title: Phytochemicals from Dodonaea viscosa and their antioxidant and anticholinesterase activities with structure-activity relationships.
abstract: Context Dodonaea viscosa (L.) Jacq (Sapindaceae) has been used in traditional medicine as antimalarial, antidiabetic and antibacterial agent, but further investigations are needed. Objective This study determines the antioxidant and anticholinesterase activities of six compounds (1-6) and two crystals (1A and 3A) isolated from D. viscosa, and discusses their structure-activity relationships. Materials and methods Antioxidant activity was evaluated using six complementary tests, i.e., β-carotene-linoleic acid; DPPH(•), ABTS(•+), superoxide scavenging, CUPRAC and metal chelating assays. Anticholinesterase activity was performed using the Elman method. Results Clerodane diterpenoids (1 and 2) and phenolics (3-6) - together with three crystals (1A, 3A and 7A) - were isolated from the aerial parts of D. viscosa. Compound 3A exhibited good antioxidant activity in DPPH (IC50: 27.44 ± 1.06 μM), superoxide (28.18 ± 1.35% inhibition at 100 μM) and CUPRAC (A0.5: 35.89 ± 0.09 μM) assays. Compound 5 (IC50: 11.02 ± 0.02 μM) indicated best activity in ABTS assay, and 6 (IC50: 14.30 ± 0.18 μM) in β-carotene-linoleic acid assay. Compounds 1 and 3 were also obtained in the crystal (1A and 3A) form. Both crystals showed antioxidant activity. Furthermore, crystal 3A was more active than 3 in all activity tests. Phenol 6 possessed moderate anticholinesterase activity against acetylcholinesterase and butyrylcholinesterase enzymes (IC50 values: 158.14 ± 1.65 and 111.60 ± 1.28 μM, respectively). Discussion and conclusion This is the first report on antioxidant and anticholinesterase activities of compounds 1, 2, 5, 6, 1A and 3A, and characterisation of 7A using XRD. Furthermore, the structure-activity relationships are also discussed in detail for the first time.
authors: a Faculty of Sciences, Department of Chemistry , Muğla Sitki Kocman University , Kötekli , Muğla , Turkey ;|b H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences , University of Karachi , Karachi , Pakistan ;|c Department of Chemistry , University of Karachi , Karachi , Pakistan ;
authors: Akhtar
authors: A
authors: Muhammad
authors: a Faculty of Sciences, Department of Chemistry , Muğla Sitki Kocman University , Kötekli , Muğla , Turkey ;
authors: Gülsen
authors: G
authors: Tel-Çayan
authors: a Faculty of Sciences, Department of Chemistry , Muğla Sitki Kocman University , Kötekli , Muğla , Turkey ;
authors: Mehmet
authors: M
authors: Öztürk
authors: a Faculty of Sciences, Department of Chemistry , Muğla Sitki Kocman University , Kötekli , Muğla , Turkey ;
authors: Mehmet Emin
authors: ME
authors: Duru
authors: a Faculty of Sciences, Department of Chemistry , Muğla Sitki Kocman University , Kötekli , Muğla , Turkey ;|b H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences , University of Karachi , Karachi , Pakistan ;
authors: Said
authors: S
authors: Nadeem
authors: c Department of Chemistry , University of Karachi , Karachi , Pakistan ;
authors: Itrat
authors: I
authors: Anis
authors: d Department of Chemistry , University of Malaya , Kuala Lumpur , Malaysia.
authors: Seik Weng
authors: SW
authors: Ng
authors: b H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences , University of Karachi , Karachi , Pakistan ;
authors: Muhammad Raza
authors: MR
authors: Shah
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology*; D052160:Benzothiazoles / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry; D002091:Butyrylcholinesterase / Q000378:metabolism; D002614:Chelating Agents / Q000302:isolation & purification / Q000494:pharmacology; D002800:Cholinesterase Inhibitors / Q000302:isolation & purification / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D016166:Free Radical Scavengers / Q000302:isolation & purification / Q000494:pharmacology; D019787:Linoleic Acid / Q000737:chemistry; D015394:Molecular Structure; D064209:Phytochemicals / Q000302:isolation & purification / Q000494:pharmacology*; D008517:Phytotherapy; D010851:Picrates / Q000737:chemistry; D010946:Plants, Medicinal; D029631:Sapindaceae / Q000737:chemistry; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000737:chemistry; D013481:Superoxides / Q000737:chemistry; D019207:beta Carotene / Q000737:chemistry
chemical_list: D000975:Antioxidants; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D002614:Chelating Agents; D002800:Cholinesterase Inhibitors; D016166:Free Radical Scavengers; D064209:Phytochemicals; D010851:Picrates; D013451:Sulfonic Acids; D019207:beta Carotene; D013481:Superoxides; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; D019787:Linoleic Acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D000110:Acetylcholinesterase; D002091:Butyrylcholinesterase
keywords: Clerodane diterpenoids; XRD study; phenolics; phytochemistry