Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts

RADUSIENE, Jolita; IVANAUSKAS, Liudas; ÇAMAŞ, Necdet; AYAN, Ali Kemal; JANULIS, Valdimaras; ÇIRAK, CÜNEYT

Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts

Cüneyt ÇIRAK, (Ondokuz Mayıs Üniversitesi, Bafra Meslek Yüksek Okulu, Samsun, Türkiye)

Jolita RADUSIENE, (Institute of Botany, Zaliuju ezeru 49, Vilnius LT-08406, LITHUANIA)

Valdimaras JANULIS, (Kaunas University of Medicine, Mickeviciaus 9, LT-44307, LITHUANIA)

Liudas IVANAUSKAS, (Kaunas University of Medicine, Mickeviciaus 9, LT-44307, LITHUANIA)

Necdet ÇAMAŞ, (Ondokuz Mayıs Üniversitesi, Bafra Meslek Yüksek Okulu, Samsun, Türkiye)

Ali Kemal AYAN (Ondokuz Mayıs Üniversitesi, Bafra Meslek Yüksek Okulu, Samsun, Türkiye)

Turkish Journal of Biology

7 0

Yıl: 2011 Cilt: 35 Sayı: 4 Sayfa Aralığı: 449 - 456 Metin Dili: Türkçe İndeks Tarihi: 29-07-2022

Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts

Öz:

Hypericum triquetrifolium Turra (Guttiferae) son yıllarda bilimsel dikkatleri üzerine çeken bir bitki olup, fenoliklerin de dahil olduğu çok sayıda biyoaktif bileşen içermektedir. Bu çalışma, ülkemizin Orta Karadeniz bölgesinde bulunan dört H. triquetrifolium populasyonunda bazı fenolik bileşenlerin (sırasıyla fenilpropan bileşiği olan klorojenik asit, ve fl avonoid bileşikleri rutin, hiperozit, apigenin-7-O-glukozit, kemferol, kersitrin, kersetin ve amentofl avon) varyasyonunu belirlemek amacıyla yürütülmüştür. Tam çiçeklenme döneminde her popülasyon için toplam 30 bitki toplanmıştır. Materyal oda sıcaklığında kurutulduktan sonra çiçek, yaprak ve sap kısımlarına ayrılmış; fenolik içerikleri belirlenmek üzere HPLC analizlerine tabi tutulmuşlardır. Popülasyonların fenolik içerikleri önemli seviyede farklı bulunmuştur. Farklı bitki kısımları içerisinde klorojenik asit, hiperozit, apigenin-7-O-glukozit, kemferol, kersetin ve amentofl avon’un esas olarak çiçeklerde, rutin ve kersitrin’in ise yapraklarda biriktiği belirlenmiştir. H. triquetrifolium’un apigenin-7-O-glukozit ve amentofl avon içerdiği ilk olarak bu çalışmada rapor edilmiştir. Popülasyonlar ve bitki kısımları arasında gözlenen kimyasal varyasyon farklı genetik, çevresel ve morfolojik faktörlerin muhtemel bir sonucu olduğu bağlamında tartışılmıştır.

Anahtar Kelime: HPLC klorojenik asit Clusiaceae flavonoidler Türkiye Hypericum triquetrifolium populasyon değişimi

Konular: Biyoloji

Türkiye’de yetişen Hypericum triquetrifolium Turra (Guttiferae) un fenolik bileşenleri: popülasyon ve bitki kısımları arasındaki varyasyon

Öz:

Hypericum triquetrifolium Turra (Guttiferae) has received considerable scientifi c interest in recent years, as it is a source of a variety of biologically active compounds including phenolics. Th e present study was conducted to determine the variation in the content of several phenolics, namely phenylpropane chlorogenic acid and fl avonoids such as rutin, hyperoside, apigenin-7-O-glucoside, kaempferol, quercitrin, quercetin and amentofl avone among four H. triquetrifolium populations from the Central Black Sea Region of Turkey. Th e aerial parts representing a total of 30 shoots were collected at full fl owering in each population. Aft er drying at room temperature, they were dissected into fl oral, leaf and stem tissues and subsequently assayed for phenolic compounds by HPLC. Th e populations varied signifi cantly in phenolic content. Among diff erent plant parts, the fl owers were found to be the principle organ for chlorogenic acid, hyperoside, apigenin-7-O-glucoside, kaempferol, quercetin and amentofl avone accumulations, while rutin and quercitrin were accumulated mainly in the leaves. Th e presence of apigenin-7-O-glucoside and amentofl avone in H. triquetrifolium is reported by us for the fi rst time. Th e chemical variation among the populations and plant parts is discussed as being possibly the result of diff erent genetic, environmental and morphological factors.

