TY - JOUR T1 - Characterization of the Volatile Profile of Bee Venom from Different Regions in Türkiye Using Gas Chromatography-Mass Spectrometry AU - Aydeniz-güneşer, Buket AU - Güneşer, Onur AU - Kekeçoğlu, Meral AU - Kolaylı, Sevgi PY - 2025 DA - January Y2 - 2024 DO - 10.15832/ankutbd.1430185 JF - Journal of Agricultural Sciences JO - J Agr Sci-Tarim Bili PB - Ankara University WT - DergiPark SN - 1300-7580 SP - 22 EP - 32 VL - 31 IS - 1 LA - en AB - The volatile organic compounds of bee venoms from four different populations of Apis mellifera anatoliaca, came from different regions in Türkiye, were analyzed using solid phase microextraction technique combined with gas chromatography-mass spectrometry. A total of 144 volatile compounds were identified in the bee venom samples. The identified volatile compounds included esters, terpenoids, alcohols, acid esters, aldehydes, ketones, and hydrocarbons. It was determined that ester-type volatile compounds characterized the bee venom obtained from the Central Anatolia Region, while bee venom from the Western Black Sea Region had a higher amount of volatile terpenes with spicy and woody aromas. Further studies are required to understand the volatile profile of bee venom, which consists of plant and animal secondary metabolites. KW - bee venom KW - Apis Mellifera Anatoliaca KW - volatile compounds KW - Gas Chromatography-Mass Spectrometry CR - Abd El-Wahed A A, Farag M A, Eraqi W A, Mersal G A, Zhao, C, Khalifa, S A & El-Seedi H R (2021). Unravelling the beehive air volatiles profile as analysed via solid phase microextraction (SPME) and chemometrics. Journal of King Saud University Science 33(5): 101449. https://doi.org/10.1016/j.jksus.2021.101449 CR - Ağan A F & Kekeçoglu M (2020). Melittin and cancer treatment: Nanotechnological perspective. Uludağ Arıcılık Dergisi 20(2): 221-231. https://doi.org/10.31467/uluaricilik.784365 CR - Al-Ghamdi A A, Al-Khaibari A M & Omar M O M (2011). Effect of honeybee race and worker age on development and histological structure of hypopharyngeal glands of honeybee. Saudi Journal of Biological Sciences 18(2): 113-116. https://doi.org/10.1016/j.sjbs.2011.01.001 CR - Ali E M (2014). Contributions of some biological activities of honey bee venom. Journal of Apicultural Research 53(4): 441-451. https://doi.org/10.3896/IBRA.1.53.4.13 CR - Ali H, Alqarni A S, Iqbal J, Owayss A A, Raweh H S & Smith B H (2019). Effect of season and behavioral activity on the hypopharyngeal glands of three honeybee Apis mellifera L. races under stressful climatic conditions of central Saudi Arabia. Journal of Hymenoptera Research 68: 85-101. https://doi.org/doi: 10.3897/jhr.68.29678 CR - Ali S H & Sayed A R (2021). Review of the synthesis and biological activity of thiazoles. Synthetic Communications 51(5): 670-700. https://doi.org/10.1080/00397911.2020.1854787 CR - Anandakumar P, Kamaraj S & Vanitha M K (2021). D‐limonene: A multifunctional compound with potent therapeutic effects. Journal of Food Biochemistry 45(1), e13566. https://doi.org/10.1111/jfbc.13566 CR - Anonymous, (2024). The goodscents company. https://www.thegoodscentscompany.com/search2.html Ando H, Kurata A & Kishimoto N (2015). Antimicrobial properties and mechanism of volatile isoamyl acetate, a main flavor component of Japanese sake (Ginjo‐shu). Journal of Applied Microbiology 118(4): 873-880. https://doi.org/10.1111/jam.12764 CR - Avsar Y K, Karagul-Yuceer Y, Drake M A, Singh T K, Yoon Y & Cadwallader K R (2004). Characterization of nutty flavor in Cheddar cheese. Journal of Dairy Science 87(7): 