Formation of bioactive benzofuran via oxidative coupling, using coconut water (Cocos nucifera L.) as biocatalyst

Luís Cezar Rodrigues, José Maria Barbosa-Filho, Sany Delany Gomes Marques, Flávio Valadares Pereira Borges, Luiz André de Araújo Silva, Irma Herrera Bravo de Laguna and Roberto Mioso

Post-Graduation Program in Development and Technological Innovation in Medicines, Department of Biotechnology, Biotechnology Research Center, Federal University of Paraíba, João Pessoa, PB, 58051-970, Brazil

Department of Pharmaceutical Sciences, Biotechnology Center, Federal University of Paraíba, João Pessoa, PB, 58051-970, Brazil

Post-Graduation Program in Development and Technological Innovation in Medicines, Federal University of Paraíba, João Pessoa, PB, 58051-970, Brazil

Department of Biology, University of Las Palmas de Gran Canaria, Las Palmas de Gran Canaria, 35017, Spain

Department of Biochemistry, Federal University of Pernambuco, Recife, PE, 50670-901, Brazil

Abstract: The capacity of simple coconut water, which contains natural peroxidases, to act as a biocatalyst for the oxidative coupling-cyclization of p-(OH)-phenylpropanoids, was evaluated in this work. As a result, dimeric forms of isoeugenol (licarin A) and methyl p-coumarate (methyl dehydrodicoumarate) were obtained. The products of the reactions were characterized by optical rotatory dispersion, and 1H-NMR and 13C-NMR spectroscopy. The oxidative coupling-cyclization mechanism for coniferyl alcohol is proposed.

Keywords: Bioprocess; biotransformation; neolignans; peroxidase; Cocos nucifera. © 2017 ACG Publications. All rights reserved.