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183 / 5,000 Türkiye'de Yetişen Epilobium angustifolium'un Çiçeği, Yaprağı ve Gövdesi İçin Esansiyel Yağların ve Çözücü Ekstraktlarının Karşılaştırmalı Kimyasal Bileşimi ve Antimikrobiyal Aktiviteleri

Year 2025, Volume: 46 Issue: 1, 27 - 34, 25.03.2025

Büşra Korkmaz , Gözde Bozdal , Şeyma Arıcı Tüfekçi , Büşra Şahin , Elif Öztürk , Şengül Alpay Karaoğlu , Serdar Makbul , Nurettin Yaylı

https://doi.org/10.17776/csj.1591654

Abstract

Epilobium angustifolium L.'nin çiçeğinden, yaprağından ve gövdesinden elde edilen uçucu yağların (EO'lar) ve katı faz mikroekstraksiyonunun (SPME) uçucu organik bileşikleri (VOC'ler) GC-FID/MS ile analiz edildi. EO'lar ve SPME'ler esas olarak, başlıca bileşik sınıfları olan monoterpenler ve aldehitlerden oluşur. Limonenin çiçekte (HD: %42,9'a karşı SPME: %95,5), yaprakta (HD: %60,3'e karşı SPME: %4,7) ve gövdede (HD: %49,06'ya karşı SPME: %93,6) başlıca bileşik olduğu bulundu. E. angustifolium'un EO'larının ve çözücü özütlerinin (n-hekzan, asetonitril ve metanol) antimikrobiyal aktivitesi dokuz mikroorganizmaya karşı in vitro tarandı. Yaprağın EO'su Mycobacterium smegmatis'e karşı en iyi aktiviteyi (10,2 µg/mL MİK) gösterdi. Tüm EO'lar ve çözücü özütleri 10,2-1300,0 µg/mL MİK değerleri aralığında Staphylococcus aureus, Bacillus cereus ve M. smegmatis'e karşı orta düzeyde aktivite gösterdi. En iyi antibakteriyel aktivite, sapın n-hekzan özütü ve çiçek örneklerinin metanol özütündeki S. aureus ve B. cereus'a karşı gözlendi.

Keywords

Epilobium angustifolium uçucu yağ SPME GC-FID/MS antimikrobiyal

Project Number

KTU-BAP (8881 and 6714)

