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The Occurrence of Flavonoids and Related Compounds in Cedrus Brevifolia A

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The Occurrence of Flavonoids and Related Compounds in Cedrus Brevifolia A plants Article The Occurrence of Flavonoids and Related Compounds in Cedrus brevifolia A. Henry ex Elwes & A. Henry Needles. Inhibitory Potencies on Lipoxygenase, Linoleic Acid Lipid Peroxidation and Antioxidant Activity Andreas Douros 1, Dimitra Hadjipavlou-Litina 2 ID , Konstantinos Nikolaou 3 and Helen Skaltsa 1,* 1 Department of Pharmacognosy & Chemistry of Natural Products, School of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece; [email protected] 2 Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University Thessaloniki, 54124 Thessaloniki, Greece; [email protected] 3 Department of Forests, Ministry of Agriculture, Natural Resources and Environment, Nicosia 1414, Cyprus; [email protected] * Correspondence: [email protected]; Tel.: +30-210-7274593 Received: 2 November 2017; Accepted: 20 December 2017; Published: 27 December 2017 Abstract: The phytochemical analysis of the polar extracts of Cedrus brevifolia needles yielded 20 compounds, namely from the methanol extract we isolated three flavonoids (1–3), one hydrolysable tannin (4), eleven phenolic derivatives (5–15) and one apocarotenoid (16), while from the methanol: water (5:1) extract we isolated four flavonoids (17–20). Chemical structures of all isolated compounds were determined by 1D, 2D-NMR (1 Dimension, 2 Dimensions Nuclear Magnetic Resonance) and UV-Vis (Ultraviolet-Visible) spectroscopy. Furthermore, the antioxidant potentials and the anti-inflammatory activities of both crude extracts and isolates were evaluated through DPPH radical scavenging capability, linoleic acid lipid peroxidation inhibition, and soybean LOX inhibition assays. This is the first report on the chemical profile of C. brevifolia needles. Catechin was the main compound derived from the methanol extract. According to our results, 4-O-β-D-glucopyranyl trans-p-coumaric acid and taxifolin were the most active ingredients. Keywords: C. brevifolia; flavonoids; catechin; simple phenols; apocarotenoids; bioactivity, antioxidant; reducing power; total antioxidant capacity; reactive oxygen species 1. Introduction Cedrus brevifolia (Pinaceae) is an important endemic tree of Cyprus flora with narrow distribution. It is well-differentiated from other species of the genus based on morphological and eco-physiological traits, such as short needles and slow growth, resistance to aphids, and the highest tolerance to drought in all cedar species [1]. In ancient times, Theophrastus (371–287 B.C.) was the first to mention the existence of Cedrus in Cyprus, Phoenicia and Syria as an important forest tree of that period [2]. Cedar wood has been highly appreciated since ancient times for building temples, palaces, and ships [2,3]. The Roman author and architect Marcus Vitruvius Pollio wrote that the material used for the roof of the Greek temple of Artemis in Ephesus was from Cedrus wood [4]. In ancient Egypt, it was known that cedar was very resistant to insects and pathogenic microorganisms, so they used its essential oil to mummify corpses [3]. Plants 2018, 7, 1; doi:10.3390/plants7010001 www.mdpi.com/journal/plants Plants 2018, 7, 1 2 of 12 InPlants South-West 2018, 7, 1 Turkey the tar extract from