1154-78-5Relevant articles and documents
Synthesis and Evaluation of Antimicrobial and Antibiofilm Properties of A-Type Procyanidin Analogues against Resistant Bacteria in Food
Alejo-Armijo, Alfonso,Glibota, Nicolás,Frías, María P.,Altarejos, Joaquín,Gálvez, Antonio,Salido, Sofía,Ortega-Morente, Elena
, p. 2151 - 2158 (2018)
Natural A-type procyanidins have shown very interesting biological activities, such as their proven antiadherence properties against pathogenic bacteria. In order to find the structural features responsible for their activities, we describe herein the design and synthesis of six A-type procyanidin analogues and the evaluation of their antimicrobial and antibiofilm properties against 12 resistant bacteria, both Gram positive and Gram negative, isolated from organic foods. The natural A-type procyanidin A-2, which had known antiadherence activity, was also tested as a reference compound for the comparative studies. Within the series, analogue 4, which had a NO2 group on ring A, showed the highest antimicrobial activity (MIC of 10 μg/mL) and was one of the best molecules at preventing biofilm formation (up to 40% decreases at 100 μg/mL) and disrupting preformed biofilms (up to 40% reductions at 0.1 μg/mL). Structure-activity relationships are also analyzed.
Thermodynamic Stability of Flavylium Salts as a Valuable Tool to Design the Synthesis of A-Type Proanthocyanidin Analogues
Alejo-Armijo, Alfonso,Jorge Parola,Pina, Fernando,Altarejos, Joaquín,Salido, Sofía
, p. 12297 - 12304 (2018)
A convenient method to synthesize A-type proanthocyanidin analogues from flavylium salts and ?€-nucleophiles has been developed. It was found that the thermodynamic stability of the starting flavylium salt, assessed by the measurement of the apparent acidity constant (K′a), was the key parameter to design effective one-pot reactions between flavylium salts and nucleophiles such as phloroglucinol and (+)-catechin. When flavylium salts have a pK′a value of 1.7 or lower, the synthesis of the corresponding 2,8-dioxabyciclo[3.3.1]nonane derivative was properly achieved.
A simple synthesis of 3-deoxyanthocyanidins and their O-glucosides
Al Bittar, Sheiraz,Mora, Nathalie,Loonis, Michèle,Dangles, Olivier
, p. 4294 - 4302 (2016/07/06)
This work deals with the chemical synthesis of simple analogs of anthocyanins, the main class of water-soluble natural pigments. Flavylium ions with hydroxyl, methoxyl and β-D-glucopyranosyloxyl substituents at positions 4′ and 7 have been prepared by straightforward chemical procedures. Moreover, the two 3-deoxyanthocyanidins of red sorghum apigeninidin (4′,5,7-trihydroxyflavylium) and luteolinidin (3′,4′,5,7-tetrahydroxyflavylium) were synthesized in a one-step protocol. Attempts to synthesize luteolinidin O-β-D-glucosides resulted in a mixture of the 5-O- and 7-O-regioisomers in low yield. A preliminary study of the 4′-β-D-glucopyranosyloxy-7-hydroxyflavylium and 7-β-D-glucopyranosyloxy-4′-hydroxy-flavylium ions shows that simply changing the glucosidation site can profoundly affect the color intensity and stability.
