Biological activities and luteolin derivatives of Verbascum eskisehirensis Karavel., Ocak & Ekici

Gözde Öztürk; Hale Gamze Ağalar; Gülsüm Yildiz; Fatih Göğer; Neşe Kirimer

Biological activities and luteolin derivatives of Verbascum eskisehirensis Karavel., Ocak & Ekici

Abstract

In this present study, the aerial parts of Verbascum eskisehirensis were dried in the shade and air-flowed area. The dried samples were macerated with 70% methanol in water for 24 h by three times. The biological activities of the extract was determined by in vitro methods. The antioxidant activity was evaluated in 2,2’-diphenyl-1 picrylhydrazyl (DPPH˙) radical scavenging assay and the trolox equivalent antioxidant capacity (TEAC) was measured the ability of the extract to scavenge the stable radical cation ABTS+ (2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)). The antibacterial effects against some clinical pathogens were tested by broth microdilution assay. The in vitro antiinflammatory activity was also examined by 5-Lipoxygenase (5-LOX) enzyme inhibitory test. In the same time, the phenolic composition of the extract was determined by LC-ESI-MS/MS system. According to results, the extract was found rich-in luteolin derivatives. The major compound was identified as luteolin-pentosyl-hexoside. The antioxidant activities of the extract were moderate. The extract showed weak antibacterial activity against tested bacteria strains. Salmonella typhimurium ATCC 13311 was more sensitive to the extract than the others. The extract showed weak antiinflammatory activity.

Keywords

References

[1] Kahraman C, Akdemir ZS, Tatli II. Promising cytotoxic activity profile, biological activities and phytochemical screening of Verbascum L. species. Med Aromatic Plant Sci Biotechnol. 2012; 6 (Special Issue 2): 63-75.
[2] Nofouzi K, Aghapour M, Ezazi A, Sheikhzadeh N, Tukmechi A, Khordadmehr M, Akbari M, Tahapour K, Mousavi M. Effects of Verbascum speciosum on Growth Performance, Intestinal Histology, Immune System and Biochemical Parameters in Rainbow Trout (Oncorhynchus mykiss). Turk J Fish Aqua Sci. 2017; 17: 145-152. [CrossRef]
[3] Mükemre M, Behçet L, Çakılcıoğlu U. Ethnobotanical study on medicinal plants in villages of Çatak (Van-Turkey). J Ethnopharmacol. 2015; 166: 361-374. [CrossRef]
[4] Dimitrova P, Georgiev MI, Khan MTH, Ivanovska N. Evaluation of Verbascum species and harpagoside in models of acute and chronic inflammation. Cent Eur J Biol. 2013; 8(2): 186-194. [CrossRef]
[5] Aysu T, Durak H. Pyrolysis of giant mullein (Verbascum thapsus L.) in a fixed-bed reactor: Effects of pyrolysis parameters on product yields and character. Energ Source Part A, Recovery, Util Environ Effects. 2016; 38(5): 661-669. [CrossRef]
[6] Brownstein KJ, Gargouri M, Folk WR, Gang DR. Iridoid and phenylethanoid/phenylpropanoid metabolite profiles of Scrophularia and Verbascum species used medicinally in North America. Metabolom. 2017; 13:133. [CrossRef]
[7] Youn IS, Han AR, Roh MS, Seo EK. Constituents of the Leaves of Verbascum blattaria. Nat Prod Commun. 2015; 10(3): 445-446.
[8] Arrif S, Lavaud C, Benkhaled M. Iridoids from Verbascum dentifolium. Biochem System Ecol. 2008; 36: 669-673. [CrossRef]

