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SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS.

Yıl 2024, Cilt: 48 Sayı: 1, 1 - 7, 20.01.2024
https://doi.org/10.33483/jfpau.1330413

Öz

Objective: This study aimed to isolate secondary metabolites from the aerial parts of endemic Centaurea aphrodisea Boiss. using several chromatographic methods and elucidate the structure of the compounds by using spectroscopic methods.
Material and Method: Aerial parts of the endemic C. aphrodisea were collected from Bozdağ (Ödemiş, İzmir) and n-hexane, chloroform and metanol extracts were prepared. The chloroform extract was investigated by using various chromatographic methods, and the structures of the isolated compounds were determined using spectroscopic methods (1D-2D NMR and LC-MS).
Result and Discussion: One elemane type sesquiterpene (methyl 8α,6α,15-trihydroxyelema-1,3,11(13)-trien-12-oate) and four flavone derivatives (cirsimaritin, 3'-O-methyl eupatorin, eupatorin and salvigenin) were isolated and identified. In addition, the presence of a phenylpropanoid glycoside (syringin) was determined in a fraction by comparison with a referance compound using TLC technique. These compounds are reported for the first time from C. aphrodisea with this study.

Destekleyen Kurum

This study was supported by the Scientific Research Projects Directorate of Ege University

Teşekkür

The authors would like to thank Prof. Serdar Gokhan Senol for identification of the plant, and Dr. Salih Gunnaz for all NMR measurements. This study was supported by the Scientific Research Projects Directorate of Ege University (Project No: 15-ECZ-003).

