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Isolation and Purification of an Antibiotic Polyketide JBIR-99 from the Marine Fungus Meyerozyma guilliermondii by High-Speed Counter-Current Chromatography

Received: 28 June 2021     Accepted: 7 July 2021     Published: 15 July 2021
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Abstract

JBIR-99 is a natural compound isolated from marine source which possesses strong antibiotic activity. An efficient approach using a combination of size exclusion chromatography with a Sephadex LH-20 and high-speed counter-current chromatography (HSCCC) has been successfully developed for the isolation and purification of a polyketide from the solid-state fermentation of Meyerozyma guilliermondii, a strain of marine fungus isolated from Indian Ocean. The active compound was isolated with purity >95% by HSCCC using an optimized solvent system composed of petroleum ether–ethyl acetate– 95% ethanol–water (5: 3: 5: 3, v/v/v/v) after size exclusion chromatography. This compound was successfully purified in the quantity of 68 mg from 120 mg of the crude extract. The structure of JBIR-99 was elucidated and assigned by 1D, 2D NMR spectroscopic, and positive HRESITOFMS. Moreover, the relative configuration of compound JBIR-99, displaying a quite complex multi-ring structure, is determined by X-ray crystallography for the first time. The purification method developed for JBIR-99 will facilitate the further investigation and development of this antibiotic agent as a lead compound. Furthermore, it is suggested that the combination of size exclusion chromatography and HSCCC could be more widely applied for the isolation and purification of polyketides from marine fungi.

Published in International Journal of Pharmacy and Chemistry (Volume 7, Issue 4)
DOI 10.11648/j.ijpc.20210704.11
Page(s) 52-57
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2021. Published by Science Publishing Group

Keywords

JBIR-99, HSCCC, Antibiotics, X-ray Crystal

References
[1] Huffman, J., Gerber, R., Du, L (2010). Recent advancements in the biosynthetic mechanisms for polyketide derived mycotoxin. Biopolymers, 93, 764–776.
[2] Wahengbam, R., Santosh, K., Giasuddin, A. and Kumaraswamy, J. (2014). Reliable differentiation of Meyerozyma guilliermondii from Meyerozyma caribbica by internal transcribed spacer restriction fingerprinting. BMC Microb. 14, 52-62.
[3] Ueda, J., Shinya, K. (2010). New xanthoquinodin-like compounds JBIR-97 -98 and -99 obtained from marine sponge-derived fungus Tritirachium sp, SpB081112MEf2. J. Antibioti., 2010, 63, 615.
[4] Wu, B., Wiese, J., Wenzel-Storjohann, A., Malien, S., Schmaljohann, R., Imhoff, J. F. (2016). Engyodontochones antibiotic polyketides from the marine fungus Engyodontium album Strain LF069. Chem. Eur. J., 2016, 22, 7452.
[5] Shibata, T.; Ishimaru, K.; Kawaguchi, S.; Yoshikawa, H.; Hama, Y. (2008). Antioxidant activities of phlorotannins isolated from Japanese Laminariacea. J. Appl. Phycol., 20, 705-711.
[6] Nakai, M., Kageyama, N., Nakahara, K., Miki, W. (2006). Phlorotannins as radical scavengers from the extract of Sargassum ringgoldianum. Mar Biotechnol. 8, 409-414.
[7] Duan, W., Ji, W., Wei, Y., Zhao, R., Chen, Z., Geng, Y., Jing, F., Wang, X. (2018). Separation and purification of fructo-oligosaccharide by high-speed counter-current chromatography coupled with precolumn derivatization. Molecules, 23, 381.
[8] Zhou, X., Yi, M., Ding, L., He, S., Yan, X. (2019). Isolation and purification of a neuroprotective phlorotannin from the marine algae Ecklonia maxima by Size Exclusion and high-speed counter-current chromatography. Mar drugs. 17, 212-219.
[9] Liu, Y., Zhou, X., Naman, C. B., Lu, Y., Ding, L., He, S. (2018). Preparative separation and purifification of trichothecene mycotoxins from the marine fungus Fusarium sp. LS68 by high-speed countercurrent chromatography in stepwise elution mode. Mar drugs. 16, 73.
[10] Wang, J., Gu, D., Wang, M., Guo, X., Li, H., Dong, Y., Guo, H., Wang, Y., Fan, M., Yang, Y. (2017). Rational approach to solvent system selection for liquid–liquid extraction–assisted sample pretreatment in counter–current chromatography. J Chromatogr B. 1053, 16-19.
[11] Shaheen, N., Lu, Y., Geng, P., Shao, Q., Wei, Y. (2017). Isolation of four phenolic compounds from Mangifera indica, L flowers by using normal phase combined with elution extrusion two-step high speed countercurrent chromatography. J Chromatogr B. 1046, 211-217.
[12] Sheldrick G, M. (2015). Crystal structure refinement with SHELXL. Acta Crystallography C. 71, 3-8.
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    Hankui Wu, Zhen Su, Jianguang Chen, Yuanping Wang, Xinyong You, et al. (2021). Isolation and Purification of an Antibiotic Polyketide JBIR-99 from the Marine Fungus Meyerozyma guilliermondii by High-Speed Counter-Current Chromatography. International Journal of Pharmacy and Chemistry, 7(4), 52-57. https://doi.org/10.11648/j.ijpc.20210704.11

