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Year 2018, Volume: 22 Issue: 3, 405 - 410, 27.06.2025

Perihan Gürbüz , Müberra Koşar , Zuhal Güvenalp , Ayşe Kuruüzüm-uz , L. Ömür Demirezer

https://doi.org/10.12991/jrp.2018.80
Cited By: 5

Abstract

References

  • [1] Coode MJE. Cistaceae. In P.H. Davis, Editor. Flora of Turkey and the East Aegean Islands. Edinburgh University Press: Edinburgh. 1965-1985, vol:1, pp. 506-523.
  • [2] Coode MJE. Cistaceae. In P.H. Davis, Mill, R., Tan, K., Editor. Flora of Turkey and the East Aegean Islands. Edinburgh University Press: Edinburgh. 1988, vol:10, pp. 61.
  • [3] Roy J, Sonie L. Germination and population dynamics of Cistus species in relation to fire. J Appl Ecol. 1992: 647-655.
  • [4] Baytop T. Therapy with Medicinal Plants in Turkey (Past and Present), Publications of the Istanbul University, İstanbul, 1984.
  • [5] Yeşilada E, Honda G, Sezik E, Tabata M, Fujita T, Tanaka T, Takeda Y, Takaishi Y. Traditional medicine in Turkey. V. Folk medicine in the inner Taurus Mountains. J Ethnopharmacol. 1995; 46(3): 133-152.
  • [6] Barrajón-Catalán E, Fernández-Arroyo S, Saura D, Guillén E, Fernández-Gutiérrez A, Segura-Carretero A, Micol V. Cistaceae aqueous extracts containing ellagitannins show antioxidant and antimicrobial capacity, and cytotoxic activity against human cancer cells. Food Chem Toxicol. 48(8-9): 2273-2282.
  • [7] Demetzos C, Mitaku S, Couladis M, Harvala C, Kokkinopoulos D. Natural metabolites of ent-13-epi-Manoyl Oxide and other cytotoxic diterpenes from the resin "LADANO" of Cistus creticus. Planta Med. 1994; 60(6): 590-591.
  • [8] Kupeli E, Orhan DD, Yesilada E. Effect of Cistus laurifolius L. leaf extracts and flavonoids on acetaminophen-induced hepatotoxicity in mice. J Ethnopharmacol. 2006; 103(3): 455-460.
  • [9] Kupeli E, Yesilada E. Flavonoids with anti-inflammatory and antinociceptive activity from Cistus laurifolius L. leaves through bioassay-guided procedures. J Ethnopharmacol. 2007; 112(3): 524-530.
  • [10] Bouamama H, Noel T, Villard J, Benharref A, Jana M. Antimicrobial activities of the leaf extracts of two Moroccan Cistus L. species. J Ethnopharmacol. 2006; 104(1-2): 104-107.
  • [11] Guvenc A, Yildiz S, Ozkan AM, Erdurak CS, Coskun M, Yilmaz G, Okuyama T, Okada Y. Antimicrobiological studies on Turkish Cistus species. Pharm Biol. 2005; 43(2): 178-183.
  • [12] Kalus U, Grigorov A, Kadecki O, Jansen JP, Kiesewetter H, Radtke H. Cistus incanus (CYSTUS052) for treating patients with infection of the upper respiratory tract: A prospective, randomised, placebo-controlled clinical study. Antivir Res. 2009; 84(3): 267-271.
  • [13] Kalus U, Kiesewetter H, Radtke H. Effect of CYSTUS052® and green tea on subjective symptoms in patients with infection of the upper respiratory tract. Phytother Res. 2010; 24(1): 96-100.
  • [14] Sadhu SK, Okuyama E, Fujimoto H, Ishibashi M, Yesilada E. Prostaglandin inhibitory and antioxidant components of Cistus laurifolius, a Turkish medicinal plant. J Ethnopharmacol. 2006; 108(3): 371-378.
  • [15] Yesilada E, Ustun O, Sezik E, Takaishi Y, Ono Y, Honda G. Inhibitory effects of Turkish folk remedies on inflammatory cytokines: interleukin-1alpha, interleukin-1beta and tumor necrosis factor alpha. J Ethnopharmacol. 1997; 58(1): 59-73.
  • [16] Attaguile G, Russo A, Campisi A, Savoca F, Acquaviva R, Ragusa N, Vanella A. Antioxidant activity and protective effect on DNA cleavage of extracts from Cistus incanus L. and Cistus monspeliensis L. Cell Biol Toxicol. 2000; 16(2): 83-90.
  • [17] Qa'Dan F, Petereit F, Mansoor K, Nahrstedt A. Antioxidant oligomeric proanthocyanidins from Cistus salvifolius. Nat Prod Res. 2006; 20(13): 1216-1224.
  • [18] Ark M, Ustun O, Yesilada E. Analgesic activity of Cistus laurifolius in mice. Pharm Biol. 2004; 42(2): 176-178.
