Umbelliferone esters with antibacterial activity produced by lipase-mediated biocatalytic pathway
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ORIGINAL RESEARCH PAPER
Umbelliferone esters with antibacterial activity produced by lipase-mediated biocatalytic pathway Vitor Soares . Maı´ra Barcellos Marini . Larissa Assis de Paula . Patrick Soares Gabry . Ana Claudia F. Amaral . Camila Ada˜o Malafaia . Ivana Correa Ramos Leal
Received: 4 February 2020 / Accepted: 29 September 2020 Ó Springer Nature B.V. 2020
Abstract Objective The present report describes the enzymatic acylation of umbelliferone with different vinyl esters as acyl donors biocatalyzed by the commercial lipase NovozymÒ 435, and the investigation for their antibacterial activity against ATCC and clinical strains isolated from hospital infection sites. Results The umbelliferone esters (1–5) were synthesized through the acylation reaction of 7-hydroxy2H-chromen-2-one with different long chain vinyl esters catalyzed by the lipase Novozym 435. The reaction conditions were: 10% Novozym 435; tetrahydrofuran:acetone (3:1) for the reactions with acetate, propionate and butyrate vinyl esters 50–90% conversion, and (9:1) for decanoate and laurate vinyl esters
V. Soares M. B. Marini L. A. de Paula P. S. Gabry C. A. Malafaia I. C. R. Leal (&) Laboratory of Natural Products and Biological Assays, Natural Products and Food Department, Pharmacy Faculty, Center of Health Sciences, Federal University of Rio de Janeiro (UFRJ), Av. Carlos Chagas Filho, N.° 373, Rio de Janeiro, RJ 21941-902, Brazil e-mail: [email protected]; [email protected] V. Soares Federal Institute of Parana´ - IFPR, Marginal Imbirama, 300, Quedas do Iguac¸u, Parana´, PR 85460-000, Brazil A. C. F. Amaral Laboratory of Medicinal Plants and Derivatives, Farmanguinhos, Fiocruz, Manguinhos, Rio de Janeiro, RJ, Brazil
10–15% conversion; acyl donor/umbelliferone molar ratio of 10:1 and 60 °C. All the umbelliferone esters were characterized NMR and (HRMS). The antibacterial activity of the products were tested using the broth microdilution method in order to determine the minimum inhibitory concentration (MIC). The results displayed by 7-laurate and 7-decanoate-umbelliferone esters showed the highest antibacterial potential, with 1 mM inhibitory activity for ATCC 33591, a methicillin and oxacillin resistant Staphylococcus aureus strain. They were also able to inhibit gram-negative bacterial strains, such as Pseudomonas aeruginosa (MIC 0.5 mM) and Klebsiella pneumoniae (MIC 1 mM). In addition, 7-laurate- and 7-decanoate-umbelliferone esters were able to inhibit all clinical strains (MIC 1 mM; except 7-laurate-umbelliferone in which MIC 0.5 mM against 55a). Conclusions This is the first study performing the biocatalysis of umbelliferone followed by the purification of the products and the antibacterial evaluation. Keywords Antibacterial activity Coumarin Novozym 435 Regioselective acylation
Introduction Coumarins and their derivatives comprise an important class of secondary metabolites produced by a
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Biotechnol Lett
large range of plant sources. Coumarins are made of ap
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