References

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  • [2] Lans C., Possible similarities between the folk medicine historically used by First Nations and American Indians in North America and the ethnoveterinary knowledge currently used in British Columbia, Canada. J. Ethnopharmacol., 192 (2016) 53-66.
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  • [21] Kukina T., Frolova T., Salnikova O., Neutral constituents of Chamaenerion angustifolium leaves, Chem. Nat. Compd., 50(2) (2014) 233-236.
  • [22] Kiss A., Kowalski J., Melzig M., Induction of neutral endopeptidase activity in PC-3 cells by an aqueous extract of Epilobium angustifolium L. and oenothein B, Phytomedicine, 13(4) (2006) 284-289.
  • [23] Kiss A.K., Bazylko A., Filipek A., Granica S., Jaszewska E., Kiarszys U., Kośmider A., Piwowarski J., Oenothein B's contribution to the anti-inflammatory and antioxidant activity of Epilobium sp., Phytomedicine, 18(7) (2011) 557-560.
  • [24] Schepetkin I.A., Kirpotina L.N., Jakiw L., Khlebnikov A.I., Blaskovich C.L., Jutila M.A., Quinnet M.T., Immunomodulatory activity of oenothein B isolated from Epilobium angustifolium, J. Immunol. Res., 183(10) (2009) 6754-6766.
  • [25] Tosun G., Kahriman N., Albay C., Karaoğlu Ş.A., Yaylı N., Antimicrobial activity and volatile constituents of the flower, leaf, and stem of Paeonia daurica grown in Turkey, Turk. J. Chem., 35(1) (2011) 145-153.
  • [26] Renda G., Özel A., Barut B., Korkmaz B., Yaylı N., The Volatile Chemical Compositions of the Essential Oil/SPME and Enzyme Inhibitory and Radical Scavenging Activities of Solvent Extracts and the Essential oils from Coronilla orientalis Miller and C. varia L. grows in Turkey, Iran. J. Pharm. Res., 18(4) (2019) 1831-1842.
  • [27] Renda G., Celik G., Korkmaz B., Karaoglu S.A., Yaylı N., Antimicrobial activity and analyses of six Geranium L. species with headspace SPME and hydrodistillation, J. Essent. Oil-Bear. Plants, 19(8) (2016) 2003-2016.
  • [28] Yaylı B., Tosun G., Karaköse M., Renda G., Yaylı N., SPME/GC-MS analysis of volatile organic compounds from three Lamiaceae species (Nepeta conferta Hedge & Lamond, Origanum onites L. and Satureja cuneifolia Ten.) growing in Turkey, Asian J. Chem., 26(9) (2014) 2541-2544.
  • [29] Yaylı N., Yaşar A., Yaylı N., Albay M., Coşkunçelebi K., Essential Oil Analysis and Antimicrobial Activity of Paeonia mascula from Turkey, Nat. Prod. Commun., 3(6) (2008) 941-944.
  • [30] Iskender N.Y., Yaylı N., Yildrim N., Cansu T.B., Terzioglu S., The volatile constituents of the flower, leaf, and stem of Verbascum wiedemannianum grown in Turkey, J. Oleo Sci., 58(3) (2009) 117-121.
  • [31] Yılmaz G., Çiçek M., Demirci B., Başer K.H.C., Composition of the essential oils of five subspecies of Scutellaria orientalis from Turkey, J. Essent. Oil Res., 32(5) (2020) 429-435.
  • [32] Verma R.S., Verma S.K., Tandon S., Padalia R.C., Darokar M.P., Chemical composition and antimicrobial activity of Java citronella (Cymbopogon winterianus Jowitt ex Bor) essential oil extracted by different methods, J. Essent. Oil Res., 32(5) (2020) 1-7.
  • [33] Adams R.P., Identification of essential oil components by gas chromatography/mass spectrometry. Allured publishing corporation Carol Stream, IL (2007).
  • [34] Üçüncü O., Yaylı N., Yaşar A., Terzioğlu S., Yaylı N., Chemical Composition of the Essential Oils from Flower, Leaf, and Stem of Senecio trapezuntinus Boiss. Grown in Turkey, Nat. Prod. Commun., 3(6) (2008) 925-928.
  • [35] Barry A.L., Standards NCCLS document, Methods for determining bactericidal activity of antimicrobial agents: approved guideline. National Committee for Clinical Laboratory Standards Wayne (1999).
  • [36] Woods G.L., Brown-Elliott B.A., Conville P.S., Desmond E.P., Hall G.S., Lin G., Pfyffer G.E., Ridderhof J.C., Siddiqi S.H., Wallace R.J., Warren N.G., Witebskyet F.G., Susceptibility testing of mycobacteria, nocardiae, and other aerobic actinomycetes. Wayne (PA): Clinical and Laboratory Standards Institute (2011).
  • [37] Kılıç G., Korkmaz B., Erik İ., Fandaklı S., Yaylı S.S., Faiz Ö., Karaoğlu Ş.A., Yaylı N., Antimicrobial, antioxidant, tyrosinase activities and volatile compounds of the essential oil and solvent extract of Epilobium hirsutum L. growing in Turkey, Turkish Journal of Analytical Chemistry, 2(2) (2020) 87-94.
  • [38] Erasto P., Viljoen A.M., Limonene-A review: Biosynthetic, ecological and pharmacological relevance, Nat. Prod. Commun., 3(7) (2008) 1190-1202.

Comparative Chemical Composition and Antimicrobial Activities of The Essential Oils and Solvent Extracts of The Flower, Leaf, And Stem of Epilobium angustifolium Growing in Türkiye

