Bicarbonate-assisted extraction of pomegranate peel (Punica granatum L.) to obtain extracts with new low molecular weight phenols and enriched in total tannins and ellagic acid
Main Article Content
Keywords
ellagic acid; food by-products; gallic acid; polyphenols; punicalagin; HPLC-DAD-MS
Abstract
Pomegranate peel is a by-product rich in ellagitannins, characterized by high molecular weight and low bioavailability. Working on several peel samples, we aimed to propose a single-step bicarbonate-assisted extraction to produce dry extracts with new phenol profiles rich in hydrolyzed tannins with potentially higher bioavailability. Compared to decoction, 0.6% sodium bicarbonate (NaHCO3) for 1 h extraction allowed 3.5–6.5-fold and 5.6– 11.3-fold increase in ellagic acid and gallic acid, respectively, with total phenols ranging from 28.3% to 35.1% w/w. Simple pomegranate peel extraction with bicarbonate can be applied to prepare botanical extracts suitable for the food supplement market, thus increasing the value of this by-product.
References
Akande, T., Khatib, M., Ola Salawu, S., Afolabi Akindahunsi, A., Di Cesare Mannelli, L., Ghelardini, C., Balli, D., Cecchi, L. and Mulinacci, N. 2022. 1H NMR and HPLC-DAD-MS for the characterization of ellagitannins and triterpenoids of less investigated Anogeissus leiocarpus DC (Combretaceae) stem bark. Food Chem. 375:131813. https://doi.org/10.1016/j.foodchem.2021.131813
Akuru, E.A., Chukwuma, C.I., Oyeagu, C.E., Erukainure, O.L., Mashile, B., Setlhodi, R., Mashele, S.S., Makhafola, T.J., Unuofin, J.O., Abifarin, T.O. and Mpendulo, T.C. 2022. Nutritional and phytochemical profile of pomegranate (“Wonderful variety”) peel and its effects on hepatic oxidative stress and metabolic alterations. J Food Biochem. 46(4):e13913. https://doi.org/10.1111/jfbc.13913
Althunibat, O.Y., Al-Mustafa, A.H., Tarawneh, K., Khleifat, K.M., Ridzwan, B.H. and Qaralleh, H.N. 2010. Protective role of Punica granatum L. peel extract against oxidative damage in experimental diabetic rats. Proc Biochem. 45(4):581–585. https://doi.org/10.1016/j.procbio.2009.12.004
Amri, Z., Ghorbel, A., Turki, M., Akrout, F.M., Ayadi, F., Elfeki, A. and Hammami, M. 2017. Effect of pomegranate extracts on brain antioxidant markers and cholinesterase activity in high fat-high fructose diet induced obesity in rat model. BMC Comp Altern Med. 17(1):339. https://doi.org/10.1186/s12906-017-1842-9
Bala, I., Bhardwaj, V., Hariharan, S. and Kumar, M.N.V.R. 2006. Analytical methods for assay of ellagic acid and its solubility studies. J Pharm Biomed Anal. 40(1):206–210. https://doi.org/10.1016/j.jpba.2005.07.006
Balli, D., Cecchi, L., Khatib, M., Bellumori, M., Cairone, F., Carradori, S., Zengin, G., Cesa, S., Innocenti, M. and Mulinacci, N. 2020. Characterization of arils juice and peel decoction of fifteen varieties of Punica granatum L.: a focus on anthocyanins, ellagitannins and polysaccharides. Antioxidants. 9(3):238. https://doi.org/10.3390/antiox9030238
Basu, A. and Penugonda, K. 2009. Pomegranate juice: a heart-healthy fruit juice. Nutr Rev. 67(1):49–56. https://doi.org/10.1111/j.1753-4887.2008.00133.x
