Origanum minutiflorum O. Schwarz et P. H. Davis essential oil: enzyme inhibitory activities and chemical composition

Gülsüm Yıldız; Betül Demirci; Halide Edip Temel; Neşe Kırımer

Origanum minutiflorum O. Schwarz et P. H. Davis essential oil: enzyme inhibitory activities and chemical composition

Abstract

The essential oil (EO) of Origanum minutiflorum O. Schwarz et P. H. Davis was obtained by the hydrodistillation method. The analysis of the EO was conducted using Gas Chromatography (GC) and Gas Chromatography/Mass Spectrometry (GC/MS). The yield of the EO was determined to be 3.9%. Fifty-six compounds were identified, constituting 97.8% of the EO. The EO was rich in carvacrol at a rate of 83.3%, and the other major compounds were p-cymene (3.0%), β-caryophyllene (1.3%), trans-sabinene hydrate (1.1%), γ-terpinene (1.1%), borneol (1.1%), and terpinene-4-ol (1.0%). While the EO (100 µg/mL) demonstrated the highest inhibition on cyclooxygenase-1 (COX-1) with 55.26%, the inhibitory activities on the other enzymes were as follows: cyclooxygenase-2 (COX-2); 33.10%, and matrix metalloproteinase-9 (MMP-9); 12.87%. The EO had no inhibition on lipoxygenase (LOX). In this research, inhibitory activity of the EO of O. minutiflorum on COXs and MMP-9 enzymes was reported for the first time.

Keywords

References

[1] Cinbilgel I, Kurt Y. Oregano and/or marjoram: Traditional oil production and ethnomedical utilization of Origanum species in southern Turkey. J Herb Med. 2019; 16: 100257. https://doi.org/10.1016/j.hermed.2019.100257
[2] Jun WJ, Han BK, Yu KW, Kim MS, Chang IS, Kim HY, Cho HY. Antioxidant effects of Origanum majorana L. on superoxide anion radicals. Food Chem. 2001; 75(4): 439-444. https://doi.org/10.1016/S0308-8146(01)00233-3
[3] Bağci Y, Kan Y, Doğu S, Çelik SA. The essential oil compositions of Origanum majorana L. cultivated in Konya and collected from Mersin-Turkey. Indian J Pharm Educ Res. 2017; 51: 463-469. https://doi.org/10.5530/ijper.51.3s.68
[4] Sharifi-Rad M, Berkay Yılmaz Y, Antika G, Salehi B, Tumer TB, Kulandaisamy Venil C, Sharifi-Rad J. Phytochemical constituents, biological activities, and health-promoting effects of the genus Origanum. Phytother Res. 2021; 35(1): 95-121. https://doi.org/10.1002/ptr.6785
[5] Esen G, Azaz AD, Kurkcuoglu M, Baser KHC, Tinmaz A. Essential oil and antimicrobial activity of wild and cultivated Origanum vulgare L. subsp. hirtum (Link) letswaart from the Marmara region, Turkey. Flavour Fragr J. 2007; 22(5): 371-376. https://doi.org/10.1002/ffj.1808
[6] Özkan A, Erdoğan A. A comparative evaluation of antioxidant and anticancer activity of essential oil from Origanum onites (Lamiaceae) and its two major phenolic components. Turk J Biol. 2011; 35(6): 735-742. https://doi.org/10.3906/biy-1011-170
[7] Becer E, Mutlu Altundag E, Başer KHC, Vatansever HS. Cytotoxic activity and antioxidant effects of Origanum onites essential oil and its two major contents, carvacrol and p-cymene on human colorectal (HCT116) and hepatocelluler carcinoma (HepG2) cell lines. J Essent Oil Res. 2022; 34(6): 514-523. https://doi.org/10.1080/10412905.2022.2107101
[8] Avola R, Granata G, Geraci C, Napoli E, Graziano ACE, Cardile V. Oregano (Origanum vulgare L.) essential oil provides anti-inflammatory activity and facilitates wound healing in a human keratinocytes cell model. Food Chem Toxicol. 2020; 144: 111586. https://doi.org/10.1016/j.fct.2020.111586

