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TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ ve ANTİOKSİDAN ETKİLERİ

Year 2017, Volume: 26 Issue: 1, 71 - 77, 01.03.2017

Abstract

Bu çalışma kapsamında Asteraceae familyasına dahil
endemik bir tür olan Tanacetum zahlbruckneri (Náb.)
Grierson bitkisinin toprak üstü kısımlarından hazırlanan
metanol ekstresinin DPPH●
, ABTS●+ radikallerini
süpürücü aktivitesi ve β-karoten-linoleik asitle oksidasyon yöntemi ile antioksidan aktiviteleri, Folin– Ciocalteu
yöntemiyle toplam fenol, flavonit ve flavonol içeriği
incelenmiştir. Metanol ekstresinden sıvı-sıvı partisyon
yöntemiyle n-hekzan, dietil eter, diklorometan ve n- butanol ekstreleri hazırlanmış, n-butanol ekstresinden
çeşitli kromatografik yöntemler kullanılarak, klorojenik
asit (1), rutin (2) ve konduritol F (3) izole edilmiştir.
Elde edilen bileşiklerin yapıları spektroskopik yöntemler (IR, 1H-NMR, 13C-NMR, 2D-NMR, IR, MS) kullanılarak
aydınlatılmıştır. Bu çalışma ile Konduritol F Tanacetum
türlerinden ilk defa izole edilmiştir. Klorojenik asit ve
rutinin bitkinin metanol ekstresindeki kantitatif tayini
Yüksek Basınçlı Sıvı Kromatografisi ile gerçekleştirilmiştir. İzole edilen bileşiklerin antioksidan aktiviteleri ölçülmüş ve klorojenik asitin aktivitesi, rutin ve
metanol ekstresinden daha yüksek bulunmuştur.

