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A High-Yield Process for Extraction of Hesperidin from Orange (Citrus sinensis L. osbeck) Peels Waste, and Its Transformation to Diosmetin, A Valuable and Bioactive Flavonoid

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Abstract

An alternative and high-yield method to obtain hesperidin, a bitter flavored flavanone glucoside, from orange (Citrus sinensis L. osbeck) peels waste is described. The proposed process, which add high-value to this kind of residue from orange juice processing industry, was based on a successful modification applied to extraction of naringin from grapefruit. This method involves extraction with methanol and crystallization in water with addition of dichloromethane, requiring shorter times and reducing of volume of solvent employed. Changing to hot extraction with methanol of fresh orange albedo led to higher yields of extraction in half the time required due to the direct method, avoiding air-dried albedo step. Application of described method led to 2.8% yield (w/w dry albedo) of hesperidin extracted in 89.4% purity determined by HPLC analysis. To add high-value to the flavanone obtained, it was subject to chemical transformation (oxidation and hydrolysis, 83% and 88% yield, respectively) into the flavone diosmetin (73% yield for 2 steps), an expensive and naturally-occurring flavonoid in low yields which exhibits a wide range of pharmacological properties.

Graphic Abstract

This paper describes high-yield process for extraction of hesperidin from orange peels waste, and their use as feedstock in the production of diosmetin.

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Fig. 1
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Acknowledgements

The authors are grateful to Brazilian Agencies CNPq (National Council for Scientific and Technological Development), CAPES (Coordination for the Improvement of Higher Education Personnel) and INCT E&A (National Institute for Science and Technology for Energy and Environment) for financial support. The authors thanks Laboratory of High Resolution Nuclear Magnetic Resonance (LAREMAR) of the Department of Chemistry (UFMG, Brazil) for conducting NMR spectra.

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Authors and Affiliations

  1. Organic Chemistry Department, Chemistry Institute, Federal University of Bahia, Salvador, BA, CEP 40170 115, Brazil

    Mauricio M. Victor, Jorge M. David, Maria V. M. Cortez, Juliana L. Leite & Gálber S. B. da Silva

  2. Nacional Institute of Science and Technology for Energy and Environmental - INCT E&A, Federal University of Bahia, Salvador, BA, CEP 40170 115, Brazil

    Mauricio M. Victor, Jorge M. David, Juliana L. Leite & Gálber S. B. da Silva

  3. Interdisciplinary Center for Energy and Environmental (CIENAM), Federal University of Bahia, Salvador, BA, CEP 40170 115, Brazil

    Mauricio M. Victor

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Victor, M.M., David, J.M., Cortez, M.V.M. et al. A High-Yield Process for Extraction of Hesperidin from Orange (Citrus sinensis L. osbeck) Peels Waste, and Its Transformation to Diosmetin, A Valuable and Bioactive Flavonoid. Waste Biomass Valor 12, 313–320 (2021). https://doi.org/10.1007/s12649-020-00982-x

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