Abstract
Antioxidant potencies of an ethanolic extract and its components from Lepidium latifolium were investigated. In this study, we found that the ethyl acetate soluble fraction of L. latifolium was a rich source of antioxidant, resulting from its high total phenolic content. To determine the antioxidant components of the ethyl acetate fraction, a bioassay-guided fractionation approach using 1,1-diphenyl-2-picrylhydrazyl, 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonate), and ferric reducing antioxidant power assays were conducted. Nine compounds were isolated and their structures were identified by MS and NMR spectral data and comparison to reported data. They are Quercetin-3-O-β-d-sophoroside-7-O-α-l-rhamnoside (1), Apetalumoside B6 (2), Kaempferol-3-O-β-d-glucopyranosyl-(1-2)-β-d-glucopyranoside-7-O-β-d-glucopyranoside (3), Kaempferol-7-O-α-l-rhamnopyranoside (4), Kaempferol-3-O-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside (5), Kaempferol-3-O-(2-O-feruloyl-β-d-glucopyranosyl-(1-2)-β-d-glucopyranoside)-7-O-glucopyranoside (6), Kaempferol-3-O-β-d-sophoroside-7-O-α-l-rhamnoside (7), Kaempferol-3-O-robinoside-7-O-(2″″-(E)-feruloyl)-sophoroside (8), Quercetin-3-O-(2,6-di-O-β-d-glucopyranosyl)-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside (9), compounds 1, 2, 4, and 8 had potent free radical scavenging activity. The IC50 values of these compounds were 9.8–12.3 and 7.4–31.4 μg/mL in DPPH and ABTS assays, respectively. The results indicate that L. latifolium is a potential natural source of antioxidants to treat several diseases related to oxidant by-products of human metabolism.
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References
Awe FB, Fagbemi TN, Ifesan BOT, Badejo AA (2013) Antioxidant properties of cold and hot water extracts of cocoa, Hibiscus flower extract, and ginger beverage blends. Food Res Int 52:490–495
Cheng SS, Yen PL, Chang ST (2015) Phytochemicals from wood extract of Cunninghamia konishii Hayata as antioxidant agents. Ind Crops Prod 64:39–44
Editorial Committee of Flora of China (1979) Flora of China, Vol. 67. Beijing Scientific Press, Beijing, p 325
Erlânio OS, Camila MBAM, Camila BN, Aline AB, Margareth LA, José GMC (2015) Phytochemical analysis and antioxidant activities of Lantana camara and Lantana montevidensis extracts. Ind Crops Prod 70:7–15
Gordon MH (1990) The mechanism of antioxidant action in vitro. In: Hudson BJF (ed) Food antioxidants. Elsevier Applied Science, London, p 1–18
Haifa A, Emna M, Wafa R, Lamia H, Slim R, Mohamaed NR, Zeineb G (2016) Phenolic composition and antioxidant activity of aqueous and ethanolic leaf extracts of six Tunisian species of genus Capparis Capparaceae. Ind Crops Prod 92:218–226
Halil IO, Ilkay K (2016) Application of response surface methodology for optimizing the recovery of phenolic compounds from hazelnut skin using differentextraction methods. Ind Crops Prod 91:114–124
Jing Z, Thomas SV, Yue G, Yadong Q, Kit C, Min-Hsiung P, Chi-Tang H, James ES, QinglIi W (2016) Phytochemistry, antioxidant capacity, total phenolic content and anti-inflammatory activity of Hibiscus sabdariffa leaves. Food Chem 190:673–680
Ji-Sun H, Hee-Young K, Seung-Taik L (2015) Antioxidant and deodorizing activities of phenolic components in chestnut inner shell extracts. Ind Crops Prod 73:99–105
Kim JE, Jung MJ, Jung HA, Woo JJ, Cheigh HS, Chung HY, Choi JS (2002) A new Kaempferol 7-O-triglucoside from the leaves of Brassica juncea L. Arch Pharm Res 25:621–630
Kosalec I, Bakmaz M, Pepeliniak S, Vladimir-Knezevic S (2004) Quantitative analysis of the flavonoids in raw propolis from northern Croatia. Acta Pharm 54:65–72
Lea DB, Carl EO, Jens KN, Niels A (2011) Polymorphism for novel tetraglycosylated flavonols in an eco-model Crucifer, Barbarea vulgaris. J Agric Food Chem 59:6947–6953
Li D, Ikeda T, Matsuoka N, Nohara T, Zhang H, Sakamoto T, Nonaka GI (2006) Cucurbitane glycosides from unripe fruits of Lo Han Kuo (Siraitia grosvenori). Chem Pharm Bull 54:1425–1435
