Comprehensive evaluation of the antioxidant capacity of Perilla frutescens leaves extract and isolation of free radical scavengers using step-wise HSCCC guided by DPPH-HPLC

References

• Halliwell, B.; Gutteridge, J.M.C. Free Radical in Biology and Medicine; Oxford Press: Oxford, UK, 1999.
   Google Scholar
• Kahl, R.; Kappus, H. Toxicology of the Synthetic Antioxidants BHA and BHT in Comparison with the Natural Antioxidant Vitamin E. Zeitschrift für Lebensmittel-Untersuchung and Forschung 1993, 19, 329–338.
   Google Scholar
• Elmastas, M.; Isildak, O.; Turkekul, I.; Temur, N. Determination of Antioxidant Activity and Antioxidant Compounds in wild Edible Mushrooms. Journal of Food Composition and Analysis 2007, 20, 337–345.
   Web of Science ®Google Scholar
• Gülçin, I.; Mshvildadze, V.; Gepdiremen, A.; Elias, R. The Antioxidant Activity of a Triterpenoid Glycoside Isolated from the Berries of Hedera colchica: 3-O-(β-D-glucopyranosyl)-Hederagenin. Phytotherapy Research 2006, 20, 130–134.
   PubMed Web of Science ®Google Scholar
• Hu, Y.; Sung, L.W.; Mokgolodi, N.C.; Zhang, Y.X.; Wen, C.X.; Xie X.L.; Liu, Y.J. Primary Identifications and Palynological Observations of Perilla in China. Journal of Systematics and Evolution 2010, 48, 133–145.
   Web of Science ®Google Scholar
• Ha, T.J.; Lee, J.H.; Lee, M.H.; Lee, B.W.; Kwon, H.S.; Park, C.H.; Shim, K.B.; Kim, H.T.; Baek, I.Y.; Jang, D.S. Isolation and Identification of Phenolic Compounds from the Seeds of Perilla frutescens (L.) and Their Inhibitory Activities Against α-Glucosidase and Aldose Reductase. Food Chemistry 2012, 135, 1397–1403.
   Google Scholar
• Igarashi, M.; Miyazaki, Y. A Review on Bioactivities of Perilla: Progress in Research on the Functions of Perilla as Medicine and Food. Evidence-based Complementary and Alternative Medicine 2013, 925342.
   PubMed Web of Science ®Google Scholar
• Meng, L.; Lozano, Y.F.; Gaydou, E.M.; Li, B. Antioxidant Activities of Polyphenols Extracted from Perilla frutescens Varieties. Molecules 2009, 14, 133–140.
   Web of Science ®Google Scholar
• Ueda, H.; Yamazaki, C.; Yamazaki, M. Luteolin as an Anti-inflammatory and Anti-Allergic Constituent of Perilla frutescens. Biological and Pharmaceutical Bulletin 2002, 25, 1197–1202.
   PubMed Web of Science ®Google Scholar
• Osakabe, N.; Yasuda, A.; Natsume, M.; Yoshikawa, T. Rosmarinic Acid Inhibits Epidermal Inflammatory Responses: Anticarcinogenic Effect of Perilla frutescens Extract in the Murine Two-Stage Skin Model. Carcinogenesis 2003, 25, 549–557.
   Web of Science ®Google Scholar
• Liu, J.; Wan, Y; Zhao, Z.; Chen, H. Determination of the Content of Rosmarinic Acid by HPLC and Analytical Comparison of Volatile Constituents by GC–MS in Different Parts of Perilla frutescens (L.) Britt. Chemistry Central Journal 2013, 7, 61.
   PubMed Web of Science ®Google Scholar
• Buchwald-Werner, S.; Fujii, H.; Schön, C.; Doebis, C. Investigation of a Perilla frutescens Special Extract - Anti-inflammatory and Immune-modulatory Properties. Agro Food Industry Hi Tech 2012, 23, 38–41.
   Web of Science ®Google Scholar
• Feng, L.J.; Yu, C.H.; Ying, K.J.; Hua, J.; Dai, X.Y. Hypolipidemic and Antioxidant Effects of Total Flavonoids of Perilla frutescens Leaves in Hyperlipidemia Rats Induced by High-fat Diet. Food Research International 2011, 44, 404–409.
   Web of Science ®Google Scholar
• Kang, R.; Helms, R.; Stout, M.J.; Jaber, H.; Chen, Z.; Nakatsu, T. Antimicrobial Activity of the Volatile Constituents of Perilla frutescens and Its Synergistic Effects with Polygodial. Journal of Agricultural and Food Chemistry 1992, 40, 2328–2330.
   Web of Science ®Google Scholar
• Nakazawa, T.; Yasuda, T.; Ueda, J.; Ohsawa, K. Antidepressant-like Effects of Apigenin and 2,4,5-Trimethoxycinnamic Acid from Perilla frutescens in the Forced Swimming Test. Biological and Pharmaceutical Bulletin 2003, 26, 474–480.