[9] Tatli II, Schuhly W, Kunert O, Bedir E, Akdemir ZS. Secondary Metabolites from the aerial parts of Verbascum dudleyanum and their biological activities. Chem Nat Comp. 2008; 44(3): 292-295.
[10] Tatli II, Takamatsu S, Khan IA, Akdemir ZS. Screening for Free Radical Scavenging and Cell Aggregation Inhibitory Activities by Secondary Metabolites from Turkish Verbascum species. Z Naturforsch. 2007; 62c: 673-678. [CrossRef]
[11] Miyase T, Horikoshi C, Yabe S, Miyasaka S, Melek FR, Kusano G. Saikosaponin homologues from Verbascum spp. The structures of Mulleinsaponins I-VII. Chem Pharm Bull. 1997; 45(12): 2029-2033. [CrossRef]
[12] Akdemir ZŞ, Tatlı İİ, Bedir E, Khan IA. Neolignan and phenylethanoid glycosides from Verbascum salviifolium Boiss. Turk J Chem. 2004; 28: 621-628.
[13] Öztürk A, Güney KB, Bani B, Güney K, Karavelioğulları FA, Pınar NM, Çeter T. Pollen morphology of some Verbascum (Scrophulariaceae) taxa in Turkey. Phytotaxa. 2018; 333(2): 209-218. [CrossRef]
[14] Karavelioğlu FA, Ocak A, Ekici M, Cabi E. Verbascum eskisehirensis sp. nov. (Scrophulariaceae) from central Anatolia, Turkey. Nord J Bot. 2009; 27: 222-227. [CrossRef]
[15] Papay V, Toth L, Osyath K, Bujtas G. On the flavonoids of Verbascum phlomoides. Pharmazie. 1980; 35(5/6): 334-335.
[16] Afifi MSA, Ahmed MM, Pezzuto JM, Kinghomt AD. Cytotoxic flavonolignans and flavones from Verbascum sinaiticum leaves. Phytochem. 1993; 34(3): 839-841. [CrossRef]
[17] Arrif S, Lavaud S, Benkhaled M. Iridoids from Verbascum dentifolium. Biochem System Ecol. 2008; 36(8): 669-673. [CrossRef]
[18] Tatlı İ, Akdemir ZS. Chemical constituents of Verbascum L. species. FABAD J Pharm Scien. 2004; 29: 93-107.
[19] Tatli İ, Akdemir ZS, Yesilada E, Kupeli E. Antiinflamatory and antinociceptive potential of major phenolics from V. salviifolium Boiss. Z Naturforsch C. 2008; 6(3): 196-202.
[20] Akdemir ZS, Tatlı İİ, Bedir E, Khan IA. Antioxidant Flavonoids from Verbascum salviifolium Boiss. FABAD J Pharm Sci. 2003; 28: 71-75.
[21] Akdemir Z, Kahraman Ç, Tatlı II, Akkol EK, Süntar I, Keles H. Bioassay-guided isolation of anti-inflammatory, antinociceptive and wound healer glycosides from the flowers of Verbascum mucronatum Lam. J Ethnopharmacol. 2011; 136: 436-443. [CrossRef]
[22] Boğa M, Ertaş A, Yılmaz MA, Kızıl M, Çeken B, Haşimi N, Özden TY, Demirci S, Yener İ, Deveci Ö. UHPLC-ESI MS/MS and GC-MS analyses on phenolic, fatty acid and essential oil of Verbascum pinetorum with antioxidant, anticholinesterase, antimicrobial and dna damage protection effects. Iran J Pharm Res. 2016; 15(3): 393-405.
[23] Danahaliloğlu, H. PhD Thesis. Determination of some chemical and biological properties of various Verbascum species growing in Hatay. Department of Chemistry, Institute of Sciences, Mustafa Kemal University, Hatay, 2014.
[24] Manav Yalçın S, Flavonoids from Verbascum cheiranthifolium Boiss. J Pharm Univ Mar. 1989; 5(2); 93-97.
[25] Gokmen A, Karaca N, Demirci F, Hohmann J, Kirmizibekmez H. Bioactivities of Verbascum bugulifolium and isolation of secondary metabolites. Planta Med Int Open. 2017; 4(S01): S1-S202. [CrossRef]
[26] Anil S, Dosler S, Mericli AH. Chemical composition and antimicrobial activity of Verbascum caesareum. Chem Nat Comp. 2016; 52(1): 125-127. [CrossRef]
[27] Boğa M, Ertaş A, Haşimi N, Demirci S, Yılmaz MA, Temel H, Kolak U. Phenolic profile, fatty acid and essential oil composition analysis and antioxidant, antialzheimer and antibacterial activities of Verbascum flavidum extracts. Chiang Mai J Sci. 2016; 43(5):1090-1101.
[28] Şen B. Master Thesis. Pharmacognostical investigation on some Verbascum Species in Marmara region. Department of Pharmacognosy, Institute of Health Science, Istanbul University, Beyazıt, İstanbul, Turkey, 2011.
[29] Güzel S. Master Thesis. Pharmacognostical investigations on Verbascum inulifolium Hub.-Mor. (Scrophulariaceae). Department of Pharmacognosy, Institute of Health Sciences, Mersin University, Mersin, Turkey, 2006.