  • [19] De Andres AI, Gomez-Serranillos MP, Iglesias I, Villar AM. Effects of extract of Cistus populifolius L. on the central nervous system. Phytother Res. 1999; 13(7): 575-579.
  • [20] Attaguile G, Perticone G, Mania G, Savoca F, Pennisi G, Salomone S. Cistus incanus and Cistus monspeliensis inhibit the contractile response in isolated rat smooth muscle. J Ethnopharmacol. 2004; 92(2-3): 245-250.
  • [21] Aziz M, Tab N, Karim A, Mekhfi H, Bnouham M, Ziyyat A, Melhaoui A, Legssyer A. Relaxant effect of aqueous extract of Cistus ladaniferus on rodent intestinal contractions. Fitoterapia. 2006; 77(6): 425-428.
  • [22] Belmokhtar M, Bouanani NE, Ziyyat A, Mekhfi H, Bnouham M, Aziz M, Mateo P, Fischmeister R, Legssyer A. Antihypertensive and endothelium-dependent vasodilator effects of aqueous extract of Cistus ladaniferus. Biochem Biophysical Res Commun. 2009; 389(1): 145-149.
  • [23] Attaguile G, Caruso A, Pennisi G, Savoca F. Gastroprotective effect of aqueous extract of Cistus incanus L. in rats. Pharm Res. 1995; 31(1): 29-32.
  • [24] Yesilada E, Gurbuz I, Ergun E. Effects of Cistus laurifolius L. flowers on gastric and duodenal lesions. J Ethnopharmacol. 1997; 55(3): 201-211.
  • [25] Yesilada E, Gurbuz I, Shibata H. Screening of Turkish anti-ulcerogenic folk remedies for anti-Helicobacter pylori activity. J Ethnopharmacol. 1999; 66(3): 289-293.
  • [26] Ustun O, Ozcelik B, Akyon Y, Abbasoglu U, Yesilada E. Flavonoids with anti-Helicobacter pylori activity from Cistus laurifolius leaves. J Ethnopharmacol. 2006; 108(3): 457-461.
  • [27] De Pascual Teresa J, Urones JG, Marcos IS, Barcala PB, Garrido NM. Diterpenoid and other components of Cistus laurifolius. Phytochemistry. 1986; 25(5): 1185-1187.
  • [28] Demirezer LO, Guvenalp Z, Kuruuzum-Uz A, Kazaz C. Labdane-type diterpenes from Cistus creticus L. Planta Med. 2007; 73(9): 953-953.
  • [29] Chaves N, Rios JJ, Gutierrez C, Escudero JC, Olias JM. Analysis of secreted flavonoids of Cistus ladanifer L. by high-performance liquid chromatography particle beam mass spectrometry. J Chromatogr A. 1998; 799(1-2): 111-115.
  • [30] Danne A, Petereit F, Nahrstedt A. Proanthocyanidins from Cistus incanus. Phytochemistry. 1993; 34(4): 1129-1133.
  • [31] Danne A, Petereit F, Nahrstedt A. Flavan-3-ols, prodelphinidins and further polyphenols from Cistus salvifolius. Phytochemistry. 1994; 37(2): 533-538.
  • [32] Saracini E, Tattini M, Traversi M, Vincieri F, Pinelli P. Simultaneous LC-DAD and LC-MS determination of ellagitannins, flavonoid glycosides, and acyl-glycosyl flavonoids in Cistus salvifolius L. leaves. Chromatographia. 2005; 62(5-6): 245-249.
  • [33] Fernández-Arroyo S, Barrajón-Catalán E, Micol V, Segura-Carretero A, Fernández-Gutiérrez A. High-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight and ion-trap tandem mass spectrometry to identify phenolic compounds from a Cistus ladanifer aqueous extract. Phytochem Anal. 2010; 21(4): 307-313.
  • [34] Santagati NA, Salerno L, Attaguile G, Savoca F, Ronsisvalle G. Simultaneous determination of catechins, rutin, and gallic acid in Cistus species extracts by HPLC with diode array detection. J Chromatogr Sci. 2008; 46(2): 150-156.
  • [35] Vogt T, Gul PG. Accumulation of flavonoids during leaf development in Cistus laurifolius. Phytochemistry. 1994; 36(3): 591-597.
  • [36] Gürbüz P, Demirezer LÖ, Güvenalp Z, Kuruüzüm-Uz A, Kazaz C. Isolation and structure elucidation of uncommon secondary metabolites from Cistus salviifolius L. Rec Nat Prod. 2015; 9(2): 175.
  • [37] Tohge T, de Souza LP, Fernie AR. On the natural diversity of phenylacylated-flavonoid and their in planta function under conditions of stress. Phytochem Rev. 2017; 1-12.

