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Inhibitory Activity of Podospermum Canum and Its Active Components

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Inhibitory Activity of Podospermum Canum and Its Active Components Bioorganic Chemistry 93 (2019) 103330 Contents lists available at ScienceDirect Bioorganic Chemistry journal homepage: www.elsevier.com/locate/bioorg Inhibitory activity of Podospermum canum and its active components on T collagenase, elastase and hyaluronidase enzymes ⁎ Özlem Bahadır Acıkaraa, Mert Ilhanb, Ekin Kurtula, Karel Šmejkald, Esra Küpeli Akkolc, a Department of Pharmacognosy, Faculty of Pharmacy, Ankara University, Tandoğan, 06100 Ankara, Turkey b Department of Pharmacognosy, Faculty of Pharmacy, Van Yüzüncü Yıl University, Tuşba 65080, Van, Turkey c Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Etiler, 06330 Ankara, Turkey d Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého tř. 1946/1, 61242 Brno, Czech Republic ARTICLE INFO ABSTRACT Keywords: Present study is aimed to investigate in vitro inhibitory effects of the extract prepared from the aerial partsof Asteraceae Podospermum canum (syn: Scorzonera cana var. jacquiniana) (Asteraceae) on hyaluronidase, collagenase, and Collagenase elastase enzymes using a bioassay-guided fractionation. Inhibitory effects of the extract, sub-extracts, fractions Elastase obtained by column chromatography, and isolated compounds on collagenase, elastase, and hyaluronidase were Hyaluronidase performed by using in vitro enzyme inhibitory assays based on spectrophotometric evaluation. The methanolic Isolation extract obtained from P. canum exhibited strong inhibitory activities on elastase and collagenase while the Podospermum canum insignificant activity was observed on hyaluronidase. Through bioactivity-guided fractionation, the ethyl acetate and remaining water sub-extracts obtained from the methanolic extract displayed significant inhibitory activities on collagenase and elastase, while petroleum ether and chloroform extracts did not show any inhibitory activity. Eleven known compounds: arbutin, 6́-O-caffeoylarbutin, cichoriin, 3,5-dicaffeoylquinic acid methyl ester, api- genin 7-O-β-glucoside, luteolin 7-O-β-glucoside, apigenin 7-O-β-rutinoside, isoorientin, orientin, vitexin, pro- catechuic acid, and new compound 4-hydroxy-benzoic acid 4-(6-O-α-rhamnopyranosyl-β-glucopyranosyl) benzyl ester have been obtained from ethyl acetate sub-extract. Results of the present study have revealed that apigenin 7-O-β-glucoside, luteolin 7-O-β-glucoside, apigenin 7-O-β-rutinoside, and isoorientin showed potent enzyme inhibitory activities. However, methanolic extract of P. canum displayed a greater inhibitory activity than fractions and isolated compounds both on collagenase and elastase. 1. Introduction arteriosclerosis, hypertension, rheumatism, kidney diseases, diabetes mellitus [5], and for wound healing [6,7]. Previous reports have re- Podospermum canum C. A. Meyer (syn.: Scorzonera cana (C.A. Meyer) vealed the significant anti-inflammatory effects of extracts of P. canum Hoffm. var. jacquiniana (W. Koch) Chamb.), a plant from Asteraceae in carrageenan-and PGE2-induced hind paw edema model at doses of family, is a perennial herb with cylindrical root-stock, entire to pin- 100 mg/kg, while no activity in serotonin induced hind paw edema and natipartite basal leaves and yellow flowers [1]. This plant which was TPA induced ear edema models. P. canum displayed also anti- formerly known as S. cana var. jacquiniana, is now systematically nociceptive activity in vivo [8]. Wound healing effects of the P. canum, classified into Podospermum genus based on studies of Mavrodiev et al. evaluated in vivo by linear incision and circular excision experimental [2], which reclassified Scorzonera, Podospermum, and Lasiospora into wound models with subsequent histopathological analysis, and an anti- separate genera. hyaluronidase activity were established as remarkable [9]. P. canum grows naturally in central and south parts of the Europe, Hyaluronidase, collagenase, and elastase are matrix metalloprotei- west part of the Syria, Iraq, Caucasia, Iran, and Anatolia [1]. P. canum is nases (MMPs), and comprise a family of ECM-degrading enzymes. They known as “karakök” or “tekesakalı” in Turkey. Its leaves are used as a play essential role in remodeling and repair of tissues. They have im- vegetable [3] and are used for their galactagogue and appetizing ac- portant role in regulation of extracellular matrix degradation and de- tivities in Turkish folk medicine [4]. Furthermore, Scorzonera plants are position which is essential for wound re-epithelialization. used as a food in Anatolia and as medicinal plants to combat Hyaluronidase, collagenase and elastase are involved in the ⁎ Corresponding author at: Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Etiler 06330, Ankara, Turkey. E-mail address: [email protected] (E. Küpeli Akkol). https://doi.org/10.1016/j.bioorg.2019.103330 Received 18 February 2019; Received in revised form 21 August 2019; Accepted 28 September 2019 Available online 30 September 2019 0045-2068/ © 2019 Elsevier Inc. All rights reserved. Ö. Bahadır Acıkara, et al. Bioorganic Chemistry 93 (2019) 103330 pathogenesis of different diseases, such as cancer, cardiovascular dis- eases, inflammation, bone destruction, fibrosis, as well as in develop- ment and healing of wounds [10–13]. The aim of the current study was to confirm medicinal usage of P. canum based on wound healing and to investigate, using bioactivity-guided fractionation and isolation, which compound(s) is/are responsible for significant wound healing activity that was established previously in vivo. 2. Materials and methods 2.1. Plant material P. canum (syn: S. cana var. jacquiniana) was collected in Çamlıdere (Ankara, Turkey, N 40°29′15.6′′; E 32°28′09.8′′, located in the north- west of the Anatolia), 100 km from the Ankara city center. Plants were growing naturally at roadsides and in the fields. The age of the har- vested plants was 5–8 months and the samples were collected during flowering period (19th of June 2016). The identification of theplant was performed by Prof. Dr. Hayri Duman (Department of Biology, Faculty of Science, Gazi University) according to the description of the plant material in the Flora of Turkey and the East Aegean Islands [1].A voucher specimen was deposited in the herbarium of the Faculty of Pharmacy at Ankara University (AEF Number: 23834). Fig. 1. Structure of 4-hydroxy-benzoic acid 4-(6-O-α-rhamnopyranosyl-β-glu- copyranosyl) benzyl ester (11). 2.2. Preparation of the plant extracts Fraction B, that contains the compounds 8, 9 and 6, was chroma- Dried and powdered aerial parts (flowers, leaves and stems; 600 g) tographed on Sephadex column to obtain 40 sub-fractions by eluting were macerated in methanol at room temperature, five times, each with methanol for obtaining 9 (12 mg) and 8 (13 mg) from sub-fractions following, in 2.5 L of methanol for 24 h. The extraction was finished by 24–29 and 34–40, respectively which were selected due to their content 1 h of a sonication. The combined extracts were filtered, and the solvent 8 and 9 in high amount than the other subfractions. On the other hands was evaporated at 40–50 °C under reduced pressure to obtain the crude 6 has already been isolated from the Fraction A, was not applied to extract (87.98 g). The crude extract was dissolved in water and then further separation procedure. subjected to partitioning by petroleum ether, chloroform, and ethyl The structures of the compounds were elucidated by using MS and acetate, respectively, to obtain four sub-extract with different polarity. 1H- and 13C NMR, 2D-NMR techniques and by comparing the results According to the results of bio-assays, the ethyl acetate fraction (4.34 g) with the literature. was selected for further separation. 2.5. In vitro enzyme inhibitory assays 2.3. General experimental procedures 2.5.1. Assessment of collagenase inhibitory activity Mass spectra were measured using a Waters 2695 Alliance The assay of collagenase inhibitory activity was based on the Micromass ZQ, LC/MS. Varian Mercury 400, 400 MHz High 1 13 spectrophotometric methods reported by Vanwart and Steinbrink [14], Performance Digital FT-NMR Spectrometer was used for H NMR, C with some modifications in order to use a microplate reader. Tricine NMR and 2D NMR (HMBC, HSQC, COSY, TOCSY, NOESY, DEPT) (in buffer was used for this assay. Collagenase from Clostridium histolyticum CD3OD). (ChC) was added to Tricine buffer (50 mM, pH 7.5, 400 mM NaCl and 10 mM CaCl ) to get a concentration of 0.8 units/mL. The substrate N- 2.4. Isolation procedure 2 [3-(2-furyl)acryloyl]-Leu-Gly-Pro-Ala (FALGPA) was added to Tricine buffer to obtain a concentration of 2 mM. In each case, the totalfinal The ethyl acetate portion, selected as the active, was separated volume of the mixture (150 μL) included Tricine buffer (25 μL), 0.8 mM using column chromatography on silica gel (40–63 μm, Merck) by FALGPA (75 μL), 0.1 units of ChC (25 μL) and 25 μL of the solution of eluting with isocratic solvent system ethyl acetate:methanol:water the tested materials in 5% DMSO (100 μg/mL). Each test material was (100:13.5:10, v/v/v). Fractions obtained from column chromatography incubated with the enzyme in buffer for 15 min before the substrate was were combined according to their TLC behavior to obtain six main added to trigger the reaction. After adding the substrate, the absorbance fractions (Fr. A-F). Fraction A and B (as the most active fractions) were at 335 nm was measured in 2 min intervals for 20 min using a Beck- used for further isolation procedures. Both Fraction A and B were mann Dual Spectrometer (Beckman, Fullerton, CA, USA). Water was subjected to Sephadex column and eluted with methanol. Fraction A used as a negative and epigallocatechin gallate (EGCG) (250 μM, gave 60 sub-fractions; sub-fraction 2 gave 1 (8 mg) and 4 (6 mg) by 0.114 mg/mL) as a positive control [15]. Measurements were done in preparative thin layer chromatography on reverse phase TLC plates three replications. The formula % inhibition = (OD – (Merck 5559) by eluting with methanol:water (1:1, v/v).
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