Chemical Profiling and Antimicrobial Activity of Essential Oils from Hypericum adenotrichum Spach. An Endemic Species

Year 2023, Volume: 27 Issue: 4, 1645 - 1657, 28.06.2025

Nagehan Saltan , Yavuz Bülent Köse , Damla Kırcı , Fatih Göğer , Betül Demirci

Abstract

The purpose of this study was to determine the content of essential oils isolated from the herba and roots of Hypericum adenotrichum Spach., an endemic, wild-growing species of Turkish flora. Gas Chromatography-Mass Spectroscopy (GC-MS) and Gas Chromatography-Flame Ionization Detector (GC-FID) were used to examine the essential oils (EO). In the essential oils of the root of H. adenotrichum, the compounds were found, with undecane (64.4%), hexadecanoic acid (5.3%), and α -copaene (3.9%) as the primary components. Three significant herba compounds, germacrene D (13.3%), hexadecanoic acid (11.3%), and cadinene (6%) were found. Moreover, in this study antimicrobial effects of EO of endemic H. adenotrichum against Escherichia coli NRRL B-3008, Staphylococcus aureus ATCC 6538, Salmonella tymphirium ATCC 14028, Staphylococcus aureus ATCC 700699, Candida albicans ATCC 90028 and Candida krusei ATTC 6258. H. adenotrichum root and herba extracts were made, and LC-MS/MS analysis was used to determine the primary constituents of the extracts. The chemicals found in the herb and root, respectively, include 3-caffeoylquinic acid, 5-caffeoylquinic acid, quercetin hexoside, quinic acid, quercetin, and catechine.