[30] Özbilgin, B. MSC Thesis. Pharmacognostical investigation on Verbascum obtusifolium Hub.- Mor. (Scrophulariaceae). Department of Pharmacognosy, Institute of Health Sciences, Mersin University, Mersin, Turkey, 2006.
[31] Foster T. Staphylacoccus. In: Baron S (Ed). Medical Microbiology, 4th Edition. The University of Texas Medical Branch at Galveston Publisher, Galveston, 1996.
[32] Foster JW, Hall HK. Adaptive acidification tolerance response of Salmonella typhimurium. J Bacterol. 1990; 172(2): 771-778.
[33] Senatore F, Rigano D, Formisano C, Grassia A, Basile A, Sorbo S. Phytogrowth-inhibitory and antibacterial activity of Verbascum sinuatum. Fitoterapia. 2007; 78: 244-247. [CrossRef]
[34] Ghasemi F, Rezaei F, Araghi A, Tabari MA. Antimicrobial activity of aqueous-alcoholic extracts and the essential oil of Verbascum thapsus L. Jundishapur J Nat Pharm Prod. 2015; 10(3): 1-5. [CrossRef]
[35] Meurer-Grimes B, McBeth DL, Hallihan B, Delph S. Antimicrobial activity in medicinal plants of the Scrophulariaceae and Acanthaceae. Pharmaceut Biol. 1996; 34: 243-248. [CrossRef]
[36] Tadeg H, Mohammed E, Asres K, Gebre-Mariam T. Antimicrobial activities of some selected traditional Ethiopian medicinal plants used in the treatment of skin disorders. J Ethnopharmacol. 2005; 100: 168-175. [CrossRef]
[37] Dülger B, Kırmızı S, Arslan H, Güleryüz G. Antimicrobial activity of three endemic Verbascum species. Pharmaceut Biol. 2002; 40(8): 587-589. [CrossRef]
[38] Dülger B, Uğurlu E, Aki C, Suerdem TB, Camdeviren A, Tazeler G. Evaluation of antimicrobial activity of some endemic Verbascum, Sideritis, and Stachys species from Turkey. Pharmaceut Biol. 2005; 43(3): 270-274. [CrossRef]
[39] Akdemir ZŞ, Tatlı II, Bedir E, Khan IA. Antimicrobial and antimalarial activities of some endemic Turkish Verbascum species. FABAD J Pharm Sci. 2003; 28: 131-135.
[40] Aligiannis N, Mitaku S, Tsitsa-Tsardis E, Harvala C, Tsaknis I, Lalas S, Haroutounian S. Methanolic extract of Verbascum macrurum as a source of natural preservatives against oxidative rancidity. J Agric Food Chem. 2003; 51: 7308-7312. [CrossRef]
[41] Abou Gazar H, Bedir E, Khan IA, Calis I. Wiedemanniosides A-E, New phenylethanoid glycosides from the roots of Verbascum wiedemannianum. Planta Med. 2003; 69: 814-819. [CrossRef]
[42] Tepe B, Sokmen M, Akpulut HA, Yumrutas O, Sokmen, A. Screening of antioxidative properties of the methanolic extracts of Pelargonium endlicherianum Fenzl., Verbascum wiedemannianum Fisch. & Mey., Sideritis libanotica Labill. subsp. linearis (Bentham) Borm., Centaurea mucronifera DC. and Hieracium cappadocicum Freyn from Turkish flora. Food Chem. 2006; 98: 9-13. [CrossRef]
[43] Duymuş HG, Göger F, Başer KHC. In vitro antioxidant properties and anthocyanin compositions of elderberry extracts. Food Chem. 2014; 155: 112-119. [CrossRef]
[44] Stanoeva JP, Stefova M, Andonovska KB and Stafilov T. LC/DAD/MS and ICP-AES assay and correlations between phenolic compounds and toxic metals in endemic Thymus alsarensis from thallium enriched Allchar locality. Nat Prod Commun. 2017; 12:167-170.
[45] Baylac S, Racine P. Inhibition of 5-lipoxygenase by essential oils and other natural fragrant extracts. Int J Aroma. 2003; 13: 138-142. [CrossRef]
[46] Tatlı II, Akdemir ZŞ. Traditional uses and biological activities of Verbascum species. FABAD J Pharm Sci. 2006; 31: 85-96.
[47] Kupeli E, Tatli II, Akdemir ZS and Yesilada E. Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham. J Ethnopharmacol. 2007; 110: 444-450. [CrossRef]
[48] Tatli II, Akkol EK, Yesilada E and Akdemir ZS. Antinociceptive and anti- inflammatory activities of seven endemic Verbascum species growing in Turkey. Pharmaceut. Biol. 2008; 46: 781-788. [CrossRef]
[49] Süntar I, Tatlı II, Akkol EK, Keleş H, Kahraman Ç and Akdemir Z. An ethnopharmacological study on Verbascum species: From conventional wound healing use to scientific verification. J Ethnopharmacol. 2010; 132: 408-413. [CrossRef]
[50] Aziz N, Kim MY and Cho JY. Anti-inflammatory effects of luteolin: A review of in vitro, in vivo and in silico studies. J Ethnopharmacol. 2018; 225: 342-358. [CrossRef]