1999-2010. https://doi.org/10.3168/jds.S0022-0302(04)70017-X CR - Bhadra S, Zhang Z, Zhou W, Ochieng F, Rockwood G A, Lippner D & Logue B A (2019). Analysis of potential cyanide antidote, dimethyl trisulfide, in whole blood by dynamic headspace gas chromatography–mass spectroscopy. Journal of Chromatography A 1591: 71-78. https://doi.org/10.1016/j.chroma.2019.01.058 CR - Bogdanov S (2016). Bee Venom: Production, composition, quality. In S. Bogdanov (Ed.), The bee venom (pp.1-8). Bee product science. https://www.bee-hexagon.net/english/bee-products/venom/ CR - Çaprazlı T & Kekeçoğlu M (2021). Bal arisi zehrinin kompozisyonunu ve üretim miktarini etkileyen faktörler. Uludag Arıcılık Dergisi (1): 132-145. https://doi.org/10.31467/uluaricilik.901279 CR - Castro-Vázquez L, Díaz-Maroto M C, González-Viñas M A, De La Fuente E & Pérez-Coello M S (2008). Influence of storage conditions on chemical composition and sensory properties of citrus honey. Journal of Agricultural and Food Chemistry 56(6): 1999-2006. https://doi.org/10.1021/jf072227k CR - Caputi L & Aprea E (2011). Use of terpenoids as natural flavouring compounds in food industry. Recent Patents on Food, Nutrition & Agriculture 3(1): 9-16. https://doi.org/10.2174/2212798411103010009 CR - Chung E S, Kim H, Lee G, Park S, Kim H & Bae H (2012). Neuro-protective effects of bee venom by suppression of neuroinflammatory responses in a mouse model of Parkinson’s disease: role of regulatory T cells. Brain, Behavior, and Immunity 26(8): 1322-1330. https://doi.org/10.1016/j.bbi.2012.08.013 CR - Ding Q, Sheikh A R, Gu X, Li J, Xia K, Sun N & Ma H (2021). Chinese propolis: Ultrasound‐assisted enhanced ethanolic extraction, volatile compounds analysis, antioxidant and antibacterial activity comparison. Food Science and Nutririton 9(1): 313-330. https://doi.org/10.1002/fsn3.1997 CR - El-Didamony S E, Amer R I & El-Osaily G H (2022). Formulation, characterization and cellular toxicity assessment of a novel bee-venom microsphere in prostate cancer treatment. Scientific Reports 12(1): 13213. https://doi.org/10.1038/s41598-022-17391-w CR - El-Saeady A A, Diab A, Shehata I A A, Nafea E A & Metwaly A A A (2016). Effect of bee venom collecting on the behavior of honeybee colonies. Journal of Plant Protection and Pathology 7(6): 347– 351. https://doi.org/10.21608/JPPP.2016.50576 CR - El Sharkawi F Z, Saleh S S & El Sayed A F M (2015). Potential anti cancer activity of snake venom, bee venom and their components in liver and breast carcinoma. International Journal of Pharmaceutical Sciences and Research 6(8): 3224. https://doi.org/10.13040/IJPSR.0975-8232 CR - Flanjak I, Kovačić M, Primorac L, Soldić A, Puškadija Z & Rajs B B (2021). Comparison between the quantity and quality of honey bee venom collected in the front and inside of the hive. Journal of Apicultural Research pp. 1-6. https://doi.org/10.1080/00218839.2021.1994262 CR - Götz M E, Sachse B, Schäfer B & Eisenreich A (2022). Myristicin and elemicin: Potentially toxic alkenylbenzenes in food. Foods 11(13): 1988. https://doi.org/10.3390/foods11131988 CR - Güneşer O & Yüceer Y K (2017). Biosynthesis of eight-carbon volatiles from tomato and pepper pomaces by fungi: Trichoderma atroviride and Aspergillus sojae. Journal of Bioscience and Bioengineering 123(4): 451-459. https://doi.org/10.1016/j.jbiosc.2016.11.013 CR - Huigens III R W, Brummel B R, Tenneti S, Garrison A T & Xiao T (2022). Pyrazine and phenazine heterocycles: Platforms for total synthesis and drug discovery. Molecules 27(3): 1112. https://doi.org/10.3390/molecules27031112 CR - Hussein