Keywords

Antimicrobial activity , GC-MS , GC-FID , Hypericum adenotrichum , LC-MS/MS

References

• [1] Crockett SL, Robson NKB. Taxonomy and Chemotaxonomy of the Genus Hypericum. Med Aromat Plant Sci Biotechnol. 2011; 5: 1-13.
• [2] Demirci B, Baser KHC, Crockett S, Khan IA. Analyses of the volatile constituents of Asian Hypericum L. species. J Essent Oil Res. 2005; 17: 659–663. https://doi.org/10.1080/10412905.2007.9699287
• [3] Güner A, Aslan S, Ekim T, Vural M, Babac MT. List of Turkish flora vascular plants. Nezahat Gokyigit Botanical Garden and Flora Research Fondation, Istanbul, 2012.
• [4] Baytop T. Türkiye’de Bitkilerle Tedavi. Nobel Press, Ankara, 2021.
• [5] Patocka J. The chemistry, pharmacology, and toxicology of the biologically active constituents of the herb Hypericum perforatum L. J Appl Biomed. 2003; 1: 61–73. https://doi.org/10.32725/jab.2003.010
• [6] Ozkan EE, Mat A. An overview on Hypericum species of Turkey. J Pharmacognosy Phytother. 2013; 5(3): 38-46. https://doi.org/10.5897/JPP2013.0260
• [7] Medina MA, Martinez-Poveda B, Amores-Sanchez MI, Quesada AR. Hyperforin: More than an antidepressant bioactive compound? Life Sci. 2006; 79: 105–111. https://doi.org/10.1016/j.lfs.2005.12.027
• [8] Davis PH, Mill RR, Tan K. Flora of Turkey and the East Aegean Islands (Supplement). Edinburgh University Press, Edinburgh, 1988.
• [9] Baytop T. Türkiyede Bitkiler ile Tedavi. Istanbul University Press, Faculty of Pharmacy, 1999. No: 3255.
• [10] Cirak C, Radusien J, Janulis V, Ivanauskas L. Chemical constituents of Hypericum adenotrichum Spach, an endemic Turkish species. Nat Prod Res. 2009; 23(13): 1189–1195. https://doi.org/10.1080/14786410802393209
• [11] Crockett SL, Schaneberg B, Khan IA. Phytochemical profiling of new and old world Hypericum (St. John's Wort) species. Phytochem Anal. 2005; 16: 479-485. https://doi.org/10.1002/pca.875
• [12] Sarimahmut M, Balikci N, Celikler S, Ari F, Ulukaya E, Guleryuz G, Ozel MZ. Evaluation of genotoxic and apoptotic potential. Regul Toxicol Pharmacol. 2016; 74: 137-146. https://doi.org/10.1016/j.yrtph.2015.11.010
• [13] Ozmen AS, Gridling M, Inghuber J, Krasteva S, Sibylle K, Madlener S, Phuong Nha Vo T, Stark N, Saiko P, Fritzer-Szekeres M, Szekeres T, Askin-Celik T, Krenn L. In vitro anti-neoplastic activity of the ethno-pharmaceutical plant Hypericum adenotrichum Spach endemic to Western Turkey. Oncol Rep. 2009; 22: 845–852. https://doi.org/10.3892/or_00000508
• [14] Kurt BZ, Gazioglu I, Sevgi E, Sönmez F. Anticholinesterase, antioxidant, antiaflatoxigenic activities of ten edible wild plants from Ordu Area, Turkey. Iran J Pharm Sci. 2018; 17(3): 1047–1056.
• [15] Maltas E, Uysal A, Yildiztugay E, Aladag M, Yildiz S, Kucukoduk M. Investigation of antioxidant and antibacterial activities of some Hypericum species. Fresenius Environ Bull. 2013; 22: 862-869.
• [16] Boga M, Ertas A, Eroglu Ozkan E, Kizil M, Ceken B, Topcu G. Phytochemical analysis, antioxidant, antimicrobial, anticholinesterase and DNA protective effects of Hypericum capitatum var. capitatum extracts. S Afr J Bot. 2016; 104: 249-257. https://doi.org/10.1016/j.sajb.2016.02.204
• [17] Ozkan EE, Ozden TY, Ozsoy N, Mat A. Evaluation of chemical composition, antioxidant and anti-acetylcholinesterase activities of Hypericum neurocalycinum and Hypericum malatyanum. S Afr J Bot. 2018; 114: 104-110. https://doi.org/10.1016/j.sajb.2017.10.022
• [18] Bender O, Liorent Martínez EJ, Zengin G, Mollica A, Ceylan R, Molina-Garcia L, Atalay A. Integration of in vitro and in silico perspectives to explain chemical characterization, biological potential and anticancer effects of Hypericum salsugineum: A pharmacologically active source for functional drug formulations. PLoS One. 2018; 13(6): 1-21. https://doi.org/10.1371/journal.pone.0197815
• [19] Ayan AK, Cirak C. Hypericin and pseudohypericin contents in some Hypericum species growing in Turkey. Pharm Biol. 2008; 46(4): 288-291. https://doi.org/10.1080/13880200701741211
• [20] Yuce-Babacan E, Bagci E. Essential oil composition of Hypericum uniglandulosum Hausskn. ex Bornm. and Hypericum lydium Boiss. from Turkey. IJNLS. 2017; 1(1): 12-16.
• [21] Erken S, Malyer H, Demirci F, Baser KHC. Chemical investigations on some Hypericum species growing in Turkey-I. Chem Nat Compd. 2001; 37: 434-438. https://doi.org/10.1023/A:1014463124907
• [22] Baser KHC, Ozek T, Nuriddinov HR, Demirci AB. Essential oils of two Hypericum species from Uzbekistan. Chem Nat Compd. 2002; 38: 54-57. https://doi.org/10.1023/A:1015781715535
