Turunçgil Kabuğu Esansiyel Yağlarının Uçucu Bileşenleri ve Ana Bileşenlerin Moleküler Bağlanma Analizleri

Öz

Turunçgil kabuğu atıkları, uçucu bileşenleri nedeniyle katma değerli ürünler için umut vadeden bir kaynaktır. Bu çalışmada, altı turunçgil türünün kabuklarından hidrodistilasyon yöntemiyle elde edilen uçucu yağ bileşimleri GC-MS analizi ile karakterize edilmiştir. Uçucu yağ verimleri önemli ölçüde farklılık gösterip ve en yüksek ve en düşük verimler sırasıyla tatlı portakal (%0.67) ve greyfurt (%0.07)’dan elde edilmiştir. Toplam 67 uçucu bileşik tanımlanmış ve limonen (%57.74-90.34) tüm yağ örneklerinde baskın bileşen olmuştur. Monoterpen hidrokarbonlar tüm türlerde baskın kimyasal sınıfı oluştururken, oksijenli monoterpenler ve seskiterpenler türe bağlı olarak varyasyon göstermiştir. Özellikle tatlı portakal yüksek linalool içeriği gösterirken, pomelo nispeten daha yüksek seskiterpen hidrokarbon içeriği ile öne çıkmıştır. Hiyerarşik kümeleme analizi ve Venn diyagramı değerlendirildiğinde kemotaksonomik farklılaşmalarına yardımcı olan hem ortak hem de türe özgü bileşiklerin bulunduğu ortaya konmuştur. Moleküler kenetlenme analizleri, D-limonen ve L-limonen enantiomerlerinin antibakteriyel hedef GyrB'ye kıyasla antifungal hedef CYP51'e daha yüksek bağlanma afinitesi gösterebileceğini ortaya koymuştur. Bu çalışma, turunçgil türlerinin sınıflandırılmasında uçucu bileşenler ve kullanımları ile potansiyel uygulamaları hakkında değerli bilgiler sağlamaktadır.

Anahtar Kelimeler

• Turunçgiller
• Turunçgil kabuğu
• Turunçgil atıkları
• Esansiyel yağ
• Hidrodistilasyon

Volatile Composition and Molecular Docking Analysis of Major Constituents from Citrus Peel Essential Oils

Öz

Citrus peel waste is a promising source of value-added products because of its volatile constituents. In this study, essential oil compositions extracted by hydrodistillation from peels of six Citrus species were characterized by GC-MS analysis. Essential oil yields varied significantly and the highest and the lowest yields were obtained from sweet orange (0.67%) and grapefruit (0.07%), respectively. A total of 67 volatile compounds were identified, and limonene (57.74-90.34%) was the dominant constituent in all oil samples. Monoterpene hydrocarbons constituted the predominant chemical class in all species, while oxygenated monoterpenes and sesquiterpenes showed species-dependent variation. In particular, sweet orange showed a high linalool content, while pomelo exhibited relatively higher sesquiterpene hydrocarbon content. Hierarchical cluster analysis and Venn diagram evaluation revealed the presence of both common and species-specific compounds helping their chemotaxonomic differentiation. Molecular docking analyses suggested that D-limonene and L-limonene enantiomers may exhibit higher binding affinity toward the antifungal target CYP51 than toward antibacterial target GyrB. This study provides valuable information for volatile compositions and uses in classification of Citrus species along with their potential applications.

Anahtar Kelimeler

• Citrus fruit
• Citrus peel
• Citrus waste
• Essential oil
• Hydrodistillation

Kaynakça

1. Asikin Y, Taira I, Inafuku S, Sumi H, Sawamura M, Takara K, Wada K, 2012. Volatile Aroma Components and Antioxidant Activities of The Flavedo Peel Extract of Unripe Shiikuwasha (Citrus depressa Hayata). Journal of food science 77 (4): C469-C475.
2. Babushok VI, Linstrom PJ, Zenkevich IG, 2011. Retention Indices for Frequently Reported Compounds of Plant Essential Oils. Journal of Physical and Chemical Reference Data 40 (4): 043101.
3. Badalamenti N, Bruno M, Schicchi R, Geraci A, Leporini M, Gervasi L, Tundis R, Loizzo MR, 2022. Chemical Compositions and Antioxidant Activities of Essential Oils, and Their Combinations, Obtained from Flavedo By-Product of Seven Cultivars of Sicilian Citrus aurantium L. Molecules 27 (5): 1580.
4. Banerjee P, Eckert, AO, Schrey AK, Preissner R, 2018. ProTox-II: a Webserver for The Prediction of Toxicity of Chemicals. Nucleic Acids Research, 46 (W1): W257-W263.
5. Banerjee P, Kemmler E, Dunkel M, Preissner R, 2024. ProTox 3.0: a Webserver for The Prediction of Toxicity of Chemicals. Nucleic Acids Research 52 (W1): W513-W520.
6. Buettner A, Schieberle P, 2001. Evaluation of Key Aroma Compounds in Hand Squeezed Grapefruit Juice (Citrus paradisi Macfayden) by Quantitation and Flavor Reconstitution Experiments. Journal of Agricultural and Food Chemistry 49 (3): 1358-1363.
7. Burnett CL, Fiume MM, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler DC, Marks JG, Shank RC, Slaga TJ, Snyder PW, Gill LJ, Heldreth B, 2019. Safety Assessment of Citrus-Derived Peel Oils as Used in Cosmetics. International Journal of Toxicology 38 (2): 33S-59S.
8. Dighe SN, Collet TA, 2020. Recent Advances in DNA Gyrase-Targeted Antimicrobial Agents. European Journal of Medicinal Chemistry 199: 112326.