A, El-Ansari M & Zahra A (2019). Effect of the honeybee hybrid and geographic region on the honeybee venom production. Journal of Plant Protection and Pathology 10(3): 171–176. https://doi.org/10.21608/jppp.2019.40922 CR - Hwang D S, Kim S K & Bae H (2015). Therapeutic effects of bee venom on immunological and neurological diseases. Toxins 7(7): 2413-2421. https://doi.org/10.3390/toxins7072413 CR - Isidorov V, Zalewski A, Zambrowski G & Swiecicka I (2023). Chemical Composition and Antimicrobial Properties of Honeybee Venom. Molecules 28(10): 4135. https://doi.org/10.3390/ molecules28104135 CR - Jeleń H & Gracka A (2016). Characterization of aroma compounds: Structure, physico‐chemical and sensory properties. In E. Guichard, C. Salles, M. Morzel, & AM. Le Bon (Eds.), Flavour: from food to perception (pp. 126-153). John Wiley & Sons, Ltd. https://doi.org/10.1002/9781118929384.ch6 CR - Jung G B, Huh J E, Lee H J, Kim D, Lee G J Park H K & Lee J D (2018). Anti-cancer effect of bee venom on human MDA-MB-231 breast cancer cells using Raman spectroscopy. Biomedical Optics Express 9(11): 5703-5718. https://doi.org/10.1364/BOE.9.005703 CR - Kaziur-Cegla W, Jochmann M A, Molt K, Bruchmann A & Schmidt T C (2022). In-tube dynamic extraction for analysis of volatile organic compounds in honey samples. Food Chemistry X, 14, Article 100337. https://doi.org/10.1016/j.fochx.2022.100337 CR - Kekeçoğlu M, Çaprazlı T, Samancı A E T, Samancı T & Önder E Y (2022). Factors affecting quality of honeybee venom. Journal of Apicultural Science 66(1): 5-14. https://doi.org/10.2478/jas-2022-0001 CR - Kekecoglu M, Sonmez E, Acar M K & Karaoglu S A (2021). Pollen analysis, chemical composition and antibacterial activity of Anatolian chestnut propolis collected from Yıgılca region. Biology Bulletin 48(7): 21-728. https://doi.org/10.1134/S106235902106011X CR - Kumar N R, Devi A, Kriti H & Kriti N (2014). Comparative biochemical studies on the poison glad and poison sac of the worker bees of three different apis species (Apis dorsata, Apis mellifera and Apis florea). International Journal of Therapeutic Applications 16: 8–16 CR - Kumar S & Aggarwal R (2019). Thiazole: A privileged motif in marine natural products. Mini-Reviews in Organic Chemistry 16(1): 26-34. https://doi.org/10.2174/1570193X15666180412152743 CR - Maga J A & Sizer C E (1973). Pyrazines in foods. Review. Journal of Agricultural and Food Chemistry 21(1): 22-30.https://doi.org/10.1021/jf60185a006 CR - Melda A, Kalaycioğlu Z, Kolayli S & Berker B (2021). Comparative determination of melittin by capillary electrophoretic methods. Journal of the Turkish Chemical Society Section A: Chemistry 8(4): 1211-1216. https://doi.org/10.18596/jotcsa.949188 CR - Miguel M G & Antunes M D (2011). Is propolis safe as an alternative medicine? Journal of Pharmacy and Bioallied Sciences 3(4): 479-495. https://doi.org/10.4103/0975-7406.90101 CR - Mortzfeld F B, Hashem C, Vranková K, Winkler M & Rudroff F (2020). Pyrazines: Synthesis and industrial application of these valuable flavor and fragrance compounds. Biotechnology Journal 15(11): 2000064. https://doi.org/10.1002/biot.202000064 CR - Ouradi H, Hanine H, Fauconnier M L, Kenne T, Rizki H, Ennahli S & Hssaini L (2021). Determination of physico-biochemical proprieties and composition in volatile constituents by solid phase micro-extraction of honey samples from different botanical and geographical origins in Morocco. Journal of Apicultural Research 60(1): 84-98. https://doi.org/10.1080/00218839.2020.1718339 CR - Özkök A (2018). Türkiye’de hızla büyüyen sektör: Arı ürünlerine