Flavonoids from two Turkish Centaurea species and their chemotaxonomic implications

Document Type: Original Article


1 Medicinal Chemistry and Natural Product Research Group, School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, United Kingdom

2 Altinbas University, Faculty of Pharmacy, Department of Pharmaceutical Botany, Istanbul, Turkey

3 Yildiz Technical University, Molecular Biology and Genetics Department, Istanbul, Turkey

4 Akdeniz University, Faculty of Science, Department of Biology, 07058, Antalya, Turkey


Centaurea asutro-anatolica Hub.-Mor. and C. kizildaghensis Uzunh., E. Doğan & H. Duman, two indigenous perennial herbs from the Turkish flora, belong to the medicinally important genus Centaurea L. (fam: Asteraceae), which comprises ca. 600 species worldwide. While various Centaurea species are well-known for producing alkaloids, flavonoids, lignans and terpenoids, there is no report on any thorough phytochemical work on any of these two species available to date. In continuation of our phytochemical and bioactivity studies on the Turkish Centaurea species, four flavonoids apigenin (1), apigenin 7,4’-dimethyl ether (2), genkwanin (3) and quercetin (4) were isolated from the methanol extracts of the aerial parts of C. austro-anatolica and C. kizildaghensis, for the very first time. The structures of the flavonoids were elucidated conclusively by spectroscopic means, i.e., UV, MS and 1D and 2D NMR data analyses. The distribution of these flavonoids (1-4) within the genus Centaurea and their possible chemotaxonomic implications within the genus Centaurea or the family Asteraceae have been discussed.

Graphical Abstract

Flavonoids from two Turkish Centaurea species and their chemotaxonomic implications


Agrawal, P.K., 1989. Carbon-13 NMR of Flavonoids. Vol. 39, Elsevier Science Publishing Company INC, Amsterdam, Oxford, New York and Tokyo.

Albayrak, S., Atasagun, B., Aksoy, A., 2017. Comparison of phenolic components and biological activities of two Centaurea sp obtained by three extraction techniques. Asian Pac. J. Trop. Med. 10, 669-676.

Avula, B., Wang, Y.H., Smillie, T.J., Mabusela, W., Vincent, L., Weitz, F., Khan, I.A., 2009. Quantitative determination of flavonoids by column high-performance liquid chromatography with mass spectrometry and ultraviolet absorption detection in Artemisia afra and comparative studies with various species of Artemisia plants. J. AOAC Int. 92, 633-644.

Ayatollahi, S.A., Shojaii, A., Kobarfard, F., Mohammadzadeh, M., Choudhary, M.I., 2009. Two flavones from Salvia leriaefolia. Iran. J. Pharm. Res. 8, 179-184.

Baytop, T., 1999. Therapy with Medicinal Plants in Turkey (Past and Present), Nobel Tip Kitabevi, Istanbul, Turkey.

Chaturvedula, V.S.P., Praksh, I., 2013. Flavonoids from Astragalus propinquus. J. Chem. Pharm. Res.

          5, 261-265.

Christensen, L.P., 1991. Flavones and other constituents from Centaurea species. Phytochemistry 30, 2663-2665.

Crawford, D.J., 1978. Flavonoid chemistry and angiosperm evolution. Bot. Rev. 44, 431-445.

Csapi, B., Hajdu, Z., Zupko, I., Berenyi, A., Forgo, P., Szabo, P., Hohmann, J., 2010. Bioactivity-guided isolation of antiproliferative compounds from Centaurea arenaria. Phytother. Res. 24, 1664-1669.

Csupor, D., Widowitz, U., Blazso, G., Lackzo-Zold, E., Tatsimo, J.S.N., Balogh, A., Boros, K., Danko, B., Bauer, R., Hohmann, J., 2013. Anti-inflammatory activities of eleven Centaurea species occurring in the Carpathian basin. Phytother. Res. 27, 540-544.

