Generic placeholder image

The Natural Products Journal

Editor-in-Chief

ISSN (Print): 2210-3155
ISSN (Online): 2210-3163

Research Article

Chemical Composition, Antioxidant, and Anti-inflammatory Activities of Whole Parts of Onobrychis crista-galli (L.) Lam

Author(s): Wassila Benchadi, Hamada Haba, Emerson Ferreira Queiroz, Laurence Marcourt, Jean-Luc Wolfender, Chawki Bensouici and Mohammed Benkhaled*

Volume 10, Issue 5, 2020

Page: [642 - 654] Pages: 13

DOI: 10.2174/2210315510666191218094623

Price: $65

Abstract

Objective: The aim of the present study is to examine the phytochemical components and the biological activities of the whole parts of Onobrychis crista-galli (L.) Lam. growing in Algeria.

Methods: The structures of the isolated compounds 1-15 were elucidated using different spectroscopic methods and by comparison with literature data. The biological evaluation of the plant was determined by the in vitro antioxidant and anti-inflammatory activities. The antioxidant activity of various extracts (petroleum ether, ethyl acetate, and n-butanol) and some isolated flavonoids was assessed by using five different test systems, namely, 1,1-diphenyl-2-picryl-hydrazil (DPPH), 2,2’- azinobis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS), cupric reducing antioxidant capacity (CUPRAC), superoxide alkaline DMSO, and β-carotene/linoleic acid tests. In addition, the total phenolic and flavonoid contents of the extracts were determined as gallic acid and quercetin equivalents, respectively. In vitro anti-inflammatory activity by protein denaturation was measured for all extracts.

Results: Phytochemical investigation of the ethyl acetate and n-butanol extracts of Onobrychis crista- galli led to the isolation for the first time of fifteen known compounds. The present study reports for the first time the isolation and identification of fifteen known compounds from this species. The ethyl acetate extract had rich phenolic content indicating (31.09 ± 0.40 mg gallic acid equivalents/g of fresh weight), while n-butanol extract displayed a high content in flavonoid compounds (60.70±0.7 mg quercetin equivalents/ g of fresh weight). This investigation indicated that the ethyl acetate extract of O. crista-galli showed the highest antioxidant activity (IC50= 17.13±0.51 μg/mL, DPPH), (IC50= 82.99±2.50 μg/mL, ABTS), and (A0.50= 94.67±0.41 μg/mL, CUPRAC), (IC50= 97.09±2.20 μg/mL, DMSO), (IC50: 36.73±1.17 μg/mL, β-carotene/linoleic acid). Furthermore, the compound luteolin 5-methyl ether (14) exhibited a good antioxidant activity in DPPH (IC50= 06.05 ± 0.15 μg /mL) and CUPRAC (A0.5= 12.57 ± 0.34 μg /mL) assays. Moreover, the ethyl acetate and nbutanol extracts of O. crista-galli evidenced a good to moderate in vitro anti-inflammatory activity.

Conclusion: The extracts of the whole plant of O. crista-galli (L.) Lam. showed potent antioxidant and anti-inflammatory activities.

Keywords: Onobrychis crista-galli (L.) Lam., flavonoids, NMR, antioxidant activity, anti-inflammatory activity, total phenolic content, total flavonoid content.