Cecchi, L., Khatib, M., Bellumori, M., Civa, V., Domizio, P., Innocenti, M., Balli, D. and Mulinacci, N. 2023. Industrial drying for agrifood by-products re-use: cases studies on pomegranate peel (Punica granatum L.) and stoned olive pomace (pâtè, Olea europaea L.). Food Chem. 403:134338. https://doi.org/10.1016/j.foodchem.2022.134338
Dadáková, K., Heinrichová, T., Lochman, J. and Kašparovský, T. 2020. Production of defense phenolics in tomato leaves of different age. Molecules. 25(21):4952. https://doi.org/10.3390/molecules25214952
Dadwal, V., Bhatt, S., Sonkhla, K., Joshi, R. and Gupta, M. 2017. Quantification of free and bound phenolics in bio-waste pomegranate peel and formulation of punicalagin rich rice. Int J Food Nutr Sci. 4(2):98–104. https://doi.org/10.15436/2377-0619.17.1321
Dey, D., Ray, R. and Hazra, B. 2015. Antimicrobial activity of pomegranate fruit constituents against drug-resistant Mycobacterium tuberculosis and β-lactamase producing Klebsiella pneumoniae. Pharm Biol. 53(10):1474–1480. https://doi.org/10.3109/13880209.2014.986687
Espín, J.C., Larrosa, M., García-Conesa, M.T. and Tomás-Barberán, F. 2013. Biological significance of urolithins, the gut microbial ellagic acid-derived metabolites: the evidence so far. Evid Based Comp Altern Med. 2013:1–15. https://doi.org/10.1155/2013/270418
Fahmy, H.A. and Farag, M.A. 2022. Ongoing and potential novel trends of pomegranate fruit peel; a comprehensive review of its health benefits and future perspectives as nutraceutical. J Food Biochem. 46(1):e14024. https://doi.org/10.1111/jfbc.14024
Fischer, U.A., Carle, R. and Kammerer, D.R. 2011. Identification and quantification of phenolic compounds from pomegranate (Punica granatum L.) peel, mesocarp, aril and differently produced juices by HPLC-DAD–ESI/MSn. Food Chem. 127(2):807–821. https://doi.org/10.1016/j.foodchem.2010.12.156
García-Villalba, R., Espín, J.C., Aaby, K., Alasalvar, C., Heinonen, M., Jacobs, G., Voorspoels, S., Koivumäki, T., Kroon, P.A., Pelvan, E., Saha, S. and Tomás-Barberán, F.A. 2015. Validated method for the characterization and quantification of extractable and nonextractable ellagitannins after acid hydrolysis in pomegranate fruits, juices, and extracts. J Agric Food Chem. 63(29):6555–6566. https://doi.org/10.1021/acs.jafc.5b02062
Gu, D., Yang, Y., Bakri, M., Chen, Q., Xin, X. and Aisa, H.A. 2013. A LC/QTOF-MS/MS application to investigate chemical compositions in a fraction with protein tyrosine phosphatase 1B inhibitory activity from Rosa Rugosa flowers: chemical compositions in an active fraction from Rosa Rugosa flowers. Phytochem Anal. 24(6):661–670. https://doi.org/10.1002/pca.2451
Haghighian, M.K., Rafraf, M., Hemmati, S., Haghravan, S. and Asghari-Jafarabadi, M. 2021. Effects of pomegranate (Punica granatum L.) peel extract supplementation on serum lipid profile and oxidative stress in obese women with knee osteoarthritis: a double blind, randomized, placebo controlled study. Adv Integ Med. 8(2):107–113. https://doi.org/10.1016/j.aimed.2020.05.001
Hemingway, R.W. and Hills, W.E. 1971. Behaviour of ellagitannins, gallic acid and ellagic acid under alkaline conditions. J Tech Assoc Pulp Paper Ind. 54(6):933–936.