Simultaneous determination of selected flavonoids from different Cistus species by HPLC-PDA

Year 2018, Volume: 22 Issue: 3, 405 - 410, 27.06.2025

Perihan Gürbüz , Müberra Koşar , Zuhal Güvenalp , Ayşe Kuruüzüm-uz , L. Ömür Demirezer

https://doi.org/10.12991/jrp.2018.80
Cited By: 5

Abstract

A rapid and simple high-performance liquid chromatography method with a Photo Diode Array (PDA) detector is developed for the simultaneous analysis of seven kaempferol, quercetin and myricetin derivatives along with an acylated flavonoid glycoside; trans-tiliroside from different Cistus species. In this study, the qualitative and quantitative analysis of the methanolic extracts of three Cistus species (C. creticus L., C. laurifolius L. and C. salviifolius L.) growing in Anatolia in terms of characterization of flavonoid compounds were performed by RP-HPLC for the first time. Trans-tiliroside, a mono-coumaroyl kaempferol glucoside was found to be the most abundant flavonoid in C. salviifolius (0.276±0.003 g/100 gextract) and C. creticus (0.253±0.001 g/100 gextract) while hyperin (0.149±0.004 g/100 gextract) and myricetin 3-O-β-galactopyranoside (0.139±0.006 g/100 gextract) were found to be the most intense flavonoids in C. laurifolius samples. The described HPLC method appears suitable for the determination of the Cistusflavonols and their glycosides and can be considered as an effective and alternative procedure for the identification and quantification of this important class of biologically active compounds.