Graphical Abstract
[1]
Quezel, P.; Santa, S. Nouvelle Flore de l’Algérie et des régions désertiques méridionales; , 1963, Vol. 1-2, .
[2]
ILDIS (International Legume Database Information Service), World Database of Legumes, Version 10.01, Available from: http://www.ildis.org/
[3]
Kavandi, A.; Jafari, A.A.; Jafarzadeh, M. Effect of seed priming on enhancement of seed germination and seedling growth of annual Sainfoin (Onobrychis crista-galli (L.) Lam.) in medium and longterm collections of gene bank J. Rangel. sci., 2018, 8(2), 117-128.
[4]
Delamarck, M.; Decandolle, M. Flore française, ou description succinctes de toutes les plantes qui croissant naturellemrnt en France chez.Agasse, rue des poitevins, Paris; , 1805, 6, p. 613.
[5]
Abdelgurfi, A.; Laouar, M. Distribution des espèces d’Onobrychis en relation avec quel-ques facteurs du milieu, en Algérie. Annales de l’institut national agronomique-El-Harrach, 2002, 32(1), 2.
[6]
Ingham, J.L. Flavonoid and isoflavonoid compounds from leaves of sainfoin (Onobrychis viciifolia). Z. Naturforsch. C, 1978, 33(1), 146-148.
[http://dx.doi.org/10.1515/znc-1978-1-227]
[7]
Russeli, G.B.; Shaw, G.J.; Christmas, P.E.; Yates, M.B.; Sutherland, O.R.W. Two 2-aryl benzofurans as insect feeding deterrents from sainfoin (Onobrychis viciifolia). Phytochemistry, 1984, 23(7), 1417-1420.
[http://dx.doi.org/10.1016/S0031-9422(00)80477-X]
[8]
Sinch, S.; Mccallum, J.; Gruber, M.Y.; Neil Towers, G.H.; Muir, A.D.; Bohm, B.A.; Koupai-Abyzani, M.R.K.; Glass, A.D.M. Biosynthesis of flanan-3-ols by leaf extracts of On-obrychis viciifolia. Phytochemistry, 1997, 44(3), 425-432.
[http://dx.doi.org/10.1016/S0031-9422(96)00415-3]
[9]
Marais, J.P.J.; Mueller-Harvey, I.; Brandt, E.V.; Ferreira, D. Polyphenols, condensed tannins, and other natural products in Onobrychis viciifolia (Sainfoin). J. Agric. Food Chem., 2000, 48(8), 3440-3447.
[http://dx.doi.org/10.1021/jf000388h ] [PMID: 10956131]
[10]
Lu, Y.; Sun, Y.; Foo, L.Y.; McNabb, W.C.; Molan, A.L. Phenolic glycosides of forage legume Onobrychis viciifolia. Phytochemistry, 2000, 55(1), 67-75.
[http://dx.doi.org/10.1016/S0031-9422(00)00143-6 ] [PMID: 11021646]
[11]
Godevac, D.; Pejin, B.; Zdunic, G.; Savikin, K.; Stesevic, D.; Vajs, V.; Millosavljevic, S. Flavonoids from the aerial parts of Onobrychis montana subsp. Scardica. J. Serb. Chem. Soc., 2008, 73(5), 525-529.
[http://dx.doi.org/10.2298/JSC0805525G]
[12]
Regos, I.; Urbanella, A.; Treutter, D. Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia). J. Agric. Food Chem., 2009, 57(13), 5843-5852.
[http://dx.doi.org/10.1021/jf900625r ] [PMID: 19456170]
[13]
Regos, I.; Treutter, D. Optimization of a high-performance liquid chromatography method for the analysis of complex polyphenol mixtures and application for sainfoin extracts (Onobrychis viciifolia). J. Chromatogr. A, 2010, 1217(40), 6169-6177.
[http://dx.doi.org/10.1016/j.chroma.2010.07.075 ] [PMID: 20817190]
[14]
Veitch, N.C.; Regos, I.; Kite, G.C.; Treutter, D. Acylated flavonol glycosides from the forage legume, Onobrychis viciifolia (sainfoin). Phytochemistry, 2011, 72(4-5), 423-429.
