Login Register Cart 0
Generic placeholder image

Current Bioactive Compounds

Editor-in-Chief

ISSN (Print): 1573-4072
ISSN (Online): 1875-6646

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Characterization of Chemical Compounds and Antioxidant Activity of Centaurea solstitialis sp. schouwii (DC.) Q. et S. (Asteraceae)

Author(s): Lamia Aliouche, Paul Mosset, Francisco León, Ignacio Brouard, Samir Benayache, Djamel Sarri and Fadila Benayache*

Volume 16, Issue 5, 2020

Page: [618 - 626] Pages: 9

DOI: 10.2174/1573407215666190213125259

Price: $65

Abstract

Background: The antioxidant activity and the total phenolic and flavonoid contents of the derived extracts (chloroform, ethyl acetate and n-butanol) of the 70% hydroalcoholic extract of the aerial parts of Centaurea solstitialis growing in Algeria was assessed. The active extracts were selected for phytochemical investigations.

Methods: The antioxidant capabilities of the extracts were assessed using 1, 1-diphenyl-2- picrylhydrazyl radical (DPPH•) scavenging and Cupric Ion Reducing Antioxidant Capacity (CUPRAC) assays. Butylhydroxyanisole (BHA), butylhydroxytoluene (BHT) and α –tocopherol were used as positive controls. The total phenolic content and total flavonoid content of the extracts were determined as gallic acid equivalents and quercetin equivalents, respectively. Chromatographic methods were used to isolate the secondary metabolites and spectrometric and spectroscopic methods were used to determine their chemical structures.

Results: The ethyl acetate extract exhibited the highest antioxidant activities followed by the n-butanol extract. The highest phenolic and flavonoid contents were found in the n-butanol extract. Phytochemical study of the ethyl acetate and n-butanol extracts led to the isolation of an undescribed guaianolide named 3-(4-hydroxybenzoyl)-cynaratriol and a known sesquiterpene lactone along with three known flavonoid glycosides. Their structures were established by spectral analyzes mainly high resolution electrospray ionisation mass spectrometry (HR-ESIMS) and 1D and 2D nuclear magnetic resonance experiments.

Conclusion: The extracts of aerial parts of C. solstitialis showed significant antioxidant activities. An undescribed sesquiterpene lactone and four known secondary metabolites were isolated from the most active extracts.

Keywords: Centaurea solstitialis, sesquiterpene lactones, flavonoids, antioxidant activity, total phenolic, flavonoid contents, hydrocarbons.