Li Y, Yili A, Liu Y, Kawuli A, Aisa HA (2014) Chemical constituents of Hippophae rhamnoides subsp. turkestanica fruits. Chem Nat Compd 50:352–360
Liu S (1999) Economic flora of Qinghai, Vol. 2. Qinghai people’s press, Qinghai, p 227
Luísa C, João P, Fernando A, Nuno RN, José MFN, Anabela R (2015) Phenolic composition, antioxidant potential and in vitro inhibitory activity of leaves and acorns of Quercus suber on key enzymes relevant for hyperglycemia and Alzheimei’s disease. Ind Crops Prod 64:45–51
Maria L, Bezerra A, Wallace ESF, Patrícia LDM, José DAS, Ricardo EA (2016) Bioactive compounds and antioxidant potential fruit of Ximenia americana L. Food Chem 192:1078–1082
Nemanja S, Tatjana M, Bojan Z, Vesna S, Violeta M, Jovana J, Ljiljana C, Branislava K, Nirit B (2016) Antibacterial and antioxidant activity of traditional medicinal plants from the Balkan Peninsula. Wageningen J Life Sci 78:21–28
Nirupama G, Dilip KR, Nigel PB, Eimear G, Mohammad BH (2016) Antioxidant-guided isolation and mass spectrometric identification of the major polyphenols in barley (Hordeum vulgare) grain. Food Chem 210:212–220
Ouyang MA, He ZD, Wu CL (2003) Anti-oxidative activity of glycosides from Ligustrum sinense. Nat Prod Res 17:381–388
Rasha RAE, Ragaa MAMMS, Ahmad F (2014) Three new flavonol glycosides from Suaeda maritima. J Asian Nat Prod Res 16(5):434–439
Reetika S, Nishi K (2015) Comparative determination of phytochemicals and antioxidant activity from leaf and fruit of Sapindus mukorrossi Gaertn.—a valuable medicinal tree. Ind Crops Prod 73:1–8
Seyed MR, Mohammad A, Arash J, Seyed HM (2015) The field efficacy of Lepidium latifolium and Zataria multiflora methanolic extracts against Varroa destructor. Parasitol Res 114:4233–4238
Shi P, Chao L, Wang T, Liu E, Han L, Zong Q, Li X, Zhang Y, Wang T (2015) New bioactive flavonoid glycosides isolated from the seeds of Lepidium apetalum Wild. Fitoterapia 103:197–205
Singh R, Singh S, Kumar S, Arora S (2007) Evaluation of antioxidant potential of ethyl acetate extract/fractions of Acacia auriculiformis A. Cunn. Food Chem Toxicol 45:1216–1223
Shimada K, Fujikawa K, Yahara K, Nakamura T (1992) Antioxidative properties of xanthum on the autoxidation of soybean oil in cyclodextrin emulsion. J Agric Food Chem 40:945–948
Tang YP, Lou FC, Wang JH (2001) Two Kaempferol triglycosides from pericarps of Sophora japonica L. China J Chin Mat Med 26:839–845
Vítor S, Eulogio JL, Sandra G, Paula C (2016) Ulex europaeus: from noxious weed to source of valuable isoflavones and flavanones. Ind Crops Prod 90:9–27
Walker RB, Everette JD (2009) Comparative reaction rates of various antioxidants with ABTS radical cation. J Agric Food Chem 57:1156–1161
Xu C, Wang L, Gao W (2015) Optimization of ultrasonic-assisted extraction for polysaccharide from Lepidium latifolium by response surface methodology. Cereals Oils 28:59–62
Yuan J, Liu X, Yang J, Cui X (2014) Forsythia suspense leaves, a plant: extraction, purification and antioxidant activity of main active compounds. Eur Food Res Technol 238:527–533
Zhang X, Hu B (1994) Study on the constituents of Lpidium latifolium. Acta Bot Boreal Occident Sin 14(4):329–333
Zheng W, Zhong Y, Sun J, Zhang P (2009) Study on the constituents of Orotachys fimbriatus. Chin Trad Herb Drug 40:859–862
Zhigang T, Anyi C, Bendui Q, Le C, Yanqun X (2014) Chemical constituents and antioxidant activity of the Musa basjoo flower. Eur Food Res Technol 239:501–508
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This research was sponsored by the Project of Discovery, Evaluation and Transformation of Active Natural Compounds, Strategic Biological Resources Service Network Program of Chinese Academy of Sciences (ZSTH-027).
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Xiang, Y., Haixia, W., Lijuan, M. et al. Isolation, purification and identification of antioxidants from Lepidium latifolium extracts. Med Chem Res 27, 37–45 (2018). https://doi.org/10.1007/s00044-017-2042-3
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DOI: https://doi.org/10.1007/s00044-017-2042-3