[http://dx.doi.org/10.1016/j.phytochem.2011.01.001 ] [PMID: 21292287]
[15]
Stringano, E.; Hayot Carbonero, C.; Smith, L.M.J.; Brown, R.H.; Mueller-Harvey, I. Proanthocyanidin diversity in the EU ‘HealthyHay’ sainfoin (Onobrychis viciifolia) germplasm collection. Phytochemistry, 2012, 77, 197-208.
[http://dx.doi.org/10.1016/j.phytochem.2012.01.013 ] [PMID: 22313998]
[16]
Thill, J.; Regos, I.; Farag, M.A.; Ahmad, A.F.; Kusek, J.; Castro, A.; Schlangen, K.; Carbonero, C.H.; Gadjev, I.Z.; Smith, L.M.J.; Halbwirth, H.; Treutter, D.; Stich, K. Polyphenol metabolism provides a screening tool for beneficial effects of Onobrychis viciifolia (sainfoin). Phytochemistry, 2012, 82, 67-80.
[http://dx.doi.org/10.1016/j.phytochem.2012.05.030 ] [PMID: 22818525]
[17]
Guler, G.O.; Zengin, G.; Karadag, F.; Mollica, A.; Picot, C.M.N.; Mahomoodally, M.F. HPLC-DAD profiles and pharmacological insights of Onobrychis argyrea subsp isaurica extracts. Comput. Biol. Chem., 2018, 76, 256-263.
[http://dx.doi.org/10.1016/j.compbiolchem.2018.07.016 ] [PMID: 30081342]
[18]
Halabalaki, M.; Aligiannis, N.; Papoutsi, Z.; Mitakou, S.; Moutsatsou, P.; Sekeris, C.; Skaltsounis, A.L. Three new arylobenzofurans from Onobrychis ebenoides and evaluation of their binding affinity for the estrogen receptor. J. Nat. Prod., 2000, 63(12), 1672-1674.
[http://dx.doi.org/10.1021/np000071b ] [PMID: 11141112]
[19]
Halabalaki, M.; Alexi, X.; Aligiannis, N.; Alexis, M.N.; Skaltsounis, A.L. Ebenfurans IV-VIII from Onobrychis ebenoides: Evidence that C-prenylation is the key determinant of the cytotoxicity of 3-formyl-2-arylbenzofurans. J. Nat. Prod., 2008, 71(11), 1934-1937.
[http://dx.doi.org/10.1021/np800134h] [PMID: 18986200]
[20]
Usta, C.; Yildirim, A.B.; Turker, A.U. Antibacterial and antitumour activities of some plants grown in Turkey. Biotechnol. Biotechnol. Equip., 2014, 28(2), 306-315.
[http://dx.doi.org/10.1080/13102818.2014.909708 ] [PMID: 26740759]
[21]
Karakoca, K.; Asan-Ozusaglam, M.; Cakmak, Y.S.; Teksen, M. Phenolic compounds, biological and antioxidant activities of Onobrychis armena Boiss. & Huet flower and root extracts. Warasan Khana Witthayasat Maha Witthayalai Chiang Mai, 2015, 42(2), 376-392.
[22]
Karamian, R.; Asadbegy, M. Antioxidant activity, total phenolic and flavonoid contents of three Onobrychis species from Iran. J. Pharm. Sci., 2016, 22(2), 112-119.
[http://dx.doi.org/10.15171/PS.2016.18]
[23]
Erbil, N.; Duzguner, V.; Durmusahya, C.; Alan, Y. Antimicrobial and antioxidant effects of Some Turkish fodder plants belongs to fabaceae family (Vicia villosa,Trifolium ochroleucum and Onobrychis altissima). Orient. J. Chem., 2015, 31, 53-58.
[http://dx.doi.org/10.13005/ojc/31.Special-Issue1.06]
[24]
Papoutsi, Z.; Kassi, E.; Halabalaki, M.; Mitakou, S.; Moutsatsou, P. Evaluation of estrogenic/antiestrogenic activity of Onobrychis ebenoides extract - interaction with estrogen receptor subtypes ERalpha and ERbeta. Toxicol. In Vitro, 2007, 21(3), 364-370.
[http://dx.doi.org/10.1016/j.tiv.2006.09.009 ] [PMID: 17092687]
[25]
