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Antimicrobial, antioxidant, tyrosinase activities and volatile compounds of the Essential oil and Solvent Extract of Epilobium hirsutum L. growing in Turkey

Year 2020, Volume: 2 Issue: 2, 87 - 94, 29.12.2020
https://doi.org/10.51435/turkjac.813224

Abstract

TThe essential oil (EO), solid phase micro extraction (SPME), and SPME of n-hexane extract of Epilobium hirsutum L. were analyzed by GC-FID/MS. A total of 35, 20, and 32 compounds were identified from E. hirsutum, accounting for 98.2% in HD, 97.6% in SPME, and 98.8% in SPME of n-hexane extract, respectively. The EO and SPME consisted mainly of alcohol (HD: 51.5% vs. SPME: 30.8%). Aromatic hydrocarbons (57.1%) was the major compounds for the SPME of n-hexane extract. Monoterpenes were the minor constituents for the EO (2.3%) and SPME (3.1%) of the E. hirsutum. (Z)-3-Hexene-1-ol (46.5%), (Z)-3-hexenyl acetate (18.2%), and cyclohexanone (38%) were major compounds for the EO, SPME, and SPME of n-hexane of the E. hirsutum, respectively. The comparative study gave that the total amount of monoterpenoids (6.3%) was found only in the EO of E. hirsutum. The antimicrobial activity of EO and solvent extracts (n-hexane, methanol, and water) of E. hirsutum were screened in vitro against nine microorganisms. The EO resulted the best activity (10 mm) against Escherichia coli. Antimicrobial activity for the methanol extract of E. hirsutum against the Pseudomonas aeruginosa, Enterococcus faecalis, and Mycobacterium smegmatis was found to be 12 mm, 12 mm, and 16 mm inhibition zone, respectively. Methanol extract gave moderate active against the Yersinia pseudotuberculosis, Staphylococcus aureus, and Bacillus cereus within 6-8 mm, respectively. Antioxidant activity of water extract were found to be 12.7647±0.0145 µm (CUPRAC) and 0.034 mg/mL (IC50, DPPH). IC50 values for the tyrosinase enzyme inhibitory activity for the methanol, and water extracts was determined to be 0.196±0.013 µg/mL and 0.160±0.09 µg/mL, respectively.

Supporting Institution

Karadeniz Technical University

References

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Year 2020, Volume: 2 Issue: 2, 87 - 94, 29.12.2020
https://doi.org/10.51435/turkjac.813224