[9] Gormez O, Diler O. In vitro antifungal activity of essential oils from Tymbra, Origanum, Satureja species and some pure compounds on the fish pathogenic fungus, Saprolegnia parasitica. Aquac Res. 2014; 45(7): 1196-1201. https://doi.org/10.1111/are.12060
[10] Koca SB, Cevikbas M. Antifungal effect of Origanum onites essential oil as an alternative to formalin in the artificial incubation of narrow-clawed crayfish (Astacus leptodactylus Eschscholtz, 1823). Aquac Res. 2015; 46(9): 2204-2210. https://doi.org/10.1111/are.12374
[11] Sarıkürkçü C, Zengin G, Oskay M, Uysal S, Ceylan R, Aktümsek A. Composition, antioxidant, antimicrobial and enzyme inhibition activities of two Origanum vulgare subspecies (subsp. vulgare and subsp. hirtum) essential oils. Ind Crops Prod. 2015; 70: 178-184. https://doi.org/10.1016/j.indcrop.2015.03.030
[12] Tonk FA, Yüce S, Bayram E, Akçali Giachino RR, Sönmez Ç, Telci I, Furan MA. Chemical and genetic variability of selected Turkish oregano (Origanum onites L.) clones. Plant Syst Evol. 2010; 288: 157-165. https://doi.org/10.1007/s00606-010-0320-3
[13] Başer KHC. The Turkish Origanum species. In: Oregano, The genera Origanum and Lippia, ed. By Kintzios SE, Taylor and Francis, London, 2002. pp. 109-126. eBook ISBN 9780429218972
[14] Lukas B, Samuel R, Mader E, Başer KHC, Duman H, Novak J. Complex evolutionary relationships in Origanum section Majorana (Lamiaceae). Bot J Linn Soc. 2013; 171(4): 667-686. https://doi.org/10.1111/boj.12022
[15] Kaplan B, Uçar Sözmen E, Turgut K. Chemical diversity of essential oils within the population of Origanum dubium Boiss. Nat Volatiles Essent Oils. 2019; 6(4): 6-12
[16] Aslim B, Yucel N. In vitro antimicrobial activity of essential oil from endemic Origanum minutiflorum on ciprofloxacin-resistant Campylobacter spp. Food Chem. 2008; 107(2): 602-606. https://doi.org/10.1016/j.foodchem.2007.08.048
[17] Oke F, Aslim B. Biological potentials and cytotoxicity of various extracts from endemic Origanum minutiflorum O. Schwarz & PH Davis. Food Chem Toxicol. 2010; 48(6): 1728-1733. https://doi.org/10.1016/j.fct.2010.03.053
[18] Elmastas M, Celik SM, Genc N, Aksit H, Erenler R, Gulcin İ. Antioxidant activity of an Anatolian herbal tea—Origanum minutiflorum: Isolation and characterization of its secondary metabolites. Int J Food Prop. 2018; 21(1): 374-384. https://doi.org/10.1080/10942912.2017.1416399
[19] Süntar I, Akkol EK, Keleş H, Oktem A, Başer KHC, Yeşilada E. A novel wound healing ointment: A formulation of Hypericum perforatum oil and sage and oregano essential oils based on traditional Turkish knowledge. J Ethnopharmacol. 2011; 134(1): 89-96. https://doi.org/10.1016/j.jep.2010.11.061
[20] Sarı AB, Üstüner-Aydal O. Antioxidant and immunostimulant effects of Origanum minutiflorum O. Schwarz et. P.H. Davis in rainbow trout. Fresenius Environ Bull. 2018; 27(2): 1013-1021.
[21] Anlaş C, Alkan FÜ, Sarı AB, Üstüner O, Bakırel T. Evaluation of the therapeutic potential of Origanum minutiflorum O. Schwarz et. PH Davis. Sağlık Bilimleri Veteriner Dergisi, Fırat Üniversitesi. 2017; 31(1): 27-32 (in Turkish).
[22] Özkan O, Aydemir I, Sarı İ, Dönmez G, Kırık FE, Savran A, Tuğlu Mİ. Investigation of cytotoxic effect of Origanum minutiflorum on cancer cells. Proceedings. 2017; 1(10): 991. https://doi.org/10.3390/proceedings1100991
[23] Özkan O, Özbey C, Aydemir I, Sari İ, Dönmez G, Kırık FE, Tuğlu Mİ. Investigation of the cytotoxic effect of Origanum minutiflorum on cancer cells. Celal Bayar Üniversitesi Sağlık Bilimleri Enstitüsü Dergisi. 2019; 6(2): 74-80 (in Turkish).
[24] Sari İ, Dönmez G, Kırık FE, Aydemir I, Özkan O, Savran A, Vural K, Tuğlu Mİ. The neurotoxic effects of Origanum minutiflorum. Proceedings. 2017; 1(10): 1026. https://doi.org/10.3390/proceedings1101026
