Mehmet ÖZTÜRK, Ebru EROL, Mehmet Emin DURU, Abdulselam ERTAŞ, Habiba MOKADDEM-DAROUI, Maya BELHADJ MOSTEFA, Fatma AYDOĞMUŞ ÖZTÜRK, Ahmed KABOUCHE, Zahia KABOUCHE

Antioxidant, anticholinesterase activities and polyphenolic constituents of cones of algerian fir (Abies numidica) by LCESI- MS/MS with chemometric approach

The fractions (Fr.1-5) of the hydromethanolic extract of Abies numidica cones were studied for theirpolyphenol constituents, antioxidant, and anticholinesterase activities. The β-carotene-linoleic acid, cupric reducingpower (CUPRAC), DPPH scavenging, and ABTS radical scavenging assays were used to determine antioxidant activity.Fr.3 exhibited the highest antioxidant activity in ABTS test (IC50: 1.29 μg/mL), b-carotene-linoleic acid test (IC50: 18.6μg/mL) and CUPRAC (A0.5: 33.8 μg/mL) assays. Three fractions (Fr.2-4) promising antioxidant activity were analyzedusing LC-MS/MS for their phenolic compositions. Taxifolin (155.9-2816.2 μg analyte/g extract), hyperoside (353.0-2045.5 μg/g), vanillin (1488.9-1529.9 μg/g), tannic acid (1281.6-1416.8 μg/g), rosmarinic acid (1063.1-1149.3 μg/g),coumarin (683.0-772.6 μg/g), quercetin (881.0 μg/g), and catechin (277.7-400.2 μg/g) were identified in the antioxidantfractions. Moreover, the anticholinesterase activity was also performed using the in vitro spectroscopic Ellman method.The antioxidant fractions exhibited moderate butyrylcholinesterase inhibitory activity. The multi-ware analysis wasperformed to understand the origin of bioactivities. According to principal component analysis, it is detected that thehyperoside, catechin, taxifolin, and tannic acid were responsible for the antioxidant activity. Therefore, the cones ofAbies numidica can be considered as potent antioxidant and anticholinesterase sources in food and pharmaceuticalindustries, commercially.

PDF

___

[1] Farjon A, Rushforth KD. A classification of Abies Miller (Pinaceae). Notes from the Royal Botanic Garden, Edinburgh 1989; 46(1): 59-79.
[2] Uçar G, Uçar MB. Geographical Variation in the Composition of Abies bornmuelleriana Mattf. Needle Oils. Rec Nat Prod. 2014; 8(1): 56-60.
[3] Baydar SN. Encyclopedia of Medicinal Plants, Palme Publishing, Istanbul, Turkey 2006.
[4] Li YL, Gao YX, Jin HZ, Shan L, Chang WL, Yang XW, Zeng HW, Wang N, Steinmetz A, Zhang WD. Chemical Constituents of Abies fabri. Phytochemistry 2015; 117: 135-143. [CrossRef]
[5] Tiwari KP, Minocha PK. A Chalcone Glycoside from Abies pindrow. Phytochemistry 1980; 19(11): 2501-2503. [CrossRef]
[6] Xia JH, Zhang SD, Li YL, Wu L, Zhu ZJ, Yang XW, Zeng HW, Li HL, Wang N, Steinmetz A, Zhang WD. Sesquiterpenoids and Triterpenoids from Abies holophylla and Their Bioactivities. Phytochemistry 2012; 74: 178-184. [CrossRef]
[7] Lavoie S, Gauthier C, Legault J, Mercier S, Mshvildadze V, Pichette A. Lanostane- and Cycloartane-Type Triterpenoids from Abies balsamea Oleoresin. Beilstein J Org Chem. 2013; 9: 1333-1339. [CrossRef]
[8] Raldugin VA, Shevtsov SA. Triterpenoids of Plant of the Genus Abies Hill. Chem Nat Comp. 1990; 26: 373-382.
[9] Yang XW, Li SM, Shen YH, Zhang WD, 2008. Phytochemical and Biological Studies of Abies species. Chem Biodivers. 2008; 5(1): 56-81. [CrossRef]
[10] Benouchenne D, Bellil I, Akkal S, Bensouici C, Khelifi D. LC–MS/MS Analysis, Antioxidant and Antibacterial Activities of Algerian Fir (Abies numidica de LANNOY ex CARRIÈRE) ethyl acetate fraction extracted from needles. J King Saud Univ – Sci. 2020; 32: 3321–3327. [CrossRef]
[11] Belhadj-Mostefa M, Abedini A, Voutquenne-Nazabadioko L, Gangloff SC, Kabouche A, Kabouche Z. Abietane Diterpenes from the Cones of Abies numidica de Lannoy ex Carrière (Pinaceae) and In Vitro Evaluation of Their Antimicrobial Properties. Nat Prod Res. 2016; 31(5): 568-571. [CrossRef]
[12] Benmerache A, Benteldjoune M, Alabdulmagid A, Abedini A, Berrehal D, Kabouche A, Gangloff SC, Voutquenne- Nazabadioko L, Kabouche Z. Chemical Composition, Antioxidant and Antibacterial Activities of Tamarix balansae J. Gay Aerial parts. Nat Prod Res. 2017; 31(24): 2828-2835. [CrossRef]
[13] Bouratoua A, Khalfallah A, Bensouici C, Kabouche Z, Alabdul Magid A, Harakat D, Voutquenne-Nazabadioko L, Kabouche A. Chemical Composition and Antioxidant Activity of Aerial Parts of Ferula longipes Coss. ex Bonnier & Maury. Nat Prod Res. 2018; 32(16): 1873-1880. [CrossRef]
[14] Cherchar H, Lehbili M, Berrehal D, Morjani H, Alabdul Magid A, Voutquenne-Nazabadioko L, Kabouche A, Kabouche A. A New 2-Alkylhydroquinone Glucoside from Phagnalon saxatile (L.) Cass. Nat Prod Res. 2018; 32(9): 1010-1016. [CrossRef]
[15] Lehbili MA, AlabdulMagid A, Kabouche A, Voutquenne-Nazabadioko L, Abedini A, Morjani H, Gangloff SC, Kabouche Z. Antibacterial, Antioxidant and Cytotoxic Activities of Triterpenes and Flavonoids from the Aerial Parts of Salvia barrelieri Etl. Nat Prod Res. 2018; 32(22): 2683-2691. [CrossRef]
[16] Bensouici C, Kabouche A, Karioti A, Öztürk M, Duru ME, Bilia AR, Kabouche Z. Compounds From Sedum caeruleum with Antioxidant, Anticholinesterase, and Antibacterial Activities. Pharm Biol. 2016; 54(1): 174-179. [CrossRef]
[17] Labed-Zouad I, Ferhat M, Öztürk M, Abaza I, Nadeem S, Kabouche A, Kabouche Z. Essential Oils Composition, Anticholinesterase and Antioxidant Activities of Pistacia atlantica Desf. Rec Nat Prod. 2017; 11(4): 411-415.
[18] Jiang Y, Han W, Shen T, Wang M-H. Antioxidant Activity and Protection from DNA Damage by Water Extract From Pine (Pinus densiflora) Bark. Prev Nutr Food Sci. 2012; 17(2): 116-121. [CrossRef]
[19] Tel G, Öztürk M, Duru ME, Dogan B, Harmandar M. Fatty Acid Composition, Antioxidant, Anticholinesterase and Tyrosinase inhibitory Activities of Four Serratula Species from Anatolia. Rec Nat Prod. 2013; 7(2): 86-95.
[20] Ertas A, Boga M, Yılmaz MA, Yesil Y, Tel G, Temel H, Hasimi N, Gazioglu I, Ozturk M, Ugurlu P. A Detailed Study on the Chemical and Biological Profiles of Essential Oil and Methanol Extract of Thymus nummularius (Anzer tea): Rosmarinic Acid. Ind Crop Prod. 2015; 67: 336-345. [CrossRef]
[21] Miller HE. A Simplified Method for the Evaluation of Antioxidants. J Am Oil Chem Soc. 1971; 48: 91-105. [CrossRef]
[22] Kabouche A, Kabouche Z, Öztürk M, Kolak U, Topçu G. Antioxidant Abietane Diterpenoids from Salvia barrelieri. Food Chem. 2007; 102(4): 1281-1287. [CrossRef]
[23] Apak R, Güçlü K, Özyürek M, Karademir SE. Novel Total Antioxidant Capacity Index for Dietary Polyphenols and Vitamins C and E, Using Their Cupric Ion Reducing Capability in the Presence of Neocuproine: CUPRAC Method. J Agric Food Chem. 2004; 52(26): 7970-7981. [CrossRef]
[24] Blois MS. Antioxidant Determinations by the Use of a Stable Free Radical. Nature 1958; 181: 1199-1200.
[25] Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant Activity Applying an Improved ABTS Radical Cation Decolorization Assay. Free Radic Biol Med. 1989; 26(9-10): 1231-1237. [CrossRef]
[26] Demirkiran O, Sabudak T, Ozturk M, Topcu G. Antioxidant and Tyrosinase Inhibitory Activities of Flavonoids from Trifolium nigrescens subsp. petrisavi. J Agric Food Chem. 2013; 61(51): 12598-12603. [CrossRef]
[27] Ellman GL, Courtney KD, Andres V, Featherston RM. A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity. Biochem Pharmacol. 1961; 7(2): 88-95. [CrossRef]
[28] Topcu G, Kolak U, Ozturk M, Boga M, Hatipoglu SD, Bahadori F, Culhaoglu B, Dirmenci T. Investigation of Anticholinesterase Activity of a Series of Salvia Extracts and the Constituents of Salvia staminea. The Nat Prod J. 2013; 3(1): 3-9.
[29] Slinkard K, Singleton VL. Total Phenol Analyses: Automation and Comparison with Manual Methods. Am J Enol Vitic. 1977; 28: 49-55.