• [23] Crockett SL, Demirci B, Baser KHC, Khan IA. Volatile Constituents of Hypericum L. Section Myriandra (Clusiaceae): Species of the H. fasciculatum Lam. Alliance. J Essent Oil Res. 2007; 20: 244-249. https://doi.org/10.1080/10412905.2008.9700003
• [24] Mathis C, Ourisson G. Chemotaxonomic study of the genus Hypericum. III. Distribution of saturated hydrocarbons and monoterpenes in the essential oils of Hypericum. Phytochemistry. 1964; 3: 133-141.
• [25] Bertoli A, Pistelli L, Morelli I, Spinelli G, Menichini F. Constituents of Hypericum hircinum oils. J Essent Oil Res. 2000; 12: 617-620. https://doi.org/10.1080/10412905.2000.9712171
• [26] Yuce-Babacan E, Bagci E. The essential oils of the aerial parts of two Hypericum taxa (Hypericum triquetrifolium and Hypericum aviculariifolium subsp. depilatum var. depilatum) (Clusiaceae) from Turkey. Nat Prod Res. 2012; 26(21): 1985-1990. https://doi.org/10.1080/14786419.2011.636743
• [27] Bagci E, Yuce E. Constituents of the essential oils of two Hypericum capitatum Choisy varieties (var. capitatum and var. luteum Robson) from Turkey. J Essent Oil-Bear Plants. 2011; 14(1): 106-113. https://doi.org/10.1080/0972060X.2011.10643908
• [28] Ozkan EE, Demirci B, Gürer CU, Kültür Ş, Başer KHC, Mat A. Essential oil composition of five endemic Hypericum species from Turkey. Med Aromat Plants. 2013; 2: 121.
• [29] Aparna V, Dileep KV, Mandal PK, Karthe P, Sadasivan C, Haridas M. Anti-inflammatory property of n-hexadecanoic acid: Structural evidence and kinetic assessment. Chem Biol Drug Des. 2012; 80: 434–439. https://doi.org/10.1111/j.1747-0285.2012.01418.x
• [30] De Oliveira PF, Alves JM, Damasceno JL, Dias HJ, Crotti AE, Tavares DC. Cytotoxicity screening of essential oils in cancer cell lines. Rev Bras Farmacogn. 2015; 25: 183–188. https://doi.org/10.1016/j.bjp.2015.02.009
• [31] Xiong L, Peng C, Zhou QM, Wan F, Xie XF, Guo L, Li XH, He CJ, Dai O. Chemical composition and antibacterial activity of essential oils from different parts of Leonurus japonicus Houtt. Molecules. 2013; 18: 963–973. https://doi.org/10.3390/molecules18010963
• [32] Birkett MA, Al Abassi S, Krober T, Chamberlain K, Hooper AM, Guerin PM, Pettersson J, Pickett JA, Slade R, Wadhams LJ. Antiectoparasitic activity of the gum resin, gum haggar, from the East Africa plant, Commiphora holtziana. Phytochemistry. 2008; 69: 1710–1715. https://doi.org/10.1016/j.phytochem.2008.02.017
• [33] Kiran SR, Devi PS. Evaluation of mosquitocidal activity of essential oil and sesquiterpenes from leaves of Chloroxylon swietenia DC. Parasitol Res. 2007; 101: 413–418. https://doi.org/10.1007/s00436-007-0485-z
• [34] Bruce TJA, Birkett MA, Blande J, Hooper AM, Martin JL, Khambay B, Prosser I, Smart LE, Wadhams LJ. Response of economically important aphids to components of Hemizygia petiolata essential oil. Pest Manag Sci. 2005; 61: 1115–1121. https://doi.org/10.1002/ps.1102
• [35] Choi D, Kang W, Park T. Anti-allergic and anti-inflammatory effects of undecane on mast cells and keratinocytes. Molecules. 2020; 25: 1554. https://doi.org/10.3390/molecules25071554
• [36] Gudzic B, Djokovic D, Vajs, Palic R, Stojanovic G. Composition and antimicrobial activity of the essential oil of Hypericum maculatum Crantz. Flavour Fragr J. 2002; 17: 392-394. https://doi.org/10.1002/ffj.1112
• [37] Kizil G, Toker Z, Ozen HC. The antimicrobial activity of essential oils of Hypericum scabrum, Hypericum scabroides and Hypericum triquetrifolium. Phytother Res. 2004; 18(4): 339-341. https://doi.org/10.1002/ptr.1460
• [38] Maggi F, Cecchini C, Cresci A, Coman M, Trillini B, Papa F, Vittori S. Chemical composition and antimicrobial activity of Hypericum hircinum L. subsp. majus essential oil. Chem Nat Compd. 2010; 46: 125-129.
• [39] Crockett S, Schaneberg B, Khan IA. Phytochemical profiling of new and old world Hypericum (St. John’s Wort) species. Phytochem Anal. 2005; 16: 479–486. https://doi.org/10.1002/pca.875
• [40] Maggi F, Ferretti G, Pocceschi N, Menghini L, Ricciutelli M. Morphological, histochemical and phytochemical investigation of the genus Hypericum of the central Italy. Fitoterapia. 2004; 75: 702–711. https://doi.org/10.1016/j.fitote.2004.09.009
• [41] Ganzera M, Zhao J, Khan IA. Hypericum perforatum – Chemical profiling and quantitative results of St. John’s Wort products by an improved high-performance liquid chromatography method. J Pharm Sci. 2002; 91: 623–629. https://doi.org/10.1002/jps.10057