[25] Antonelli M, Kushner I. It's time to redefine inflammation. The FASEB J. 2017; 31(5): 1787-1791. https://doi.org/10.1096/fj.201601326R
[26] Bäck M, Yurdagul Jr A, Tabas I, Öörni K, Kovanen PT. Inflammation and its resolution in atherosclerosis: Mediators and therapeutic opportunities. Nat Rev Cardiol. 2019; 16(7): 389-406. https://doi.org/10.1038/s41569-019-0169-2
[27] Shirato K, Kizaki T. SARS-CoV-2 spike protein S1 subunit induces pro-inflammatory responses via toll-like receptor 4 signaling in murine and human macrophages. Heliyon. 2021; 7(2): e06187. https://doi.org/10.1016/j.heliyon.2021.e06187
[28] Maruyama M, Rhee C, Utsunomiya T, Zhang N, Ueno M, Yao Z, Goodman SB. Modulation of the inflammatory response and bone healing. Front Endocrinol. 2020; 11: 386. https://doi.org/10.3389/fendo.2020.00386
[29] Sun QY, Zhou HH, Mao XY. Emerging roles of 5-lipoxygenase phosphorylation in inflammation and cell death. Oxid Med Cell Longev. 2019; 2019: 2749173. https://doi.org/10.1155/2019/2749173
[30] Butovich IA, Lukyanova SM. Inhibition of lipoxygenases and cyclooxygenases by linoleyl hydroxamic acid: comparative in vitro studies. J Lipid Res. 2008; 49(6): 1284-1294. https://doi.org/10.1194/jlr.M700602-JLR200
[31] Ouellet M, Percival MD. Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995; 306 (1): 247-251. https://doi.org/10.1042/bj3060247
[32] Rouzer CA, Marnett LJ. Cyclooxygenases: structural and functional insights. J Lipid Res. 2009; 50: S29-S34. https://doi.org/10.1194/jlr.R800042-JLR200
[33] Limongelli V, Bonomi M, Marinelli L, Gervasio FL, Cavalli A, Novellino E, Parrinello M. Molecular basis of cyclooxygenase enzymes (COXs) selective inhibition. Proc Natl Acad Sci. 2010; 107 (12): 5411-5416. https://doi.org/10.1073/pnas.0913377107
[34] Charlier C, Michaux C. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. Eur J Med Chem. 2003; 38 (7-8): 645-659. https://doi.org/10.1016/S0223-5234(03)00115-6
[35] Corbel M, Belleguic C, Boichot E, Lagente V. Involvement of gelatinases (MMP-2 and MMP-9) in the development of airway inflammation and pulmonary fibrosis. Cell Biol Toxicol. 2002; 18 (1): 51-61. https://doi.org/10.1023/a:1014471213371
[36] Halade GV, Jin YF, Lindsey ML. Matrix metalloproteinase (MMP)-9: a proximal biomarker for cardiac remodeling and a distal biomarker for inflammation. Pharmacol Ther. 2013; 139 (1): 32-40. https://doi.org/10.1016/j.pharmthera.2013.03.009
[37] Gutierrez FRS, Lalu MM, Mariano FS, Milanezi CM, Jonathan C, Gerlach RF, Silva JS. Increased activities of cardiac matrix metalloproteinases matrix metalloproteinase (MMP)-2 and MMP-9 are associated with mortality during the acute phase of experimental Trypanosoma cruzi infection. J Infect Dis. 2008; 197 (10): 1468-1476. https://doi.org/10.1086/587487
[38] Lee HM, Ciancio SG, Tuter G, Ryan ME, Komaroff E, Golub LM. Subantimicrobial dose doxycycline efficacy as a matrix metalloproteinase inhibitor in chronic periodontitis patients is enhanced when combined with a non-steroidal anti-inflammatory drug. J Periodontol. 2004; 75: 453–463. https://doi.org/10.1902/jop.2004.75.3.453
[39] Zhang Y, Gu Y, Lee HM, Hambardjieva E, Vranková K, Golub LM, Johnson F. Design, synthesis and biological activity of new polyenolic inhibitors of matrix metalloproteinases: a focus on chemically-modified curcumins. Curr Med Chem. 2012; 19 (25): 4348-4358. https://doi.org/10.2174/092986712802884295
[40] Hanáková Z, Hosek J, Kutil Z, Temml V, Landa P, Vanek T, Smejkal K. Anti-inflammatory activity of natural geranylated flavonoids: Cyclooxygenase and lipoxygenase inhibitory properties and proteomic analysis. J Nat Prod. 2017; 80(4): 999-1006. https://doi.org/10.1021/acs.jnatprod.6b01011
