@misc{10481/84037, year = {2023}, month = {6}, url = {https://hdl.handle.net/10481/84037}, abstract = {Developing new types of effective antimicrobial compounds derived from natural products is of interest for the food industry. Some analogs to A-type proanthocyanidins have shown promising antimicrobial and antibiofilm activities against foodborne bacteria. We report herein the synthesis of seven additional analogs with NO2 group at A-ring and their abilities for inhibiting the growth and the biofilm formation by twenty-one foodborne bacteria. Among them, analog 4 (one OH at B-ring; two OHs at D-ring) showed the highest antimicrobial activity. The best results with these new analogs were obtained in terms of their antibiofilm activities: analog 1 (two OHs at B-ring; one OH at D-ring) inhibited at least 75% of biofilm formation by six strains at all of the concentrations tested, analog 2 (two OHs at B-ring; two OHs at D-ring; one CH3 at C-ring) also showed antibiofilm activity on thirteen of the bacteria tested, and analog 5 (one OH at B-ring; one OH at D-ring) was able to disrupt preformed biofilms in eleven strains. The description of new and more active analogs of natural compounds and the elucidation of their structure-activity relationships may contribute to the active development of new food packaging for preventing biofilm formation and lengthening the food shelf life.}, organization = {Andalusian Consejería de Economía y Conocimiento (FEDER program 2014–2020: grant number 1380669),}, organization = {Spain, and the Spanish Ministerio de Ciencia}, organization = {Innovación y Universidades (grant RTI2018-098560-B-C22,}, organization = {FEDER funds of the European Union)}, organization = {(Grant RTI2018-098560-B-C22, co-financed by the FEDER funds of the European Union}, organization = {Centro de Instrumentación Científico-Técnica (CICT) of the University of Jaén, Spain.}, publisher = {MDPI}, keywords = {A-type proanthocyanidin analogs}, keywords = {Flavylium chemistry}, keywords = {Antimicrobial activity}, keywords = {Antibiofilm activity}, keywords = {Antioxidant activity}, title = {Synthesis of Analogs to A-Type Proanthocyanidin Natural Products with Enhanced Antimicrobial Properties against Foodborne Microorganisms}, doi = {10.3390/molecules28124844}, author = {Cobo Molinos, Antonio}, }