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Effect of the Enzymatic Treatment of Phenolic-Rich Pigments from Purple Corn (Zea mays L.): Evaluation of Thermal Stability and Alpha-Glucosidase Inhibition

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Abstract

The impact of enzymatic treatment of Candida antarctica lipase B on a phenolics-rich extract from purple corn (Zea mays L.) (PCE) was evaluated. PCE was obtained by solid–liquid extraction with 80% ethanol. PCE was treated with lipase B in acetonitrile using octanoic acid as acyl donor for 72 h. Acylated and non-acylated PCE were tested for thermal stability at 80 °C, ɑ-glucosidase inhibitory activity, and molecular docking. The enzymatic treatment promoted the generation of a reaction product identified by HPLC along with a bathochromic shift (530 to 570 nm) in the extract. Enzymatic treatment increased (p < 0.05) the half-life of total anthocyanins in solution at 80 °C from 6.05 to 10.05 h. Additionally, enhanced (p < 0.05) the ɑ-glucosidase inhibitory activity at a concentration of 0.5 mg eq. C3G/mL (11.7% non-acylated and 33.2% acylated). Molecular docking using predicted acylated structures of major anthocyanins in PCE was correlated with biochemical evaluation on ɑ-glucosidase; for instance, cyanidin-3-(6″-n-octanoyl)-glucoside (−9.4 kcal/mol) had a more favorable binding energy than non-acylated cyanidin-3-O-glucoside (−8.4 kcal/mol) with the catalytic site of ɑ-glucosidase. A ligand–protein interaction analysis showed that the acyl group plays an important role in stabilizing anthocyanins in the catalytic cavity of ɑ-glucosidase. Our results suggest that treatment with lipase B is a promising strategy to improve technological and biological potential of pigments from purple corn.

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Data Availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author upon reasonable request.

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Acknowledgements

The authors thank M.T. Celestino Aparicio Martínez, purple corn producer, for kindly providing the samples for this study.

Funding

Jimena Yañez Apam was supported by a CONACyT scholarship number 1078514. This project was financially supported by the Young Investigator Award on Food Science and Technology 2021 from the Mexican Academy of Sciences, received by Diego Luna-Vital, and a seed funding provided by the Institute for Obesity Research—Tecnologico de Monterrey, Mexico.

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  1. Tecnologico de Monterrey, School of Engineering and Science, Ave. Eugenio Garza Sada 2501, 64849, Monterrey, N.L., Mexico

    Jimena Yañez Apam

  2. Department of Chemical Engineering, Centro Universitario de Ciencias Exactas e Ingenierías, Universidad de Guadalajara, Blvd. Gral. Marcelino García Barragán 1421, Olímpica, 44430, Guadalajara, Jal., Mexico

    Azucena Herrera-González

  3. Tecnologico de Monterrey, The Institute for Obesity Research, Ave. Eugenio Garza Sada 2501, 64849, Monterrey, N.L., Mexico

    Jimena Yañez Apam, Astrid Domínguez Uscanga, Jorge Alberto Fragoso-Medina & Diego A. Luna-Vital

  4. Laboratorio de Química de Productos Naturales, Red de Estudios Moleculares Avanzados, Instituto de Ecología A. C., Carretera Antigua a Coatepec 351, 91073, Xalapa, Ver., Mexico

    José Antonio Guerrero-Analco & Juan Luis Monribot-Villanueva

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Jimena Yañez Apam performed the experiments, analyzed the data, and wrote the manuscript text. Azucena Herrera-González, Astrid Domínguez-Uscanga, Jose Antonio Guerrero Analco, Juan Luis Monribot-Villanueva, and Jorge Alberto Fragoso Medina provided guidance, specialized equipment, and data curation. Diego Armando Luna-Vital conceived the project, provided guidance and funding, and contributed to writing the manuscript. All authors reviewed the manuscript.

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Correspondence to Diego A. Luna-Vital.

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Yañez Apam, J., Herrera-González, A., Domínguez Uscanga, A. et al. Effect of the Enzymatic Treatment of Phenolic-Rich Pigments from Purple Corn (Zea mays L.): Evaluation of Thermal Stability and Alpha-Glucosidase Inhibition. Food Bioprocess Technol 16, 2055–2069 (2023). https://doi.org/10.1007/s11947-023-03021-4

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