Chemical Composition of Hydrodistillated Essential Oil of Heracleum antasiaticum MANDEN (L.) and its Antimicrobial Activity Against Food-Borne Microorganisms

Year 2025, Volume: 39 Issue: 2, 467 - 475, 27.08.2025

Furkan Çoban , Bülent Çetin , Hakan Özer , Zehra Toktay , Beyzanur Budak , Hilal Angın , Ali Kandemir

https://doi.org/10.15316/selcukjafsci.1683861

Abstract

The essential oil obtained by hydrodistillation from the aerial parts of Heracleum antasiaticum MANDEN from Türkiye was analyzed by GC and GC-MS. Forty-five compounds were characterized, representing 92.7 % of the total components detected, and elemicin (27.8%), apiole (26.2%), n-octanol (4.9%), α-zingiberene (3.9%), octyl acetate (3.8%), and (E)-γ-bisabolene (3.1%) were identified as predominant components. In addition, in this study, the essential oil was tested for its antimicrobial activity against 23 different food-borne microorganisms including 20 bacteria, 1 fungi and 2 yeast species. The essential oil of Heracleum antasiaticum exhibited considerable inhibitory effects against all bacteria, fungi and yeast species tested.

Keywords

Heracleum antasiaticum , essential oil , elemicin , apiole , antimicrobial activity

(L.) Heracleum antasiaticum MANDEN Türüne Ait Hidrodistilasyonla Elde Edilen Uçucu Yağın Kimyasal Bileşimi ve Gıda Kaynaklı Mikroorganizmalara Karşı Antimikrobiyal Aktivitesi

Abstract

Türkiye'de yetişen Heracleum antasiaticum MANDEN türünün toprak üstü kısımlarından hidrodistilasyon yöntemiyle elde edilen uçucu yağ, GC ve GC-MS analizleri ile incelenmiştir. Analizler sonucunda toplam bileşenlerin %92,7’sini temsil eden kırk beş bileşik karakterize edilmiştir. Bu bileşikler arasında elemisin (%27,8), apiol (%26,2), n-oktanol (%4,9), α-zingiberen (%3,9), oktil asetat (%3,8) ve (E)-γ-bisabolen (%3,1) en baskın bileşenler olarak belirlenmiştir. Ayrıca bu çalışmada, elde edilen uçucu yağın 20 bakteri, 1 mantar ve 2 maya türü olmak üzere toplam 23 farklı gıda kaynaklı mikroorganizmaya karşı antimikrobiyal aktivitesi test edilmiştir. Heracleum antasiaticum uçucu yağı, test edilen tüm bakteri, mantar ve maya türleri üzerinde önemli düzeyde inhibe edici etki göstermiştir.

Keywords

Heracleum antasiaticum , essential oil , elemicin , apiole , antimicrobial activity