[41] Belal A, Elanany MA, Raafat M, Hamza HT, Mehany AB. Calendula officinalis phytochemicals for the treatment of wounds through matrix metalloproteinases-8 and 9 (MMP-8 and MMP-9): In silico approach. Nat Prod Commun. 2022; 17(5): 1934578X221098848. https://doi.org/10.1177/1934578X221098848
[42] Başer KHC, Tümen G, Sezik E. The essential oil of Origanum minutiflorum O. Schwarz and PH Davis. J Essent Oil Res. 1991; 3(6): 445-446. https://doi.org/10.1080/10412905.1991.9697982
[43] Kırımer N, Başer KHC, Tümen G. Carvacrol-rich plants in Turkey. Chem Nat Compd. 1995; 31(1): 37-41. https://doi.org/10.1007/BF01167568
[44] Baydar H. The effect of different harvesting times on essential oil content and essential oil components of highland thyme (Origanum minutiflorum O. Schwarz et P.H. Davis). Akdeniz University Journal of the Faculty of Agriculture. 2005; 18 (2): 175-178.
[45] Figueredo G, Cabassu P, Chalchat JC, Pasquier B. Studies of Mediterranean Oregano populations. VII: Chemical composition of essential oils of carvacrol-rich Oregano of various origins. J Essent Oil Res. 2006; 18(3): 244-249. https://doi.org/10.1080/10412905.2006.9699077
[46] Özkum D, Kürkçüoğlu M, Tipirdamaz R, Başer KHC. Essential oils from wild and micropropagated plants of Origanum minutiflorum O. Schwarz et Davis. J Essent Oil Res. 2010; 22: 135-137. https://doi.org/10.1080/10412905.2010.9700284
[47] Toker R, Gölükcü M, Tokgöz H. Effects of distillation times on essential oil compositions of Origanum minutiflorum O. Schwarz Et. PH Davis. J Essent Oil Res. 2017; 29(4): 330-335. https://doi.org/10.1080/10412905.2016.1276026
[48] Babushok VI, Linstrom PJ, Zenkevich IG. Retention indices for frequently reported compounds of plant essential oils. J Phys Chem Ref Data. 2011; 40(4): 043101. https://doi.org/10.1063/1.3653552
[49] Loizzo MR, Menichini F, Conforti F, Tundis R, Bonesi M, Saab AM, Frega NG. Chemical analysis, antioxidant, antiinflammatory and anticholinesterase activities of Origanum ehrenbergii Boiss. and Origanum syriacum L. essential oils. Food Chem. 2009; 117(1): 174-180. https://doi.org/10.1016/j.foodchem.2009.03.095
[50] Ocana-Fuentes A, Arranz-Gutierrez E, Senorans FJ, Reglero G. Supercritical fluid extraction of oregano (Origanum vulgare) essentials oils: anti-inflammatory properties based on cytokine response on THP-1 macrophages. Food Chem Toxicol. 2010; 48(6): 1568-1575. https://doi.org/10.1016/j.fct.2010.03.026
[51] El Kharraf S, El-Guendouz S, Farah A, Bennani B, Mateus MC, Miguel MG. Hydrodistillation and simultaneous hydrodistillation-steam distillation of Rosmarinus officinalis and Origanum compactum: Antioxidant, anti-inflammatory, and antibacterial effect of the essential oils. Ind Crops Prod. 2021; 168: 113591. https://doi.org/10.1016/j.indcrop.2021.113591
[52] Al-Mijalli SH, Mrabti NN, Ouassou H, Sheikh RA, Assaggaf H, Bakrim S, Mrabti HN. Chemical composition and antioxidant, antimicrobial, and anti-inflammatory properties of Origanum compactum Benth essential oils from two regions: in vitro and in vivo evidence and in silico molecular investigations. Molecules. 2022; 27(21): 7329. https://doi.org/10.3390/molecules27217329
[53] Demirci F, Teralı K, Karadağ AE, Biltekin SN, Ak Sakallı E, Demirci B, Koşar M, Başer KHC. In vitro and in silico evaluation of ACE2 and LOX inhibitory activity of Origanum essential oils and carvacrol. Planta Med. 2022; Epub ahead of print.
[54] Landa P, Kokoska L, Pribylova M, Vanek T, Marsik P. In vitro anti-inflammatory activity of carvacrol: Inhibitory effect on COX-2 catalyzed prostaglandin E2 biosynthesis. Arch Pharm Res. 2009; 32(1): 75-78. https://doi.org/10.1007/s12272-009-1120-6