Kaynakça

  • 1. Garcia-Jacas, N., Susanna, A., Mozaffarian, V., Ilarslan, R. (2000). The natural delimitation of Centaurea (Asteraceae : Cardueae): ITS sequence analysis of the Centaurea jacea group. Plant Systematics and Evolution, 223, 185-199. [CrossRef]
  • 2. Uysal, T. (2012). Centaurea L. In: A. Guner, S. Aslan, T. Ekim, M. Vural and M.T. Babac (Eds.), Türkiye Bitkileri Listesi (Damarlı Bitkiler), (pp. 127-140). İstanbul: Nezahat Gökyiğit Botanik Bahçesi ve Flora Araştırmaları Derneği.
  • 3. Akkol, E.K., Arif, R., Ergun, F., Yesilada, E. (2009). Sesquiterpene lactones with antinociceptive and antipyretic activity from two Centaurea species. Journal of Ethnopharmacology, 122(2), 210-215. [CrossRef]
  • 4. Ozcelik, B., Gurbuz, I., Karaoglu, T., Yesilada, E. (2009). Antiviral and antimicrobial activities of three sesquiterpene lactones from Centaurea solstitialis L. ssp solstitialis. Microbiological Research, 164(5), 545-552. [CrossRef]
  • 5. Erel, S.B., Demir, S., Nalbantsoy, A., Ballar, P., Khan, S., Yavasoglu, N.U.K., Karaalp, C. (2014). Bioactivity screening of five Centaurea species and in vivo anti-inflammatory activity of C. athoa. Pharmaceutical Biology, 52(6), 775-781. [CrossRef]
  • 6. Bruno, M., Bancheva, S., Rosselli, S., Maggio, A. (2013). Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, C-13 NMR spectral data and biological properties. Phytochemistry, 95, 19-93. [CrossRef]
  • 7. Formisano, C., Rigano, D., Senatore, F., Bancheva, S., Maggio, A., Rosselli, S., Bruno, M. (2012). Flavonoids in Subtribe Centaureinae (Cass.) Dumort. (Tribe Cardueae, Asteraceae): Distribution and 13C-NMR spectral data. Chemistry & Biodiversity, 9(10), 2096-2158. [CrossRef]
  • 8. Karamenderes, C., Konyalioglu, S., Khan, S., Khan, I.A. (2007). Total phenolic contents, free radical scavenging activities and inhibitory effects on the activation of NF-kappa B of eight Centaurea L. species. Phytotherapy Research, 21, 488-491. [CrossRef]
  • 9. Baykan Erel, S., Ballar, P., Karaalp, C. (2014). Antioxidant activities of phenolic compounds of Centaurea ensiformis P.H. Davis. Turkish Journal of Pharmaceutical Sciences, 11(1), 19-24.
  • 10. Gurbuz, I., Yesilada, E. (2007). Evaluation of the anti-ulcerogenic effect of sesquiterpene lactones from Centaurea solstitialis L. ssp. solstitialis by using various in vivo and biochemical techniques. Journal of Ethnopharmacology, 112, 284-291. [CrossRef]
  • 11. Demiroz, T., Albayrak, G., Nalbantsoy, A., Gocmen, B., Baykan, S. (2018). Anti-inflammatory properties of Centaurea calolepis Boiss. and cnicin against Macrovipera lebetina obtusa (Dwigubsky, 1832) and Montivipera xanthina (Gray, 1849) venoms in rat. Toxicon, 152, 37-42. [CrossRef]
  • 12. Wagenitz, G. (1975). Centaurea L. In: P.H. Davis (Ed.), Flora of Turkey and East Aegean Islands, (pp. 501-502). Edinburgh: Edinburgh University Press.
  • 13. Erel, S.B., Demirci, B., Demir, S., Karaalp, C., Baser, K.H.C. (2013). Composition of the essential oils of Centaurea aphrodisea, C. polyclada, C. athoa, C. hyalolepis and C. iberica. Journal of Essential Oil Research, 25(2), 79-84. [CrossRef]
  • 14. Cardona, L., Fernandez, I., Pedro, J.R., Vidal, R. (1992). Polyoxygenated terpenes and cyanogenic glucosides from Centaurea aspera var subinermis. Phytochemistry, 31(10), 3507-3509. [CrossRef]
  • 15. Demir, S., Karaalp, C., Bedir, E. (2017). Specialized metabolites from the aerial parts of Centaurea polyclada DC. Phytochemistry, 143, 12-18. [CrossRef]
  • 16. Salan, U., Topcu, G., Oksuz, S. (2001). Flavonoids of Centaurea kilaea and C. salonitana. Journal of Faculty of Pharmacy of Istanbul University, 34, 55-61.
  • 17. Cardona, L., Bardon, A., Garcia, B., Pedro, J.R. (1993). Eudesmane and elemane derivatives from Onopordon acaulon. Phytochemistry, 33(6), 1457-1460. [CrossRef]
  • 18. Formisano, C., Rigano, D., Russo, A., Cardile, V., Caggia, S., Arnold, N.A., Mari, A., Piacente, S., Rosselli, S., Senatore, F., Bruno, M. (2012). Phytochemical profile and apoptotic activity of Onopordum cynarocephalum. Planta Medica, 78(15), 1651-1660. [CrossRef]
  • 19. Bai, N., He, K., Roller, M., Lai, C.S., Shao, X., Pan, M.H., Bily, A., Ho, C.T. (2011). Flavonoid glycosides from Microtea debilis and their cytotoxic and anti-inflammatory effects. Fitoterapia, 82(2), 168-172. [CrossRef]
  • 20. Khademian, A., Tabefam, M., Mazarei, Z., Kanani, M.R., Sepehri, H., Delphi, L., Danton, O., Hamburger, M., Farimani, M.M. (2021). Chemical constituents and cytotoxic activity of Stachys pilifera Benth. South African Journal of Botany, 139, 226-229. [CrossRef]
  • 21. Pathak, G., Singh, S., Kumari, P., Raza, W., Hussain, Y., Meena, A. (2021). Cirsimaritin, a lung squamous carcinoma cells (NCIH-520) proliferation inhibitor. Journal of Biomolecular Structure & Dynamics, 39(9), 3312-3323. [CrossRef]
  • 22. Noori, S., Hassan, Z.M., Yaghmaei, B., Dolatkhah, M. (2013). Antitumor and immunomodulatory effects of salvigenin on tumor bearing mice. Cellular Immunology, 286(1-2), 16-21. [CrossRef]
  • 23. Shao, H., Chen, J.Y., Li, A., Ma, L.L., Tang, Y.Z., Chen, H.Z., Chen, Y.P., Liu, J.Y. (2023). Salvigenin suppresses hepatocellular carcinoma glycolysis and chemoresistance through inactivating the PI3K/AKT/GSK-3 beta pathway. Applied Biochemistry and Biotechnology, 195(8), 5217-5237. [CrossRef]