Abstract

References

  • [1] D.A. Baum, K.J. Sytsma, P.C. Hoch, A phylogenetic analysis of Epilobium (Onagraceae) based on nuclear ribosomal DNA sequences. Syst Bot, 19, 1994, 363-388.
  • [2] D. Chamberlain, P.H. Raven, Epilobium L. Flora of Turkey and The East Aegean Islan, pp. 183-196, Edinburgh Universty Press, 1972.
  • [3] N. Zeybek, U. Zeybek, Pharmaceutical botany, Ege University Faculty of Pharmacy Publication, Izmir, 1994.
  • [4] T. Ege, The pharmacological and therapeutic potentials of Epilobium hirsutum L, Int. J Pharm Sci Rev Res, 57, 2019, 20-23.
  • [5] S. Karakaya, I. Suntar, Ö.F. Yakinci, O. Sytar, S. Ceribasi, B. Dursunoglu, H. Ozbek, Z. Guvenalp, In vivo bioactivity assessment on Epilobium species: A particular focus on Epilobium angustifolium and its components on enzymes connected with the healing process, J Ethnopharmacol, 262, 2020, 113-207.
  • [6] S. Granica, J.P. Piwowarski, M.E. Czerwińska, A.K. Kiss, Phytochemistry, pharmacology and traditional uses of different Epilobium species J. (Onagraceae): a review, J Ethnopharmacol, 156, 2014, 316–346.
  • [7] L. Pirvu, V. Nicorescu, C. Hlevca, D.I. Udeanu, I. Nicorescu, Antimicrobial and synergistic activity of some whole and selective Epilobium hirsutum L. (great willowherb) extracts tested on standard and wild Staphylococcus aureus strains, Farmacia, 63, 2015, 690-695.
  • [8] A. Vitalone, J. McColl, D. Thome, L.G. Costa, B. Tita, Characterization of the effect of Epilobium extracts on human cell proliferation, Pharmacology, 69, 2003, 79-87.
  • [9] A. Sayik, A.S. Yusufoğlu, A. Leyla, G. Türker, B. Aydin, L. Arslan, Dna-binding, biological activities and chemical composition of wild growing Epilobium angustifolium L. extracts from Çanakkale, Turkey, J Turkish Chem Soc, 4, 2017, 811-840.
  • [10] R. Jacquet, Methods of use for oenothein A and oenothein B from Epilobium species to treat inflammation or improve hormone balance in postmenopausal women, U S Pat Appl Publ, 2020, US 20200179426, A1 20200611.
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  • [12] I. Nitescu, D. Cucu, D. Lapa, O. Contz, Studies on a new method for photochemical screening using chromatography of medicinal plants, Farmacia, 42, 1994, 41-43.
  • [13] D. Cando, D. Morcuende, M. Utrera, M. Estevez, Phenolic-rich extracts from Willowherb (Epilobium hirsutum L.) inhibit lipid oxidation but accelerate protein carbonylation and discoloration of beef patties, Eur Food Res Technol 238, 2014, 741-751.
  • [14] I. Remmel, L. Vares, L. Toom, V. Matto, A. Raal, Phenolic compounds in five Epilobium species collected from Estonia Nat Prod Commun, 7, 2012, 1323-1324.
  • [15] M. Pelc, O. Kosakowska, Z. Weglarz, J. Przybyl, A. Geszprych, Sterols and fatty acids in the seeds of evening primrose (Oenothera sp.) and willow herb (Epilobium sp.), Herba Pol, 51, 2005, 20-24.
  • [16] M.A. Nawwar, M.S. Marzouk, W. Nigge, M. Linscheid, High-performance liquid chromatographic/electrospray ionization mass spectrometric screening for polyphenolic compounds of Epilobium hirsutum - the structure of the unique ellagitannin epilobamide-A, J Mass Spectrom, 32, 1997, 645-654.
  • [17] J. De Pascual Teresa, B. Corrales, M. Grande, A review on presence of Oleanolic acid in Natural Products, Anales de Quimica, 75, 1979, 135-139. [18] S. Ivancheva, N. Manolova, J. Serkedjieva, V. Dimov, N. Ivanovska, Polyphenols from Bulgarian medicinal plants with anti-infectious activity, Basic Life Sci 59, 1992, 717-728.
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  • [20] B.H. Tóth, B. Blazics, Á. Kéry, Polyphenol composition and antioxidant capacity of Epilobium species. J Pharm Biomed, 49, 2009, 26-31.
  • [21] A. Vitalone, F. Bordi, C. Baldazzi, G. Mazzanti, L. Saso, B. Tita, Anti-proliferative effect on a prostatic epithelial cell line (PZ-HPV-7) by Epilobium angustifolium L., Il Farmaco, 56, 2001, 483-489.
  • [22] E. Ruszová, J. Cheel, S. Pávek, M. Moravcová, M. Hermannová, I. Matějková, J. Spilková, V. Velebný, and L. Kubala, Epilobium angustifolium extract demonstrates multiple effects on dermal fibroblasts in vitro and skin photo-protection in vivo, Gen Physiol Biophys, 32, 2013, 347-359.
  • [23] V. Kaškonienė, M. Stankevičius, T. Drevinskas, I. Akuneca, P. Kaškonas, K.B. Survilienė , A. Maruška, O. Ragažinskienė, O. Kornyšova, V. Briedis, R. Ugenskienė, Evaluation of phytochemical composition of fresh and dried raw material of introduced Chamerion angustifolium L. using chromatographic, spectrophotometric and chemometric techniques, Phytochemistry, 115, 2015, 184-193.
  • [24] H.C Onar, A. Yusufoglu, G. Turker, R. Yanardag, Elastase, tyrosinase and lipoxygenase inhibition and antioxidant activity of an aqueous extract from Epilobium angustifolium L. leave, J Med Plants Res, 6, 2012, 716-726.