Graphical Abstract

[1]
Khammar, A.; Djeddi, S. Pharmacological and biological properties of Centaurea species. Eur. J. Sci. Res., 2012, 84(3), 398-416.
[2]
Arif, R.; Küpeli, E.; Ergun, F. The biological activity of Centaurea species. G U J. Sci., 2004, 17(4), 149-164.
[3]
Yeşilada, E.; Gürbüz, I.; Shibata, H. Screening of Turkish anti-ulcerogenic folk remedies for anti-Helicobacter pylori activity. J. Ethnopharmacol., 1999, 66(3), 289-293.
[http://dx.doi.org/10.1016/S0378-8741(98)00219-0] [PMID: 10473175]
[4]
Albayrak, S.; Atasagun, B.; Aksoy, A. Comparison of phenolic components and biological activities of two Centaurea sp. obtained by three extraction techniques. Asian Pac. J. Trop. Med., 2017, 10(6), 599-606.
[http://dx.doi.org/10.1016/j.apjtm.2017.06.010] [PMID: 28756926]
[5]
Zengin, G.; Cakmak, Y.S.; Guler, G.O.; Aktumsek, A. In vitro antioxidant capacities and fatty acid compositions of three Centaurea species collected from Central Anatolia region of Turkey. Food Chem. Toxicol., 2010, 48(10), 2638-2641.
[http://dx.doi.org/10.1016/j.fct.2010.06.033] [PMID: 20600531]
[6]
Aktumsek, A.; Zengin, G.; Guler, G.O.; Cakmak, Y.S.; Duran, A. Antioxidant potentials and anticholinesterase activities of methanolic and aqueous extracts of three endemic Centaurea L. species. Food Chem. Toxicol., 2013, 55, 290-296.
[http://dx.doi.org/10.1016/j.fct.2013.01.018] [PMID: 23357566]
[7]
Koca, U.; Süntar, I.P.; Keles, H.; Yeşilada, E.; Akkol, E.K. In vivo anti-inflammatory and wound healing activities of Centaurea iberica Trev. ex Spreng. J. Ethnopharmacol., 2009, 126(3), 551-556.
[http://dx.doi.org/10.1016/j.jep.2009.08.017] [PMID: 19703541]
[8]
Zater, H.; Huet, J.; Fontaine, V.; Benayache, S.; Stévigny, C.; Duez, P.; Benayache, F. Chemical constituents, cytotoxic, antifungal and antimicrobial properties of Centaurea diluta Ait. subsp. algeriensis (Coss. & Dur.) Maire. Asian Pac. J. Trop. Med., 2016, 9(6), 554-561.
[http://dx.doi.org/10.1016/j.apjtm.2016.04.016] [PMID: 27262066]
[9]
El-Najjar, N.; Dakdouki, S.; Darwiche, N.; El-Sabban, M.; Saliba, N.A.; Gali-Muhtasib, H. Anti-colon cancer effects of Salograviolide A isolated from Centaurea ainetensis. Oncol. Rep., 2008, 19(4), 897-904.
[http://dx.doi.org/10.3892/or.19.4.897] [PMID: 18357373]
[10]
Cassady, J.M.; Hokanson, G.C. 3α, 16α-dihydroxytaraxene-3-acetate: a new triterpene from Centaurea solstitialis. Phytochemistry, 1978, 17(2), 324-325.
[http://dx.doi.org/10.1016/S0031-9422(00)94180-3]
[11]
Merrill, G.B.; Stevens, K.L. Sesquiterpene lactones from Centaurea solstitialis. Phytochemistry, 1985, 24(9), 2013-2018.
[http://dx.doi.org/10.1016/S0031-9422(00)83113-1]
[12]
Kamanzi, K.; Raynaud, J. Contribution to the study of the flavone glycosides of Centaurea solstitialis L. Plant Med. Phytother, 1976, 10, 78-84.
[13]
Hamburger, M.; Wolfender, J.L.; Hostettmann, K. Search for chlorinated sesquiterpene lactones in the neurotoxic thistle Centaurea solstitialis by liquid chromatography-mass spectrometry, and model studies on their possible artifactual formation. Nat. Toxins, 1993, 1(6), 315-327.
[http://dx.doi.org/10.1002/nt.2620010602] [PMID: 8167953]
[14]
Cassady, J.M.; Abramson, D.; Cowall, P.; Chang, C.; Mc Laughlin, J.L.; Aynehchi, Y.J. Centaurepensin: A cytotoxic constituent of Centaurea solstitialis and C. repens (Asteraceae). J. Nat. Prod., 1979, 42(4), 427-429.
[http://dx.doi.org/10.1021/np50004a013]
[15]
Erenler, R.; Sen, O.; Yaglioglu, A.S.; Demirtaş, I. Bioactivity-guided isolation of antiproliferative sesquiterpene lactones from Centaurea solstitialis L. sp. solstitialis. Comb. Chem. High Throughput Screen., 2016, 19(1), 66-72.
