Extraction, purification, characterization and antioxidant activities of heat-resistance phenolic compounds from lemon pulp

Document Type: Original Article

Authors

1 Department of Chemistry, Faculty of Natural Sciences, Cankiri Karatekin University, 18100, Çankiri, Turkey

2 Department of Chemistry, Faculty of Science and Arts, Ondokuz Mayis University, Samsun, Turkey

Abstract

Lemon as a citrus species is widely cultivated in the Mediterranean region, Turkey. The lemon pulp has been characterized as a rich source of phenolic and flavonoid compounds, phenolic acid as well as novel coumarin derivatives. It is usually obtained within the juice production in the food industries. In the current report, lemon pulp was initially dried and immediately after subjected to extraction with hot water and ethyl acetate. This study deals with the isolation of secondary metabolites along with determinations of 32 phenolic contents. After isolation of major components using Sephadex LH-20 column and silica gel, 11 phenolic components were totally characterized using the 1D and 2D NMR techniques. Lemon pulp known as citrus peel has been recognized as a potential source of coumarin, limonoids, and methoxylated flavones. The antioxidant activities of the limonin (LMN) and lemon pulp ethyl acetate extract (LPEA) were evaluated using in vitro methods involving total antioxidant activity, reducing power, inhibition of lipid peroxidation, scavenging activities of DPPH∙, H2O2 and ABTS+. and compared with standards at 10, 25, 50 and 100 μg.mL-1. According to the finding of this research, LMN and LPEA showed strong in vitro antioxidant activities and also were significantly exhibited an increase to be in a dose-dependent manner, (p <0.05).

Graphical Abstract

Extraction, purification, characterization and antioxidant activities of heat-resistance phenolic compounds from lemon pulp

Keywords

Main Subjects


Antolovich, M., Prenzler, P.D., Patsalides, E., McDonald, S., Robards, K., 2002. Methods for testing antioxidant activity. Analyst 127(1), 183-198.

Blois, M.S., 1958. Antioxidant determinations by the use of a stable free radical. Nature 181, 1199-1200.

Bocco, A., Cuvelier, M.-E., Richard, H., Berset, C., 1998. Antioxidant activity and phenolic composition of citrus peel and seed extracts. J. Agric. Food Chem. 46(6), 2123-2129.

Bursal, E., Köksal, E., 2011. Evaluation of reducing power and radical scavenging activities of water and ethanol extracts from sumac (Rhus coriaria L.). Food Res. Int. 44(7), 2217-2221.

Choi, C.W., Kim, S.C., Hwang, S.S., Choi, B.K., Ahn, H.J., Lee, M.Y., Park, S.H., Kim, S.K., 2002. Antioxidant activity and free radical scavenging capacity between Korean medicinal plants and flavonoids by assay-guided comparison. Plant Sci. 163(6), 1161-1168.

Del Rıo, J., Fuster, M., Gomez, P., Porras, I., Garcıa-Lidon, A., Ortuno, A., 2004. Citrus limon: a source of flavonoids of pharmaceutical interest. Food Chem. 84(3), 457-461.

Demirtas, I., Erenler, R., Elmastas, M., Goktasoglu, A., 2013. Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction. Food Chem. 136(1), 34-40.

Dinis, T.C., Madeira, V.M., Almeida, L.M., 1994. Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch. Biochem. Biophys. 315(1), 161-169.

Erenler, R., Sen, O., Aksit, H., Demirtas, I., Yaglioglu, A.S., Elmastas, M., Telci, İ., 2016. Isolation and identification of chemical constituents from Origanum majorana and investigation of antiproliferative and antioxidant activities. J. Sci. Food Agric. 96(3), 822-836.

Erlund, I., Meririnne, E., Alfthan, G., Aro, A., 2001. Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice. J. Nut. 131(2), 235-241.

Frankel, E.N., 2014. Lipid oxidation, Elsevier.

Gecibesler, I.H., Demirtas, I., Behcet, L., Tufekci, A.R., 2017. Two new flavonoids and other phytochemicals from endemic Phryna ortegioides (Fish. & CA Mey.) Pax & K. Hoffm and their antioxidant potentials. Rec. Nat. Prod. 11(3), 290-298.

Haber, F., Weiss, J., 1934. The catalytic decomposition of hydrogen peroxide by iron salts. In: Proceedings of the Royal Society of London A: Mathematical, Physical and Engineering Sciences, Vol. 861, The Royal Society, pp. 332-351.