Hernández-Corroto, E., Marina, M.L. and García, M.C. 2019. Extraction and identification by high resolution mass spectrometry of bioactive substances in different extracts obtained from pomegranate peel. J Chrom A. 1594:82–92. https://doi.org/10.1016/j.chroma.2019.02.018
Khatib, M., Campo, M., Bellumori, M., Cecchi, L., Vignolini, P., Innocenti, M. and Mulinacci, N. 2023. Tannins from different parts of the chestnut trunk (Castanea Sativa Mill.): a green and effective extraction method and their profiling by high-performance liquid chromatography-diode array detector-mass spectrometry. ACS Food Sci Tech. 3(11):1903–1912. https://doi.org/10.1021/acsfoodscitech.3c00272
Khatib, M., Innocenti, M., Giuliani, C., Al- Tamimi, A., Romani, A. and Mulinacci N. 2017. Mesocarp and exocarp of laffan and wonderful pomegranate varieties: by-products as a source of Ellagitannins. Int J Food Nutr Sci. 4(1):60–66. https://doi.org/10.15436/2377-0619.17.1465
Li, Y., Guo, C., Yang, J., Wei, J., Xu, J. and Cheng, S. 2006. Evaluation of antioxidant properties of pomegranate peel extract in comparison with pomegranate pulp extract. Food Chem. 96(2):254–260. https://doi.org/10.1016/j.foodchem.2005.02.033
Li, Y., Ye, T., Yang, F., Hu, M., Liang, L., He, H., Li, Z., Zeng, A., Li, Y., Yao, Y., Xie, Y., An, Z. and Li, S. 2016. Punica granatum (pomegranate) peel extract exerts potent antitumor and anti-metastasis activity in thyroid cancer. RSC Adv. 6(87):84523–84535. https://doi.org/10.1039/C6RA13167K
Liu, B., Lei, W., Hu, L. and Zhao, J. 2013. Mild alkaline hydrolysis is an efficient and low-cost method for improving the free phenolic content and health benefit of pomegranate peel extract. J Food Process Preserv. 37:694–700.
Liu, R., Li, J., Cheng, Y., Huo, T., Xue, J., Liu, Y., Liu, J. and Chen, X. 2015. Effects of ellagic acid-rich extract of pomegranates peel on regulation of cholesterol metabolism and its molecular mechanism in hamsters. Food Funct. 6(3):780–787. https://doi.org/10.1039/C4FO00759J
Long, J., Guo, Y., Yang, J., Henning, S.N., Lee, R., Rasmussen, A., Zhang, L., Lu, Q., Heber, D. and Li, Z. 2019. Bioavailability and bioactivity of free ellagic acid compared to pomegranate juice. Food Funct. 10:6582–6588. https://doi.org/10.1039/C9FO01683J
Lv, O., Wang, L., Li, J., Ma, Q. and Zhao, W. 2016. Effects of pomegranate peel polyphenols on lipid accumulation and cholesterol metabolic transformation in L-02 human hepatic cells via the PPARγ-ABCA1/CYP7A1 pathway. Food Funct. 7(12):4976–4983. https://doi.org/10.1039/C6FO01261B
Man, G., Xu, L., Wang, Y., Liao, X. and Xu, Z. 2022. Profiling phenolic composition in pomegranate peel from nine selected cultivars using UHPLC-QTOF-MS and UPLC-QQQ-MS. Front Nutr. 8:807447. https://doi.org/10.3389/fnut.2021.807447
Mastrogiovanni, F., Mukhopadhya, A., Lacetera, N., Ryan, M., Romani, A., Bernini, R. and Sweeney, T. 2019. Anti-inflammatory effects of pomegranate peel extracts on in vitro human intestinal CaCo-2 cells and ex vivo porcine colonic tissue explants. Nutrients. 11(3):548. https://doi.org/10.3390/nu11030548
Mo, F., Lv, B., An, T., Miao, J., Liu, J., Zhang, J., Zhang, Z., Ma, M., Yang, X., Zhao, D., Zhang, D., Gao, S. and Jiang, G. 2019. Protective mechanism of punicalagin against endoplasmic reticulum stress in the liver of mice with type 2 diabetes mellitus. J Funct Foods. 56:57–64. https://doi.org/10.1016/j.jff.2019.03.006