• [42] Smelcerovic A, Verma V, Spiteller M, Puri SC, Nabi Qazi G. Phytochemical analysis and genetic characterization of six Hypericum species from Serbia. Phytochemistry. 2006; 67: 171–178. https://doi.org/10.1016/j.phytochem.2005.10.021
• [43] Tatsis EC, Boeren S, Exarchou V, Troganis AN, Vervoort J, Gerothanassis IP. Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS. Phytochemistry. 2007; 68: 383–391. https://doi.org/10.1016/j.phytochem.2006.11.026
• [44] Kitanov GM. Hypericin and pseudohypericin in some Hypericum species. Biochem Syst Ecol. 2001; 29: 171–178. https://doi.org/10.1016/S0305-1978(00)00032-6
• [45] Cirak C, Radusiene J, Karabuk B, Janulis V, Ivanuaskas L. Variation of bioactive compounds in Hypericum perforatum growing in Turkey during its phenological cycle. J Integr Plant Biol. 2007; 49: 615–620. https://doi.org/10.1111/j.1744-7909.2007.00479.x
• [46] Cirak C, Radusiene J, Saglam B. Variation of bioactive substances in Hypericum montbretii during plant growth. Nat Prod Res. 2008; 22: 246–252. https://doi.org/10.1080/14786410701642623
• [47] Kazlauskas S, Bagdonaite E. Quantitative analysis of active substances in St. John’s wort (Hypericum perforatum L.) by the high performance liquid chromatography method. Medicina (Kaunas). 2004; 40(10): 975–981.
• [48] Chu YH, Chang CL, Hsu HF. Flavonoid content of several vegetables and their antioxidant activity. J Sci Food Agric. 2000; 80: 561–566. https://doi.org/10.1002/(SICI)1097-0010(200004)80:5%3C561::AID-JSFA574%3E3.0.CO;2-%23
• [49] Rainha N, Koci K, Coelho AV, Bptşsta J, Fernandes-Ferreira M. HPLC–UV–ESI-MS analysis of phenolic compounds and antioxidant properties of Hypericum undulatum shoot cultures and wild-growing plants. Phytochemistry. 2013; 86: 83-91. https://doi.org/10.1016/j.phytochem.2012.10.006
• [50] Cirak C, Radusiene J, Janulis V, Ivanuaskas L, Camas N, Ayan AK. Phenolic constituents of Hypericum triquetrifolium Turra (Guttiferae) growing in Turkey: variation among populations and plant parts. Turk J Biol. 2011; 35: 449-456. https://doi.org/10.3906/biy-1002-36
• [51] Cirak C, Radusiene J, Stanius Z, Camas N, Caliskan O, Odabas MS. Secondary metabolites of Hypericum orientale L. growing in Turkey: variation among populations and plant parts. Acta Physiol Plant. 2012; 34: 1313–1320. https://doi.org/10.1007/s11738-012-0928-8
• [52] Smelcerovic A, Zuehlke S, Spiteller M, Raabe N, Ozen T. Phenolic constituents of 17 Hypericum species from Turkey. Biochem Syst Ecol. 2008; 36: 316-319. https://doi.org/10.1016/j.bse.2007.09.002
• [53] Camas N, Radusiene J, Ivanauskas L, Jakstas V, Cirak C. Altitudinal changes in the content of bioactive substances in Hypericum orientale and Hypericum pallens. Acta Physiol Plant. 2014; 36: 675–686. https://doi.org/10.1007/s11738-013-1446-z
• [54] Kurt D, Caliskan O, Odabas M, Radusiene J, Cirak C. Modeling the altitudinal variation in secondary metabolite contents of Hypericum orientale from Turkey. Int Biol Biomed J. 2018; 4: 199-205.
• [55] Cirak C, Radusiene J, Camas N, Caliskan O, Odabas MS. Changes in the contents of main secondary metabolites in two Turkish Hypericum species during plant development. Pharm Biol. 2013; 51(3): 391-399. https://doi.org/10.3109/13880209.2012.733012
• [56] Taylor TA, Unakal CG. Staphylococcus aureus in StatPearls Publishing, Treasure Island (FL), 2017.
• [57] Karadag AE, Ustundag-Okur N, Demirci B, Demirci F. Rosmarinus officinalis L. essential oil encapsulated in new microemulsion formulations for enhanced antimicrobial activity. J Surfactants Deterg. 2021; 25(1): 95-103. https://doi.org/10.1002/jsde.12549
• [58] Saltan N, Kirci D, Kose YB, Demirci B. Chemical compositions and antimicrobial activity of Prunella vulgaris L. Int J Agric Environ Food Sci. (Special Issue 1), 2018; 186-189. https://doi.org/10.31015/jaefs.18032
• [59] Mc Lafferty FW, Stauffer DB. The Wiley/NBS Registry of Mass Spectral Data, J Wiley and Sons, New York, 1989.
• [60] Hochmuth DH. MassFinder 4.0 (Hochmuth Scientific Consulting, Hamburg, Germany, 2008).
• [61] National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved Standard-M27A2. CLSI, Wayne PA, USA, 2002.
• [62] National Committee for Clinical Laboratory Standards. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically. Approved Standard-M7A7. Wayne PA, USA, 2006.
• [63] Göger F, Köse YB, Göger G, Demirci F. Phytochemical characterization of phenolics by LC-MS/MS and biological evaluation of Ajuga orientalis from Turkey. Bangladesh J Pharmacol. 2015; 10: 639-644. https://doi.org/10.3329/bjp.v10i3.23500