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Biotransformation of ruscogenins by Cunninghamella blakesleeana NRRL 1369 and neoruscogenin by endophytic fungus Neosartorya hiratsukae
Phytochemistry ( IF 3.8 ) Pub Date : 2018-04-22
Özge Özçinar, Özgür Tağ, Hasan Yusufoglu, Bijen Kivçak, Erdal Bedir

Biotransformation of steroidal ruscogenins (neoruscogenin and ruscogenin) was carried out with Cunninghamella blakesleeana NRRL 1369 and endophytic fungus Neosartorya hiratsukae yielding mainly P450 monooxygenase products together with a glycosylated compound. Fermentation of ruscogenins (75:25, neoruscogenin-ruscogenin mixture) with C. blakesleeana yielded 8 previously undescribed hydroxylated compounds. Furthermore, microbial transformation of neoruscogenin by endophytic fungus N. hiratsukae afforded three previously undescribed neoruscogenin derivatives. While hydroxylation at C-7, C-12, C-14, C-21 with further oxidation at C-1 and C-7 were observed with C. blakesleeana, N. hiratsukae biotransformation provided C-7 and C-12 hydroxylated compounds along with C-12 oxidized and C-1(O) glycosylated derivatives. The structures of the metabolites were elucidated by 1-D (1H, 13C and DEPT135) and 2-D NMR (COSY, HMBC, HMQC, NOESY, ROESY) as well as HR-MS analyses.



中文翻译:

内生真菌Neurosartorya hiratsukae对Cunninghamella blakesleeana NRRL 1369对ruscogenins的生物转化和对neuroruscogenin的生物转化

甾体类糖原蛋白(neususcogenin和ruscogenin)的生物转化是用Cunninghamella blakesleeana NRRL 1369和内生真菌Neosartorya hiratsukae进行的,主要产生P450单加氧酶产物以及糖基化化合物。乳木菌素(75:25,新乳木素-乳木素的混合物)与黑头梭菌的发酵产生了8种先前未描述的羟基化化合物。此外,通过内生真菌hiratsukae对新新霉素的微生物转化提供了三种先前未描述的新新霉素的衍生物。观察到C. blakesleeanaN。hiratsukae在C-7,C-12,C-14,C-21处发生羟基化反应,并在C-1和C-7处进一步氧化生物转化提供了C-7和C-12羟基化的化合物以及C-12氧化的和C-1(O)糖基化的衍生物。通过1-D(1 H,13 C和DEPT135)和2-D NMR(COSY,HMBC,HMQC,NOESY,ROESY)以及HR-MS分析阐明了代谢物的结构。

更新日期:2018-04-25
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