Mourtzinos, I. and Goula, A. 2019. Polyphenols in agricultural byproducts and food waste. In: Polyphenols in Plants. Academic Press, Elsevier, Amsterdam, the Netherlands, pp. 23–44. https://doi.org/10.1016/B978-0-12-813768-0.00002-5
Plumb, G.W., De Pascual-Teresa, S., Santos-Buelga, C., Rivas-Gonzalo, J.C., and Williamson, G. 2002. Antioxidant properties of gallocatechin and prodelphinidins from pomegranate peel. Redox Rep. 7(1):41–46. https://doi.org/10.1179/135100002125000172
Sentandreu, E., Cerdán-Calero, M. and Sendra, J.M. 2013. Phenolic profile characterization of pomegranate (Punica granatum) juice by high-performance liquid chromatography with diode array detection coupled to an electrospray ion trap mass analyzer. J Food Comp Anal. 30(1):32–40. https://doi.org/10.1016/j.jfca.2013.01.003
Shahidi, F. and Peng, H. 2018. Bioaccessibility and bioavailability of phenolic compounds. J Food Bioact. 4(7):11–68. https://doi.org/10.31665/JFB.2018.4162
Sun, J., Chu, Y.-F., Wu, X. and Liu, R.H. 2002. Antioxidant and antiproliferative activities of common fruits. J Agric Food Chem. 50(25):7449–7454. https://doi.org/10.1021/jf0207530
Sun, S., Huang, S., Shi, Y., Shao, Y., Qiu, J., Sedjoah, R.-C. A.-A., Yan, Z., Ding, L., Zou, D. and Xin, Z. 2021. Extraction, isolation, characterization and antimicrobial activities of non-extractable polyphenols from pomegranate peel. Food Chem. 351:129232. https://doi.org/10.1016/j.foodchem.2021.129232
Tanaka, T., Nonaka, G. and Nishioka, I. 1990. Tannins and related compounds. C. Reaction of dehydrohexahydroxydiphenic acid esters with bases, and its application to the structure determination of pomegranate tannins, granatins A and B. Chem Pharm Bullettin. 38:2424-2428, https://doi.org/10.1248/cpb.38.2424
Tuominen, A. and Sundman, T. 2013. Stability and oxidation products of hydrolysable tannins in basic conditions detected by HPLC/DAD-ESI/QTOF/MS: stability of hydrolysable tannins in basic conditions. Phytochem Analysis. 24(5):424–435. https://doi.org/10.1002/pca.2456
Venusova, E., Kolesarova, A., Horky, P. and Slama, P. 2021. Physiological and immune functions of punicalagin. Nutrients. 13:2150. https://doi.org/10.3390/nu13072150
Verotta, L., Panzella, L., Antenucci, S., Calvenzani, V., Tomay, F., Petroni, K., Caneva, E. and Napolitano, A. 2018. Fermented pomegranate wastes as sustainable source of ellagic acid: antioxidant properties, anti-inflammatory action, and controlled release under simulated digestion conditions. Food Chem. 246:129–136. https://doi.org/10.1016/j.foodchem.2017.10.131
Xiang, Q., Li, M., Wen, J., Ren, F., Yang, Z., Jiang, X. and Chen, Y. 2022. The bioactivity and applications of pomegranate peel extract: a review. J Food Biochem. 46(7):e14105. https://doi.org/10.1111/jfbc.14105
Zhai, X., Zhu, C., Zhang, Y., Sun, J., Alim, A. and Yang, X. 2018. Chemical characteristics, antioxidant capacities and hepatoprotection of polysaccharides from pomegranate peel. Carbohydr Polym. 202:461–469. https://doi.org/10.1016/j.carbpol.2018.09.013
Zhang, B., Zhang, Y., Li, H., Deng, Z. and Tsao, R. 2020. A review on insoluble-bound phenolics in plant-based food matrix and their contribution to human health with future perspectives. Trends Food Sci Technol. 105:347–362. https://doi.org/10.1016/j.tifs.2020.09.029