  • [25] B.T. Hevesi, P.J. Houghton, S. Habtemariam, Á. Kéry, Antioxidant and anti-inflammatory effect of Epilobium parviflorum Schreb, Phytother Res, 23, 2009, 719-724.
  • [26] A.K. Kiss, A. Bazylko, A. Filipek, S. Granica, E. Jaszewska, U. Kiarszys, A. Kośmider, J. Piwowarski, Oenothein Bʼs contribution to the anti-inflammatory and antioxidant activity of Epilobium sp. Phytomedicine, 18, 2011, 557-560.
  • [27] H. Juan, W. Sametz, A. Hiermann, Anti-inflammatory effects of a substance extracted from Epilobium angustifolium, Agents and Actions, 23, 1988, 106-107.
  • [28] W.J. Bartfay, E. Bartfay, J.G. Johnson, Gram-negative and Gram-positive antibacterial properties of the whole plant extract of Willowherb (Epilobium angustifolium), Biol Res Nurs, 14,2012, 85-89.
  • [29] L. Battinelli, B. Tita, M.G. Evandri, G. Mazzanti, Antimicrobial activity of Epilobium spp. Extracts, Il Farmaco, 56, 2001, 345–348.
  • [30] I. Kosalec, N. Kopjar, D. Kremer, Antimicrobial activity of Willowherb (Epilobium angustifolium L.) leaves and flowers, Curr Drug Targets,14, 2013, 986-991.
  • [31] Q. Zeng, J. Wu, P. Lin, Chemical composition and antimicrobial activity of the essential oil from Epilobium angustifolium. Chem Natl Compd, 52, 2016, 1113-1115.
  • [32] S. Silló, E. Varga, Á. Belák, A. Maráz, Phytochemical and antimicrobial investigation of Epilobium angustifolium L., Acta Pharm Hung, 84, 2014, 105-110.
  • [33] B. Tita, H. Abdel-Haq, A. Vitalone, G. Mazzanti, L. Saso, Analgesic properties of Epilobium angustifolium, evaluated by the hot plate test and the writhing test, Il Farmaco 56, 2001, 341–343.
  • [34] M. Stolarczyk, M. Naruszewicz, A.K. Kiss, Extracts from Epilobium sp. herbs induce apoptosis in human hormone-dependent prostate cancer cells by activating the mitochondrial pathway, J Pharm Pharmacol, 65, 2013, 1044-1054.
  • [35] F. Pourmorad, M.A. Ebrahimzadeh, M. Mahmoudi, S. Yasini, Antinociceptive activity of methanolic extract of Epilobium hirsutum, Pak J Biol Sci, 10, 2007, 2764-2767.
  • [36] F. Vitali, G. Fonte, A. Saija, B. Tita, Inhibition of intestinal motility and secretion by extracts of Epilobium spp. in mice, J Ethnopharmacol, 107, 2006, 342–348.
  • [37] E. Ehsan, M.R. Akhgar, A. Kariminik, Chemical constituents and antibacterial activity of the essential oil from Epilobium hirsutum, J Biodivers Environ Sci, 7, 2015, 338-344.
  • [38] I. Erik, G. Kiliç, E. Öztürk, Ş.A. Karaoğlu, N. Yaylı, Chemical composition, antimicrobial and lipase enzyme activity of essential oil and solvent extracts from Serapias orientalis subs. orientalis, Turk J Chem, in press 2020. DOI: 10.3906/kim-2005-51.
  • [39] G. Tosun, N. Kahriman, C. Albay, Ş.A. Karaoğlu, N. Yaylı, Antimicrobial activity and volatile constituents of the flower, leaf, and stem of Paeonia daurica grown in Turkey, Turk J Chem, 35, 2011, 145-153.
  • [40] G. Renda, A. Özel, B. Barut, B. Korkmaz, N. Yaylı, 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, 2019, 1831-1842.
  • [41] B. Yaylı, G. Tosun, M. Karaköse, G. Renda, N. Yaylı, 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, 2014, 2541-2544.
  • [42] N. Yaylı, A. Yaşar, N. Yaylı, M. Albay, K. Coşkunçelebi, Essential oil analysis and antimicrobial activity of Paeonia mascula from Turkey, Nat. Prod. Commun, 3, 2008, 941-944.
  • [43] R.P. Adams, Identification of essential oil components by gas chromatography/mass spectrometry, Allured publishing corporation Carol Stream, IL, 2007.
  • [44] G.L. Woods, B.A. Brown-Elliott, P.S. Conville, E.P. Desmond, G.S. Hall, G. Lin, G.E. Pfyffer, J.C. Ridderhof, S.H. Siddiqi, R.J. Wallace Jr, N.G. Warren, F.G. Witebskyet, Susceptibility testing of mycobacteria, nocardiae, and other aerobic actinomycetes, Wayne (PA): Clinical and Laboratory Standards Institute, 2011.
  • [45] A.L. Barry, Standards NCCLS document, Methods for determining bactericidal activity of antimicrobial agents: approved guideline. National Committee for Clinical Laboratory Standards Wayne, 1999.
  • [46] R. Apak, K. Güçlü, B. Demirata, M. Özyürek, E.S. Çelik, B. Bektaşoğlu, I.K. Berker, D. Özyurt, Comparative evaluation of various total antioxidant capacity assays applied to phenolic compounds with the CUPRAC assay, Molecules, 12, 2007,1496-1547.
  • [47] M.S. Blois, Antioxidant determinations by the use of a stable free radical, Nature, 181, 1958, 1199–1200.
  • [48] R. Fu, Y. Zhang, Y. Guo, F. Chen, Antioxidant and tyrosinase inhibition activities of the ethanol-insoluble fraction of water extract of Sapium sebiferum (L.) Roxb. Leaves, S. Afr. J. Bot, 93, 2014, 98–104.
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There are 51 citations in total.