Curkovic-Perica, M., Likic, S., Rusak, G., 2014. Phenolic compounds in Centaurea rupestris tissues and their antiphytovial activity. Croat. Chem. Acta 87, 79-84.

De Oliveira, J.A.M., Bernardi, D.I., Balbinot, R.B., Avincola, A.D., Pilau, E., do Carmo, M.R.B., Sarragiotto, M.H., Baldoqui, D.C., 2017. Chemotaxonomic value of flavonoids in Chromolaena congesta (Asteraceae). Biochem. Syst. Ecol. 70, 7-13.

Emerenciano, V.P., Militao, J.S.L.T., Campos, C.C., Romoff, P., Kaplan, M.A.C., Zambon, M., Brant, A.J.C., 2001. Flavonoids as chemotaxonomic markers for Asteraceae. Biochem. Syst. Ecol. 29, 947-957.

Flamini, G., Bulleri, C., Morelli, I., Manunta, A., 2000. A new flavonoid glycoside from Centaurea horrida. J. Nat. Prod. 63, 662-663.

Flamini, G., Pardini, M., Morelli, I., 2001. A flavonoid sulphate and other compounds from the roots of Centaurea bracteata. Phytochemistry 58, 1229-1233.

Flamini, G., Stoppelli, G., Morelli, I., Ertugrul, K., Dural, H., Tugay, O., Demirelma, H., 2004. Secondary metabolites from Centaurea isaurica from Turkey and their chemotaxonomic significance. Biochem. Syst. Ecol. 32, 553-557.

Forgo, P., Zupko, I., Molnar, J., Vasas, A., Dombi, G., Hohmann, J., 2012. Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. Fitoterapia 83, 921-925.

Gokbel, H., Ozcan, M.M., Duran, A., Hamurcu, M., Celik, M., Uslu, N., Demiral, T., 2015. Mineral contents and bioactive properties of Centaurea spp. leave and seeds. Iran. J. Chem. Chem. Eng.

          34, 79-88.

Gonnet, J.F., 1993. Flavonoid glycoside variation in wild specimens of Centaurea triumfetti (Compositae) and comments on its relationships with Centaurea montana based on flavonoid fingerprints. Biochem. Syst. Ecol. 21, 389-396.

Granger, M., Samson, E., Sauvage, S., Majumdar, A., Nigam, P., Nahar, L., Celik, S., Sarker, S.D., 2009. Bioactivity of the extracts of Centaurea polyclada DC. (Asteraceae). Arch. Biol. Sci. 61, 447-452.

Gulcemal, D., Alankus-Caliskan, O., Karaalp, C., Ors, A.U., Ballar, P., Bedird, E., 2010. Phenolic glycosides with antiproteasomal activity from Centaurea urvillei DC. subsp. urvillei. Carbohydr. Res. 345, 2529-2533.

Hammoud, L., Seghiri, R., Benayache, S., Mosset, P., Lobstein, A., Chaabi, M., Leon, F., Brouard, I., Bermejo, J., Benayache, F., 2012. A new flavonoid and other constituents from Centaurea nicaeensis All. var. walliana M. Nat. Prod. Res. 26, 203-208.

Kamanzi, K., Raynaud, J., Voirin, B., 1982. Flavone glycosides of the leaves of Centaurea collina Compositae. Plantes Med. Phytotherapie 16, 30-33.

Koehler, I., Jenett-Siems, K., Siems, K., Hernandez, M.A., Ibarra, R.A., Berendsohn, W.G., Bienzle, U., Eich, E., 2002. In vitro antiplasmodial investigation of medicinal plants from El Salvador.          Z. Naturforsch. C 57, 277-281.

Kraft, C., Jenett-Siems, K., Siems, K., Jakupovic, J., Mavi, S., Bienzle, U., Eich, E., 2003. In vitro antiplasmodial evaluation of medicinal plants from Zimbabwe. Phytother. Res. 17, 123-128.