References

  • Korkmaz M, Kandemir A, Ilhan V, et al. Tanacetum erzincanense (Asteraceae), a new species from Erzincan, Turkey. Turk J Bot 2015; 39: 96-104.
  • Bagci E, Kursat M, Kocak A, et al. Composition and antimicrobial activity of the essential oils of Tanacetum balsamita L. subsp balsamita and T. chiliophyllum (Fisch et Mey.) Schultz Bip. var. chiliophyllum (Asteraceae) from Turkey. J Essent Oil Bear Pl 2008; 11: 476-484.
  • Baytop T. Türkiye’de Biktiler ile Tedavi (Geçmişte ve Bugün). Nobel Tıp Kitabevleri, İstanbul 1999.
  • Tournier H, Schinella G, De Balsa EM, et al. Effect of the chloroform extract of Tanacetum vulgare and one of its active principles, parthenolide, on experimental gastric ulcer in rats. J Pharm Pharmacol 1999; 51: 215-219.
  • Kurkina AV, Khusainova AI, Daeva ED, et al. Flavonoids from Tanacetum vulgare flowers. Chem Nat Compd 2011; 47: 284-285.
  • Wu CQ, Chen F, Rushing JW, et al. Antiproliferative activities of parthenolide and golden feverfew extract against three human cancer cell lines. J Med Food 2006; 9: 55-61.
  • Pajak B, Gajkowska B, Orzechowski A. Molecular basis of parthenolide-dependent proapoptotic activity in cancer cells. Folia Histochem Cytobiol 2008; 46: 129-135.
  • Ozek G, Ozek T, Iscan G, et al. Composition and antimicrobial activity of the essential oil of Tanacetum cadmeum (Boiss.) heywood subsp orientale grierson. J Essent Oil Res 2007; 19: 392- 395.
  • Datta S, Saxena DB. Pesticidal properties of parthenin (from Parthenium hysterophorus) and related compounds. Pest Manag Sci 2001; 57: 95- 101.
  • Sulsen VP, Cazorla SI, Frank FM, et al. Natural terpenoids from Ambrosia species are active in vitro and in vivo against human pathogenic Trypanosomatids. Plos Negl Trop Dis 2013; 7.
  • Maxia A, Sanna C, Piras A, et al. Chemical composition and biological activity of Tanacetum audibertii (Req.) DC. (Asteraceae), an endemic species of Sardinia Island, Italy. Ind Crops Prod 2015; 65: 472-476.
  • Móricz ÁM, Häbe TT, Böszörményi A, et al. Tracking and identification of antibacterial components in the essential oil of Tanacetum vulgare L. by the combination of high-performance thin-layer chromatography with direct bioautography and mass spectrometry. J Chromatogr A 2015; 1422: 310-317.
  • Mostafa EM. Rateb ANG, El-Hawary SS, El-Shamy AM. Phytochemical and biological investigation of Tanacetum parthenium (L.) cultivated in Egypt. J Med Plants Res 2007; 1 (1): 18-26.
  • Petrovic SD, Dobric S, Bokonjic DB, et al. Evaluation of Tanacetum larvatum for an anti-inflammatory activity and for the protection against indomethacin-induced ulcerogenesis in rats. J Ethnopharmacol 2003; 87: 109-113.
  • Rustaiyan A, Sedaghat S. Two new guaianolides from Tanacetum fruticulosum Ledeb. Acta Hort 2005; 677:65-69.
  • Mükemre M, Behçet L, Çakılcıoğlu U. Ethnobotanical study on medicinal plants in villages of Çatak (Van-Turkey). J Ethnopharmacol 2015; 166: 361-374.
  • Polatoğlu K, Demirci B, Gören N, et al. Essential oil composition of endemic Tanacetum zahlbruckneri (Náb.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey. Nat Prod Res 2011; 25: 576-584.
  • Singleton VL, Orthofer R, Lamuela-Raventos RM. Analysis of total phenols and other oxidation substrates and antioxidants by means of folin- ciocalteu reagent. Methods Enzymol 1999; 299: 152 -178.
  • Zhishen J, Mengcheng T, Jianming W. The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals. Food Chem 1999; 64: 555-559.
  • Miliauskas G, Venskutonis PR, Van Beek TA. Screening of radical scavenging activity of some medicinal and aromatic plant extracts. Food Chem 2004; 85: 231-237.
  • Koşar M, Dorman D, Başer K, et al. An improved HPLC post-column methodology for the identification of free radical scavenging phytochemicals in complex mixtures. Chromatographia 2004; 60: 635-638.
  • Gyamfi MA, Yonamine M, Aniya Y. Free-radical scavenging action of medicinal herbs from Ghana: Thonningia sanguinea on experimentally-induced liver injuries. General Pharmacology: The Vascular System 1999; 32: 661-667.
  • Re R, Pellegrini N, Proteggente A, et al. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 1999; 26: 1231-1237.
  • Oomah BD, Mazza G. Flavonoids and antioxidative activities in buckwheat. J Agricult Food Chem 1996; 44: 1746-1750.
  • Jin U-H, Lee J-Y, Kang S-K, et al. A phenolic compound, 5-caffeoylquinic acid (chlorogenic acid), is a new type and strong matrix metalloproteinase- 9 inhibitor: Isolation and identification from methanol extract of Euonymus alatus. Life Sci 2005; 77: 2760-2769.
  • Sprogøe K, Stærk D, Jäger AK, et al. Targeted natural product isolation guided by HPLC–SPE–NMR: Constituents of Hubertia species. J Nat Prod 2007; 70: 1472-1477.
  • De Bruyn A, Anteunis M, De Gussem R, et al. 1H- NMR study of L-rhamnose, methyl α-L- rhamnopyranoside, and 4-O-β-D-galactopyranosyl- L-rhamnose in deuterium oxide. Carbohydr Res 1976; 47: 158-163.
  • Xiao Z, Wu H, Wu T, et al. Kaempferol and quercetin flavonoids from Rosa rugosa. Chem Nat Compd 2006; 42: 736-737.
  • Çağlar FP. Tanacetum zahlbruckneri (Nãb.) Grierson Bitkisi Üzerinde Fitokimyasal Araştırmalar. Yüksek Lisans Tezi, Yıldız Teknik Üniversitesi Fen Bilimleri Enstitüsü, İstanbul 2007.
  • Papaioannou P, Lazari D, Karioti A, et al. Phenolic compounds with antioxidant activity from Anthemis tinctoria L.(Asteraceae). Z Naturforsch C 2007; 62: 326-330.
  • Honda K, Ômura H, Hayashi N, et al. Conduritols as oviposition stimulants for the danaid butterfly, parantica sita, identified from a host plant, Marsdenia tomentosa. J Chem Ecol 2004; 30: 2285- 2296.
  • Balci M, Sütbeyaz Y, Seçen H. Conduritols and related compounds. Tetrahedron 1990; 46: 3715- 3742.
  • Kılbaş B, Balci M. Recent advances in inositol chemistry: Synthesis and applications. Tetrahedron 2011; 67: 2355-2389.