C. libani, under the common name katran, is used2 internally of 12 and externallyIn South-West to heal wounds, Turkey fightthe tar parasites, extract from and cureC. libani various, under diseases the common [3]. It isname noteworthy katran, is that used the tar extractinternally has been and proposed externally to beto recognizedheal wounds, for fight its therapeutic parasites, valueand cure by thevarious French diseases pharmacopoeia [3]. It is [5]. C. brevifolianoteworthybark that is a the source tar extract of compounds has been proposed with antioxidant to be recognized capacity for and its therapeutic 15-lipoxygenase value by inhibitory the activityFrench [6]; C. pharmacopoeia deodara needles [5]. waterC. brevifolia extract bark exhibits is a source antibacterial of compounds activity with [7]. antioxidant capacity and Taking15-lipoxygenase in consideration inhibitory theactivity importance [6]; C. deodara and needles uses of waterCedrus extractspecies, exhibits this antibacterial study was designedactivity to [7]. investigate the chemical composition of the methanol and the aqueous methanol [MeOH:H2O (5:1)] extracts preparedTaking in fromconsideration needles the of importanceC. brevifolia andand uses to of evaluate Cedrus species, their total this antioxidantstudy was designed capacity to and investigate the chemical composition of the methanol and the aqueous methanol [MeOH:H2O (5:1)] anti-inflammatory activity, as well as of the isolates. extracts prepared from needles of C. brevifolia and to evaluate their total antioxidant capacity and 2. Resultsanti-inflammatory activity, as well as of the isolates. The2. Results methanol extract (6.5 g) yielded taxifolin (1)[8], astragalin (2)[9], isorhamnetin 3-O-β-D-glucoside (3)[10], (−The)-catechin methanol (4)[11 extract], benzoate (6.5 glucosideg) yielded (5)[ taxifolin12], benzyl- (1)β -[8],D-glucoside astragalin (6 )[(132) ],[9], benzyl- isorhamnetinβ-D-rutinoside (7)[143-],O 2-methoxy-phenyl--β-D-glucoside (3) [10],β-D (-glucoside−)-catechin ((84)[) [11],15], 3,4-dimethoxyphenyl-benzoate glucoside (5) [12],β-D -glucosidebenzyl-β-D-glucoside (9)[16], raspberry (6) ketone[13], (10 benzyl-)[17], p-anisicβ-D-rutinoside acid (11(7))[ [14],18], 2-methoxy-phenyl- 4-hydroxybenzoicβ- acidD-glucoside 4-O-β- D(8-glucoside) [15], 3,4-dimethoxyphenyl- (12)[19], p-coumaric acidβ (13-D,-glucoside 6.0 mg) (9 and) [16], its raspberry glucoside ketone (14)[ (1020) ,21[17],], transp-anisic-vaginoside acid (11) ([18],15)[ 4-hydroxybenzoic22] and abscisic acid alcohol glucoside4-O-β (-16D-glucoside)[23]. The (12 methanol:water) [19], p-coumaric (5:1) acid extract (13, afforded 6.0 mg) kaempferol-3- and its glucosideO-β-rutinoside (14) [20,21], (17)[ 24], kaempferide-3-trans-vaginosideO-β-rutinoside (15) [22] and (18 )[abscisic25], tiliroside alcohol glucoside (19)[26], (16 and) [23]. syringetin The methanol:water 3-O-β-D-glucoside (5:1) extract (20)[ 27] (Figureafforded1). Furthermore, kaempferol-3 both-O- crudeβ-rutinoside extracts (17 and) [24], isolated kaempferide-3- compoundsO-β were-rutinoside examined (18) for[25], their tiliroside inhibitory (19) [26], and syringetin 3-O-β-D-glucoside (20) [27] (Figure 1). Furthermore, both crude extracts and potency on lipoxygenase and lipid peroxidation, as well as for their antioxidant activity, in comparison to isolated compounds were examined for their inhibitory potency on lipoxygenase and lipid0 knownperoxidation, antioxidants, as e.g.,well caffeicas for acid,their nor-dihydroguareticantioxidant activity, in acid comparison (NDGA) to and known trolox. antioxidants AAPH (2,2 e.g.