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Pharmacy 250 15-Lipoxygenase Inhibition

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Pharmacy 250 15-Lipoxygenase Inhibition Rev. Med. Chir. Soc. Med. Nat., Iaşi – 2013 – vol. 117, no. 1 PHARMACY ORIGINAL PAPERS 15-LIPOXYGENASE INHIBITION, SUPEROXIDE AND HYDROXYL RADICALS SCAVENGING ACTIVITIES OF CEDRUS BREVIFOLIA BARK EXTRACTS Elena Creţu1, Adriana Trifan2, Ana Clara Aprotosoaie2, Anca Miron2 University of Medicine and Pharmacy "Grigore T. Popa" – Iasi Faculty of Pharmacy 1. Ph. D. student 2. Discipline of Pharmacognosy 15-LIPOXYGENASE INHIBITION, SUPEROXIDE AND HYDROXYL RADICALS SCAV- ENGING ACTIVITIES OF CEDRUS BREVIFOLIA BARK EXTRACTS (Abstract): Cedrus brevifolia (Hook. f.) Henry, a species endemic to Cyprus, has not been studied regarding its constituents and potential biological activities. Material and methods: A crude extract from Cedrus brevifolia bark and its four fractions (diethyl ether, ethyl acetate, n-butanol and aque- ous fractions) were investigated regarding their capacity to inhibit 15-lipoxygenase and scav- enge reactive oxygen species (superoxide anion and hydroxyl radicals). Catechin was used as positive control in all antioxidant assays. Results and discussion: In the superoxide anion rad- ical scavenging assay, the crude extract showed the highest activity (EC 50 = 57.73±1.25 µg/mL) comparable to that of the positive control, catechin (EC50 = 52.60±1.65 µg/mL). All other frac- tions exhibited noticeable scavenging effects against superoxide radical, their EC 50 values ranging from 76.33±3.50 to 91.06±4.45 µg/mL. The ethyl acetate and n-butanol fractions were the most active in the hydroxyl radical scavenging (EC50 = 580.20±18.72 and 792.10±15.36 µg/mL, respectively) and 15-lipoxygenase inhibition assays (EC50 = 34.0±0.9 and 40.96±0.45 µg/mL, respectively). Conclusions: Cedrus brevifolia bark is a valuable source of compounds with reactive oxygen species and 15-lipoxygenase inhibitory activities. These results support further studies for the identification and isolation of the bioactive constituents. Keywords: CEDRUS BREVIFOLIA, 15-LIPOXYGENASE, SUPEROXIDE ANION RADICAL, HY- DROXYL RADICAL In living cells, reactive oxygen species ROS (1). In low levels, ROS have im- (ROS) (superoxide anion, hydroxyl, perox- portant physiological roles (defence against yl and alkoxyl radicals, hydrogen peroxide, pathogens, cellular signaling) while in high singlet oxygen, hypochlorous acid) are concentrations they become harmful as produced during normal activities such as they damage cells constituents such as mitochondrial respiration, peroxisomal lipids, proteins, carbohydrates, DNA (oxi- beta-oxidation, cytochrome P450 metabo- dative stress). Oxidative stress plays a key lism. Pathological processes such as in- role in the development of cancer, cardio- flammation, exposure to ultraviolet and vascular, neurodegenerative and rheumatic gamma-irradiation are additional sources of diseases, diabetes mellitus (2, 3). One of 250 15-lipoxygenase inhibition, superoxide and hydroxyl radicals scavenging activities of Cedrus brevifolia the most important factors associated with rate in drought conditions in comparison carcinogenesis is DNA damage produced with other species of cedar (C. libani, C. by ROS. During cell division, these oxida- atlantica) (7, 8). A genetic diversity study tive lesions lead to mutations of the genes using AFLP (Amplified Fragment Length that regulate cell growth and differentia- Polymorfism) fingerprinting technique was tion. Lipid peroxidation indirectly induces performed on 17 populations of cedar. For DNA mutagenic lesions. Final products of C. brevifolia, found in small and fragment- lipid peroxidation (epoxides, aldehydes) ed populations, one of the highest levels of diffuse from the site of production and bind intrapopulational diversity was noticed. covalently to DNA, leading to exocyclic This unexpected pattern of diversity and adducts with mutagenic potential. The differentiation suggests a population in overexpression of NOX enzymes (NADPH evolution rather than one in decline (9). oxidases that transfer electrons across The present study was designed to eval- membranes generating superoxide anion uate the antioxidant potential (15- radical and other ROS) is implicated in lipoxygenase inhibition, superoxide and ischaemia/reperfusion injury, hypertension hydroxyl radicals scavenging activities) of and neurodegeneration but also in age- C. brevifolia bark extracts. associated hearing loss, cataract and retinal degeneration (1-3). In rheumatoid arthritis, MATERIAL AND METHODS ROS damage the cartilage, extracellular Chemicals. (+) Catechin hydrate, nitro- colagen and DNA (4). In diabetes mellitus, bluetetrazolium (NBT), phenazine meth- the increased production of superoxide osulphate (PMS), iron (II) sulfate heptahy- anion radical activates