Li, K., Li, X-M., Wang, B-G., 2008. Chemical constituents from herb of Gueldenstaedtia stenophylla. Zhongguo Zhong Yao Za Zhi 33, 1711-1713.

Mabry, T.J., Markham, K.R., Thomas, M.B., 1970. The Systematic Identification of Flavonoids. Springer-Verlag, Berlin.

Mishio, T., Takeda, K., Iwashina, T., 2015. Anthocyanins and other flavonoids as flower pigments from eleven Centaurea species. Nat. Prod. Commun. 10, 447-450.

Mouffok, S., Haba, H., Lavaud, C., Long, C., Benkhaled, M., 2012. Chemical constituents of Centaurea omphalotricha Coss. & Durieu ex Batt. & Trab. Rec. Nat. Prod. 6, 292-295.

Nakasugi, T., Komai, K., 1998. Antimutagens in the Brazilian folk medicinal carqueja (Baccharis trimera Less.). J. Agric. Food Chem. 46, 2560-2564.

Negrete, R.E., Backhouse, N., Bravo, B., Erazo, S., Garcia, R., Avendano, S., 1987. Some flavonoids of  Centaurea floccose Hook. and Arn. Plantes Med. Phytotherapie 21, 168-172.

Negrete, R.E., Latorre, I., Backhouse, N., Pena, R., Delporte, C., 1988. Anatomical and phytochemical studies flavonoids and a lactone from Centaurea chilensis Hooker and Arnold. Plantes Med. Phytotherapie 22, 1-10.

Narain, N.K., 1976. Spectroscopic studies of a less abundant flavone, genkwanin. Spectrosc. Lett. 9, 865-875.

Nikolova, M., Bancheva, S., 2013. Surface flavonoids of Centaurea stenolepis and the local endemics Centaurea davidovii and C. parilica (Asteraceae, sect. Lepteranthus) from Bulgaria. Phytologia Balcan. 19, 357-360.

Oksuz, S., Putun, E., 1987. Flavonoids of Centaurea kotschyi var Kotschyi. DOGA Turk Kimya Derg. 11, 66-71.

Peter, A., Dosa, G., 2002. Detection of phenoloids in some Hungarian Inula and Centaurea species.         Acta Bot. Hung. 44, 129-135.

Piao, G.C., Li, Y.X., Yuan, H.D., Jin, G.Z., 2012. Cytotoxic fraction from Artemisia sacrorum Ledeb. against three human cancer cell lines and separation and identification of its compounds. Nat. Prod. Res. 26, 1483-1491.

Pirvu, L., Dragomir, C., Schiopu, S., Mihul, S.C., 2012. Vegetal extracts with gastroprotective activity. Part I. Extracts obtained from Centaurea cyanus L. raw material. Rom. Biotech. Lett. 17, 7169-7176.

Sarker, S.D., Savchenko, T., Whiting, P., Sik, V., Dinan, L.N., 1997. Moschamine, cis-moschamine, moschamindole and moschamindolol: four novel indole alkaloids from Centaurea moschata. Nat. Prod. Lett. 9, 189-199.

Sarker, S.D., Kumarasamy, Y., Shoeb, M., Celik, S., Yucel, E., Middleton, M., Nahar, L., 2005. Antibacterial and antioxidant activities of three Turkish species of the genus Centaurea. Orient. Pharm. Exp. Med. 5, 246-250.

Sarker, S.D., Shoeb, M., Celik, S., Jaspars, M., Nahar, L., Kong-Thoo-Lin, P., MacManus, S.M., 2007. Extracts of Centaurea bornmuelleri and Centaurea huber-morathii inhibit the growth of colon cancer cells in vitro. Orient. Pharm. Exp. Med. 7, 336-340.

Sarker, S.D.,Nahar, L., Gujja, S., Begum, S., Celik, S., 2012. Bioactivity of Centaurea persica Boiss. (Asteraceae). Arch. Biol. Sci. 64, 517-523.

