Hydroxylation of 1,8-cineole by Mucor ramannianusand Aspergillus niger

Revista de microbiologia

Ramos, Aline de Souza¹  Teixeira, Bruna Gomes²  Ferreira, José Luiz Pinto³  Ribeiro, Joyce Benzaquem⁴ 

[1] Farmanguinhos, Manguinhos, Brazil;Universidade Federal Fluminense, Niterói, Brazil;Universidade Federal do Amazonas, Manaus, Brazil;Universidade Federal do Rio de Janeiro, Cidade Universitária, Brazil

关键词: biotransformation;    monoterpene;    1;    8-cineole;    Mucor ramannianus;    Aspergillus niger.;   

DOI  :  10.1590/S1517-838246120131020

学科分类：农业科学（综合）

来源: Sociedade Brasileira de Microbiologia / Brazilian Society for Microbiology

【 摘 要 】

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 Eucalyptuscultivation 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. ramannianuswas 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.

【 授权许可】

CC BY-NC