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Datura Innoxia and Dipsacus Laciniatus Biological Activity And Biocatalysis and Agricultural Biotechnology 19 (2019) 101163 Contents lists available at ScienceDirect Biocatalysis and Agricultural Biotechnology journal homepage: www.elsevier.com/locate/bab Datura innoxia and Dipsacus laciniatus: Biological activity and phenolic composition T ∗ Mohamed Ali Benabderrahima, Cengiz Sarikurkcub, , Walid Elfallehc, Mehmet Sabih Ozerd a Arid Land and Oasis Cropping Laboratory, Institute of Arid Land, Route Eljorf, University of Gabes, 4119, Medenine, Tunisia b Department of Analytical Chemistry, Faculty of Pharmacy, Süleyman Demirel University, Isparta, Turkey c Laboratoire Energie, Eau, Environnement et Procèdes, (LEEEP), LR18ES35, Ecole Nationaled'Ingénieurs de Gabès, Université de Gabès, 6072, Gabès, Tunisia d Department of Chemistry, Faculty of Science and Literature, Manisa Celal Bayar University, Manisa, Turkey ARTICLE INFO ABSTRACT Keywords: In the present study, we investigated the phenolic composition of the methanol extract from the aboveground of Datura innoxia two plants of Turkish flora; Datura innoxia and Dipsacus laciniatus. In addition, the antioxidant (phosphomo- Dipsacus laciniatus lybdenum, CUPRAC, FRAP, DPPH, ABTS) and enzyme inhibitory activities (α-amylase and tyrosinase), and total (+)-catechin phenolic and flavonoids contents were determined in these plant extracts. The results showed high significant (−)-epicatechin differences among plants (p ≤ 0.05) for the antioxidant capacities measured with the different methods, the Chlorogenic acid enzyme inhibitory activities, and the all identified phenolic compounds except for hyperoside. From a total of 23 Antioxidant activity identified phenolic compounds, 19 were found in both plants. The main flavonoids identified were (+)-catechin and (−)-epicatechin and hyperoside. (+)-Catechin and (−)-epicatechin showed very high concentrations in D. innoxia (12937.39 ± 108.86 and 24147.64 ± 2512.35 μg/g of dry plant, respectively) and in D. laciniatus (4947.99 ± 14.18 and 13171.30 ± 2410.76 μg/g of dry plant, respectively). Hyperoside had interesting con- tents with comparable values (115.11 ± 16.20 in D. innoxia, and 110.77 ± 16.32 μg/g of dry plant in D. la- ciniatus). The major phenolic acid was chlorogenic acid especially in D. laciniatus (12124.22 ± 598.13 μg/g of dry plant). These compounds were correlated to the high antioxidant and enzyme inhibitory activities for both species and confirm their medicinal traditional uses. Hence, further screening of bioactive compounds in dif- ferent organs such as flowers and roots of these plants is crucial for the discovering of new source of natural antioxidants and enzyme inhibitors. 1. Introduction Datura innoxia Mill. originates from Central America. It is an annual ornamental plant with attractive flowers and is alien of Turkey (Uludag Floristic analysis has shown that our planet has approximately et al., 2017) growing in the gardens for decorative purposes. It is pre- 500,000 plant species, and about 120,000 plant species can be used to sent as both cultivated plant and as well as wild population. Despite D. create biologically active products that could be used in treatment of innoxia is extremely toxic plant, there is evidence that in Serbian Voj- many diseases (Kallassy, 2017). Several bioactive compounds found in vodina province it is cultivated as medicinal plant (Lakušić et al., 2017). medicinal plants showed high activities against many diseases (rheu- However, little information is available on its phenolic composition and matic, inflammatory, microbiologic origins … etc.) (Mukhtar et al., bioactive properties. In genus Datura, some phytochemicals were 2008; Prakash et al., 2007). In Turkey, it is estimated that the Turkish screened in D. metel such as alkaloid, phenols, flavonoids, tannins, sa- flora has more than 10,000 species of vascular plants (about 34% are ponins and sterols (Okwu and Igara, 2009). endemic) (Kizilarslan and Özhatay, 2012). Ethnobotanical studies re- Dipsacus laciniatus, native to Eurasia, is an invasive weed species ported that a wide range of Turkish plants are used for medicinal (Sforza, 2004). In Turkey, it is very largely distributed in north Turkey purposes in the traditional medicine (Sadikoglu and Alpinar, 2004). (from Ankara to the Black Sea), but rare or absent in the rest of the Despite their high potential biological activities, a lot of plants are not country (Sforza, 2004). Plants appear to be a mixture of rapidly well characterized and still under debate such as Datura inoxia and growing rosettes and rosettes with the development of reproductive Dipsacus laciniatus. structures (Bentivegna and Smeda, 2011). In the other side, this species ∗ Corresponding author. E-mail address: [email