Keywords

Cistus Cistaceae flavonols HPLC-PDA

References

  • [1] Coode MJE. Cistaceae. In P.H. Davis, Editor. Flora of Turkey and the East Aegean Islands. Edinburgh University Press: Edinburgh. 1965-1985, vol:1, pp. 506-523.
  • [2] Coode MJE. Cistaceae. In P.H. Davis, Mill, R., Tan, K., Editor. Flora of Turkey and the East Aegean Islands. Edinburgh University Press: Edinburgh. 1988, vol:10, pp. 61.
  • [3] Roy J, Sonie L. Germination and population dynamics of Cistus species in relation to fire. J Appl Ecol. 1992: 647-655.
  • [4] Baytop T. Therapy with Medicinal Plants in Turkey (Past and Present), Publications of the Istanbul University, İstanbul, 1984.
  • [5] Yeşilada E, Honda G, Sezik E, Tabata M, Fujita T, Tanaka T, Takeda Y, Takaishi Y. Traditional medicine in Turkey. V. Folk medicine in the inner Taurus Mountains. J Ethnopharmacol. 1995; 46(3): 133-152.
  • [6] Barrajón-Catalán E, Fernández-Arroyo S, Saura D, Guillén E, Fernández-Gutiérrez A, Segura-Carretero A, Micol V. Cistaceae aqueous extracts containing ellagitannins show antioxidant and antimicrobial capacity, and cytotoxic activity against human cancer cells. Food Chem Toxicol. 48(8-9): 2273-2282.
  • [7] Demetzos C, Mitaku S, Couladis M, Harvala C, Kokkinopoulos D. Natural metabolites of ent-13-epi-Manoyl Oxide and other cytotoxic diterpenes from the resin "LADANO" of Cistus creticus. Planta Med. 1994; 60(6): 590-591.
  • [8] Kupeli E, Orhan DD, Yesilada E. Effect of Cistus laurifolius L. leaf extracts and flavonoids on acetaminophen-induced hepatotoxicity in mice. J Ethnopharmacol. 2006; 103(3): 455-460.
  • [9] Kupeli E, Yesilada E. Flavonoids with anti-inflammatory and antinociceptive activity from Cistus laurifolius L. leaves through bioassay-guided procedures. J Ethnopharmacol. 2007; 112(3): 524-530.
  • [10] Bouamama H, Noel T, Villard J, Benharref A, Jana M. Antimicrobial activities of the leaf extracts of two Moroccan Cistus L. species. J Ethnopharmacol. 2006; 104(1-2): 104-107.
  • [11] Guvenc A, Yildiz S, Ozkan AM, Erdurak CS, Coskun M, Yilmaz G, Okuyama T, Okada Y. Antimicrobiological studies on Turkish Cistus species. Pharm Biol. 2005; 43(2): 178-183.
  • [12] Kalus U, Grigorov A, Kadecki O, Jansen JP, Kiesewetter H, Radtke H. Cistus incanus (CYSTUS052) for treating patients with infection of the upper respiratory tract: A prospective, randomised, placebo-controlled clinical study. Antivir Res. 2009; 84(3): 267-271.
  • [13] Kalus U, Kiesewetter H, Radtke H. Effect of CYSTUS052® and green tea on subjective symptoms in patients with infection of the upper respiratory tract. Phytother Res. 2010; 24(1): 96-100.
  • [14] Sadhu SK, Okuyama E, Fujimoto H, Ishibashi M, Yesilada E. Prostaglandin inhibitory and antioxidant components of Cistus laurifolius, a Turkish medicinal plant. J Ethnopharmacol. 2006; 108(3): 371-378.
  • [15] Yesilada E, Ustun O, Sezik E, Takaishi Y, Ono Y, Honda G. Inhibitory effects of Turkish folk remedies on inflammatory cytokines: interleukin-1alpha, interleukin-1beta and tumor necrosis factor alpha. J Ethnopharmacol. 1997; 58(1): 59-73.
  • [16] Attaguile G, Russo A, Campisi A, Savoca F, Acquaviva R, Ragusa N, Vanella A. Antioxidant activity and protective effect on DNA cleavage of extracts from Cistus incanus L. and Cistus monspeliensis L. Cell Biol Toxicol. 2000; 16(2): 83-90.
  • [17] Qa'Dan F, Petereit F, Mansoor K, Nahrstedt A. Antioxidant oligomeric proanthocyanidins from Cistus salvifolius. Nat Prod Res. 2006; 20(13): 1216-1224.
  • [18] Ark M, Ustun O, Yesilada E. Analgesic activity of Cistus laurifolius in mice. Pharm Biol. 2004; 42(2): 176-178.