Zengin, G.; Guler, G.O.; Aktumsek, A.; Ceylan, R.; Picot, C.M.N.; Mahomoodally, M.F. Enzyme inhibitory properties, antioxidant activities, and phytochemical profile of three medicinal plants from Turkey. Adv. Pharmacol. Sci., 2015.
[http://dx.doi.org/10.1155/2015/410675] [PMID: 26798334]
[26]
Blois, M.S. Antioxidant determinations by the use of a stable free radical. Nature, 1958, 181(4617), 1119-1200.
[http://dx.doi.org/10.1038/1811199a0]
[27]
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., 1999, 26(9-10), 1231-1237.
[http://dx.doi.org/10.1016/S0891-5849(98)00315-3 ] [PMID: 10381194]
[28]
Apak, R.; Güçlü, K.; Ozyürek, M.; Karademir, S.E. 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.
[http://dx.doi.org/10.1021/jf048741x ] [PMID: 15612784]
[29]
Kunchandy, E.; Rao, M.N.A. Oxygen radical scavenging activity of curcumin. Int. J. Pharm., 1990, 58(3), 237-240.
[http://dx.doi.org/10.1016/0378-5173(90)90201-E]
[30]
Marco, G.J. A rapid method for evaluation of antioxidants. J. Am. Oil Chem. Soc., 1968, 45, 594-595.
[http://dx.doi.org/10.1007/BF02668958]
[31]
Karthik, K.; Kumar, P.B.R.; Priya, R.V.; Kumar, K.S.; Rathore, R.S.B. Evaluation of anti inflammatory activity of Canthium parviflorum by in vitro method. Indian J. Res. Pharm. Biotech., 2013, 1(5), 729-3471.
[32]
Kuwabara, H.; Mouri, K.; Otsuka, H.; Kasai, R.; Yamasaki, K. Tricin from a Malagasy connaraceous plant with potent antihistaminic activity. J. Nat. Prod., 2003, 66(9), 1273-1275.
[http://dx.doi.org/10.1021/np030020p ] [PMID: 14510616]
[33]
Ghanadian, S.M.; Ayatollahi, A.M.; Afsharypour, S.; Hareem, S.; Abdalla, O.M.; Jules Kezetas Bankeu, J. Flavonol glyco-sides from Euphorbia microsciadia Bioss. with their Immunomodulatory activities. Iran. J. Pharm. Res., 2012, 11(3), 925-930.
[PMID: 24250520]
[34]
Marin, P.D.; Grayer, R.J.; Grujic-Jovanovic, S.; Kite, G.C.; Veitch, N.C. Glycosides of tricetin methyl ethers as chemosystematic markers in Stachys subgenus Betonica. Phytochemistry, 2004, 65(9), 1247-1253.
[http://dx.doi.org/10.1016/j.phytochem.2004.04.014] [PMID: 15184009]
[35]
Panda, S.; Kar, A. Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-O-glucoside. Biofactors, 2007, 31(3-4), 201-210.
[http://dx.doi.org/10.1002/biof.5520310307 ] [PMID: 18997283]
[36]
Lee, K.H.; Tagahara, K.; Suzuki, H.; Wu, R.Y.; Haruna, M.; Hall, I.H.; Huang, H.C.; Ito, K.; Iida, T.; Lai, J.S. Antitumor agents. 49 tricin, kaempferol-3-O-β-D-glucopyranoside and (+)-nortrachelo-genin, antileukemic principles from Wikstroemia indica. J. Nat. Prod., 1981, 44(5), 530-535.
[http://dx.doi.org/10.1021/np50017a003 ] [PMID: 7320737]
[37]
Luk’yanchikov, M.S. Polyphenols of Onobrychis bobrovii. Chem. Nat. Compd., 1982, 18(2), 237-237.
[http://dx.doi.org/10.1007/BF00577212]
[38]
Yuldashev, M.P.; Batirov, E.Kh.; Malikov, V.M. Flavonoids of the epigeal part of Onobrychis arenaria. Chem. Nat. Compd., 1996, 32(4), 590-591.
[http://dx.doi.org/10.1007/BF01372623]
[39]
Heshmati Afshar, F.; Delazar, A.; Nazemiyeh, H.; Khodaie, L.; Bamdad Moghaddam, S. Phenolic derivatives of Artemisia spicigera C. Koch growing in Iran. Iran. J. Pharm. Res., 2015, 14(4), 1241-1246.