protected] (C. Sarikurkcu). https://doi.org/10.1016/j.bcab.2019.101163 Received 23 April 2019; Received in revised form 15 May 2019; Accepted 15 May 2019 Available online 17 May 2019 1878-8181/ © 2019 Elsevier Ltd. All rights reserved. M.A. Benabderrahim, et al. Biocatalysis and Agricultural Biotechnology 19 (2019) 101163 is used in the processing of wool (Rector et al., 2006). Also, D. laciniatus 2.3. Phenolic composition analysis by LC–ESI–MS/MS (Liquid is cultivated for its attractive purple flowers, its attractiveness to but- Chromatography–Electrospray Tandem mass spectrometry) terflies, and as natural enemies of crop pests (Judd, 1983). The benefits of this species for human health and their phytochemical composition Total phenolic and flavonoid contents in the extracts were firstly are still unclear. In fact, plants of genus Dipsacus have been used as determined spectrophotometrically by calculating as gallic acid and medicinal agents to treat several diseases (Alzheimer's disease, cancer, quercetin equivalents, respectively (Zengin et al., 2015a, 2015b). Then lime disease, fibromyalgia, etc.) (Zhao and Shi, 2011). Previous studies phenolic composition in the extracts were detected by LC–ESI–MS/MS on plants of the genus Dipsacus has reported many biological activities (Cittan and Çelik, 2018) using experimental conditions given in detail such as antimicrobial activity, cytoprotective capacities, inhibition of in the supplementary file. HIV-1 reverse transcriptase, and antinociceptive effects, etc. (Zhao and Shi, 2011). Dipsacus asper herbs have been documented to have neu- 2.4. Antioxidantand enzyme inhibition activities roprotective compounds for treating or preventing neurodegenerative ff diseases such as the phenolic acid 3,5-dica eoylquinic acid (Kim et al., Diverse assays such as free radical scavenging [on 1,1-diphenyl-2- ff ˙ 2005). The neuroprotective agents could have a supressor e ect of picrylhydrazyl (DPPH) radical and 2,2-azino-bis (3-ethylbenzothia- fl neuroin ammation inducing the attenuation of neuronal damage zloine-6-sulphonic acid) radical cation (ABTS·+)] (Zengin et al., (Mollica et al., 2012). To the best of our knowledge, there is very few 2015b), phosphomolybdenum (Zengin et al., 2015a), ferrous ion che- fi information on the phytochemical composition, the bene ts and the lating (Tepe et al., 2011), and reducing power [cupric ion reducing potential uses both Datura innoxia and Dipsacus laciniatus. (CUPRAC), and ferric reducing antioxidant power (FRAP)] (Apak et al., In this context, this study aims to screen the phenolic composition of 2006; Kocak et al., 2016) were used to screen the antioxidant activities the aerial parts of D. innoxia and D. laciniatus. Methanol was used to of the two plant extractsusing experimental conditions given in detail in extract bioactive molecules from the plant material. The antioxidant the supplementary file. The activity is expressed as both IC50 and EC50 (phosphomolybdenum, CUPRAC, FRAP, DPPH, ABTS) and enzyme in- value (the sample concentration providing 50% of radical scavenging/ α fl hibitory activities ( -amylase and tyrosinase), total phenolic and a- ferrous ion chelating, or 0.500 absorbance for the reducing power/ fi vonoids, and the phenolic pro les of D. innoxia and D. laciniatus extracts phosphomolybdenum assays, respectively) and standard (Trolox or were determined. EDTA) equivalents (μg/g extract). Enzyme inhibitory activities of the methanol extracts were mea- sured toward α-amylase and tyrosinase using experimental conditions 2. Materials and methods given in detail in the supplementary file (Zengin et al., 2015c). The enzyme inhibitory activity is expressed as both standard (kojic acid and 2.1. Plant material acarbose) equivalents and IC50 values (the sample concentration pro- viding 50% of enzyme inhibition). The aerial parts of Datura innoxia Mill. (Solanaceae) and Dipsacus laciniatus L. (Dipsacaceae) were collected from Senir town, Keciborlu, 2.5. Statistical analysis Isparta-Turkeyon 10 June 2016 (846 m, 37° 47′ 27.03″N 30° 13′ 28.01″E) and Karakent village, Burdur-Turkey on 10 July 2016 (925 m, All the experiments were repeated in triplicate and the results were 37° 41′ 42.89″N 30° 03′ 50.73″E), respectively. The plants were de- given as the mean value and the standard deviation (mean ± SD). posited and recognized by Prof. Dr. Hasan Ozcelik from the Department Statistical significance was analyzed by using ANOVA (one-way ana- of Biology, Süleyman Demirel University, Isparta-Turkey. lysis of variance) and Tukey's honestly significant difference post hoc test and Student's t-test with α = 0.05 for biological activity assays and phenolic composition (SPSS v. 22.0 software package). 2.2. Preparation of the extracts Five grams of air-dried samples of the aerial parts of each plant was 3. Results and discussion
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