Year 2025, Volume: 46 Issue: 1, 27 - 34, 25.03.2025

Büşra Korkmaz , Gözde Bozdal , Şeyma Arıcı Tüfekçi , Büşra Şahin , Elif Öztürk , Şengül Alpay Karaoğlu , Serdar Makbul , Nurettin Yaylı

https://doi.org/10.17776/csj.1591654

Abstract

Volatile organic compounds (VOCs) of essential oils (EOs) and solid phase microextract (SPME) obtained from the flower, leaf, and stem of Epilobium angustifolium L. were analyzed by GC-FID/MS. The EOs and SPMEs consist mainly of monoterpenes and aldehydes, which are major classes of compounds. Limonene was found to be a major compound in flower (HD: 42.9% vs. SPME: 95.5%), in leaf (HD: 60.3% vs. SPME: 4.7%), and in stem (HD: 49.06% vs. SPME: 93.6%). The antimicrobial activity of EOs and the solvent extracts (n-hexane, acetonitrile, and methanol) of E. angustifolium were screened in vitro against nine microorganisms. The EO of the leaf showed the best activity (10.2 µg/mL MIC) against Mycobacterium smegmatis. All the EOs and the solvent extracts gave moderate activity against the Staphylococcus aureus, Bacillus cereus, and M. smegmatis within the range of 10.2-1300.0 µg/mL MIC values. The best antibacterial activity was observed against S. aureus and B. cereus in the n-hexane extract of stem and methanol extract of flower samples.

Keywords

Epilobium angustifolium Essential oil SPME GC-FID/MS Antimicrobial

Project Number

KTU-BAP (8881 and 6714)