[http://dx.doi.org/10.2174/1386207319666151203002117] [PMID: 26632440]
[16]
Yeşilada, E.; Gürbüz, I.; Bedir, E.; Tatli, I.; Khan, I.A. Isolation of anti-ulcerogenic sesquiterpene lactones from Centaurea solstitialis L. ssp. solstitialis through bioassay-guided fractionation procedures in rats. J. Ethnopharmacol., 2004, 95(2-3), 213-219.
[http://dx.doi.org/10.1016/j.jep.2004.07.021] [PMID: 15507339]
[17]
Ozçelik, B.; Gürbüz, I.; Karaoglu, T.; Yeşilada, E. Antiviral and antimicrobial activities of three sesquiterpene lactones from Centaurea solstitialis L. ssp. solstitialis. Microbiol. Res., 2009, 164(5), 545-552.
[http://dx.doi.org/10.1016/j.micres.2007.05.006] [PMID: 17614269]
[18]
Gürbüz, I.; Yeşilada, E. Evaluation of the anti-ulcerogenic effect of sesquiterpene lactones from Centaurea solstitialis L. ssp. solstitialis by using various in vivo and biochemical techniques. J. Ethnopharmacol., 2007, 112(2), 284-291.
[http://dx.doi.org/10.1016/j.jep.2007.03.009] [PMID: 17418988]
[19]
Kilic, O. Essential oil compounds of three Centaurea L. taxa from Turkey and their chemotaxonomy. J. Med. Plants Res., 2013, 7(19), 1344-1350.
[20]
Bruno, M.; Diaz, J.G.; Herz, W. Guaianolides and lignans from Centaurea solstitialis subsp. schouwii. Phytochemistry, 1991, 30(12), 4165-4166.
[http://dx.doi.org/10.1016/0031-9422(91)83490-C]
[21]
Oksüz, S.; Glark, R.J.; Herz, W. A guaianolide diol monoacetate from Centaurea behen and C. solstitialis ssp. schouwii. Phytochemistry, 1993, 33(5), 1267-1268.
[http://dx.doi.org/10.1016/0031-9422(93)85063-W] [PMID: 7763477]
[22]
Senatore, F.; Formisano, C.; Raio, A.; Bellone, G.; Bruno, M. Volatile components from flower-heads of Centaurea nicaeensis All., C. parlatoris Helder and C. solstitialis L. ssp. schouwii (DC.) Dostál growing wild in southern Italy and their biological activity. Nat. Prod. Res., 2008, 22(10), 825-832.
[http://dx.doi.org/10.1080/14786410500410719] [PMID: 18626815]
[23]
Licata, M.; Tuttolomondo, T.; Leto, C.; Virga, G.; Bonsangue, G.; Cammalleri, I.; Gennaro, M.C.; La Bella, S. A survey of wild plant species for food use in Sicily (Italy) results of a 3-year study four regional parks.J. Ethnobiol. Ethnomed; 2016 12 p, 12(14)
[24]
Boussaha, S.; Bekhouche, K.; Boudjerda, A.; Leόn, F.; Koldaş, S.; Yaglioglu, A.S.; Demirtaş, I.; Brouard, I.; Marchioni, E.; Zama, D.; Benayache, S.; Benayache, F. Chemical constituents, in vitro antioxidant and antiproliferative activities of Perralderia coronopifolia Coss. subsp. eu-coronopifolia M. var. typica M. extract. Rec. Nat. Prod., 2015, 9(3), 312-322.
[25]
Aliouche, L.; Larguet, H.; Amrani, A.; León, F.; Brouard, I.; Benayache, S.; Zama, D.; Meraihi, Z.; Benayache, F. Isolation, antioxidant and antimicrobial activities of ecdysteroids from Serratula cichoracea. Curr. Bioact. Compd., 2018, 14(1), 60-66.
[http://dx.doi.org/10.2174/1573407214666171211154922]
[26]
Seghiri, R.; Boumaza, O.; Mekkiou, R.; Benayache, S.; Mosset, P.; Quintana, J.; Estévez, F.; León, F.; Bermejo, J.; Benayache, F. A flavonoid with cytotoxic activity and other constituents from Centaurea africana. Phytochem. Lett., 2009, 2(3), 114-118.
[http://dx.doi.org/10.1016/j.phytol.2009.03.002]
[27]
Hammoud, L.; Seghiri, R.; Benayache, S.; Mosset, P.; Lobstein, A.; Chaabi, M.; León, F.; Brouard, I.; Bermejo, J.; Benayache, F. A new flavonoid and other constituents from Centaurea nicaeensis All. var. walliana M. Nat. Prod. Res., 2012, 26(3), 203-208.
[http://dx.doi.org/10.1080/14786419.2010.534995] [PMID: 21815723]
[28]
Kolli, E.H.; León, F.; Benayache, F.; Estévez, S.; Quintana, J.; Estévez, F.; Brouard, I.; Bermejo, J.; Benayache, S. Cytotoxic sesquiterpene lactones and other constituents from Centaurea omphalotricha. J. Braz. Chem. Soc., 2012, 23(5), 977-983.