Anahtar Kelime: flavonoids Turkey Hypericum triquetrifolium population change HPLC chlorogenic acid Clusiaceae

Konular: Biyoloji

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Davis PH. Flora of Turkey and the East Aegean Islands. Edinburgh University Press. Edinburgh; 1988.
2. Baytop T. Th erapy with Medicinal Plants in Turkey. İstanbul University Press, İstanbul; 1999.
3. Apaydın S, Zeybek U, Ince I et al. Hypericum triquetrifolium Turra. extract exhibits antinociceptive activity in the mouse. J Ethnopharmacol 3: 307-312, 1999.
4. Ozturk B, Apaydin S, Goldeli E et al. Hypericum triquetrifolium Turra. extract exhibits antiinfl ammatory activity in the rat. J Ethnopharmacol 80: 207-209, 2002.
5. Conforti F, Statti GA, Tundis R et al. Antioxidant activity of methanolic extract of Hypericum triquetrifolium Turra aerial part. Fitoterapia 6: 479-483, 2002.
6. Pistelli L, Bertoli A, Morelli I et al. Chemical and antibacterial evaluation of Hypericum triquetrifolium Turra. Phytother Res 19: 787-791, 2005.
7. Fraternalea D, Bertoli A, Giamperi L et al. Antifungal evaluation of Hypericum triquetrifolium polar extracts against Fusarium spp. Nat Prod Commun 1: 1117-1122, 2006.
8. Conforti F, Loizzo MR, Statti AG et al. Cytotoxic activity of antioxidant constituents from Hypericum triquetrifolium Tura. Nat Prod Res 21: 42-46, 2007.
9. Kitanov GM. Hypericin and pseudohypericin in some Hypericum species. Biochem Syst Ecol 29: 171-178, 2001.
10. Radušienė J, Bagdonaite E, Kazlauskas S. Morphological and chemical evaluation on Hypericum perforatum and H. maculatum in Lithuania. Acta Hort (ISHS) 629: 55-62, 2004.
11. Bertoli A, Menichini F, Mazzetti M et al. Volatile constituents of the leaves and fl owers of Hypericum triquetrifolium Tura. Flavour Fragr J 18: 91-94, 2003.
12. Tanaka N, Takaishi Y. Xanthones from Hypericum chinense. Phytochemistry 67: 2146-2151, 2006.
13. Dall’Agnol R, Ferraz A, Bernardi AP et al. Antimicrobial activity of some Hypericum species. Phytomedicine 10: 511-516, 2003.
14. Greeson J, Sanford B, Monti DA. St. John’s wort (Hypericum perforatum L.): A review of the current pharmacological, toxicological and clinical literature. Psychopharmacol 153: 402-414, 2001.
15. Russo A, Acquaviva R, Campisi A et al. Biofl avonoids as antiradicals, antioxidants and DNA cleavage protectors. Cell Biol Toxicol 16: 91-98, 2000.
16. Gülçin İ, Elias R, Gepdiremen A et al. Antioxidant secoiridoids from fringe tree (Chionanthus virginicus L.). Wood Sci Technol 43: 195-212, 2009.
17. Gülçin İ. Comparison of in vitro antioxidant and antiradical activities of L-tyrosine and L-Dopa. Amino Acids 32: 431-438, 2007.
18. Isfahlan AJ, Mahmoodzadeh A, Hasanzadeh A et al. Antioxidant and antiradical activities of phenolic extracts from Iranian almond (Prunus amygdalus L.) hulls and shells. Turk J Biol 34: 165-173, 2010.
19. Chu YH, Chang CL, Hsu HF. Flavonoid content of several vegetables and their antioxidant activity. J Sci Food Agric 80: 561-566, 2000.
20. Noldner M, Schotz K. Rutin is essential for the antidepressant activity of Hypericum perforatum extracts in the forced swimming test. Planta Med 68: 577-80, 2002.
21. Gastpar M, Zeller K. Hypericum-extrakt STW3 und sertralin zur behandlung der mittelschweren depression. Psychopharmakotherapie 12: 146-153, 2005.
22. Marfonti P, Repcak M. Secondary metabolites during fl ower ontogenesis of Hypericum perforatum L. Zahradnictvi 21: 37-44, 1994.
23. Tekel’ova D, Repcak M, Zemkova E et al. Quantitative changes of dianthrones, hyperforin and fl avonoids content in the fl ower ontogenesis of Hypericum perforatum. Planta Med 66: 778-780, 2000.
24. Kazlauskas S, Bagdonaite E. Quantitative analysis of active substances in St. John’s wort (Hypericum perforatum L.) by the high performance liquid chromatography method. Medicina (Kaunas) 40: 975-981, 2004.
25. Abreu IN, Porto ALM, Marsaioli AJ et al. Distrubution of bioactive substances from Hypericum brasiliense during plant growth. Plant Sci 167: 949-954, 2004.
26. Ozen T, Ayan AK, Çırak C et al. Total phenol content of some Hypericum species growing in Turkey. Chem Nat Compd 41: 232-233, 2005.
27. Martonfi P, Repcak M, Zanvit P. Secondary metabolites variation in Hypericum maculatum and its relatives. Biochem Syst Ecol 34: 56-59, 2006.
28. Ayan AK, Çırak C, Yanar O. Variations in total phenolics during ontogenetic, morphogenetic, and diurnal cycles in Hypericum species from Turkey. J Plant Biol 49: 432-440, 2006.
29. Çırak C, Radušienė J, Janulis V et al. Variation of bioactive secondary metabolites in Hypericum origanifolium during its phenological cycle. Acta Physiol Plant 29: 197-203, 2007.
30. Çırak C, Radušienė J, Janulis V et al. Chemical constituents of some Hypericum species growing in Turkey. J Plant Biol 50: 632-635, 2007.
31. Çırak C, Radušienė J, Sağlam B. Variation of bioactive substances in Hypericum montbretii during plant growth. Nat Prod Res 22: 246-252, 2008.
32. Toker Z. Variation of total hypericin, phenolic and fl avonoid compounds in Hypericum triquetrifolium during its phenological cycle. Pharm Biol 47: 285-288, 2009.
33. Ayan AK, Çırak C. Hypericin and pseudohypericin contents in some Hypericum species growing in Turkey. Pharm Biol 46: 288-291, 2008.
34. Gülçin İ, Kireçci E, Akkemik E et al. Antioxidant and antimicrobial activities of an aquatic plant: Duckweed (Lemna minor L.). Turk J Biol 34: 175-188, 2010.
35. Kovacs G, Kuzovkina IN, Szoke E et al. HPLC determination of fl avonoids in hairy-root cultures of Scutellaria baicalensis Georgi. Chromatographia 60: 81-85, 2004.
36. Bergonzi MC, Bilia AR, Gallori S et al. Variability in the content of the constituents of Hypericum perforatum L. and some commercial extracts. Drug Dev Ind Pharm 27: 491-497,2001.
37. Ciccarelli D, Andreucci AC, Pagni AM. Translucent glands and secretory canals in Hypericum perforatum, Morphological, anatomical and histochemical studies during the course of onthogenesis. Ann Bot-London 88: 637-644, 2001.
38. Maggi F, Ferretti G, Pocceschi N et al. Morphological, histochemical and phytochemical investigation of the genus Hypericum of the Central Italy. Fitoterapia 75: 702-711, 2004.