References

• Adams RP (2007). Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. Allured Publishing Co., Carol Stream, Illinois, USA. p.104.
• Akcin A, Seyis F, Akcin TA, Cayci YT, Coban AY (2013). Chemical composition and antimicrobial activity of the essential oil of endemic Heracleum platytaenium Boiss. from Turkey. Journal of Essential Oil Bearing Plants 16(2), 166–171.
• Amaike S, Keller NP (2011). Aspergillus flavus. Annual Review of Phytopathology 49, 107–133.
• Baser K, Kürkçüoglu M, Adigüzel N, Aytac Z, Joulain D, Laurent R (2000). Composition of the essential oil of Heracleum paphlagonicum Czeczott. Journal of Essential Oil Research 12(3), 385–386.
• Chu SS, Cao J, Liu QZ, Du SS, Deng ZW, Liu ZL (2012). Chemical composition and insecticidal activity of Heracleum moellendorffii Hance essential oil. Chemija 23(2), 108–112.
• Çetin B, Özer H, Çakir A, Mete E, Tosun M, Öztürk E, Polat T, Kandemir A (2009). Chemical composition of hydrodistilled essential oil of Artemisia incana (L.) Druce and antimicrobial activity against foodborne microorganisms. Chemistry & Biodiversity 6(12), 2302–2310.
• Çetin B, Özer H, Cakir A, Polat T, Dursun A, Mete E, Öztürk E, Ekinci M (2010). Antimicrobial activities of essential oil and hexane extract of Florence fennel [Foeniculum vulgare var. azoricum (Mill.) Thell.] against foodborne microorganisms. Journal of Medicinal Food 13(1), 196–204.
• Davis P, Tan K, Mill R (1988). Flora of Turkey and the Aegean Islands. Edinburgh University Press, Edinburgh, UK. Vol. 10.
• Davis PH (1972). Heracleum L. In: Davis PH (Ed), Flora of Turkey and East Aegean Islands, Vol. 4, Edinburgh University Press, Edinburgh, UK, pp. 488–500.
• Duman H (2000). Flora of Turkey and East Aegean Islands. Edinburgh University Press, Edinburgh, UK. Vol. 11, p.144.
• Ergene A, Tan S, Mirici S, Güler P, Yıldırım S (2007). Antimicrobial activity of Heracleum antasiaticum. In: I International Medicinal and Aromatic Plants Conference on Culinary Herbs, 16–20 April 2007, Antalya, Turkey. Acta Horticulturae 826: 267–270.
• Firuzi O, Asadollahi M, Gholami M, Javidnia K (2010). Composition and biological activities of essential oils from four Heracleum species. Food Chemistry 122(1), 117–122.
• Gul HI, Ojanen T, Hänninen O (2002). Antifungal evaluation of bis Mannich bases derived from acetophenones and their corresponding piperidinols and stability studies. Biological and Pharmaceutical Bulletin 25(10), 1307–1310.
• Guleria S, Saini R, Jaitak V, Kaul V, Lal B, Rahi P, Gulati A, Singh B (2011). Composition and antimicrobial activity of the essential oil of Heracleum thomsonii (Clarke) from the cold desert of the western Himalayas. Natural Product Research 25(13), 1250–1260.
• Habibi Z, Eshaghi R, Mohammadi M, Yousefi M (2010). Chemical composition and antibacterial activity of essential oil of Heracleum rechingeri Manden from Iran. Natural Product Research 24(11), 1013–1017.
• Harrigan WF (1998). Laboratory Methods in Food Microbiology. Gulf Professional Publishing, San Diego, USA. İ şcan G, Demirci F, Kürkçüoğlu M, Kıvanç M, Can Başer KH (2003). The bioactive essential oil of Heracleum sphondylium L. subsp. ternatum (Velen.) Brummitt. Zeitschrift für Naturforschung C 58(3–4), 195–200.
• Jagannath N, Ramakrishnaiah H, Krishna V, Gowda PJ (2012). Chemical composition and antimicrobial activity of essential oil of Heracleum rigens. Natural Product Communications 7(7), 943–946.
• Jennings W (1980). Qualitative Analysis of Flavor and Fragrance Volatiles by Glass Capillary Gas Chromatography. Elsevier, Amsterdam, Netherlands.
• John GH, Holt NR, Krieg PH (1994). Bergey’s Manual of Determinative Bacteriology (9th Edition). Williams & Wilkins, Baltimore, USA.
• Karimi AG, Ito M (2012). Sedative effect of vapor inhalation of essential oil from Heracleum afghanicum Kitamura seeds. Journal of Essential Oil Research 24(6), 571–577.
• Karuppusamy S, Muthuraja G (2010). Radical scavenging activities of Heracleum aquilegifolium Wight (Apiaceae) fruit oils in vitro. Zeitschrift für Naturforschung C 65(11–12), 653–659.
• Kazemi M, Rostami H (2015). Chemical composition, antimicrobial and antioxidant activities of the essential oil of Psammogeton canescens. Natural Product Research 29(3), 277–280.
• Li W, Chen L, Wu C, Xin J (2013). Analysis of the essential oil from seed of Heracleum moellendorffii Hance cultivated in northeast China. Asian Journal of Chemistry 25(8), 4701–4704.
• Logacheva M, Valiejo-Roman C, Pimenov M (2008). ITS phylogeny of West Asian Heracleum species and related taxa of Umbelliferae–Tordylieae WDJ Koch, with notes on evolution of their psbA-trnH sequences. Plant Systematics and Evolution 270, 139–157.
• Maggi F, Quassinti L, Bramucci M, Lupidi G, Petrelli D, Vitali LA, Papa F, Vittori S (2014). Composition and biological activities of hogweed [Heracleum sphondylium L. subsp. ternatum (Velen.) Brummitt] essential oil and its main components octyl acetate and octyl butyrate. Natural Product Research 28(17), 1354–1363.
• Miladinović D, Ilić B, Mihajilov-Krstev TM, Nikolić D, Cvetković O, Marković M, Miladinović L (2013). Antibacterial activity of the essential oil of Heracleum sibiricum. Natural Product Communications 8(9), 1309–1311.
• Murray PR, Baron EJ, Pfaller MA, Tenover FC, Yolken RH (1995). Manual of Clinical Microbiology. American Society for Microbiology, Washington, DC, USA.
• Najafabadi RE, Mohammadi M, Yousefi M, Habibi Z (2011). Chemical composition and antibacterial activity of essential oils from flowers, seeds and stems of Heracleum rechingeri (Manden) from Iran. Journal of Essential Oil Bearing Plants 14(6), 746–750.
• Pavlović I, Petrović S, Radenković M, Milenković M, Couladis M, Branković S, Drobac MP, Niketić M (2012). Composition, antimicrobial, antiradical and spasmolytic activity of Ferula heuffelii Griseb. ex Heuffel (Apiaceae) essential oil. Food Chemistry 130(2), 310–315.
• Radjabian T, Salimi A, Rahmani N, Shockravi A, Mozaffarian V (2013). Essential oil composition of some wild populations of Heracleum persicum Desf. Ex Fischer growing in Iran. Journal of Essential Oil Bearing Plants 16(6), 841–849.
• Sefidkon F, Dabiri M, Mohammad N (2002). Analysis of the oil of Heracleum persicum L. (leaves and flowers). Journal of Essential Oil Research 14(4), 295–297.
• Tavares AC, Gonçalves MJ, Cavaleiro C, Cruz MT, Lopes MC, Canhoto J, Salgueiro LR (2008). Essential oil of Daucus carota subsp. halophilus: composition, antifungal activity and cytotoxicity. Journal of Ethnopharmacology 119(1), 129–134.
• Tkachenko K (2009). Essential oils from roots of certain Heracleum species. Chemistry of Natural Compounds 45(4), 578–580.
• Ušjak L, Petrović S, Drobac M, Soković M, Stanojković T, Ćirić A, Niketić M (2017). Essential oils of three cow parsnips–composition and activity against nosocomial and foodborne pathogens and food contaminants. Food & Function 8(1), 278–290.
• Yousefirad M, Karimzadeh R (2008). Chemical composition of the essential oil of Heracleum persicum seeds of Iran. Asian Journal of Chemistry 20(5), 3345–3348.
• Yuca H, Sefalı A, Aydın B, Karadayı M, Gülşahin Y, Yazıcı A, Karakaya S, Demirci B, Çoban F, Özdemir E, Demir AY, Güvenalp Z (2024). Phytochemical analysis and biological evaluation of essential oils and extracts from Heracleum pastinacifolium subsp. incanum (Boiss. & A. Huet) PH Davis, an endemic plant from Turkey. Natural Product Research 4, 1–11.