9. FAOSTAT, 2025. Statistical Database. https://www.fao.org/faostat/en/#data (Accessed April 10, 2026).
10. González-Mas MC, Rambla JL, Alamar MC, Gutiérrez A, Granell A, 2011. Comparative Analysis of The Volatile Fraction of Fruit Juice from Different Citrus species. PLoS One 6(7): e22016.
11. González-Mas MC, Rambla JL, López-Gresa MP, Blázquez MA, Granell A, 2019. Volatile Compounds in Citrus Essential Oils: A Comprehensive Review. Frontiers in Plant science 10: 433929.
12. Hosni K, Zahed N, Chrif R, Abid I, Medfei W, Kallel M, Brahim NB, Sebei H, 2010. Composition of Peel Essential Oils from Four Selected Tunisian Citrus species: Evidence for The Genotypic Influence. Food Chemistry 123(4): 1098-1104.
13. Huang YQ, Tan YX, Watanabe Y, Liao MX, Li QM, Wang K, Zhou Y, 2026. Assessment of The Antibacterial and Antioxidant Properties of Major Volatile Components in The Flavedo Peel Extract of Citrus. Journal of Food Measurement and Characterization 1-15.
14. Jing L, Lei Z, Zhang G, Pilon AC, Huhman DV, Xie R, Xi W, Zhou Z, Sumner LW, 2015. Metabolite Profiles of Essential Oils in Citrus Peels and Their Taxonomic Implications. Metabolomics 11(4): 952-963.
15. Jongedijk E, Cankar K, Buchhaupt M, Schrader J, Bouwmeester H, Beekwilder J, 2016. Biotechnological Production of Limonene in Microorganisms. Applied Microbiology and Biotechnology 100(7): 2927-2938.
16. Kelebek H, Selli S, 2011. Determination of Volatile, Phenolic, Organic Acid and Sugar Components in a Turkish cv. Dortyol (Citrus sinensis L. Osbeck) Orange Juice. Journal of the Science of Food and Agriculture 91(10): 1855-1862.
17. Lin J, Rouseff RL, Barros S, Naim M, 2002. Aroma Composition Changes in Early Season Grapefruit Juice Produced from Thermal Concentration. Journal of Agricultural and Food Chemistry 50(4): 813-819.
18. Liu Y, Yang X, Gan J, Chen S, Xiao ZX, Cao Y, 2022. CB-Dock2: Improved Protein-Ligand Blind Docking by Integrating Cavity Detection, Docking and Homologous Template Fitting. Nucleic Acids Research 50(W1): W159-W164.
19. Liu C, Cheng Y, Zhang H, Deng X, Chen F, Xu J, 2012. Volatile Constituents of Wild Citrus Mangshanyegan (Citrus nobilis Lauriro) Peel Oil. Journal of Agricultural and Food Chemistry, 60 (10):2617-2628.
20. Lu Q, Huang N, Peng Y, Zhu C, Pan S, 2019. Peel Oils from Three Citrus species: Volatile Constituents, Antioxidant Activities and Related Contributions of Individual Components. Journal of Food Science and Technology 56(10): 4492-4502.
21. Mai R, Li Y, Ren J, Fan G, Yang J, 2025. Machine Learning in The Citrus Essential Oil Industry: A Comprehensive Review on Process Optimization, Authentication, and Flavor and Bioactive Compound Development. Trends in Food Science & Technology 165: 105347.
22. Meryem S, Mohamed D, Nour-Eddine C, Faouzi E, 2023. Chemical Composition, Antibacterial and Antioxidant Properties of Three Moroccan Citrus Peel Essential Oils. Scientific African 20: e01592.
23. Metsalu T, Vilo J, 2015. ClustVis: a Web Tool for Visualizing Clustering of Multivariate Data Using Principal Component Analysis and Heatmap. Nucleic Acids Research 43(W1): W566-W570.
24. Mutlucan M, Önder S, 2025. Citrus Seeds as Potential Vegetable Oil Resources: Oil Content and Some Quality Characteristics of Oil. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 29(3): 602-609.
25. NIST Chemistry WebBook, 2025. NIST Standard Reference Database Number 69, Gaithersburg, National Institute of Standards and Technology. https://webbook.nist.gov/chemistry/ (Accessed April 2, 2026).
26. Önder S, Periz ÇD, Ulusoy S, Erbaş S, Önder D, Tonguç M, 2024. Chemical Composition and Biological Activities of Essential Oils of Seven Cultivated Apiaceae Species. Scientific Reports 14(1): 10052.
