Microbial β-glycosylation of entacapone by Cunninghamella echinulata ATCC 9245

Microbial transformation of ambrisentan to its glycosides by Cunninghamella elegans

“…Considering the mass difference between the standard and the new molecule (162 m / z ) we observed fragmentation related to glucoside conjugation (C 28 H 33 N 2 O 9 ) in the molecule of AMB with consequent loss of one hydrogen atom of the drug molecule (Figure ). These results corroborate the findings by Lustosa et al (), which performed biotranformation by Cunninghamella enchinulata and identified entacapone glycoside with a mass difference of m / z 162 for the standard structure. These outcomes suggest the incorporation of a glycoside molecule into ambrisentan.…”

“…Cunninghamella is a genus that has frequently been proposed for glycosylation reactions and it is a very interesting tool in the production of molecules with improved pharmacological profiles. It was suggested that the conversion based on microbial specific reactions was useful for the production of new AMB derivatives (Lustosa et al, ; Miyakoshi et al, ).…”

“…Biotransformation studies of biologically active compounds through microorganisms, mainly by filamentous fungi, and their possible glycosylated derivatives have been extensively investigated because biotransformation shows advantages such as one‐step simple reaction and eco‐friendly production. Cunninghamella is a genus of filamentous fungi that has frequently been proposed for glycosylation reactions and it is a very interesting tool in the production of molecules with improved pharmacological profiles (Lustosa, Menegatti, Braga, Lião, & Oliveira, ; Miyakoshi, Azami, & Kuzuyama, ; Mukhopadhyay, Kartha, Russell, & Field, ; Shao‐Hua, Chen‐Hui, ZHANG, & Bo‐Yang, ).…”

Biotransformação da B-lapachona utilizando culturas microbianas: uma alternativa para estudos de metabolismo in vitro

“…Fungos do gênero Cunninghamella se destacam pela capacidade de mimetizar o metabolismo de mamíferos, sendo capazes de catalisar reações tanto de fase I como de fase II (ABOURASHED et al, 2012;ASHAA e VIDYAVATHI, 2009). A espécie C. echinulata foi capaz de catalisar glicosilações em moléculas de interesse farmacêutico (LUSTOSA et al, 2012;MIYAKOSHI et al, 2010). Essa espécie também catalisou hidroxilações em cadeias carbônicas (MAATOOQ et al, 2010;LAMM et al, 2009).…”

“…Porém, essa é a primeira vez que derivados glicosilados da β-lapachona são relatados. O fungo C. echinulada é conhecido por catalisar reações de glicosilação (LUSTOSA et al, 2012;MIYAKOSHI et al, 2010 uma molécula de glicose na hidroxila livre dessa naftoquinona (OTTEN e ROSAZZA, 1981). Porém, com o procedimento de transformação microbiana da β-lapachona, esse fungo filamentoso não propiciou a obtenção de derivados com rendimento significativo, após sete dias de incubação.…”