[55] Wagner H, Wierer M, Bauer R. In vitro inhibition of prostaglandin biosynthesis by essential oils and phenolic compounds. Planta Med. 1986; (3): 184-187.
[56] Mahtaj LG, Feizpour A, Kianmehr M, Soukhtanloo M, Boskabady MH. The effect of carvacrol on systemic inflammation in guinea pigs model of COPD induced by cigarette smoke exposure. Pharmacol Rep. 2015; 67(1): 140-145. https://doi.org/10.1016/j.pharep.2014.08.017
[57] Subramaniyan J, Krishnan G, Balan R, Divya MGJ, Ramasamy E, Ramalingam S, Thiruvengadam D. Carvacrol modulates instability of xenobiotic metabolizing enzymes and downregulates the expressions of PCNA, MMP-2, and MMP-9 during diethylnitrosamine-induced hepatocarcinogenesis in rats. Mol Cell Biochem. 2014; 395(1-2): 65-76. https://doi.org/10.1007/s11010-014-2112-5
[58] Przybyłowska M, Dzierzbicka K, Kowalski S, Chmielewska K, Inkielewicz-Stepniak I. Therapeutic potential of multifunctional derivatives of cholinesterase inhibitors. Curr Neuropharmacol. 2021; 19(8): 1323. https://doi.org/10.2174/1570159X19666201218103434
[59] Orhan İ, Kartal M, Kan Y, Şener B. Activity of essential oils and individual components against acetyland butyrylcholinesterase. Z Naturforsch. C 2008; 63(7-8): 547-553. https://doi.org/10.1515/znc-2008-7-813
[60] de Cássia da Silveira e Sá R, Andrade LN, de Sousa DP. A review on anti-inflammatory activity of monoterpenes. Molecules. 2013; 18(1): 1227-1254. https://doi.org/10.3390/molecules18011227
[61] Fidyt K, Fiedorowicz A, Strządała L, Szumny A. β-Caryophyllene and β-caryophyllene oxide-natural compounds of anticancer and analgesic properties. Cancer Med. 2016; 5(10): 3007-3017. https://doi.org/10.1002/cam4.816
[62] de Santana MF, Guimaraes AG, Chaves DO, Silva JC, Bonjardim LR, Lucca Júnior WD, Quintans-Júnior LJ. The anti-hyperalgesic and anti-inflammatory profiles of p-cymene: Evidence for the involvement of opioid system and cytokines. Pharm Biol. 2015; 53(11): 1583-1590. https://doi.org/10.3109/13880209.2014.993040
[63] Zhong W, Chi G, Jiang L, Soromou LW, Chen N, Huo M, Feng H. p-Cymene modulates in vitro and in vivo cytokine production by inhibiting MAPK and NF-κB activation. Inflammation. 2013; 36: 529-537. https://doi.org/10.1007/s10753-012-9574-y
[64] Khan AUR, Huang K, Jinzhong Z, Zhu T, Morsi Y, Aldalbahi A, Mo X. PLCL/Silk fibroin based antibacterial nano wound dressing encapsulating Oregano essential oil: Fabrication, characterization and biological evaluation. Colloids and Surf B: Biointerfaces. 2020; 196: 111352-111352. https://doi.org/10.1016/j.colsurfb.2020.111352
[65] Plati F, Paraskevopoulou A. Micro-and nano-encapsulation as tools for essential oils advantages’ exploitation in food applications: The case of Oregano essential oil. Food Bioproc Tech. 2022; 15(5): 949-977. https://doi.org/10.1007/s11947-021-02746-4
[66] Perumalsamy H, Shanmugam R, Kim JR, Anandapadmanaban G, Huq M, Dua K, Balusamy SR. Nanoemulsion and encapsulation strategy of hydrophobic oregano essential oil increased human prostate cancer cell death via apoptosis by attenuating lipid metabolism. Bioinorg Chem Appl. 2022. https://doi.org/10.1155/2022/9569226
[67] McLafferty FW, Stauffer DB. The wiley/NBS registry of mass spectral data. J. Wiley and Sons, New York, 1989.
[68] Koenig WA, Joulain D, Hochmuth DH. Terpenoids and related constituents of essential oils. MassFinder 3, ed. By Hochmuth DH. Hamburg, Germany, 2004.
[69] Baylac S, Racine P. Inhibition of 5-lipoxygenase by essential oils and other natural fragrant extracts. Int J Aromather. 2003; 13(2-3): 138-142. https://doi.org/10.1016/S0962-4562(03)00083-3