  • [19] De Andres AI, Gomez-Serranillos MP, Iglesias I, Villar AM. Effects of extract of Cistus populifolius L. on the central nervous system. Phytother Res. 1999; 13(7): 575-579.
  • [20] Attaguile G, Perticone G, Mania G, Savoca F, Pennisi G, Salomone S. Cistus incanus and Cistus monspeliensis inhibit the contractile response in isolated rat smooth muscle. J Ethnopharmacol. 2004; 92(2-3): 245-250.
  • [21] Aziz M, Tab N, Karim A, Mekhfi H, Bnouham M, Ziyyat A, Melhaoui A, Legssyer A. Relaxant effect of aqueous extract of Cistus ladaniferus on rodent intestinal contractions. Fitoterapia. 2006; 77(6): 425-428.
  • [22] Belmokhtar M, Bouanani NE, Ziyyat A, Mekhfi H, Bnouham M, Aziz M, Mateo P, Fischmeister R, Legssyer A. Antihypertensive and endothelium-dependent vasodilator effects of aqueous extract of Cistus ladaniferus. Biochem Biophysical Res Commun. 2009; 389(1): 145-149.
  • [23] Attaguile G, Caruso A, Pennisi G, Savoca F. Gastroprotective effect of aqueous extract of Cistus incanus L. in rats. Pharm Res. 1995; 31(1): 29-32.
  • [24] Yesilada E, Gurbuz I, Ergun E. Effects of Cistus laurifolius L. flowers on gastric and duodenal lesions. J Ethnopharmacol. 1997; 55(3): 201-211.
  • [25] Yesilada E, Gurbuz I, Shibata H. Screening of Turkish anti-ulcerogenic folk remedies for anti-Helicobacter pylori activity. J Ethnopharmacol. 1999; 66(3): 289-293.
  • [26] Ustun O, Ozcelik B, Akyon Y, Abbasoglu U, Yesilada E. Flavonoids with anti-Helicobacter pylori activity from Cistus laurifolius leaves. J Ethnopharmacol. 2006; 108(3): 457-461.
  • [27] De Pascual Teresa J, Urones JG, Marcos IS, Barcala PB, Garrido NM. Diterpenoid and other components of Cistus laurifolius. Phytochemistry. 1986; 25(5): 1185-1187.
  • [28] Demirezer LO, Guvenalp Z, Kuruuzum-Uz A, Kazaz C. Labdane-type diterpenes from Cistus creticus L. Planta Med. 2007; 73(9): 953-953.
  • [29] Chaves N, Rios JJ, Gutierrez C, Escudero JC, Olias JM. Analysis of secreted flavonoids of Cistus ladanifer L. by high-performance liquid chromatography particle beam mass spectrometry. J Chromatogr A. 1998; 799(1-2): 111-115.
  • [30] Danne A, Petereit F, Nahrstedt A. Proanthocyanidins from Cistus incanus. Phytochemistry. 1993; 34(4): 1129-1133.
  • [31] Danne A, Petereit F, Nahrstedt A. Flavan-3-ols, prodelphinidins and further polyphenols from Cistus salvifolius. Phytochemistry. 1994; 37(2): 533-538.
  • [32] Saracini E, Tattini M, Traversi M, Vincieri F, Pinelli P. Simultaneous LC-DAD and LC-MS determination of ellagitannins, flavonoid glycosides, and acyl-glycosyl flavonoids in Cistus salvifolius L. leaves. Chromatographia. 2005; 62(5-6): 245-249.
  • [33] Fernández-Arroyo S, Barrajón-Catalán E, Micol V, Segura-Carretero A, Fernández-Gutiérrez A. High-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight and ion-trap tandem mass spectrometry to identify phenolic compounds from a Cistus ladanifer aqueous extract. Phytochem Anal. 2010; 21(4): 307-313.
  • [34] Santagati NA, Salerno L, Attaguile G, Savoca F, Ronsisvalle G. Simultaneous determination of catechins, rutin, and gallic acid in Cistus species extracts by HPLC with diode array detection. J Chromatogr Sci. 2008; 46(2): 150-156.
  • [35] Vogt T, Gul PG. Accumulation of flavonoids during leaf development in Cistus laurifolius. Phytochemistry. 1994; 36(3): 591-597.
  • [36] Gürbüz P, Demirezer LÖ, Güvenalp Z, Kuruüzüm-Uz A, Kazaz C. Isolation and structure elucidation of uncommon secondary metabolites from Cistus salviifolius L. Rec Nat Prod. 2015; 9(2): 175.
  • [37] Tohge T, de Souza LP, Fernie AR. On the natural diversity of phenylacylated-flavonoid and their in planta function under conditions of stress. Phytochem Rev. 2017; 1-12.
There are 37 citations in total.