   PubMed Web of Science ®Google Scholar
• Nitta, M.; Lee, J.K.; Ohnishi, O. Asian perilla Crops and Their Weedy Forms: Their Cultivation, Utilization and Genetic Relationships. Economic Botany 2003, 57, 245–253.
   Web of Science ®Google Scholar
• Paek, J.H.; Shin, K.H.; Kang, Y.H.; Lee, J.Y.; Lim, S.S. Rapid Identification of Aldose Reductase Inhibitory Compounds from Perilla frutescens. BioMed Research International 2013, 679463.
   PubMed Web of Science ®Google Scholar
• Wang Z.; Kwon, S.H.; Hwang, S.H.; Kang, Y.H.; Lee, J.Y.; Lim, S.S. Competitive Binding Experiments can Reduce the False Positive Results of Affinity-based Ultrafiltration-HPLC: A Case Study for Identification of Potent Xanthine Oxidase Inhibitors from Perilla frutescens Extract. Journal of Chromatography B 2017, 1048, 30–37.
   PubMed Web of Science ®Google Scholar
• Park, S.H.; Paek, J.H.; Shin, D.; Lee, J.Y.; Lim, S.S.; Kang, Y.H. Purple perilla Extracts with α-Asarone Enhance Cholesterol Efflux from Oxidized LDL-exposed Macrophages. International Journal of Molecular Medicine 2015, 35, 957–965.
   PubMed Web of Science ®Google Scholar
• Hwang, S.H.; Kwon, S.H.; Kang, Y.H.; Lee, J.Y.; Lim, S.S. Rapid High Performance Liquid Chromatography Determination and Optimization of Extraction Parameters of the α-Asarone Isolated from Perilla frutescens L. Molecules 2017, 22, 270.
   Web of Science ®Google Scholar
• Banno, N.; Akihisa, T.; Tokuda, H.; Yasukawa, K.; Higashihara, H.; Ukiya, M.; Watanabe, K.; Kimura, Y.; Hasegawa, J.I.; Nishino, H. Triterpene Acids from the Leaves of Perilla frutescens and Their Anti-inflammatory and Antitumor-promoting Effects. Bioscience, Biotechnology, and Biochemistry 2004, 68, 85–90.
   Google Scholar
• Wang, J.W.; Xia, Z.H.; Chu, J.H.; Tan, R.X. Simultaneous Production of Anthocyanin and Triterpenoids in Suspension Cultures of Perilla frutescens. Enzyme and Microbial Technology 2004, 34, 651–656.
   Web of Science ®Google Scholar
• Meng, L.; Lozano, Y.; Bombarda, I.; Gaydou, E.M.; Li, B. Polyphenol Extraction from Eight Perilla frutescens Cultivars. Comptes Rendus Chimie 2009, 12, 602–611.
   Web of Science ®Google Scholar
• Hazra, B.; Biswas, S.; Mandal, N. Antioxidant and Free Radical Scavenging Activity of Spondias pinnata. BMC Complementary and Alternative Medicine 2008, 8, 63.
   PubMed Web of Science ®Google Scholar
• Dai, X.; Huang, Q.; Zhou, B.; Gong, Z.; Liu, Z.; Shi, S. Preparative Isolation and Purification of Seven Main Antioxidants from Eucommia ulmoides Oliv. (Du-zhong) Leaves Using HSCCC Guided by DPPH-HPLC Experiment. Food Chemistry 2013, 139, 563–570.
   PubMed Web of Science ®Google Scholar
• Shi, S.; Ma, Y.; Zhang, Y.; Liu, L.; Liu, Q.; Peng, M.; Xiong, X. Systematic Separation and Purification of 18 Antioxidants from Pueraria lobate Flower Using HSCCC Target-Guided by DPPH–HPLC Experiment. Separation and Purification Technology 2012, 89, 225–233.
   Web of Science ®Google Scholar
• Sun, L.Q.; Ding, X.P.; Qi, J.; Yu, H.; He, S.A.; Zhang, J.; Ge, H.X.; Yu, B.Y. Antioxidant Anthocyanins Screening Through Spectrum–Effect Relationships and DPPH-HPLC-DAD Analysis on Nine Cultivars of Introduced Rabbiteye Blueberry in China. Food Chemistry 2012, 132, 759–765.
   Web of Science ®Google Scholar
• Yang, F.; Zhang, T.; Tian, G.; Cao, H.; Liu, Q.; Ito, Y. Preparative Isolation and Purification of hydroxyanthraquinones from Rheum officinale Baill by High-Speed Counter-Current Chromatography Using pH-modulated Stepwise Elution. Journal of Chromatography A 1999, 858, 103–107.
