title: Hydroxylation of 1,8-cineole by Mucor ramannianus and Aspergillus niger.
abstract: The monoterpenoid 1,8-cineole is obtained from the leaves of Eucalyptus globulus and it has important biological activities. It is a cheap natural substrate because it is a by-product of the Eucalyptus cultivation for wood and pulp production. In this study, it was evaluated the potential of three filamentous fungi in the biotransformation of 1,8-cineole. The study was divided in two steps: first, reactions were carried out with 1,8-cineole at 1 g/L for 24 h; afterwards, reactions were carried out with substrate at 5 g/L for 5 days. The substrate was hydroxylated into 2-exo-hydroxy-1,8-cineole and 3-exo-hydroxy-1,8-cineole by fungi Mucor ramannianus and Aspergillus niger with high stereoselectivity. Trichoderma harzianum was also tested but no transformation was detected. M. ramannianus led to higher than 99% of conversion within 24 h with a starting high substrate concentration (1 g/L). When substrate was added at 5 g/L, only M. ramannianus was able to catalyze the reaction, but the conversion level was 21.7% after 5 days. Both products have defined stereochemistry and could be used as chiral synthons. Furthermore, biological activity has been described for 3-exo-hydroxy-1,8-cineol. To the best of our knowledge, this is the first report on the use of M. ramannianus in this reaction.
authors.affiliation: Fundação Oswaldo Cruz, Farmanguinhos, Manguinhos, Rio de Janeiro, RJ, Brazil.
authors.forename: Aline de Souza
authors.initials: Ade S
authors.lastname: Ramos
authors.affiliation: Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, Rio de Janeiro, RJ, Brazil.
authors.forename: Joyce Benzaquem
authors.initials: JB
authors.lastname: Ribeiro
authors.affiliation: Fundação Oswaldo Cruz, Farmanguinhos, Manguinhos, Rio de Janeiro, RJ, Brazil.
authors.forename: Bruna Gomes
authors.initials: BG
authors.lastname: Teixeira
authors.affiliation: Fundação Oswaldo Cruz, Farmanguinhos, Manguinhos, Rio de Janeiro, RJ, Brazil. ; Faculdade de Farmácia, Universidade Federal Fluminense, Niterói, RJ, Brazil.
authors.forename: José Luiz Pinto
authors.initials: JL
authors.lastname: Ferreira
authors.affiliation: Departamento de Química, Universidade Federal do Amazonas, Manaus, AM, Brazil.
authors.forename: Jefferson Rocha de A
authors.initials: JR
authors.lastname: Silva
authors.affiliation: Fundação Oswaldo Cruz, Farmanguinhos, Manguinhos, Rio de Janeiro, RJ, Brazil.
authors.forename: Alexandre do Amaral
authors.initials: Ado A
authors.lastname: Ferreira
authors.affiliation: Instituto de Química, Universidade Federal do Rio de Janeiro, Cidade Universitária, Rio de Janeiro, RJ, Brazil.
authors.forename: Rodrigo Octavio Mendonça Alves
authors.initials: RO
authors.lastname: de Souza
authors.affiliation: Fundação Oswaldo Cruz, Farmanguinhos, Manguinhos, Rio de Janeiro, RJ, Brazil.
authors.forename: Ana Claudia F
authors.initials: AC
authors.lastname: Amaral
mesh_terms: D001234:Aspergillus niger / Q000378:metabolism*; D003511:Cyclohexanols / Q000378:metabolism*; D000077591:Eucalyptol; D005052:Eucalyptus / Q000737:chemistry*; D006900:Hydroxylation; D039821:Monoterpenes / Q000378:metabolism*; D009090:Mucorales / Q000378:metabolism*; D013997:Time Factors; D014242:Trichoderma / Q000378:metabolism
chemical_list: D003511:Cyclohexanols; D039821:Monoterpenes; D000077591:Eucalyptol
keywords: 1,8-cineole; Aspergillus niger; Mucor ramannianus; biotransformation; monoterpene