Details

Primary Language English
Subjects Pharmacognosy
Journal Section Articles
Authors

Perihan Gürbüz 0000-0002-3056-411X

Müberra Koşar 0000-0002-1559-998X

Zuhal Güvenalp 0000-0002-8803-8147

Ayşe Kuruüzüm-uz 0000-0003-3373-4759

L. Ömür Demirezer 0000-0002-5284-0744

Publication Date June 27, 2025
Published in Issue Year 2018 Volume: 22 Issue: 3

Cite

APA Gürbüz, P., Koşar, M., Güvenalp, Z., Kuruüzüm-uz, A., et al. (2025). Simultaneous determination of selected flavonoids from different Cistus species by HPLC-PDA. Journal of Research in Pharmacy, 22(3), 405-410. https://doi.org/10.12991/jrp.2018.80
AMA Gürbüz P, Koşar M, Güvenalp Z, Kuruüzüm-uz A, Demirezer LÖ. Simultaneous determination of selected flavonoids from different Cistus species by HPLC-PDA. J. Res. Pharm. June 2025;22(3):405-410. doi:10.12991/jrp.2018.80
Chicago Gürbüz, Perihan, Müberra Koşar, Zuhal Güvenalp, Ayşe Kuruüzüm-uz, and L. Ömür Demirezer. “Simultaneous Determination of Selected Flavonoids from Different Cistus Species by HPLC-PDA”. Journal of Research in Pharmacy 22, no. 3 (June 2025): 405-10. https://doi.org/10.12991/jrp.2018.80.
EndNote Gürbüz P, Koşar M, Güvenalp Z, Kuruüzüm-uz A, Demirezer LÖ (June 1, 2025) Simultaneous determination of selected flavonoids from different Cistus species by HPLC-PDA. Journal of Research in Pharmacy 22 3 405–410.
IEEE P. Gürbüz, M. Koşar, Z. Güvenalp, A. Kuruüzüm-uz, and L. Ö. Demirezer, “Simultaneous determination of selected flavonoids from different Cistus species by HPLC-PDA”, J. Res. Pharm., vol. 22, no. 3, pp. 405–410, 2025, doi: 10.12991/jrp.2018.80.
ISNAD Gürbüz, Perihan et al. “Simultaneous Determination of Selected Flavonoids from Different Cistus Species by HPLC-PDA”. Journal of Research in Pharmacy 22/3 (June 2025), 405-410. https://doi.org/10.12991/jrp.2018.80.
JAMA Gürbüz P, Koşar M, Güvenalp Z, Kuruüzüm-uz A, Demirezer LÖ. Simultaneous determination of selected flavonoids from different Cistus species by HPLC-PDA. J. Res. Pharm. 2025;22:405–410.
MLA Gürbüz, Perihan et al. “Simultaneous Determination of Selected Flavonoids from Different Cistus Species by HPLC-PDA”. Journal of Research in Pharmacy, vol. 22, no. 3, 2025, pp. 405-10, doi:10.12991/jrp.2018.80.
Vancouver Gürbüz P, Koşar M, Güvenalp Z, Kuruüzüm-uz A, Demirezer LÖ. Simultaneous determination of selected flavonoids from different Cistus species by HPLC-PDA. J. Res. Pharm. 2025;22(3):405-10.

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