ENDEMİK CENTAUREA APHRODISEA BOISS.’İN SEKONDER METABOLİTLERİ

Yıl 2024, Cilt: 48 Sayı: 1, 1 - 7, 20.01.2024
https://doi.org/10.33483/jfpau.1330413

Öz

Amaç: Bu çalışmada endemik Centaurea aphrodisea Boiss. bitkisinin toprak üstü kısımlarında bulunan sekonder metabolitlerin, kromatografik yöntemlerle saflaştırılması ve spektroskopik yöntemlerlede yapılarının aydınlatılması amaçlanmıştır.
Gereç ve Yöntem: Bu çalışmada, endemik C. aphrodisea’nın toprak üstü kısımları Bozdağ’dan (Ödemiş, İzmir) toplanmış, ve n-hekzan, kloroform ve metanol ekstreleri hazırlanmıştır. Kloroform ekstresi çeşitli kromatografik yöntemler kullanılarak incelenmiş ve izole edilen bileşiklerin yapıları spektroskopik yöntemler (1D-2D NMR ve LC-MS) kullanılarak aydınlatılmıştır.
Sonuç ve Tartışma: Bir eleman tip seskiterpen (metil 8α,6α,15-trihidroksielema-1,3,11(13)-trien-12-oat) ve dört flavon türevi (sirsimaritin, 3'-O-metil öpatorin, öpatorin ve salvigenin) izole edilerek yapıları aydınlatılmıştır. Ayrıca İTK tekniği ve şahit bileşikler kullanılarak bir fraksiyonda fenilpropanoit glikozitinin (siringin) varlığı saptanmıştır. Bu bileşikler C. aphrodisea’dan tarafımızca ilk kez rapor edilmektedir.