Details

Primary Language

English

Subjects

Pharmacognosy

Journal Section

Research Article

Authors

Gözde Öztürk ^*
Türkiye

Hale Gamze Ağalar
Türkiye

Gülsüm Yildiz This is me
Türkiye

Fatih Göğer
Türkiye

Neşe Kirimer This is me
Türkiye

Publication Date

June 27, 2025

Submission Date

December 17, 2018

Acceptance Date

February 1, 2019

Published in Issue

Year 2019 Volume: 23 Number: 3

IZ

https://izlik.org/JA66XB36FB

Cite

RIS / Bibtex

APA

Öztürk, G., Ağalar, H. G., Yildiz, G., Göğer, F., & Kirimer, N. (2025). Biological activities and luteolin derivatives of Verbascum eskisehirensis Karavel., Ocak & Ekici. Journal of Research in Pharmacy, 23(3), 532-542. https://izlik.org/JA66XB36FB

AMA

1.Öztürk G, Ağalar HG, Yildiz G, Göğer F, Kirimer N. Biological activities and luteolin derivatives of Verbascum eskisehirensis Karavel., Ocak & Ekici. J. Res. Pharm. 2025;23(3):532-542. https://izlik.org/JA66XB36FB

Chicago

Öztürk, Gözde, Hale Gamze Ağalar, Gülsüm Yildiz, Fatih Göğer, and Neşe Kirimer. 2025. “Biological Activities and Luteolin Derivatives of Verbascum Eskisehirensis Karavel., Ocak & Ekici”. Journal of Research in Pharmacy 23 (3): 532-42. https://izlik.org/JA66XB36FB.

EndNote

Öztürk G, Ağalar HG, Yildiz G, Göğer F, Kirimer N (June 1, 2025) Biological activities and luteolin derivatives of Verbascum eskisehirensis Karavel., Ocak & Ekici. Journal of Research in Pharmacy 23 3 532–542.

IEEE

[1]G. Öztürk, H. G. Ağalar, G. Yildiz, F. Göğer, and N. Kirimer, “Biological activities and luteolin derivatives of Verbascum eskisehirensis Karavel., Ocak & Ekici”, J. Res. Pharm., vol. 23, no. 3, pp. 532–542, June 2025, [Online]. Available: https://izlik.org/JA66XB36FB

ISNAD

Öztürk, Gözde - Ağalar, Hale Gamze - Yildiz, Gülsüm - Göğer, Fatih - Kirimer, Neşe. “Biological Activities and Luteolin Derivatives of Verbascum Eskisehirensis Karavel., Ocak & Ekici”. Journal of Research in Pharmacy 23/3 (June 1, 2025): 532-542. https://izlik.org/JA66XB36FB.

JAMA

1.Öztürk G, Ağalar HG, Yildiz G, Göğer F, Kirimer N. Biological activities and luteolin derivatives of Verbascum eskisehirensis Karavel., Ocak & Ekici. J. Res. Pharm. 2025;23:532–542.

MLA

Öztürk, Gözde, et al. “Biological Activities and Luteolin Derivatives of Verbascum Eskisehirensis Karavel., Ocak & Ekici”. Journal of Research in Pharmacy, vol. 23, no. 3, June 2025, pp. 532-4, https://izlik.org/JA66XB36FB.

Vancouver

1.Gözde Öztürk, Hale Gamze Ağalar, Gülsüm Yildiz, Fatih Göğer, Neşe Kirimer. Biological activities and luteolin derivatives of Verbascum eskisehirensis Karavel., Ocak & Ekici. J. Res. Pharm. [Internet]. 2025 Jun. 1;23(3):532-4. Available from: https://izlik.org/JA66XB36FB