Details

Primary Language English
Subjects Analytical Chemistry
Journal Section Research Articles
Authors

Gözde Kılıç 0000-0003-1248-7912

Büşra Korkmaz 0000-0002-3747-8855

İshak Erik This is me 0000-0002-9729-1013

Seda Fandaklı This is me 0000-0002-8199-3336

Sevde Seher Yaylı This is me 0000-0002-5923-9302

Özlem Faiz This is me 0000-0003-2447-0763

Şengül Alpay Karaoğlu 0000-0003-1047-8350

Nurettin Yaylı 0000-0003-4174-3014

Publication Date December 29, 2020
Submission Date October 20, 2020
Acceptance Date November 21, 2020
Published in Issue Year 2020 Volume: 2 Issue: 2

Cite

APA Kılıç, G., Korkmaz, B., Erik, İ., Fandaklı, S., et al. (2020). 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), 87-94. https://doi.org/10.51435/turkjac.813224
AMA Kılıç G, Korkmaz B, Erik İ, Fandaklı S, Yaylı SS, Faiz Ö, Alpay Karaoğlu Ş, Yaylı N. Antimicrobial, antioxidant, tyrosinase activities and volatile compounds of the Essential oil and Solvent Extract of Epilobium hirsutum L. growing in Turkey. TurkJAC. December 2020;2(2):87-94. doi:10.51435/turkjac.813224
Chicago Kılıç, Gözde, Büşra Korkmaz, İshak Erik, Seda Fandaklı, Sevde Seher Yaylı, Özlem Faiz, Şengül Alpay Karaoğlu, and Nurettin Yaylı. “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, no. 2 (December 2020): 87-94. https://doi.org/10.51435/turkjac.813224.
EndNote Kılıç G, Korkmaz B, Erik İ, Fandaklı S, Yaylı SS, Faiz Ö, Alpay Karaoğlu Ş, Yaylı N (December 1, 2020) 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 87–94.
IEEE G. Kılıç, B. Korkmaz, İ. Erik, S. Fandaklı, S. S. Yaylı, Ö. Faiz, Ş. Alpay Karaoğlu, and N. Yaylı, “Antimicrobial, antioxidant, tyrosinase activities and volatile compounds of the Essential oil and Solvent Extract of Epilobium hirsutum L. growing in Turkey”, TurkJAC, vol. 2, no. 2, pp. 87–94, 2020, doi: 10.51435/turkjac.813224.
ISNAD Kılıç, Gözde et al. “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 (December 2020), 87-94. https://doi.org/10.51435/turkjac.813224.
JAMA Kılıç G, Korkmaz B, Erik İ, Fandaklı S, Yaylı SS, Faiz Ö, Alpay Karaoğlu Ş, Yaylı N. Antimicrobial, antioxidant, tyrosinase activities and volatile compounds of the Essential oil and Solvent Extract of Epilobium hirsutum L. growing in Turkey. TurkJAC. 2020;2:87–94.
MLA Kılıç, Gözde et al. “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, vol. 2, no. 2, 2020, pp. 87-94, doi:10.51435/turkjac.813224.
Vancouver Kılıç G, Korkmaz B, Erik İ, Fandaklı S, Yaylı SS, Faiz Ö, Alpay Karaoğlu Ş, Yaylı N. Antimicrobial, antioxidant, tyrosinase activities and volatile compounds of the Essential oil and Solvent Extract of Epilobium hirsutum L. growing in Turkey. TurkJAC. 2020;2(2):87-94.

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