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Biotransformation and recovery of the isoflavones genistein and daidzein from industrial antibiotic fermentations

  • Applied microbial and cell physiology
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Abstract

The objective of this study was to follow the metabolic fate of isoflavone glucosides from the soybean meal in a model industrial fermentation to determine if commercially useful isoflavones could be harvested as coproducts from the spent broth at the end of the fermentation. The isoflavone aglycones, genistein, and daidzein together make up 0.1–0.2 % of the soybean meal by weight but serve no known function in the manufacturing process. After feeding genistein to washed cells of the erythromycin-producing organism, Saccharopolyspora erythraea, the first biotransformation product (Gbp1) was determined by X-ray crystallography to be genistein-7-O-α-rhamnoside (rhamnosylgenistein). Subsequent feeding of rhamnosylgenistein to growing cells of Saccharopolyspora erythraea led to the production of a second biotransformation product, Gbp2. Chromatographic evidence suggested that Gbp2 accumulated in the spent broth of the erythromycin fermentation. When the spent broth was hydrolyzed with acid or industrial enzyme preparations, the isoflavone biotransformation products were returned back to their parental forms, genistein and daidzein, which were then recovered as coproducts. Desirable features of this method are that it does not require modification of the erythromycin manufacturing process or genetic engineering of the producing organism to be put into practice. A preliminary investigation of five additional antibiotic fermentations of industrial importance also found isoflavone coproduct potential.

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Acknowledgments

We acknowledge the Small Business Innovation Research program and the National Institutes of Health for grants R43 CA93165 and R44 CA93165 from the National Center for Complementary and Alternative Medicine. We acknowledge Igor Brikun, Andrey Fedashtchin, Noelle Kwan, Ben Leach, Cheryl Iverson, and John Aikens for the helpful discussions.

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Author notes

  1. Andrew R. Reeves

    Present address: Coskata, Inc, 4575 Weaver Pkwy., Suite 100, Warrenville, IL, 60555, USA

  2. Ramya Seshadri

    Present address: Abbott Molecular, 1300 East Touhy Avenue, Des Plaines, IL, 60018, USA

  3. Melissa C. Gonzalez

    Present address: Department of Cellular and Molecular Biology, Northwestern University, 303 East Chicago Avenue, Chicago, IL, 60611, USA

Authors and Affiliations

  1. Fermalogic, Inc, 920 N. Franklin St, Chicago, IL, 60610, USA

    J. Mark Weber, Andrew R. Reeves, Ramya Seshadri, William H. Cernota, Melissa C. Gonzalez & Roy K. Wesley

  2. School of Chemical Sciences, University of Illinois, 505 S Matthews Ave, Urbana, IL, 61801, USA

    Danielle L. Gray

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  1. J. Mark Weber
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Correspondence to J. Mark Weber.

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Weber, J.M., Reeves, A.R., Seshadri, R. et al. Biotransformation and recovery of the isoflavones genistein and daidzein from industrial antibiotic fermentations. Appl Microbiol Biotechnol 97, 6427–6437 (2013). https://doi.org/10.1007/s00253-013-4839-4

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  • DOI: https://doi.org/10.1007/s00253-013-4839-4

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