Glycosylation and sulfation of emodin by Gliocladium deliquescens NRRL 1086.
The present study was designed to explore the substrate scope and biocatalytic capability of Gliocladium deliquescens NRRL 1086 on phenolic natural products. Emodin was subjected to the fermentation culture of Gliocladium deliquescens NRRL 1086 according to the standard two-stage protocol. The biotransformation process was monitored by HPLC-DAD-MS, the main product was isolated by column chromatography, and the structure was elucidated on the basis of NMR spectroscopy. Emodin could be fully metabolized by Gliocladium deliquescens NRRL 1086, resulting in high yield of emodin 6-O-β-D-glucopyranoside and small amount of sulfated product. In conclusion, our results may provide a convenient method to prepare emodin 6-O-β-D-glucopyranoside and the microbe catalyzed glucosylation/sulfation will give an inspiration to pharmacokinetic model studies in vitro.
State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China.
Shao-Hua
SH
Xu
State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China; Shanxi University of Traditional Chinese Medicine, Taiyuan 030024, China.
Chen-Hui
CH
DU
State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China. Electronic address: wilson1978@163.com.
Jian
J
Zhang
Department of Complex Prescription of TCM, China Pharmaceutical University, Nanjing 211198, China. Electronic address: boyangyu59@163.com.
Bo-Yang
BY
Yu
D019149:Bioreactors; D001711:Biotransformation; D004642:Emodin / Q000378:metabolism*; D005285:Fermentation; D020462:Gliocladium / Q000378:metabolism*; D005960:Glucosides / Q000378:metabolism*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010636:Phenols / Q000378:metabolism; D010936:Plant Extracts / Q000378:metabolism*
C117506:6''-O-glucopyranoside; D005960:Glucosides; D010636:Phenols; D010936:Plant Extracts; D004642:Emodin
Emodin; Gliocladium deliquescens NRRL 1086; Microbial glycosylation; Sulfation