-azobis (2-amidino-propane)caffeic acid, nor-dihydroguaretic dihydrochloride), acid DPPH (NDGA) (2,2-diphenyl-1-picrylhydrazyl) and trolox. AAPH (2,2′-azobis and (2-amidino-propane) soybean lipoxygenase (LOX)dihydrochloride), assays were used DPPH for the (2,2-dip tests.henyl-1-picrylhydrazyl) This is the first report onand the soyb chemicalean lipoxygenase profile of C. (LOX) brevifolia assaysneedles. Catechinwere was used the for main the tests. compound This is the derived first report from on the the methanol chemical extractprofile (Seeof C. Supplementarybrevifolia needles. Data, Catechin Table S1. Accordingwas the to main our results compound of the derivedin vitro fromtests, the both methan extractsol extract were (See found Supplementary to possess potential Data, Table antioxidant S1. activityAccording due to their to our high results phenolic of the contents. in vitro Moreover, tests, both 4-O extracts-β-D-glucopyranyl were foundtrans to possess-p-coumaric potential acid and taxifolinantioxidant were the mostactivity active due ingredients to their (Figureshigh phenolic2–4, Table contents.1). Moreover, 4-O-β-D-glucopyranyl trans-p-coumaric acid and taxifolin were the most active ingredients (Figures 2–4, Table 1). OH H HO O OH H OH OH O 1 2: R=Η 4 3: R= -OCH3 6: R=H 5 8: R1= OCH3 R2= R3=Η 7: R= L-rha 9: R1= Η, R2= OCH3, R3= OCH3 10 11: R= CH3 13: R=H 12: R=D-glu 14: R=D-glu Figure 1. Cont. Plants 2018, 7, 1 3 of 12 Plants 2018, 7, 1 3 of 12 Plants 2018, 7, 1 3 of 12 16 15 16 15 17 17 19 19 18 20 18 20 FigureFigure 1. 1. StructuresStructures of of isolated isolated compounds compounds from from C.C. brevifolia brevifolia needlesneedles.. Figure 1. Structures of isolated compounds from C. brevifolia needles. FigureFigure 2. Reducing 2. Reducing ability ability (RA (RA %)%) at 0.1 0.1 mM. mM. Interaction Interaction with with DPPH. DPPH. Plants 2018, 7, 1 4 of 12 Figure 2. Reducing ability (RA %) at 0.1 mM. Interaction with DPPH. FigureFigure 3. % Inhibition3. % Inhibition of soybeanof soybean lipoxygenase lipoxygenase (LOX)(LOX) at at 0.1 0.1 mM. mM. Figure 4. Percent inhibition of lipid peroxidation induced by AAPH at 0.1 mM. Table 1. In vitro reducing ability (RA %) in DPPH assay, soybean lipoxygenase inhibition (% LOX inhbt) and anti-lipid peroxidation activity (A-LP %). RA # % ± SD, RA # % ± SD, % LOX ± SD A-LP % ± SD Compound DPPH, (20 min) DPPH, (60 min) Inhbt @ (0.1 mM) @ (0.1 mM) 1 84 ± 1.8 * 100 ± 2.1 ** no 61 ± 0.6 ** 4 86 ± 2.2 ** 100 ± 3.1 ** no 13 ± 0.3 * 5 5 ± 0.1 * no 29 ± 1.1 ** 9 ± 0.1 * 6 8 ± 0.3 ** no no 9 ± 0.1 * 7 2 ± 0.0 * no no no 8 9.8 ± 0.4 * no no 7 ± 0.1 * 9 41 ± 1.0 ** 42 ± 1.3 ** no 31 ± 0.7 * 10 24 ± 0.8 ** no 8.5 ± 0.1 ** 18 ± 0.6 ** Plants 2018, 7, 1 4 of 12 Plants 2018, 7, 1 4 of 12 Figure 3. % Inhibition of soybean lipoxygenase (LOX) at 0.1 mM. Figure 4. Percent inhibition of lipid peroxidation induced by AAPH at 0.1 mM. Figure 4. Percent inhibition of lipid peroxidation induced by AAPH at 0.1 mM. Table 1. In vitro reducing ability (RA %) in DPPH assay, soybean lipoxygenase inhibition (%Table LOX 1.inhbt)In vitro andreducing anti-lipid ability peroxidation (RA %) in DPPHactivity assay, (A-LP soybean %).
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