genel bir bakış. Palme Yayın Dağıtım. Paulino B N, Silva G N, Araújo F F, Néri-Numa I A, Pastore G M, Bicas J L & Molina G (2022). Beyond natural aromas: The bioactive and technological potential of monoterpenes. Trends in Food Science & Technology 128: 188-201 CR - Pawliszyn J (1999). Quantitative aspects of SPME. In: J. Pawliszyn (Ed.), Applications of solid phase microextraction (pp. 3-21). Royal Society of Chemistry. https://doi.org/10.1039/9781847550149 CR - Ramos O Y, Salomón V, Libonatti C, Cepeda R, Maldonado L & Basualdo M (2018). Effect of botanical and physicochemical composition of Argentinean honeys on the inhibitory action against food pathogens. LWT 87: 457-463. https://doi.org/10.1016/j.lwt.2017.09.014. CR - Rockwood G A, Thompson D E & Petrikovics I (2016). Dimethyl trisulfide: A novel cyanide countermeasure. Toxicology & Industrial Health, 32(12): 2009-2016. https://doi.org/10.1177/0748233715622713 CR - Salehi B, Upadhyay S, Erdogan Orhan I, Kumar Jugran A, Jayaweera L D S A, Dias D, Sharopov F, Taheri Y, Martins N, Baghalpour N, Cho W C & Sharifi-Rad J (2019). Therapeutic potential of α-and β-pinene: A miracle gift of nature. Biomolecules 9(11): 738. https://doi.org/10.3390/biom9110738 CR - Samancı T & Kekeçoglu M (2019). Comparison of commercial and Anatolian bee venom in terms of chemical composition. Uludag Arıcılık Dergisi 19(1): 60-67. https://doi.org/10.31467/uluaricilik.527986 CR - Seneme E F, Dos Santos D C, Silva E M R, Franco Y E M & Longato G B (2021). Pharmacological and therapeutic potential of myristicin: A literature review. Molecules, 26 (19), 5914. https://doi.org/10.3390/molecules26195914 CR - Somwongin S, Chantawannakul P & Chaiyana W (2018). Antioxidant activity and irritation property of venoms from Apis species. Toxicon, 145: 32–39. https://doi.org/10.1016/j.toxicon.2018.02.049 CR - Souza-Silva ÉA, Gionfriddo E & Pawliszyn J (2015). A critical review of the state of the art of solid-phase microextraction of complex matrices II. Food analysis. TrAC Trends in Analytical Chemistry 71: 236-248.https://doi.org/10.1016/j.trac.2015.04.018 CR - Tanugur-Samanci A E & Kekeçoglu M (2021). An evaluation of the chemical content and microbiological contamination of Anatolian bee venom. Plos One, 16, 1-14, https://doi.org/10.1371/journalpone.0255161 CR - Uzuner S Ç, Birinci E, Tetikoğlu S, Birinci C & Kolaylı S (2021). Distinct epigenetic reprogramming, mitochondrial patterns, cellular morphology, and cytotoxicity after bee venom treatment. Recent Patents on Anti-Cancer Drug Discovery 16(3): 377-392. https://doi.org/10.2174/1574892816666210422125058 CR - Wager B R & Breed M D (2000). Does honey bee sting alarm pheromone give orientation information to defensive bees? Annals of the Entomological Society of America 93(6): 1329-1332.https://doi.org/10.1603/0013-8746(2000)093[1329:DHBSAP]2.0.CO;2 CR - Yehye W A, Rahman N A, Ariffin A, Abd Hamid S B, Alhadi A A, Kadir F A & Yaeghoobi M (2015). Understanding the chemistry behind the antioxidant activities of butylated hydroxytoluene (BHT): A review. European Journal of Medicinal Chemistry 101: 295-312. https://doi.org/10.1016/j.ejmech.2015.06.026 CR - Zidan H A E G, Mostafa Z K, Ibrahim M A, Haggag S I, Darwish D A & Elfiky A A (2018). Venom composition of Egyptian and Carniolan honeybee. Apis mellifera L. affected by collection methods. Egyptian Academic Journal of Biological Sciences 11(4): 59–71. https://doi.org/10.21608/EAJBSA.2018.17733 UR - https://doi.org/10.15832/ankutbd.1430185 L1 - https://dergipark.org.tr/en/download/article-file/3700861 ER -