APA	ÇIRAK C, RADUSIENE J, JANULIS V, IVANAUSKAS L, ÇAMAŞ N, AYAN A (2011). Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. , 449 - 456.
Chicago	ÇIRAK CÜNEYT,RADUSIENE Jolita,JANULIS Valdimaras,IVANAUSKAS Liudas,ÇAMAŞ Necdet,AYAN Ali Kemal Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. (2011): 449 - 456.
MLA	ÇIRAK CÜNEYT,RADUSIENE Jolita,JANULIS Valdimaras,IVANAUSKAS Liudas,ÇAMAŞ Necdet,AYAN Ali Kemal Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. , 2011, ss.449 - 456.
AMA	ÇIRAK C,RADUSIENE J,JANULIS V,IVANAUSKAS L,ÇAMAŞ N,AYAN A Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. . 2011; 449 - 456.
Vancouver	ÇIRAK C,RADUSIENE J,JANULIS V,IVANAUSKAS L,ÇAMAŞ N,AYAN A Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. . 2011; 449 - 456.
IEEE	ÇIRAK C,RADUSIENE J,JANULIS V,IVANAUSKAS L,ÇAMAŞ N,AYAN A "Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts." , ss.449 - 456, 2011.
ISNAD	ÇIRAK, CÜNEYT vd. "Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts". (2011), 449-456.

APA	ÇIRAK C, RADUSIENE J, JANULIS V, IVANAUSKAS L, ÇAMAŞ N, AYAN A (2011). Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. Turkish Journal of Biology, 35(4), 449 - 456.
Chicago	ÇIRAK CÜNEYT,RADUSIENE Jolita,JANULIS Valdimaras,IVANAUSKAS Liudas,ÇAMAŞ Necdet,AYAN Ali Kemal Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. Turkish Journal of Biology 35, no.4 (2011): 449 - 456.
MLA	ÇIRAK CÜNEYT,RADUSIENE Jolita,JANULIS Valdimaras,IVANAUSKAS Liudas,ÇAMAŞ Necdet,AYAN Ali Kemal Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. Turkish Journal of Biology, vol.35, no.4, 2011, ss.449 - 456.
AMA	ÇIRAK C,RADUSIENE J,JANULIS V,IVANAUSKAS L,ÇAMAŞ N,AYAN A Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. Turkish Journal of Biology. 2011; 35(4): 449 - 456.
Vancouver	ÇIRAK C,RADUSIENE J,JANULIS V,IVANAUSKAS L,ÇAMAŞ N,AYAN A Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. Turkish Journal of Biology. 2011; 35(4): 449 - 456.
IEEE	ÇIRAK C,RADUSIENE J,JANULIS V,IVANAUSKAS L,ÇAMAŞ N,AYAN A "Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts." Turkish Journal of Biology, 35, ss.449 - 456, 2011.
ISNAD	ÇIRAK, CÜNEYT vd. "Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts". Turkish Journal of Biology 35/4 (2011), 449-456.