   PubMed Web of Science ®Google Scholar
• Marston, A.; Hostettmann, K. Developments in the Application of Counter-Current Chromatography to Plant Analysis. Journal of Chromatography A 2006, 1112, 181–194.
   PubMed Web of Science ®Google Scholar
• Oliveria, R.R.; Leitão, G.G.; Moraes, M.C.C.; Kaplan, M.A.C. Lopes, D.; Carauta, J.P.P. Gradient Elution for Triterpene Separation from Cecropia lyratiloba Miquel by HSCCC. Journal of Liquid Chromatography and Related Technologies 2005, 28, 1985–1992.
   Web of Science ®Google Scholar
• da Silva, V.P.; Oliveira, R.R.; Figueiredo, M.R. Isolation of Limonoids from Seeds of Carapa guianensis Aublet (Meliaceae) by High-speed Countercurrent Chromatography. Phytochemical Analysis 2009, 20, 77–81.
   PubMed Web of Science ®Google Scholar
• Du, Q.; Jerz, G.; Chen, P.; Winterhalter, P. Preparation of Ursane Triterpenoids from Centella asiatica Using High Speed Countercurrent Chromatography with Step-Gradient Elution. Journal of Liquid Chromatography Related Technologies 2004, 27, 2201–2215.
   Web of Science ®Google Scholar
• Su, X.Y.; Wang, Z.Y.; Liu, J.R. In vitro and in vivo Antioxidant Activity of Pinus koraiensis Seed Extract Containing Phenolic Compounds . Food Chemistry 2009, 117, 681–686.
   Google Scholar
• Winterbourn, C.C.; Metodiewa, D. Reactivity of Biologically Important Thiol Compounds with Superoxide and Hydrogen Peroxide. Free Radical Biology and Medicine 1999, 27, 322–328.
   PubMed Web of Science ®Google Scholar
• Hsu, B.; Coupar, I.M.; Ng, K. Antioxidant Activity of Hot Water Extract from the Fruit of the Doum palm, Hyphaene thebaica. Food Chemistry 2006, 98, 317–328.
   Web of Science ®Google Scholar
• Nitha, B.; De, S.; Adhikari, S.K.; Devasagayam, T.P.A. Evaluation of Free Radical Scavenging Activity of Morel Mushroom, Morchella esculenta Mycelia: A Potential Source of Therapeutically Useful Antioxidants. Pharmaceutical Biology 2010, 48, 453–460.
   Google Scholar
• Oliveira, D.R.; Schaffer, L.F.; Busanello, A.; Barbosa, C.P.; Peroza, L.R.; Freitaas, C.M.; Krum, B.N.; Bressan, G.N.; Boligon, A.A.; Athayde, M.L.; Menezes, I.R.A.; Fachinetto, R. Silymarin has Antioxidant Potential and Changes the Activity of Na+/K+-ATPase and Monoamine Oxidase in vitro. Industrial Crops and Products 2015, 70, 347–355.
   Web of Science ®Google Scholar
• Amarowicz, R.; Pegg, R.B.; Rahimi-Moghaddam, P.; Barl, B.; Weil, J.A. Free-radical Scavenging Capacity and Antioxidant Activity of Selected Plant Species from the Canadian Prairies. Food Chem. 2004, 84, 551–562.
   Web of Science ®Google Scholar
• Wang, Z.; Hwang, S.H.; Lim, S.S. Chemoenzymatically Synthesized Policosanyl Phenolates as Autoxidation Inhibitors. European Journal of Lipid Science and Technology 2015, 117, 300–310.
   Web of Science ®Google Scholar
• Jun, H.I.; Kim, B.T.; Song, G.S.; Kim, Y.S. Structural Characterization of Phenolic Antioxidants from Purple Perilla (Perilla frutescens var. acuta) Leaves. Food Chemistry 2014, 148, 367–372.
   PubMed Web of Science ®Google Scholar
• Chen, J.H.; Xia, Z.H.; Tan, R.X. High-performance Liquid Chromatographic Analysis of Bioactive triterpenes in Perilla frutescens. Journal of Pharmaceutical and Biomedical Analysis 2003, 32, 1175–1179.
   PubMed Web of Science ®Google Scholar
• Sawabe, A.; Satake, T.; Alzawa, R.; Sakatani, K.; Nishinoto, K.; Ozeki, C.; Hamada, Y.; Komemushi, S. Toward Use of the Leaves of Perilla frutescens (L.) Britton var. Acuta Kuto (Red Perilla) with Japanese Dietary Pickled Plum (umeboshi). Journal of Oleo Science 2006, 55, 413–422.
   Google Scholar
• Masahiro, T.; Risa, M.; Harutaka, Y.; Kazuhiro, C. Novel Antioxidants Isolated from Perilla frutescens Britton var. crispa (Thunb.). Bioscience, Biotechnology, and Biochemistry 1996, 60, 1093–1095.