Secondary Metabolites and Antioxidant Activities of Tanacetum Zahlbruckneri(Náb.)Grierson

Year 2017, Volume: 26 Issue: 1, 71 - 77, 01.03.2017

Abstract

In the current study, antioxidant activity of methanol
extract prepared from Tanacetum zahlbruckneri
(Asteraceae) was studied with DPPH●, ABTS+ radical
scavenging and beta-carotene-linoleic acid cooxidation
assays. Total phenol, flavonoid and flavonol contents of
extracts were determined with Folin- Ciocalteu method. n-Hexane, diethyl ether, dichloromethane and n-butanol
extracts were prepared from methanol extract with
solvent partitioning and chlorogenic acid, rutin and
conduritol F were isolated from n-BuOH extract with
various chromatographic methods. Structures of the
compounds were elucidated by extensive 1D- and 2D- NMR spectroscopic analysis in combination with IR, MS
experiments. Conduritol F was isolated for the first time
from Tanacetum species. Quantitative analyses of
chlorogenic acid and rutin in MEOH extract were determined with High Pressure Liquid Chromatography
(HPLC). Antioxidant activities of isolated compounds
were studied and chlorogenic acid was found to be
more active than rutin and methanol extract.

References

  • Korkmaz M, Kandemir A, Ilhan V, et al. Tanacetum erzincanense (Asteraceae), a new species from Erzincan, Turkey. Turk J Bot 2015; 39: 96-104.
  • Bagci E, Kursat M, Kocak A, et al. Composition and antimicrobial activity of the essential oils of Tanacetum balsamita L. subsp balsamita and T. chiliophyllum (Fisch et Mey.) Schultz Bip. var. chiliophyllum (Asteraceae) from Turkey. J Essent Oil Bear Pl 2008; 11: 476-484.
  • Baytop T. Türkiye’de Biktiler ile Tedavi (Geçmişte ve Bugün). Nobel Tıp Kitabevleri, İstanbul 1999.
  • Tournier H, Schinella G, De Balsa EM, et al. Effect of the chloroform extract of Tanacetum vulgare and one of its active principles, parthenolide, on experimental gastric ulcer in rats. J Pharm Pharmacol 1999; 51: 215-219.
  • Kurkina AV, Khusainova AI, Daeva ED, et al. Flavonoids from Tanacetum vulgare flowers. Chem Nat Compd 2011; 47: 284-285.
  • Wu CQ, Chen F, Rushing JW, et al. Antiproliferative activities of parthenolide and golden feverfew extract against three human cancer cell lines. J Med Food 2006; 9: 55-61.
  • Pajak B, Gajkowska B, Orzechowski A. Molecular basis of parthenolide-dependent proapoptotic activity in cancer cells. Folia Histochem Cytobiol 2008; 46: 129-135.
  • Ozek G, Ozek T, Iscan G, et al. Composition and antimicrobial activity of the essential oil of Tanacetum cadmeum (Boiss.) heywood subsp orientale grierson. J Essent Oil Res 2007; 19: 392- 395.
  • Datta S, Saxena DB. Pesticidal properties of parthenin (from Parthenium hysterophorus) and related compounds. Pest Manag Sci 2001; 57: 95- 101.
  • Sulsen VP, Cazorla SI, Frank FM, et al. Natural terpenoids from Ambrosia species are active in vitro and in vivo against human pathogenic Trypanosomatids. Plos Negl Trop Dis 2013; 7.
  • Maxia A, Sanna C, Piras A, et al. Chemical composition and biological activity of Tanacetum audibertii (Req.) DC. (Asteraceae), an endemic species of Sardinia Island, Italy. Ind Crops Prod 2015; 65: 472-476.
  • Móricz ÁM, Häbe TT, Böszörményi A, et al. Tracking and identification of antibacterial components in the essential oil of Tanacetum vulgare L. by the combination of high-performance thin-layer chromatography with direct bioautography and mass spectrometry. J Chromatogr A 2015; 1422: 310-317.