References

  • [1] Schepetkin I.A., Ramstead A.G., Kirpotina L.N., Voyich J.M., Jutila M.A., Quinn M.T., Therapeutic potential of polyphenols from Epilobium angustifolium (Fireweed), Phytother. Res., 30(8) (2016) 1287-1297.
  • [2] Lans C., Possible similarities between the folk medicine historically used by First Nations and American Indians in North America and the ethnoveterinary knowledge currently used in British Columbia, Canada. J. Ethnopharmacol., 192 (2016) 53-66.
  • [3] Zeybek N., Zeybek U., Pharmaceutical botany. Ege University Faculty of Pharmacy Publication, Izmir (1994).
  • [4] Granica S., Piwowarski J.P., Czerwińska M.E., Kiss A.K., Phytochemistry, pharmacology and traditional uses of different Epilobium species (Onagraceae): A review, J. Ethnopharmacol., 156 (2014) 316-346.
  • [5] Sayik A., Yusufoğlu A.S., Leyla A., Türker G., Aydin B., Arslan L., DNA-Binding, Biological Activities and Chemical Composition of Wild Growing Epilobium angustifolium L. Extracts from Çanakkale, Turkey, J. Turk. Chem. Society, 4(3) (2017) 811-840.
  • [6] Vitalone A., Guizzetti M., Costa L.G., Tita B., Extracts of various species of Epilobium inhibit proliferation of human prostate cells. J. Pharm. Pharmacol., 55(5) (2003) 683-690.
  • [7] Vitalone A., Bordi F., Baldazzi C., Mazzanti G., Saso L., B. Tita, Anti-proliferative effect on a prostatic epithelial cell line (PZ-HPV-7) by Epilobium angustifolium L., Farmaco. 56 (5-7) (2001) 483-489.
  • [8] Ruszová E., Cheel J., Pávek S., Moravcová M., Hermannová M., Matějková I., Spilková J., Velebný V., Kubala L., Epilobium angustifolium extract demonstrates multiple effects on dermal fibroblasts in vitro and skin photo-protection in vivo, Gen. Physiol. Biophys., 32(3) (2013) 347-359.
  • [9] Tóth B.H., Blazics B., Kéry Á., Polyphenol composition and antioxidant capacity of Epilobium species. J. Pharm. Biomed. Anal., 49(1) (2009) 26-31.
  • [10] Onar H.C., Yusufoglu A., Turker G., Yanardağ R., Elastase, tyrosinase and lipoxygenase inhibition and antioxidant activity of an aqueous extract from Epilobium angustifolium L. leaves, J. Med. Plant Res., 6(5) (2012) 716-726.
  • [11] Juan H., Sametz W., Hiermann A., Anti-inflammatory effects of a substance extracted from Epilobium angustifolium, Agents and Actions, 23(1-2) (1988) 106-107.
  • [12] Kosalec I., Kopjar N., Kremer D., Antimicrobial activity of Willowherb (Epilobium angustifolium L.) leaves and flowers, Curr. Drug Targets, 14(9) (2013) 986-991.
  • [13] Zeng Q., Wu J., Lin P., Chemical composition and antimicrobial activity of the essential oil from Epilobium angustifolium, Chem. Nat. Compd., 52(6) (2016) 1113-1115.
  • [14] Battinelli L., Tita B., Evandri M.G., Mazzanti G., Antimicrobial activity of Epilobium spp. Extracts, Farmaco., 56(5-7) (2001) 345-348.
  • [15] Silló S., Varga E., Belák Á., Maráz A., Phytochemical and antimicrobial investigation of Epilobium angustifolium L, Acta Pharm. Hung., 84(3) (2014) 105-110.
  • [16] Baum D.A., Sytsma K.J., Hoch P.C., A phylogenetic analysis of Epilobium (Onagraceae) based on nuclear ribosomal DNA sequences, Systematic Botany, 19(3) (1994) 363-388.
  • [17] Chamberlain D., Raven P.H., Epilobium L. Flora of Turkey and The East Aegean Island., Edinburgh University Press (1972) 183-196.
  • [18] Kaškonienė V., Stankevičius M., Drevinskas T., Akuneca I., Kaškonas P., Survilienė K.B., Maruška A., Ragažinskienė O., Kornyšova O., Briedis V., Ugenskienė R., Evaluation of phytochemical composition of fresh and dried raw material of introduced Chamerion angustifolium L. using chromatographic, spectrophotometric and chemometric techniques, Phytochem., 115 (2015) 184-193.
  • [19] Kaškonienė V., Maruška A., Akuņeca I., Stankevičius M., Ragažinskienė O., Bartkuvienė V., Kornyšova O., Briedis V., Ugenskienė R., Screening of antioxidant activity and volatile compounds composition of Chamerion angustifolium (L.) Holub ecotypes were grown in Lithuania, Nat. Prod. Res., 30(12) (2016) 1373-1381.
  • [20] Nowak A., Duchnik W., Makuch E., Kucharski L., Ossowicz-Rupniewska P., Cybulska K., Sulikowski T., Moritz M., Klimowicz A., Epilobium angustifolium L. Essential oil-biological activity and enhancement of the skin penetration of drugs-in vitro study, Molecules, 26(23) (2021) 7188.
  • [21] Kukina T., Frolova T., Salnikova O., Neutral constituents of Chamaenerion angustifolium leaves, Chem. Nat. Compd., 50(2) (2014) 233-236.
  • [22] Kiss A., Kowalski J., Melzig M., Induction of neutral endopeptidase activity in PC-3 cells by an aqueous extract of Epilobium angustifolium L. and oenothein B, Phytomedicine, 13(4) (2006) 284-289.