Kaynakça

  • 1. Garcia-Jacas, N., Susanna, A., Mozaffarian, V., Ilarslan, R. (2000). The natural delimitation of Centaurea (Asteraceae : Cardueae): ITS sequence analysis of the Centaurea jacea group. Plant Systematics and Evolution, 223, 185-199. [CrossRef]
  • 2. Uysal, T. (2012). Centaurea L. In: A. Guner, S. Aslan, T. Ekim, M. Vural and M.T. Babac (Eds.), Türkiye Bitkileri Listesi (Damarlı Bitkiler), (pp. 127-140). İstanbul: Nezahat Gökyiğit Botanik Bahçesi ve Flora Araştırmaları Derneği.
  • 3. Akkol, E.K., Arif, R., Ergun, F., Yesilada, E. (2009). Sesquiterpene lactones with antinociceptive and antipyretic activity from two Centaurea species. Journal of Ethnopharmacology, 122(2), 210-215. [CrossRef]
  • 4. Ozcelik, B., Gurbuz, I., Karaoglu, T., Yesilada, E. (2009). Antiviral and antimicrobial activities of three sesquiterpene lactones from Centaurea solstitialis L. ssp solstitialis. Microbiological Research, 164(5), 545-552. [CrossRef]
  • 5. Erel, S.B., Demir, S., Nalbantsoy, A., Ballar, P., Khan, S., Yavasoglu, N.U.K., Karaalp, C. (2014). Bioactivity screening of five Centaurea species and in vivo anti-inflammatory activity of C. athoa. Pharmaceutical Biology, 52(6), 775-781. [CrossRef]
  • 6. Bruno, M., Bancheva, S., Rosselli, S., Maggio, A. (2013). Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, C-13 NMR spectral data and biological properties. Phytochemistry, 95, 19-93. [CrossRef]
  • 7. Formisano, C., Rigano, D., Senatore, F., Bancheva, S., Maggio, A., Rosselli, S., Bruno, M. (2012). Flavonoids in Subtribe Centaureinae (Cass.) Dumort. (Tribe Cardueae, Asteraceae): Distribution and 13C-NMR spectral data. Chemistry & Biodiversity, 9(10), 2096-2158. [CrossRef]
  • 8. Karamenderes, C., Konyalioglu, S., Khan, S., Khan, I.A. (2007). Total phenolic contents, free radical scavenging activities and inhibitory effects on the activation of NF-kappa B of eight Centaurea L. species. Phytotherapy Research, 21, 488-491. [CrossRef]
  • 9. Baykan Erel, S., Ballar, P., Karaalp, C. (2014). Antioxidant activities of phenolic compounds of Centaurea ensiformis P.H. Davis. Turkish Journal of Pharmaceutical Sciences, 11(1), 19-24.
  • 10. Gurbuz, I., Yesilada, E. (2007). Evaluation of the anti-ulcerogenic effect of sesquiterpene lactones from Centaurea solstitialis L. ssp. solstitialis by using various in vivo and biochemical techniques. Journal of Ethnopharmacology, 112, 284-291. [CrossRef]
  • 11. Demiroz, T., Albayrak, G., Nalbantsoy, A., Gocmen, B., Baykan, S. (2018). Anti-inflammatory properties of Centaurea calolepis Boiss. and cnicin against Macrovipera lebetina obtusa (Dwigubsky, 1832) and Montivipera xanthina (Gray, 1849) venoms in rat. Toxicon, 152, 37-42. [CrossRef]
  • 12. Wagenitz, G. (1975). Centaurea L. In: P.H. Davis (Ed.), Flora of Turkey and East Aegean Islands, (pp. 501-502). Edinburgh: Edinburgh University Press.
  • 13. Erel, S.B., Demirci, B., Demir, S., Karaalp, C., Baser, K.H.C. (2013). Composition of the essential oils of Centaurea aphrodisea, C. polyclada, C. athoa, C. hyalolepis and C. iberica. Journal of Essential Oil Research, 25(2), 79-84. [CrossRef]
  • 14. Cardona, L., Fernandez, I., Pedro, J.R., Vidal, R. (1992). Polyoxygenated terpenes and cyanogenic glucosides from Centaurea aspera var subinermis. Phytochemistry, 31(10), 3507-3509. [CrossRef]
  • 15. Demir, S., Karaalp, C., Bedir, E. (2017). Specialized metabolites from the aerial parts of Centaurea polyclada DC. Phytochemistry, 143, 12-18. [CrossRef]
  • 16. Salan, U., Topcu, G., Oksuz, S. (2001). Flavonoids of Centaurea kilaea and C. salonitana. Journal of Faculty of Pharmacy of Istanbul University, 34, 55-61.
  • 17. Cardona, L., Bardon, A., Garcia, B., Pedro, J.R. (1993). Eudesmane and elemane derivatives from Onopordon acaulon. Phytochemistry, 33(6), 1457-1460. [CrossRef]
  • 18. Formisano, C., Rigano, D., Russo, A., Cardile, V., Caggia, S., Arnold, N.A., Mari, A., Piacente, S., Rosselli, S., Senatore, F., Bruno, M. (2012). Phytochemical profile and apoptotic activity of Onopordum cynarocephalum. Planta Medica, 78(15), 1651-1660. [CrossRef]
  • 19. Bai, N., He, K., Roller, M., Lai, C.S., Shao, X., Pan, M.H., Bily, A., Ho, C.T. (2011). Flavonoid glycosides from Microtea debilis and their cytotoxic and anti-inflammatory effects. Fitoterapia, 82(2), 168-172. [CrossRef]
  • 20. Khademian, A., Tabefam, M., Mazarei, Z., Kanani, M.R., Sepehri, H., Delphi, L., Danton, O., Hamburger, M., Farimani, M.M. (2021). Chemical constituents and cytotoxic activity of Stachys pilifera Benth. South African Journal of Botany, 139, 226-229. [CrossRef]
  • 21. Pathak, G., Singh, S., Kumari, P., Raza, W., Hussain, Y., Meena, A. (2021). Cirsimaritin, a lung squamous carcinoma cells (NCIH-520) proliferation inhibitor. Journal of Biomolecular Structure & Dynamics, 39(9), 3312-3323. [CrossRef]
  • 22. Noori, S., Hassan, Z.M., Yaghmaei, B., Dolatkhah, M. (2013). Antitumor and immunomodulatory effects of salvigenin on tumor bearing mice. Cellular Immunology, 286(1-2), 16-21. [CrossRef]
  • 23. Shao, H., Chen, J.Y., Li, A., Ma, L.L., Tang, Y.Z., Chen, H.Z., Chen, Y.P., Liu, J.Y. (2023). Salvigenin suppresses hepatocellular carcinoma glycolysis and chemoresistance through inactivating the PI3K/AKT/GSK-3 beta pathway. Applied Biochemistry and Biotechnology, 195(8), 5217-5237. [CrossRef]