  • Mostafa EM. Rateb ANG, El-Hawary SS, El-Shamy AM. Phytochemical and biological investigation of Tanacetum parthenium (L.) cultivated in Egypt. J Med Plants Res 2007; 1 (1): 18-26.
  • Petrovic SD, Dobric S, Bokonjic DB, et al. Evaluation of Tanacetum larvatum for an anti-inflammatory activity and for the protection against indomethacin-induced ulcerogenesis in rats. J Ethnopharmacol 2003; 87: 109-113.
  • Rustaiyan A, Sedaghat S. Two new guaianolides from Tanacetum fruticulosum Ledeb. Acta Hort 2005; 677:65-69.
  • Mükemre M, Behçet L, Çakılcıoğlu U. Ethnobotanical study on medicinal plants in villages of Çatak (Van-Turkey). J Ethnopharmacol 2015; 166: 361-374.
  • Polatoğlu K, Demirci B, Gören N, et al. Essential oil composition of endemic Tanacetum zahlbruckneri (Náb.) and Tanacetum tabrisianum (Boiss.) Sosn. and Takht. from Turkey. Nat Prod Res 2011; 25: 576-584.
  • Singleton VL, Orthofer R, Lamuela-Raventos RM. Analysis of total phenols and other oxidation substrates and antioxidants by means of folin- ciocalteu reagent. Methods Enzymol 1999; 299: 152 -178.
  • Zhishen J, Mengcheng T, Jianming W. The determination of flavonoid contents in mulberry and their scavenging effects on superoxide radicals. Food Chem 1999; 64: 555-559.
  • Miliauskas G, Venskutonis PR, Van Beek TA. Screening of radical scavenging activity of some medicinal and aromatic plant extracts. Food Chem 2004; 85: 231-237.
  • Koşar M, Dorman D, Başer K, et al. An improved HPLC post-column methodology for the identification of free radical scavenging phytochemicals in complex mixtures. Chromatographia 2004; 60: 635-638.
  • Gyamfi MA, Yonamine M, Aniya Y. Free-radical scavenging action of medicinal herbs from Ghana: Thonningia sanguinea on experimentally-induced liver injuries. General Pharmacology: The Vascular System 1999; 32: 661-667.
  • Re R, Pellegrini N, Proteggente A, et al. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 1999; 26: 1231-1237.
  • Oomah BD, Mazza G. Flavonoids and antioxidative activities in buckwheat. J Agricult Food Chem 1996; 44: 1746-1750.
  • Jin U-H, Lee J-Y, Kang S-K, et al. A phenolic compound, 5-caffeoylquinic acid (chlorogenic acid), is a new type and strong matrix metalloproteinase- 9 inhibitor: Isolation and identification from methanol extract of Euonymus alatus. Life Sci 2005; 77: 2760-2769.
  • Sprogøe K, Stærk D, Jäger AK, et al. Targeted natural product isolation guided by HPLC–SPE–NMR: Constituents of Hubertia species. J Nat Prod 2007; 70: 1472-1477.
  • De Bruyn A, Anteunis M, De Gussem R, et al. 1H- NMR study of L-rhamnose, methyl α-L- rhamnopyranoside, and 4-O-β-D-galactopyranosyl- L-rhamnose in deuterium oxide. Carbohydr Res 1976; 47: 158-163.
  • Xiao Z, Wu H, Wu T, et al. Kaempferol and quercetin flavonoids from Rosa rugosa. Chem Nat Compd 2006; 42: 736-737.
  • Çağlar FP. Tanacetum zahlbruckneri (Nãb.) Grierson Bitkisi Üzerinde Fitokimyasal Araştırmalar. Yüksek Lisans Tezi, Yıldız Teknik Üniversitesi Fen Bilimleri Enstitüsü, İstanbul 2007.
  • Papaioannou P, Lazari D, Karioti A, et al. Phenolic compounds with antioxidant activity from Anthemis tinctoria L.(Asteraceae). Z Naturforsch C 2007; 62: 326-330.
  • Honda K, Ômura H, Hayashi N, et al. Conduritols as oviposition stimulants for the danaid butterfly, parantica sita, identified from a host plant, Marsdenia tomentosa. J Chem Ecol 2004; 30: 2285- 2296.
  • Balci M, Sütbeyaz Y, Seçen H. Conduritols and related compounds. Tetrahedron 1990; 46: 3715- 3742.
  • Kılbaş B, Balci M. Recent advances in inositol chemistry: Synthesis and applications. Tetrahedron 2011; 67: 2355-2389.
There are 33 citations in total.