Akuru, E.A., Chukwuma, C.I., Oyeagu, C.E., Erukainure, O.L., Mashile, B., Setlhodi, R., Mashele, S.S., Makhafola, T.J., Unuofin, J.O., Abifarin, T.O. and Mpendulo, T.C. 2022. Nutritional and phytochemical profile of pomegranate (“Wonderful variety”) peel and its effects on hepatic oxidative stress and metabolic alterations. J Food Biochem. 46(4):e13913. https://doi.org/10.1111/jfbc.13913
Althunibat, O.Y., Al-Mustafa, A.H., Tarawneh, K., Khleifat, K.M., Ridzwan, B.H. and Qaralleh, H.N. 2010. Protective role of Punica granatum L. peel extract against oxidative damage in experimental diabetic rats. Proc Biochem. 45(4):581–585. https://doi.org/10.1016/j.procbio.2009.12.004
Amri, Z., Ghorbel, A., Turki, M., Akrout, F.M., Ayadi, F., Elfeki, A. and Hammami, M. 2017. Effect of pomegranate extracts on brain antioxidant markers and cholinesterase activity in high fat-high fructose diet induced obesity in rat model. BMC Comp Altern Med. 17(1):339. https://doi.org/10.1186/s12906-017-1842-9
Bala, I., Bhardwaj, V., Hariharan, S. and Kumar, M.N.V.R. 2006. Analytical methods for assay of ellagic acid and its solubility studies. J Pharm Biomed Anal. 40(1):206–210. https://doi.org/10.1016/j.jpba.2005.07.006
Balli, D., Cecchi, L., Khatib, M., Bellumori, M., Cairone, F., Carradori, S., Zengin, G., Cesa, S., Innocenti, M. and Mulinacci, N. 2020. Characterization of arils juice and peel decoction of fifteen varieties of Punica granatum L.: a focus on anthocyanins, ellagitannins and polysaccharides. Antioxidants. 9(3):238. https://doi.org/10.3390/antiox9030238
Basu, A. and Penugonda, K. 2009. Pomegranate juice: a heart-healthy fruit juice. Nutr Rev. 67(1):49–56. https://doi.org/10.1111/j.1753-4887.2008.00133.x
Cecchi, L., Khatib, M., Bellumori, M., Civa, V., Domizio, P., Innocenti, M., Balli, D. and Mulinacci, N. 2023. Industrial drying for agrifood by-products re-use: cases studies on pomegranate peel (Punica granatum L.) and stoned olive pomace (pâtè, Olea europaea L.). Food Chem. 403:134338. https://doi.org/10.1016/j.foodchem.2022.134338
Dadáková, K., Heinrichová, T., Lochman, J. and Kašparovský, T. 2020. Production of defense phenolics in tomato leaves of different age. Molecules. 25(21):4952. https://doi.org/10.3390/molecules25214952
Dadwal, V., Bhatt, S., Sonkhla, K., Joshi, R. and Gupta, M. 2017. Quantification of free and bound phenolics in bio-waste pomegranate peel and formulation of punicalagin rich rice. Int J Food Nutr Sci. 4(2):98–104. https://doi.org/10.15436/2377-0619.17.1321
Dey, D., Ray, R. and Hazra, B. 2015. Antimicrobial activity of pomegranate fruit constituents against drug-resistant Mycobacterium tuberculosis and β-lactamase producing Klebsiella pneumoniae. Pharm Biol. 53(10):1474–1480. https://doi.org/10.3109/13880209.2014.986687
Espín, J.C., Larrosa, M., García-Conesa, M.T. and Tomás-Barberán, F. 2013. Biological significance of urolithins, the gut microbial ellagic acid-derived metabolites: the evidence so far. Evid Based Comp Altern Med. 2013:1–15. https://doi.org/10.1155/2013/270418
Fahmy, H.A. and Farag, M.A. 2022. Ongoing and potential novel trends of pomegranate fruit peel; a comprehensive review of its health benefits and future perspectives as nutraceutical. J Food Biochem. 46(1):e14024. https://doi.org/10.1111/jfbc.14024