Details

Primary Language

English

Subjects

Pharmacognosy

Journal Section

Research Article

Authors

Gülsüm Yıldız ^*
0000-0002-1697-7380
Türkiye

Betül Demirci
0000-0003-2343-746X
Türkiye

Halide Edip Temel
0000-0002-5233-1165
Türkiye

Neşe Kırımer
0000-0001-7866-7719
Türkiye

Publication Date

June 28, 2025

Submission Date

January 6, 2023

Acceptance Date

March 1, 2023

Published in Issue

Year 2023 Volume: 27 Number: 5

IZ

https://izlik.org/JA64CE43DS

Cite

RIS / Bibtex

APA

Yıldız, G., Demirci, B., Temel, H. E., & Kırımer, N. (2025). Origanum minutiflorum O. Schwarz et P. H. Davis essential oil: enzyme inhibitory activities and chemical composition. Journal of Research in Pharmacy, 27(5), 2160-2169. https://izlik.org/JA64CE43DS

AMA

1.Yıldız G, Demirci B, Temel HE, Kırımer N. Origanum minutiflorum O. Schwarz et P. H. Davis essential oil: enzyme inhibitory activities and chemical composition. J. Res. Pharm. 2025;27(5):2160-2169. https://izlik.org/JA64CE43DS

Chicago

Yıldız, Gülsüm, Betül Demirci, Halide Edip Temel, and Neşe Kırımer. 2025. “Origanum Minutiflorum O. Schwarz et P. H. Davis Essential Oil: Enzyme Inhibitory Activities and Chemical Composition”. Journal of Research in Pharmacy 27 (5): 2160-69. https://izlik.org/JA64CE43DS.

EndNote

Yıldız G, Demirci B, Temel HE, Kırımer N (July 1, 2025) Origanum minutiflorum O. Schwarz et P. H. Davis essential oil: enzyme inhibitory activities and chemical composition. Journal of Research in Pharmacy 27 5 2160–2169.

IEEE

[1]G. Yıldız, B. Demirci, H. E. Temel, and N. Kırımer, “Origanum minutiflorum O. Schwarz et P. H. Davis essential oil: enzyme inhibitory activities and chemical composition”, J. Res. Pharm., vol. 27, no. 5, pp. 2160–2169, July 2025, [Online]. Available: https://izlik.org/JA64CE43DS

ISNAD

Yıldız, Gülsüm - Demirci, Betül - Temel, Halide Edip - Kırımer, Neşe. “Origanum Minutiflorum O. Schwarz et P. H. Davis Essential Oil: Enzyme Inhibitory Activities and Chemical Composition”. Journal of Research in Pharmacy 27/5 (July 1, 2025): 2160-2169. https://izlik.org/JA64CE43DS.

JAMA

1.Yıldız G, Demirci B, Temel HE, Kırımer N. Origanum minutiflorum O. Schwarz et P. H. Davis essential oil: enzyme inhibitory activities and chemical composition. J. Res. Pharm. 2025;27:2160–2169.

MLA

Yıldız, Gülsüm, et al. “Origanum Minutiflorum O. Schwarz et P. H. Davis Essential Oil: Enzyme Inhibitory Activities and Chemical Composition”. Journal of Research in Pharmacy, vol. 27, no. 5, July 2025, pp. 2160-9, https://izlik.org/JA64CE43DS.

Vancouver

1.Gülsüm Yıldız, Betül Demirci, Halide Edip Temel, Neşe Kırımer. Origanum minutiflorum O. Schwarz et P. H. Davis essential oil: enzyme inhibitory activities and chemical composition. J. Res. Pharm. [Internet]. 2025 Jul. 1;27(5):2160-9. Available from: https://izlik.org/JA64CE43DS