Details

Other ID JA78MB38HK
Journal Section Research Article
Authors

Perihan Gürbüz

Duygu Eroğlu This is me

Şengül Dilem Doğan This is me

Gökçe Şeker Karatoprak This is me

Mehmet Yavuz Paksoy This is me

Müberra Koşar This is me

Publication Date March 1, 2017
Submission Date March 1, 2017
Published in Issue Year 2017 Volume: 26 Issue: 1

Cite

APA Gürbüz, P., Eroğlu, D., Doğan, Ş. D., Karatoprak, G. Ş., et al. (2017). TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ ve ANTİOKSİDAN ETKİLERİ. Sağlık Bilimleri Dergisi, 26(1), 71-77.
AMA Gürbüz P, Eroğlu D, Doğan ŞD, Karatoprak GŞ, Paksoy MY, Koşar M. TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ ve ANTİOKSİDAN ETKİLERİ. JHS. March 2017;26(1):71-77.
Chicago Gürbüz, Perihan, Duygu Eroğlu, Şengül Dilem Doğan, Gökçe Şeker Karatoprak, Mehmet Yavuz Paksoy, and Müberra Koşar. “TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ Ve ANTİOKSİDAN ETKİLERİ”. Sağlık Bilimleri Dergisi 26, no. 1 (March 2017): 71-77.
EndNote Gürbüz P, Eroğlu D, Doğan ŞD, Karatoprak GŞ, Paksoy MY, Koşar M (March 1, 2017) TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ ve ANTİOKSİDAN ETKİLERİ. Sağlık Bilimleri Dergisi 26 1 71–77.
IEEE P. Gürbüz, D. Eroğlu, Ş. D. Doğan, G. Ş. Karatoprak, M. Y. Paksoy, and M. Koşar, “TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ ve ANTİOKSİDAN ETKİLERİ”, JHS, vol. 26, no. 1, pp. 71–77, 2017.
ISNAD Gürbüz, Perihan et al. “TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ Ve ANTİOKSİDAN ETKİLERİ”. Sağlık Bilimleri Dergisi 26/1 (March 2017), 71-77.
JAMA Gürbüz P, Eroğlu D, Doğan ŞD, Karatoprak GŞ, Paksoy MY, Koşar M. TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ ve ANTİOKSİDAN ETKİLERİ. JHS. 2017;26:71–77.
MLA Gürbüz, Perihan et al. “TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ Ve ANTİOKSİDAN ETKİLERİ”. Sağlık Bilimleri Dergisi, vol. 26, no. 1, 2017, pp. 71-77.
Vancouver Gürbüz P, Eroğlu D, Doğan ŞD, Karatoprak GŞ, Paksoy MY, Koşar M. TANACETUM ZAHLBRUCKNERI (NÁB.) GRIERSON’ NUN SEKONDER METABOLİTLERİ ve ANTİOKSİDAN ETKİLERİ. JHS. 2017;26(1):71-7.