/02)
Seven ferulic acid esters of 1-alkanols ranging in carbon length from C16 to C28 were synthesized and an HPLC protocol for their separation developed. Extracts prepared from wound healing potato (Solanum tuberosum) tubers and analysed by HPLC indicated th