   Google Scholar
• Kalam, S.; Gul, M.Z.; Singh, R.; Ankati, S. Free Radicals: Implications in Etiology of Chronic Diseases and Their Amelioration Through Nutraceuticals. Pharmacologia 2015, 6, 11–20.
   Google Scholar
• Giese, E.C.; Gascon, J.; Anzelmo, G.; Barbosa, A.M.; Alves da Cunha, M.A.; Dekker, R.F.H. Free-Radical Scavenging Properties and Antioxidant Activities of Botryosphaeran and Some Other β-D-glucans. International Journal of Biological Macromolecules 2015, 72, 125–130.
   PubMed Web of Science ®Google Scholar
• Johansen, J.S.; Harris, A.K.; Rychly, D.J.; Ergul, A. Oxidative Stress and the Use of Antioxidants in Diabetes: Linking Basic Science to Clinical Practice. Cardiovascular Diabetology 2005, 4, 5.
   PubMed Web of Science ®Google Scholar
• Gliszczyńska-Świgło, A. Antioxidant Activity of Water Soluble Vitamins in the TEAC (Trolox Equivalent Antioxidant Capacity) and the FRAP (Ferric Reducing Antioxidant Power) Assays. Food Chemistry 2006, 96, 131–136.
   Web of Science ®Google Scholar
• Ozgen, M.; Reese, R.N.; Tulio Jr, A.Z.; Scheerens, J.C.; Miller, A.R. Modified 2,2-Azino-Bis-3-Ethylbenzothiazoline-6-Sulfonic Acid (ABTS) Method to Measure Antioxidant Capacity of Selected Small Fruits and Comparison to Ferric Reducing Antioxidant Power (FRAP) and 2,2’-Diphenyl-1-Picrylhydrazyl (DPPH) Methods. Journal of Agricultural and Food Chemistry 2006, 54, 1151–1157.
   PubMed Web of Science ®Google Scholar
• Leiss, K.A.; Maltese, F.; Choi, Y.H.; Verpoorte, R.; Klinkhamer, P.G.L. Identification of Chlorogenic Acid as a Resistance Factor for Thrips in Chrysanthemum. Plant Physiology 2009, 150, 1567–1575.
   PubMed Web of Science ®Google Scholar
• Jung, H.A.; Park, J.C.; Chung, H.Y.; Kim, J.; Choi, J.S. Antioxidant Flavonoids and Chlorogenic Acid from the Leaves of Eriobotrya japonica. Archives of Pharmacal Research 1999, 22, 213–218.
   PubMed Web of Science ®Google Scholar
• Li, H.J.; Luo, Y.G.; He, Z.H.; Zhang, G.L. Chemical Constituents from Lonicera saccata. Chinese Journal of Applied and Environmental Biology 2007, 13, 188–191.
   Google Scholar
• Sobolev, V.S.; Horn, B.W.; Potter, T.L.; Deyrup, S.T.; Gloer, J.B. Production of Stilbenoids and Phenolic Acids by the Peanut Plant at Early Stages of Growth. Journal of Agricultural and Food Chemistry 2006, 54, 3505–3511.
   PubMed Web of Science ®Google Scholar
• Wang, M.; Li, J.; Rangarajan, M.; Shao, Y.; Lavoie, E.J.; Huang, T.C.; Ho, C.T. Antioxidative Phenolic Compounds from Sage (Salvia officinalis). Journal of Agricultural and Food Chemistry 2007, 46, 4869–4873.
   Web of Science ®Google Scholar
• Kim, N.M.; Kim, J.; Chung, H.Y.; Choi, J.S. Isolation of Luteolin 7-O-Rutinoside and Esculetin with Potential Antioxidant Activity from the Aerial Parts of Artemisia montana. Archives of Pharmacal Research 2000, 23, 237–239.
   PubMed Web of Science ®Google Scholar
• Machida, K.; Osawa, K. Quantitative Analysis of Methoxylated Flavonoids in iyo (Citrus iyo) Peels by High-Performance Liquid Chromatography. Yakugaku Zasshi 1989, 109, 192–194.
   PubMed Web of Science ®Google Scholar
• Cuvelier, M.E.; Richard, H.; Berset, C. Comparison of the Antioxidative Activity of Some Acid-Phenols: Structure-Activity’ Relationship. Bioscience, Biotechnology, and Biochemistry 1992, 56, 324–325.
   Web of Science ®Google Scholar
• Benavente-García, O.; Castillo, J.; Lorenta, J.; Ortuño, A.; Del Rio, J.A. Antioxidant Activity of Phenolics Extracted from Olea europaea L. Leaves. Food Chemistry 2000, 68, 457–462.
   Web of Science ®Google Scholar