Fischer, U.A., Carle, R. and Kammerer, D.R. 2011. Identification and quantification of phenolic compounds from pomegranate (Punica granatum L.) peel, mesocarp, aril and differently produced juices by HPLC-DAD–ESI/MSn. Food Chem. 127(2):807–821. https://doi.org/10.1016/j.foodchem.2010.12.156
García-Villalba, R., Espín, J.C., Aaby, K., Alasalvar, C., Heinonen, M., Jacobs, G., Voorspoels, S., Koivumäki, T., Kroon, P.A., Pelvan, E., Saha, S. and Tomás-Barberán, F.A. 2015. Validated method for the characterization and quantification of extractable and nonextractable ellagitannins after acid hydrolysis in pomegranate fruits, juices, and extracts. J Agric Food Chem. 63(29):6555–6566. https://doi.org/10.1021/acs.jafc.5b02062
Gu, D., Yang, Y., Bakri, M., Chen, Q., Xin, X. and Aisa, H.A. 2013. A LC/QTOF-MS/MS application to investigate chemical compositions in a fraction with protein tyrosine phosphatase 1B inhibitory activity from Rosa Rugosa flowers: chemical compositions in an active fraction from Rosa Rugosa flowers. Phytochem Anal. 24(6):661–670. https://doi.org/10.1002/pca.2451
Haghighian, M.K., Rafraf, M., Hemmati, S., Haghravan, S. and Asghari-Jafarabadi, M. 2021. Effects of pomegranate (Punica granatum L.) peel extract supplementation on serum lipid profile and oxidative stress in obese women with knee osteoarthritis: a double blind, randomized, placebo controlled study. Adv Integ Med. 8(2):107–113. https://doi.org/10.1016/j.aimed.2020.05.001
Hemingway, R.W. and Hills, W.E. 1971. Behaviour of ellagitannins, gallic acid and ellagic acid under alkaline conditions. J Tech Assoc Pulp Paper Ind. 54(6):933–936.
Hernández-Corroto, E., Marina, M.L. and García, M.C. 2019. Extraction and identification by high resolution mass spectrometry of bioactive substances in different extracts obtained from pomegranate peel. J Chrom A. 1594:82–92. https://doi.org/10.1016/j.chroma.2019.02.018
Khatib, M., Campo, M., Bellumori, M., Cecchi, L., Vignolini, P., Innocenti, M. and Mulinacci, N. 2023. Tannins from different parts of the chestnut trunk (Castanea Sativa Mill.): a green and effective extraction method and their profiling by high-performance liquid chromatography-diode array detector-mass spectrometry. ACS Food Sci Tech. 3(11):1903–1912. https://doi.org/10.1021/acsfoodscitech.3c00272
Khatib, M., Innocenti, M., Giuliani, C., Al- Tamimi, A., Romani, A. and Mulinacci N. 2017. Mesocarp and exocarp of laffan and wonderful pomegranate varieties: by-products as a source of Ellagitannins. Int J Food Nutr Sci. 4(1):60–66. https://doi.org/10.15436/2377-0619.17.1465
Li, Y., Guo, C., Yang, J., Wei, J., Xu, J. and Cheng, S. 2006. Evaluation of antioxidant properties of pomegranate peel extract in comparison with pomegranate pulp extract. Food Chem. 96(2):254–260. https://doi.org/10.1016/j.foodchem.2005.02.033
Li, Y., Ye, T., Yang, F., Hu, M., Liang, L., He, H., Li, Z., Zeng, A., Li, Y., Yao, Y., Xie, Y., An, Z. and Li, S. 2016. Punica granatum (pomegranate) peel extract exerts potent antitumor and anti-metastasis activity in thyroid cancer. RSC Adv. 6(87):84523–84535. https://doi.org/10.1039/C6RA13167K
Liu, B., Lei, W., Hu, L. and Zhao, J. 2013. Mild alkaline hydrolysis is an efficient and low-cost method for improving the free phenolic content and health benefit of pomegranate peel extract. J Food Process Preserv. 37:694–700.