M’hiri, N., Ioannou, I., Ghoul, M., Mihoubi Boudhrioua, N., 2017. Phytochemical characteristics of citrus peel and effect of conventional and nonconventional processing on phenolic compounds: A review. Food Rev. Int. 33(6), 587-619.

Mazimba, O., 2017. Umbelliferone: Sources, chemistry and bioactivities review. Bull. Fac. Pharm. Cairo Univ. In press.

Miyake, Y., Hiramitsu, M., 2011. Isolation and extraction of antimicrobial substances against oral bacteria from lemon peel. J. Food Sci. Tech. 48(5), 635-639.

Miyake, Y., Yamamoto, K., Morimitsu, Y., Osawa, T., 1997a. Isolation of C-glucosylflavone from lemon peel and antioxidative activity of flavonoid compounds in lemon fruit. J. Agric. Food Chem. 45(12), 4619-4623.

Miyake, Y., Yamamoto, K., Morimitsu, Y., Osawa, T., 1998. Characteristics of antioxidative flavonoid glycosides in lemon fruit. Food Sci. Technol. Int. 4(1), 48-53.

Miyake, Y., Yamamoto, K., Osawa, T., 1997b. Isolation of eriocitrin (eriodictyol 7-rutinoside) from lemon fruit (citrus limon BURM. f.) and its antioxidative activity. Food Sci. Technol. Int. 3(1), 84-89.

Murakami, A., Kuki, W., Takahashi, Y., Yonei, H., Nakamura, Y., Ohto, Y., Ohigashi, H., Koshimizu, K., 1997. Auraptene, a citrus coumarin, inhibits 12‐0‐tetradecanoylphorbol‐13‐acetate‐induced tumor promotion in icr mouse skin, possibly through suppression of superoxide generation in leukocytes. Cancer Sci. 88(5), 443-452.

Nogata, Y., Ohta, H., Sumida, T., Sekiya, K., 2003. Effect of extraction method on the concentrations of selected bioactive compounds in mandarin juice. J. Agric. Food Chem. 51(25), 7346-7351.

Oyaizu, M., 1986. Studies on products of browning reaction--antioxidative activities of products of browning reaction prepared from glucosamine. Jpn. J. Nutr. 4, 307-315.

Ozen, T., Yenigun, S., Altun, M., Demirtas, I., 2017. Phytochemical constituents, ches and urease inhibition, antiproliferative and antioxidant properties of Elaeagnus umbellata Thunb. Comb. Chem & High Throughput Screening 20, 558-577.

Poprac, P., Jomova, K., Simunkova, M., Kollar, V., Rhodes, C.J., Valko, M., 2017. Targeting free radicals in oxidative stress-related human diseases. Trends in Pharmacol. Sci. 38(7), 592-607.

Prieto, P., Pineda, M., Aguilar, M., 1999. Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: specific application to the determination of vitamin E. Anal. Biochem. 269(2), 337-341.

Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., Rice-Evans, C., 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic. Biol. Med. 26(9), 1231-1237.

So, F.V., Guthrie, N., Chambers, A.F., Moussa, M., Carroll, K.K., 1996. Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices. Nutr. Cancer 26(2), 167-181.

Sun, C., Chen, K., Chen, Y., Chen, Q., 2005. Contents and antioxidant capacity of limonin and nomilin in different tissues of citrus fruit of four cultivars during fruit growth and maturation. Food Chem. 93(4), 599-605.

Wang, Y.-C., Chuang, Y.-C., Hsu, H.-W., 2008. The flavonoid, carotenoid and pectin content in peels of citrus cultivated in Taiwan. Food Chem. 106(1), 277-284.

Yildiz, I., Sen, O., Erenler, R., Demirtas, I., Behcet, L., 2017. Bioactivity-guided isolation of flavonoids from Cynanchum acutum L. subsp. sibiricum (Willd.) Rech. f. and investigation of their antiproliferative activity. Nat. Prod. Res. 1-5.

Zhao, G.-R., Xiang, Z.-J., Ye, T.-X., Yuan, Y.-J., Guo, Z.-X., 2006. Antioxidant activities of Salvia miltiorrhiza and Panax notoginseng. Food Chem. 99(4), 767-774.