130734-47-3Relevant articles and documents
Effect of 1-ethyl-3-methylimidazolium acetate on the oxidation of caffeic acid benzyl ester: An electrochemical and theoretical study
Pantoja-Hernández, Maurizio A.,Alemán-Vilis, Josué A.,Sánchez, Analilia,Salas-Reyes, Magali,López-Bonilla, Judith,Matus, Myrna H.,Domínguez, Zaira
, (2020)
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.
Synthesis, DNA/RNA-interaction and biological activity of benzo[k,l]xanthene lignans
?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
, (2020/09/11)
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.
Synthesis of Diverse Hydroxycinnamoyl Phenylethanoid Esters Using Escherichia coli
Song, Min Kyung,Cho, A Ra,Sim, Geunyoung,Ahn, Joong-Hoon
, p. 2028 - 2035 (2019/02/26)
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.