polyol and hex- drate, linoleic acid, lipoxidase from soy- osamine pathways, increases the production bean (15-LO), hydrogen peroxide solution of advanced glycation end products (AGEs) were obtained from Fluka (Steinheim, and the expression of their receptors thus Germany). Sodium salicylate and dimethyl leading to diabetes complications (athero- sulfoxide (DMSO) were purchased from sclerosis, cardiomyopathy) (5). Antioxi- Sigma-Aldrich (Steinheim, Germany). Tris dants are able to delay or prevent diseases (hydroxymethyl)aminomethane (Tris) and associated with oxidative stress (2, 3). beta-nicotinamide adenine dinucleotide Therefore, there is an increasing interest in reduced (NADH) were supplied by Merck finding new antioxidants, especially from (Darmstadt, Germany). All other solvents natural sources. and reagents were of analytical grade. Cedrus brevifolia (Hook. f.) Henry Equipments. For UV/VIS measure- (Cyprus cedar) is a conifer belonging to: ments, a Jasco V-550 spectrophotometer division-Pinophyta, class-Pinopsida, order- was employed. Pinales, family-Pinaceae, genus-Cedrus. Plant material.C. brevifolia bark was The present natural geographic distribution supplied by the Cyprus Department of For- of Cedrus species is limited to the Himala- ests of the Ministry of Agriculture, Natural yan Mountains (1500-3200 m) and the Resources and Environment in March Mediterranean coast (1000-2200 m) (6). 2008. Few studies on C. brevifolia reported an Preparation of bark extracts. Dried and increased sensitivity and a limited growth powdered bark was extracted with 80% 251 Elena Creţu et al. methanol (v/v); the crude extract (CbE) nm after 5 min incubaton at 25°C. Percent was further fractionated by successive superoxide anion radical scavenging activi- liquid-liquid partition. The diethyl ether ty was calculated as follows: (CbE1), ethyl acetate (CbE2), n-butanol Superoxide anion radical scavenging ac- (CbE3) and aqueous (CbE4) fractions were tivity (%) = 100 × (Acontrol – Asample)/Acontrol, obtained according to a methodology de- where Acontrol is the absorbance of control scribed previously (Elena Creţu, submit- and Asample is the absorbance in presence of ted). The polyphenolic content and profile extracts/catechin (11). The assay was car- of C. brevifolia bark extracts were studied ried out in triplicate and the results were and reported (Elena Creţu, submitted). expressed as mean values ± SD. 15-Lipoxygenase inhibition assay. Ex- Hydroxyl radical scavenging assay. Ex- tracts and catechin (positive control) were tracts and catechin (positive control) were dissolved in DMSO in concentrations rang- dissolved in DMSO in different concentra- ing from 0.31 to 5 mg/mL. The reaction tions ranging from 4 to 12 mg/mL. The mixture consisted of extracts/catechin and final reaction mixture contained ex- 0.2 M borate buffer (pH 9.0) containing 15- tracts/catechin, 1.5 mM iron (II) sulfate LO (10000 U/mL). After 10 min incubation heptahydrate, 20 mM sodium salicylate and at 25°C, the substrate (linoleic acid in bo- 6 mM hydrogen peroxide. The mixture was rate buffer) was added. Absorbance of the incubated at 37°C for 30 min. After cool- reaction mixture was measured at λ = 234 ing, the absorbance was measured at λ = nm after 30 and 90 s reaction time. Percent 562 nm. Percent hydroxyl radical scaveng- 15-LO inhibition was calculated using the ing activity was calculated using the for- formula: mula: Inhibition of 15-LO (%) = 100 × [(Acon- Hydroxyl radical scavenging activity trol, 90 – Acontrol, 30) – (Asample, 90 – Asample, (%) = 100 × (Acontrol – Asample)/Acontrol, 30)/(Acontrol, 90 – Acontrol, 30)], where Acontrol, 30 where Acontrol is the absorbance of control and Acontrol, 90 are the absorbances of the and Asample is the absorbance in presence of control after 30 and 90 s reaction time, extracts/catechin (12). The assay was per- respectively. Asample, 30 and Asample, 90 are the formed in triplicate and the results were absorbances of the mixtures containing expressed as mean values ± SD. extracts/catechin after 30 and 90 s reaction time, respectively (10). The assay was RESULTS AND DISCUSSION carried out in triplicate and the results were 15-Lipoxygenase inhibition assay. 15- expressed as mean values ± SD. LO plays a major role in the development Superoxide anion radical scavenging of atherosclerosis. The enzyme oxidizes assay. Extracts and catechin (positive con- circulating low-density lipoproteins (LDL) trol) were dissolved in DMSO in a concen- initiating the formation of the atheroscle- tration range of 0.039 − 1.25 mg/mL. The rotic plaques in the arterial wall. 15-LO is reaction mixture consisted of ex- also responsible for other processes in- tracts/catechin and 16 mM Tris-HCl buffer volved in atherogenesis such as endothelial (pH 8.0) containing 557 μM NADH, 45 μM injury, proinflammatory
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