Liu, R., Li, J., Cheng, Y., Huo, T., Xue, J., Liu, Y., Liu, J. and Chen, X. 2015. Effects of ellagic acid-rich extract of pomegranates peel on regulation of cholesterol metabolism and its molecular mechanism in hamsters. Food Funct. 6(3):780–787. https://doi.org/10.1039/C4FO00759J
Long, J., Guo, Y., Yang, J., Henning, S.N., Lee, R., Rasmussen, A., Zhang, L., Lu, Q., Heber, D. and Li, Z. 2019. Bioavailability and bioactivity of free ellagic acid compared to pomegranate juice. Food Funct. 10:6582–6588. https://doi.org/10.1039/C9FO01683J
Lv, O., Wang, L., Li, J., Ma, Q. and Zhao, W. 2016. Effects of pomegranate peel polyphenols on lipid accumulation and cholesterol metabolic transformation in L-02 human hepatic cells via the PPARγ-ABCA1/CYP7A1 pathway. Food Funct. 7(12):4976–4983. https://doi.org/10.1039/C6FO01261B
Man, G., Xu, L., Wang, Y., Liao, X. and Xu, Z. 2022. Profiling phenolic composition in pomegranate peel from nine selected cultivars using UHPLC-QTOF-MS and UPLC-QQQ-MS. Front Nutr. 8:807447. https://doi.org/10.3389/fnut.2021.807447
Mastrogiovanni, F., Mukhopadhya, A., Lacetera, N., Ryan, M., Romani, A., Bernini, R. and Sweeney, T. 2019. Anti-inflammatory effects of pomegranate peel extracts on in vitro human intestinal CaCo-2 cells and ex vivo porcine colonic tissue explants. Nutrients. 11(3):548. https://doi.org/10.3390/nu11030548
Mo, F., Lv, B., An, T., Miao, J., Liu, J., Zhang, J., Zhang, Z., Ma, M., Yang, X., Zhao, D., Zhang, D., Gao, S. and Jiang, G. 2019. Protective mechanism of punicalagin against endoplasmic reticulum stress in the liver of mice with type 2 diabetes mellitus. J Funct Foods. 56:57–64. https://doi.org/10.1016/j.jff.2019.03.006
Mourtzinos, I. and Goula, A. 2019. Polyphenols in agricultural byproducts and food waste. In: Polyphenols in Plants. Academic Press, Elsevier, Amsterdam, the Netherlands, pp. 23–44. https://doi.org/10.1016/B978-0-12-813768-0.00002-5
Plumb, G.W., De Pascual-Teresa, S., Santos-Buelga, C., Rivas-Gonzalo, J.C., and Williamson, G. 2002. Antioxidant properties of gallocatechin and prodelphinidins from pomegranate peel. Redox Rep. 7(1):41–46. https://doi.org/10.1179/135100002125000172
Sentandreu, E., Cerdán-Calero, M. and Sendra, J.M. 2013. Phenolic profile characterization of pomegranate (Punica granatum) juice by high-performance liquid chromatography with diode array detection coupled to an electrospray ion trap mass analyzer. J Food Comp Anal. 30(1):32–40. https://doi.org/10.1016/j.jfca.2013.01.003
Shahidi, F. and Peng, H. 2018. Bioaccessibility and bioavailability of phenolic compounds. J Food Bioact. 4(7):11–68. https://doi.org/10.31665/JFB.2018.4162
Sun, J., Chu, Y.-F., Wu, X. and Liu, R.H. 2002. Antioxidant and antiproliferative activities of common fruits. J Agric Food Chem. 50(25):7449–7454. https://doi.org/10.1021/jf0207530
Sun, S., Huang, S., Shi, Y., Shao, Y., Qiu, J., Sedjoah, R.-C. A.-A., Yan, Z., Ding, L., Zou, D. and Xin, Z. 2021. Extraction, isolation, characterization and antimicrobial activities of non-extractable polyphenols from pomegranate peel. Food Chem. 351:129232. https://doi.org/10.1016/j.foodchem.2021.129232