Shoeb, M., Celik, S., Jaspars, M., Kumarasamy, Y., MacManus, S.M., Nahar, L., Thoo-Lin, P.K., Sarker, S.D., 2005. Isolation, structure elucidation and bioactivity of schischkiniin, a unique indole alkaloid from the seeds of Centaurea schischkini. Tetrahedron 61, 9001-9006.

Shoeb, M., MacManus, S.M., Jaspars, M., Kong-Thoo-Lin, P., Nahar, L., Celik, S., Sarker, S.D., 2007a. Bioactivity of two Turkish Centaurea species, and their major constituents. Braz. J. Pharmacog. 17, 155-159.

Shoeb, M., Jaspars, M., MacManus, S.M., Celik, S., Nahar, L., Kong-Thoo-Lin, P., Sarker, S.D., 2007b. Anti-colon cancer potential of phenolic compounds from the aerial parts of Centaurea gigantea (Asteraceae). J. Nat. Med. 61, 164-169.

Shoeb, M., Jaspars, M., MacManus, S.M., Celik, S., Nahar, L., Kong-Thoo-Lin, P., Sarker, S.D., 2007c. Two salonitenolide derivatives from the aerial parts of Centaurea gigantea inhibit the growth of colorectal cancer cells in vitro. Nat. Prod. Commun. 2, 121-125.

Shoeb, M., MacManus, S.M., Celik, S., Jaspars, M., Kong-Thoo-Lin, P., Nahar, L., Sarker, S.D., 2007d. Bioactivity of the extracts and the isolation of lignans and a sesquiterpene from the aerial parts of Centaurea pamphylica (Asteraceae). Daru 15, 118-122.

Shoeb, M., MacManus, S.M., Jaspars, M., Nahar, L., Kong-Thoo-Lin, P., Celik, S., Sarker, S.D., 2007e. Lignans and flavonoids from the seeds of Centaurea bornmuelleri Hausskn. Ex. Bornm. and Centaurea huber-morathii Wagenitz. Pol. J. Chem. 81, 39-44.

Tesevic, V., Aljancic, I., Milosavljevic, S., Vajs, V., Dordevic, I., Jadranin, M., Menkovic, N., Matevski, V., 2014. Secondary metabolites of three endemic Centaurea L. species. J. Serb. Chem. Soc. 79, 1355-1362.

Tuzun, B.S., Hajdu, Z., Orban-Gyapai, O., Zomborszki, Z. P., Jedlinszki, N., Forgo, P., Kivcak, B., Hohmann, J., 2017. Isolation of chemical constituents of Centaurea virgata Lam. and xanthine oxidase inhibitory activity of the plant extract and compounds. Med. Chem. 13, 498-502.

Ugur, A., Sarac, N., Ceylan, O., Duru, M.E., 2009. Chemical composition of endemic Centaurea autro-anatolica and studies of its antimicrobial activity against multi-resistant bacteria. Acta Pharm. 59, 463-472.

Ulubelen, A., Oksuz, S., 1982. Cytotoxic flavones from Centaurea urvillei. J. Nat. Prod. 45, 373-373.

Uzunhisarcıklı, E., Doğan, E., Duman, H., 2007. A new species of Centaurea L. (Cardueae: Asteraceae) from Turkey. Bot. J. Linn. Soc. 153, 61-66.

Wagenitz, G., 1975.Centaurea L. In: Davis PH, Ed. Flora of Turkey and the East Aegean Islands, Vol. 5. Edinburgh University Press, Edinburgh, 493-494.

Youssef, D., Frahm, A.W., 1995. Constituents of the Egyptian Centaurea scoparia. 3. Phenolic constituents of the aerial parts. Planta Med. 61, 570-573.

Zheng, X-D., Hu, H-B., Chen, H., Zheng, S-Z., Shen, X-W., 2004. Studies on chemical components of Centaurea repens. Xibei Zhiwu Xuebao 24, 1932-1935.