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    ACS Style

    Hankui Wu; Zhen Su; Jianguang Chen; Yuanping Wang; Xinyong You, et al. Isolation and Purification of an Antibiotic Polyketide JBIR-99 from the Marine Fungus Meyerozyma guilliermondii by High-Speed Counter-Current Chromatography. Int. J. Pharm. Chem. 2021, 7(4), 52-57. doi: 10.11648/j.ijpc.20210704.11

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    AMA Style

    Hankui Wu, Zhen Su, Jianguang Chen, Yuanping Wang, Xinyong You, et al. Isolation and Purification of an Antibiotic Polyketide JBIR-99 from the Marine Fungus Meyerozyma guilliermondii by High-Speed Counter-Current Chromatography. Int J Pharm Chem. 2021;7(4):52-57. doi: 10.11648/j.ijpc.20210704.11

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  • @article{10.11648/j.ijpc.20210704.11,
      author = {Hankui Wu and Zhen Su and Jianguang Chen and Yuanping Wang and Xinyong You and Kunpeng Zhang and Xiaobin Li},
      title = {Isolation and Purification of an Antibiotic Polyketide JBIR-99 from the Marine Fungus Meyerozyma guilliermondii by High-Speed Counter-Current Chromatography},
      journal = {International Journal of Pharmacy and Chemistry},
      volume = {7},
      number = {4},
      pages = {52-57},
      doi = {10.11648/j.ijpc.20210704.11},
      url = {https://doi.org/10.11648/j.ijpc.20210704.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijpc.20210704.11},
      abstract = {JBIR-99 is a natural compound isolated from marine source which possesses strong antibiotic activity. An efficient approach using a combination of size exclusion chromatography with a Sephadex LH-20 and high-speed counter-current chromatography (HSCCC) has been successfully developed for the isolation and purification of a polyketide from the solid-state fermentation of Meyerozyma guilliermondii, a strain of marine fungus isolated from Indian Ocean. The active compound was isolated with purity >95% by HSCCC using an optimized solvent system composed of petroleum ether–ethyl acetate– 95% ethanol–water (5: 3: 5: 3, v/v/v/v) after size exclusion chromatography. This compound was successfully purified in the quantity of 68 mg from 120 mg of the crude extract. The structure of JBIR-99 was elucidated and assigned by 1D, 2D NMR spectroscopic, and positive HRESITOFMS. Moreover, the relative configuration of compound JBIR-99, displaying a quite complex multi-ring structure, is determined by X-ray crystallography for the first time. The purification method developed for JBIR-99 will facilitate the further investigation and development of this antibiotic agent as a lead compound. Furthermore, it is suggested that the combination of size exclusion chromatography and HSCCC could be more widely applied for the isolation and purification of polyketides from marine fungi.},
     year = {2021}
    }
    

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  • TY  - JOUR
    T1  - Isolation and Purification of an Antibiotic Polyketide JBIR-99 from the Marine Fungus Meyerozyma guilliermondii by High-Speed Counter-Current Chromatography
    AU  - Hankui Wu
    AU  - Zhen Su
    AU  - Jianguang Chen
    AU  - Yuanping Wang
    AU  - Xinyong You
    AU  - Kunpeng Zhang
    AU  - Xiaobin Li
    Y1  - 2021/07/15
    PY  - 2021
    N1  - https://doi.org/10.11648/j.ijpc.20210704.11
    DO  - 10.11648/j.ijpc.20210704.11
    T2  - International Journal of Pharmacy and Chemistry
    JF  - International Journal of Pharmacy and Chemistry
    JO  - International Journal of Pharmacy and Chemistry
    SP  - 52
    EP  - 57
    PB  - Science Publishing Group
    SN  - 2575-5749
    UR  - https://doi.org/10.11648/j.ijpc.20210704.11
    AB  - JBIR-99 is a natural compound isolated from marine source which possesses strong antibiotic activity. An efficient approach using a combination of size exclusion chromatography with a Sephadex LH-20 and high-speed counter-current chromatography (HSCCC) has been successfully developed for the isolation and purification of a polyketide from the solid-state fermentation of Meyerozyma guilliermondii, a strain of marine fungus isolated from Indian Ocean. The active compound was isolated with purity >95% by HSCCC using an optimized solvent system composed of petroleum ether–ethyl acetate– 95% ethanol–water (5: 3: 5: 3, v/v/v/v) after size exclusion chromatography. This compound was successfully purified in the quantity of 68 mg from 120 mg of the crude extract. The structure of JBIR-99 was elucidated and assigned by 1D, 2D NMR spectroscopic, and positive HRESITOFMS. Moreover, the relative configuration of compound JBIR-99, displaying a quite complex multi-ring structure, is determined by X-ray crystallography for the first time. The purification method developed for JBIR-99 will facilitate the further investigation and development of this antibiotic agent as a lead compound. Furthermore, it is suggested that the combination of size exclusion chromatography and HSCCC could be more widely applied for the isolation and purification of polyketides from marine fungi.
    VL  - 7
    IS  - 4
    ER  - 

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Author Information
  • School of Biotechnology and Food Engineering, Anyang Institute of Technology, Anyang, China

  • School of Biotechnology and Food Engineering, Anyang Institute of Technology, Anyang, China

  • School of Biotechnology and Food Engineering, Anyang Institute of Technology, Anyang, China

  • School of Biotechnology and Food Engineering, Anyang Institute of Technology, Anyang, China

  • School of Biotechnology and Food Engineering, Anyang Institute of Technology, Anyang, China

  • School of Biotechnology and Food Engineering, Anyang Institute of Technology, Anyang, China

  • Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), Jinan, China

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