Tanaka, T., Nonaka, G. and Nishioka, I. 1990. Tannins and related compounds. C. Reaction of dehydrohexahydroxydiphenic acid esters with bases, and its application to the structure determination of pomegranate tannins, granatins A and B. Chem Pharm Bullettin. 38:2424-2428, https://doi.org/10.1248/cpb.38.2424
Tuominen, A. and Sundman, T. 2013. Stability and oxidation products of hydrolysable tannins in basic conditions detected by HPLC/DAD-ESI/QTOF/MS: stability of hydrolysable tannins in basic conditions. Phytochem Analysis. 24(5):424–435. https://doi.org/10.1002/pca.2456
Venusova, E., Kolesarova, A., Horky, P. and Slama, P. 2021. Physiological and immune functions of punicalagin. Nutrients. 13:2150. https://doi.org/10.3390/nu13072150
Verotta, L., Panzella, L., Antenucci, S., Calvenzani, V., Tomay, F., Petroni, K., Caneva, E. and Napolitano, A. 2018. Fermented pomegranate wastes as sustainable source of ellagic acid: antioxidant properties, anti-inflammatory action, and controlled release under simulated digestion conditions. Food Chem. 246:129–136. https://doi.org/10.1016/j.foodchem.2017.10.131
Xiang, Q., Li, M., Wen, J., Ren, F., Yang, Z., Jiang, X. and Chen, Y. 2022. The bioactivity and applications of pomegranate peel extract: a review. J Food Biochem. 46(7):e14105. https://doi.org/10.1111/jfbc.14105
Zhai, X., Zhu, C., Zhang, Y., Sun, J., Alim, A. and Yang, X. 2018. Chemical characteristics, antioxidant capacities and hepatoprotection of polysaccharides from pomegranate peel. Carbohydr Polym. 202:461–469. https://doi.org/10.1016/j.carbpol.2018.09.013
Zhang, B., Zhang, Y., Li, H., Deng, Z. and Tsao, R. 2020. A review on insoluble-bound phenolics in plant-based food matrix and their contribution to human health with future perspectives. Trends Food Sci Technol. 105:347–362. https://doi.org/10.1016/j.tifs.2020.09.029
Article Sidebar
Published
Oct 1, 2025
Article Details
How to Cite
D'Agostino, S., Ugolini, T., Freschini, D., Khatib, M., Cecchi, L., Zanoni, B., Zonfrillo, B., Innocenti, M., Bellumori, M., & Mulinacci, N. . (2025). Bicarbonate-assisted extraction of pomegranate peel (Punica granatum L.) to obtain extracts with new low molecular weight phenols and enriched in total tannins and ellagic acid. Italian Journal of Food Science, 37(4), 47-73. https://doi.org/10.15586/ijfs.v37i4.2996
Section
Paper
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Copyright Agreement with Authors
Before publication, after the acceptance of the manuscript, Authors have to sign a Publication Agreement with "Italian Journal of Food Science", granting and assigning to "Italian Journal of Food Science" the perpetual right to distribute the work free of charge by any means and in any parts of the world, including the communication to the public through the journal website.
License for Published Contents
http://creativecommons.org/licenses/by-nc-nd/4.0/
How to Cite
D'Agostino, S., Ugolini, T., Freschini, D., Khatib, M., Cecchi, L., Zanoni, B., Zonfrillo, B., Innocenti, M., Bellumori, M., & Mulinacci, N. . (2025). Bicarbonate-assisted extraction of pomegranate peel (Punica granatum L.) to obtain extracts with new low molecular weight phenols and enriched in total tannins and ellagic acid. Italian Journal of Food Science, 37(4), 47-73. https://doi.org/10.15586/ijfs.v37i4.2996