27. Peana AT, D'Aquila PS, Panin F, Serra G, Pippia P, Moretti MDL, 2002. Anti-Inflammatory Activity of Linalool and Linalyl Acetate Constituents of Essential Oils. Phytomedicine 9 (8): 721-726.
28. Penić M, Grassino AN, Aladić K, Jokić S, Jerković I, Dent M, 2026. Effects of Enzymatic Pretreatment on Yield and Volatile Composition of Citrus Peel Essential Oils. Molecules 31(4): 657.
29. Perez-Cacho PR, Rouseff R, 2008. Processing and Storage Effects on Orange Juice Aroma: A Review. Journal of Agricultural and Food Chemistry 56(21): 9785-9796.
30. PubChem, 2021. National Center for Biotechnology Information: PubChem compound summary. Limonene, (-)- | C10H16 | CID 439250 - PubChem. (Accessed April 19, 2026).
31. Qiao Y, Xie BJ, Zhang Y, Zhou HY, Pan SY, 2007. Study on Aroma Components in Fruit from Three Different Satsuma Mandarin Varieties. Agricultural Sciences in China 6(12): 1487-1493.
32. Ren JN, Tai YN, Dong M, Shao JH, Yang SZ, Pan SY, Fan G, 2015. Characterisation of Free and Bound Volatile Compounds from Six Different Varieties of Citrus Fruits. Food Chemistry 185: 25-32.
33. Ruma YN, Keniya MV, Tyndall JD, Monk BC, 2022. Characterisation of Candida parapsilosis CYP51 as a Drug Target Using Saccharomyces cerevisiae as Host. Journal of Fungi 8(1): 69.
34. Schnee C, Köllner TG, Held M, Turlings TC, Gershenzon J, Degenhardt J, 2006. The Products of a Single Maize Sesquiterpene Synthase Form a Volatile Defense Signal that Attracts Natural Enemies of Maize Herbivores. Proceedings of The National Academy of Sciences 103(4): 1129-1134.
35. Scora RW, Malik MN, 1970. Chemical Characterization of Citrus As a Tool in Phylogeny. Taxon 19(2): 215-228.
36. Shaw D, Tripathi AD, Paul V, Agarwal A, Mishra PK, Kumar M, 2023. Valorization of Essential Oils from Citrus Peel Powder Using Hydro-Distillation. Sustainable Chemistry and Pharmacy 32: 101036.
37. Spencer AC, Panda SS, 2023. DNA Gyrase As a Target for Quinolones. Biomedicines 11(2): 371.
38. Tikunov YM., de Vos RCH, Gonzaݩlez Paramaݩs AM, Hall RD, Bovy AG, 2010. A Role for Differential Glycoconjugation in The Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach. Plant Physiology 152(1): 55-70.
39. Tisserand R, Young R, 2013. Essential Oil Safety: a Guide for Health Care Professionals. Elsevier Health Sciences. Amsterdam, 757pp, The Netherlands.
40. Tonguç F, Erdoğan Ü, Önder S, Tonguç M, 2025. Essential Oil Composition of Oleaster (Elaeagnus angustifolia L.) Flowers and Comparative Assessment of Metabolic and Antioxidant Potential of Flower and Leaf Extracts. Artvin Çoruh Üniversitesi Orman Fakültesi Dergisi 26(2): 402-409.
41. Vigushin DM, Poon GK, Boddy A, English J, Halbert GW, Pagonis C, Jarman M, Coomes RC, 1998. Phase I and Pharmacokinetic Study of D-limonene in Patients with Advanced Cancer. Cancer Chemotherapy and Pharmacology 42(2): 111-117.
42. Wu GA, Terol J, Ibanez V, López-García A, Pérez-Román E, Borredá C, Domingo C, Tadeo FR, Carbonell-Caballero J, Alonso R, Curk F, Du D, Ollitrault P, Roose ML, Dopazo J, Gmitter FG, Rokhsar DS, Talon M, (2018). Genomics of The Origin and Evolution of Citrus. Nature 554 (7692): 311-316.
43. Wu T, Li Y, Qiu G, Yang B, Wang L, Wang S, 2025. Design and Discovery of Novel Antifungal Inhibitors Targeting 14α-Demethylase: F11 As a Promising Antifungal Candidate. Results in Chemistry 16: 102411.
44. Yang J, Park MJ, 2025. Antioxidant Effects of Essential Oils from the Peels of Citrus Cultivars. Molecules 30(4): 833.
45. Zareiyan F, Khajehsharifi H, 2021. Analyzing Bioactive Compounds in Essential Oil of Citrus maxima and Citrus sinensis Peel. Journal of Essential Oil Bearing Plants 24(4): 677-682.
46. Zhang H, Xie Y, Liu C, Chen S, Hu S, Xie Z, Deng X, Xu J, 2017. Comprehensive Comparative Analysis of Volatile Compounds in Citrus Fruits of Different Species. Food Chemistry 230: 316-326.