  • [23] Kiss A.K., Bazylko A., Filipek A., Granica S., Jaszewska E., Kiarszys U., Kośmider A., Piwowarski J., Oenothein B's contribution to the anti-inflammatory and antioxidant activity of Epilobium sp., Phytomedicine, 18(7) (2011) 557-560.
  • [24] Schepetkin I.A., Kirpotina L.N., Jakiw L., Khlebnikov A.I., Blaskovich C.L., Jutila M.A., Quinnet M.T., Immunomodulatory activity of oenothein B isolated from Epilobium angustifolium, J. Immunol. Res., 183(10) (2009) 6754-6766.
  • [25] Tosun G., Kahriman N., Albay C., Karaoğlu Ş.A., Yaylı N., Antimicrobial activity and volatile constituents of the flower, leaf, and stem of Paeonia daurica grown in Turkey, Turk. J. Chem., 35(1) (2011) 145-153.
  • [26] Renda G., Özel A., Barut B., Korkmaz B., Yaylı N., The Volatile Chemical Compositions of the Essential Oil/SPME and Enzyme Inhibitory and Radical Scavenging Activities of Solvent Extracts and the Essential oils from Coronilla orientalis Miller and C. varia L. grows in Turkey, Iran. J. Pharm. Res., 18(4) (2019) 1831-1842.
  • [27] Renda G., Celik G., Korkmaz B., Karaoglu S.A., Yaylı N., Antimicrobial activity and analyses of six Geranium L. species with headspace SPME and hydrodistillation, J. Essent. Oil-Bear. Plants, 19(8) (2016) 2003-2016.
  • [28] Yaylı B., Tosun G., Karaköse M., Renda G., Yaylı N., SPME/GC-MS analysis of volatile organic compounds from three Lamiaceae species (Nepeta conferta Hedge & Lamond, Origanum onites L. and Satureja cuneifolia Ten.) growing in Turkey, Asian J. Chem., 26(9) (2014) 2541-2544.
  • [29] Yaylı N., Yaşar A., Yaylı N., Albay M., Coşkunçelebi K., Essential Oil Analysis and Antimicrobial Activity of Paeonia mascula from Turkey, Nat. Prod. Commun., 3(6) (2008) 941-944.
  • [30] Iskender N.Y., Yaylı N., Yildrim N., Cansu T.B., Terzioglu S., The volatile constituents of the flower, leaf, and stem of Verbascum wiedemannianum grown in Turkey, J. Oleo Sci., 58(3) (2009) 117-121.
  • [31] Yılmaz G., Çiçek M., Demirci B., Başer K.H.C., Composition of the essential oils of five subspecies of Scutellaria orientalis from Turkey, J. Essent. Oil Res., 32(5) (2020) 429-435.
  • [32] Verma R.S., Verma S.K., Tandon S., Padalia R.C., Darokar M.P., Chemical composition and antimicrobial activity of Java citronella (Cymbopogon winterianus Jowitt ex Bor) essential oil extracted by different methods, J. Essent. Oil Res., 32(5) (2020) 1-7.
  • [33] Adams R.P., Identification of essential oil components by gas chromatography/mass spectrometry. Allured publishing corporation Carol Stream, IL (2007).
  • [34] Üçüncü O., Yaylı N., Yaşar A., Terzioğlu S., Yaylı N., Chemical Composition of the Essential Oils from Flower, Leaf, and Stem of Senecio trapezuntinus Boiss. Grown in Turkey, Nat. Prod. Commun., 3(6) (2008) 925-928.
  • [35] Barry A.L., Standards NCCLS document, Methods for determining bactericidal activity of antimicrobial agents: approved guideline. National Committee for Clinical Laboratory Standards Wayne (1999).
  • [36] Woods G.L., Brown-Elliott B.A., Conville P.S., Desmond E.P., Hall G.S., Lin G., Pfyffer G.E., Ridderhof J.C., Siddiqi S.H., Wallace R.J., Warren N.G., Witebskyet F.G., Susceptibility testing of mycobacteria, nocardiae, and other aerobic actinomycetes. Wayne (PA): Clinical and Laboratory Standards Institute (2011).
  • [37] Kılıç G., Korkmaz B., Erik İ., Fandaklı S., Yaylı S.S., Faiz Ö., Karaoğlu Ş.A., Yaylı N., Antimicrobial, antioxidant, tyrosinase activities and volatile compounds of the essential oil and solvent extract of Epilobium hirsutum L. growing in Turkey, Turkish Journal of Analytical Chemistry, 2(2) (2020) 87-94.
  • [38] Erasto P., Viljoen A.M., Limonene-A review: Biosynthetic, ecological and pharmacological relevance, Nat. Prod. Commun., 3(7) (2008) 1190-1202.
There are 38 citations in total.

Details

Primary Language English
Subjects Pharmacognosy, Natural Products and Bioactive Compounds
Journal Section Natural Sciences
Authors

Büşra Korkmaz 0000-0002-3747-8855

Gözde Bozdal 0000-0003-1248-7912

Şeyma Arıcı Tüfekçi 0009-0001-4791-8287

Büşra Şahin 0000-0002-2727-9801

Elif Öztürk 0000-0002-0809-6145

Şengül Alpay Karaoğlu 0000-0003-1047-8350

Serdar Makbul 0000-0001-8798-0926

Nurettin Yaylı 0000-0003-4174-3014

Project Number KTU-BAP (8881 and 6714)
Publication Date March 25, 2025
Submission Date November 28, 2024
Acceptance Date February 12, 2025
Published in Issue Year 2025Volume: 46 Issue: 1

Cite

APA Korkmaz, B., Bozdal, G., Arıcı Tüfekçi, Ş., Şahin, B., et al. (2025). Comparative Chemical Composition and Antimicrobial Activities of The Essential Oils and Solvent Extracts of The Flower, Leaf, And Stem of Epilobium angustifolium Growing in Türkiye. Cumhuriyet Science Journal, 46(1), 27-34. https://doi.org/10.17776/csj.1591654
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