[http://dx.doi.org/10.1590/S0103-50532012000500026]
[29]
Bicha, S.; Chalard, P.; Hammoud, L.; León, F.; Brouard, I.; Garcia, V.G.; Lobstein, A.; Bentamene, A.; Benayache, S.; Bermejo, J.; Benayache, F. Maroccanin: A new α-lactone and other constituents from Centaurea maroccana Ball. (Asteraceae). Rec. Nat. Prod., 2013, 7, 114-118.
[30]
Baali, N.; Baali, S.; Bentamen, A.; Benayache, S.; Benayache, F.; Amedah, S. Ameliorative effect of Centaurea maroccana and Centaurea acaulis against nephrotoxicity induced by carbon tetrachloride. Curr. Bioact. Compd., 2018.
[http://dx.doi.org/10.2174/1573407214666180820151905]
[31]
Quezel, P.; Santa, S. Nouvelle flore de l’Algérie et des régions désertiques méridionales.Editions du C.N.R.S, Paris, 1963 2, p. 1026.
[32]
Slinkard, K.; Singleton, V.L. Total phenol analyses: automation and comparison with manual methods. Am. J. Enol. Vitic., 1977, 28, 49-55.
[33]
Turkoglu, A.; Duru, M.E.; Mercan, N.; Kivrak, I.; Gezer, K. Antioxidant and antimicrobial activity of Laetiporus sulphurous (Bull.) Murrill. Food Chem., 2007, 101(1), 267-273.
[http://dx.doi.org/10.1016/j.foodchem.2006.01.025]
[34]
Blois, M.S. Antioxidant determinations by the use of a stable free radical. Nature, 1958, 181, 1199-1200.
[http://dx.doi.org/10.1038/1811199a0]
[35]
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]
[36]
Bernhard, H.O.; Thiele, K. Pretsch. E. Cynaratriol, ein neues Guajanolid aus der Kardone Cynara cardunculus L. und der Artischocke C. scolymus L. (Compositae). Helv. Chim. Acta, 1979, 62(4), 1288-1297.
[http://dx.doi.org/10.1002/hlca.19790620440]
[37]
López-Rodríguez, M.; P García, V.; Zater, H.; Benayache, S.; Benayache, F. Cynaratriol, a sesquiterpene lactone from Centaurea musimomum. Acta Crystallogr. Sect. E Struct. Rep. Online, 2009, 65(Pt 8), o1867-o1868.
[http://dx.doi.org/10.1107/S1600536809026701] [PMID: 21583563]
[38]
Zater, H. Magister Thesis, University Mentouri: Constantine, Algeria. November. 2004.
[39]
Stevens, K.L.; Witt, S.C.; Kunt, S.; Haddon, W.F.; Benson, M. Picrolide A, an unusual sesquiterpene lactone from Acroptilon repens. J. Nat. Prod., 1991, 54(1), 276-280.
[http://dx.doi.org/10.1021/np50073a034]
[40]
Öksüz, S.; Topcu, G. Guaianolides from Centaurea glastifolia. Phytochemistry, 1994, 37(2), 487-490.
[http://dx.doi.org/10.1016/0031-9422(94)85084-4]
[41]
Medjroubi, K.; Benayache, F.; León, F.; Bermejo, J. Complete assignment of the 13C of 1H NMR spectra of two Known guaianolides isolated from Centaurea musimomum. Rev. Colomb. Quim., 2003, 32, 17-25.
[42]
Diantini, A.; Subarnas, A.; Lestari, K.; Halimah, E.; Susilawati, Y.; Supriyatna, S.; Julaeha, E.; Achmad, T.H.; Suradji, E.W.; Yamazaki, C.; Kobayashi, K.; Koyama, H.; Abdulah, R. Kaempferol-3-O-rhamnoside isolated from the leaves of Schima wallichii Korth. inhibits MCF-7 breast cancer cell proliferation through activation of the caspase cascade pathway. Oncol. Lett., 2012, 3(5), 1069-1072.
[http://dx.doi.org/10.3892/ol.2012.596] [PMID: 22783393]
[43]
Chemam, Y.; Benayache, S.; Marchioni, E.; Zhao, M.; Mosset, P.; Benayache, F. On-Line screening, isolation and identification of antioxidant compounds of Helianthemum ruficomum. Molecules, 2017, 22(2), 239.
[http://dx.doi.org/10.3390/molecules22020239] [PMID: 28208718]
[44]
Wei, X.; Huang, H.; Wu, P.; Cao, H.; Ye, W. Phenolic constituents from Mikania micrantha. Biochem. Syst. Ecol., 2004, 32(11), 1091-1096.
[http://dx.doi.org/10.1016/j.bse.2004.04.013]

Rights & Permissions Print Cite
Article Metrics
12
World Immunization Week
© 2024 Bentham Science Publishers | Privacy Policy