[PMID: 26664392]
[40]
Ince, S.; Ekici, H.; Yurdakok, B. Determination of in vitro antioxidant activity of the sainfoin (Onobrychis Viciifolia) extracts. Ankara Univ. Vet. Fak. Derg., 2012, 59, 23-27.
[http://dx.doi.org/10.1501/Vetfak_0000002496]
[41]
Husain, S.R.; Cillard, J.; Cillard, P. Hydroxyl radical scavenging activity of flavonoids. Phytochemistry, 1987, 26(9), 2489-2491.
[http://dx.doi.org/10.1016/S0031-9422(00)83860-1]
[42]
Lin, C.Z.; Zhu, C.C.; Hu, M.; Wu, A.Z.; Bairu, Z.D.; Kangsa, S.Q. Structure-activity relationships of antioxidant activity in vitro about flavonoids isolated from Pyrethrum tatsienense. J. Intercult. Ethnopharmacol., 2014, 3(3), 123-127.
[http://dx.doi.org/10.5455/jice.20140619030232 ] [PMID: 26401360]
[43]
Heim, K.E.; Tagliaferro, A.R.; Bobilya, D.J. Flavonoid antioxidants: Chemistry, metabolism and structure-activity relationships. J. Nutr. Biochem., 2002, 13(10), 572-584.
[http://dx.doi.org/10.1016/S0955-2863(02)00208-5 ] [PMID: 12550068]
[44]
Bektas, E.; Kaltalioglu, K.; Sahin, H.; Turkmen, Z.; Kandemir, A. Analysis of phenolic compounds, antioxidant and antimicro-bial properties of some endemic medicinal plants Int. J. Second. Metab., 2018, 5(2), 75-86.
[45]
Shahidi, F.; Wanasundara, P.K.; Wanasundara, P.D. Phenolic antioxidants. Crit. Rev. Food Sci. Nutr., 1992, 32(1), 67-103.
[http://dx.doi.org/10.1080/10408399209527581 ] [PMID: 1290586]
[46]
Kumar, S.; Pandey, A.K. Chemistry and biological activities of flavonoids: An overview. Scient. World J., 2013.
[http://dx.doi.org/10.1155/2013/162750 ] [PMID: 24470791]
[47]
Halim, A.; Aurang Zeb, M.; Ullah Khan, S. In-vitro anti inflammatory activity of Indigofera heterantha roots. ots. Pharm. Pharmacol. Int. J., 2018, 6(4), 307-308.
[48]
Heydari, H.; Saltan Işcan, G.; Eryilmaz, M.; Bahadir Acikara, Ö.; Yilmaz Sarialtin, S.; Tekin, M.; Çoban, T. Antimicrobial and anti inflammatory activity of some Lathyrus L. (Fabaceae) species growing in Turkey. Turk J Pharm Sci, 2019, 16(2), 240-245.
[http://dx.doi.org/10.4274/tjps.galenos.2018.86719 ] [PMID: 32454720]
[49]
Singh, R.K.; Pandey, B.L.; Tripathi, M.; Pandey, V.B. anti inflammatory effect of (+)-pinitol. Fitoterapia, 2001, 72(2), 168-170.
[http://dx.doi.org/10.1016/S0367-326X(00)00267-7 ] [PMID: 11223227]
[50]
Riaz, A.; Rasul, A.; Hussain, G.; Zahoor, M.K.; Jabeen, F.; Subhani, Z.; Younis, T.; Ali, M.; Sarfraz, I.; Selamoglu, Z. Astragalin: A bioactive phytochemical with potential therapeutic activities. Adv. Pharmacol. Sci., 2018.
[http://dx.doi.org/10.1155/2018/9794625 ] [PMID: 29853868]
[51]
Kang, B.M.; An, B.K.; Jung, W.S.; Jung, H.K.; Cho, J.H.; Cho, H.W.; Jang, S.J.; Yun, Y.B.; Kuk, Y.I. anti inflammatory effect of tricin isolated from Alopecurus aequalis Sobol. on the LPS-induced inflammatory response in RAW 264.7 cells. Int. J. Mol. Med., 2016, 38(5), 1614-1620.
[http://dx.doi.org/10.3892/ijmm.2016.2765 ] [PMID: 28025993]
[52]
Garbor, M. The anti inflammatory actions of flavonoids. Akademia ki-ado: Budapest, Hungary, 1972, pp. 698-699.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy