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Acylation of flavonol glycosides using protein extracts of Croton species (Euphorbiaceae)

  • Biochemistry & Physiology - Original Article
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Abstract

Acylation of flavonoid glycosides enhances their chemical stability, lipo-solubility and antioxidant activity, improving their medicinal potential. Enzymatic acylation of flavonoid glycosides is advantageous compared to chemical procedures, as these reactions proceed at mild conditions and the acyl group is inserted at specific positions. In the present work, enriched leaf protein extracts of Croton floribundus Spreng and C. urucurana Baillon (Euphorbiaceae) were used as sources of enzymes in approaches to obtain p-coumaroyl derivatives of 3-O-glycosides of kaempferol and quercetin, as well as 7-O-quercetagetin glucoside. Tiliroside (1), helichrysoside (2) and quercetin-3-O-(6″-p-coumaroyl)-galactoside (3) were detected by HPLC–DAD and UPLC/MS as products of acylation reaction, using protein extracts of C. urucurana and either p-coumaroyl-CoA or p-coumaric acid plus CoA and ATP. Protein extracts of C. floribundus Spreng were effective toward the acylation of kaempferol-3-O-glucoside. Although acyltransferases seem to be ubiquitous in Croton, the ability to acylate different flavonol glycosides might largely depend on the species. Acyltransferases in the protein extracts are versatile at acylating flavonoids with distinct aglycones and distinct sugar substituents. The failure to attain acylated products of quercetagetin-7-O-glucoside indicates that Croton acyltransferases are regioselective, with a target on 3-O-sugars of flavonoids.

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Acknowledgements

The authors thank Dr. Cláudia Maria Furlan (University of São Paulo, Dept. of Botany for constructive suggestions and Dr. Alexandra C. H. Frankland Sawaya (University of Campinas, Faculty of Pharmaceutical Sciences) for her kind allowance to perform analyses with the UPLC/MS apparatus system of her laboratory. The work was benefited with resources derived from grant 2007/02518-6 of FAPESP (Fundação de Amparo à Pesquisa no Estado de São Paulo). IC and AS are fellow and senior fellow researcher, respectively, of CNPq (Conselho Nacional do Desenvolvimento Científico e Tecnológico, Brazil).

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Authors and Affiliations

  1. Department of Botany, Institute of Biosciences, University of São Paulo, Rua do Matão 277, São Paulo, SP, 05508-090, Brazil

    Jocimar Oliani, Igor Cesarino, Maria Luiza Faria Salatino & Antonio Salatino

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  1. Jocimar Oliani
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  2. Igor Cesarino
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  3. Maria Luiza Faria Salatino
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  4. Antonio Salatino
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Contributions

J.O. contributed to formal analysis, investigation, review; I.C. contributed to methodology, formal analysis, investigation, review; M.L.F.S. contributed to investigation, project administration, review; A.S. contributed to conceptualization, project administration, funding acquisition, original draft, review and editing.

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Correspondence to Jocimar Oliani.

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The authors declare that they have no known competing financial interests or personal relationship that could have appeared to influence the work reported in this paper.

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Oliani, J., Cesarino, I., Salatino, M.L.F. et al. Acylation of flavonol glycosides using protein extracts of Croton species (Euphorbiaceae). Braz. J. Bot 44, 601–609 (2021). https://doi.org/10.1007/s40415-021-00748-2

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  • DOI: https://doi.org/10.1007/s40415-021-00748-2

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