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Microbial conversion of ruscogenin by Gliocladium deliquescens NRRL1086: glycosylation at C-1

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Abstract

The glycosylation of ruscogenin (1) by Gliocladium deliquescens NRRL 1086 was observed and gave a regioselectively glycosylated product identified as ruscogenin 1-O-β-D-glucopyranoside (2) by infrared, mass spectrometry, and nuclear magnetic resonance spectra. Time-course studies indicated that it appeared to be favorable to accumulate 2 when ruscogenin was added to the 24-h-old stage II culture, and the yield of 2 was about 20.1% during 120∼168 h. It was noted that additional carbohydrates could significantly increase glycoside formation and the yield of 2 even reached as high as 68% compared with the control 20.1%. The primary investigation about the characteristics of the enzyme resulted that the reaction was blocked by β-glycosidase inhibitor imidazole, however, was enhanced remarkably by glycosyltransferase inhibitor sodium dodecyl sulfate. To our knowledge, this is the first reported case of producing steroidal saponin by microbial transformation, and G. deliquescens NRRL1086 would be a practical and highly efficient tool in producing natural ruscogenin monoside.

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Acknowledgment

This work was supported by the National Nature Science Foundation of China (NSFC No. 20602040, 30672603). Thanks also give to the financial support from the State Administration of Foreign Expert Affairs of China (no. 111-2-07) and the “111 Project” from the Ministry of Education of China.

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Authors and Affiliations

  1. Department of Complex Prescription of TCM, China Pharmaceutical University, 639 Long Mian Road, Nanjing, 211198, People’s Republic of China

    Nai-Dong Chen & Jian Zhang

  2. Key Laboratory of Modern Chinese Medicines, Ministry of Education, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing, 210038, People’s Republic of China

    Ji-Hua Liu & Bo-Yang Yu

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  1. Nai-Dong Chen
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  2. Jian Zhang
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  3. Ji-Hua Liu
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  4. Bo-Yang Yu
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Correspondence to Jian Zhang or Bo-Yang Yu.

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Chen, ND., Zhang, J., Liu, JH. et al. Microbial conversion of ruscogenin by Gliocladium deliquescens NRRL1086: glycosylation at C-1. Appl Microbiol Biotechnol 86, 491–497 (2010). https://doi.org/10.1007/s00253-009-2315-y

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