Ayrıntılar

Birincil Dil İngilizce
Konular Farmasotik Botanik
Bölüm Araştırma Makalesi
Yazarlar

Fazilet GÜRER 0000-0001-7210-4245

Serdar DEMİR 0000-0001-6572-8818

Şüra BAYKAN 0000-0002-3624-4811

Canan KARAALP 0000-0002-4787-3779

Proje Numarası Project No: 15-ECZ-003
Erken Görünüm Tarihi 12 Ekim 2023
Yayımlanma Tarihi 20 Ocak 2024
Gönderilme Tarihi 20 Temmuz 2023
Kabul Tarihi 19 Eylül 2023
Yayımlandığı Sayı Yıl 2024 Cilt: 48 Sayı: 1

Kaynak Göster

APA GÜRER, F., DEMİR, S., BAYKAN, Ş., KARAALP, C. (2024). SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS. Journal of Faculty of Pharmacy of Ankara University, 48(1), 1-7. https://doi.org/10.33483/jfpau.1330413
AMA GÜRER F, DEMİR S, BAYKAN Ş, KARAALP C. SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS. Ankara Ecz. Fak. Derg. Ocak 2024;48(1):1-7. doi:10.33483/jfpau.1330413
Chicago GÜRER, Fazilet, Serdar DEMİR, Şüra BAYKAN, ve Canan KARAALP. “SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS”. Journal of Faculty of Pharmacy of Ankara University 48, sy. 1 (Ocak 2024): 1-7. https://doi.org/10.33483/jfpau.1330413.
EndNote GÜRER F, DEMİR S, BAYKAN Ş, KARAALP C (01 Ocak 2024) SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS. Journal of Faculty of Pharmacy of Ankara University 48 1 1–7.
IEEE F. GÜRER, S. DEMİR, Ş. BAYKAN, ve C. KARAALP, “SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS”., Ankara Ecz. Fak. Derg., c. 48, sy. 1, ss. 1–7, 2024, doi: 10.33483/jfpau.1330413.
ISNAD GÜRER, Fazilet vd. “SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS”. Journal of Faculty of Pharmacy of Ankara University 48/1 (Ocak 2024), 1-7. https://doi.org/10.33483/jfpau.1330413.
JAMA GÜRER F, DEMİR S, BAYKAN Ş, KARAALP C. SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS. Ankara Ecz. Fak. Derg. 2024;48:1–7.
MLA GÜRER, Fazilet vd. “SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS”. Journal of Faculty of Pharmacy of Ankara University, c. 48, sy. 1, 2024, ss. 1-7, doi:10.33483/jfpau.1330413.
Vancouver GÜRER F, DEMİR S, BAYKAN Ş, KARAALP C. SECONDARY METABOLITES OF ENDEMIC CENTAUREA APHRODISEA BOISS. Ankara Ecz. Fak. Derg. 2024;48(1):1-7.

Kapsam ve Amaç

Ankara Üniversitesi Eczacılık Fakültesi Dergisi, açık erişim, hakemli bir dergi olup Türkçe veya İngilizce olarak farmasötik bilimler alanındaki önemli gelişmeleri içeren orijinal araştırmalar, derlemeler ve kısa bildiriler için uluslararası bir yayım ortamıdır. Bilimsel toplantılarda sunulan bildiriler supleman özel sayısı olarak dergide yayımlanabilir. Ayrıca, tüm farmasötik alandaki gelecek ve önceki ulusal ve uluslararası bilimsel toplantılar ile sosyal aktiviteleri içerir.