GC–MS Profiling and Molecular Docking Analysis of Ferula huber-morathii and Ferula longipedunculata (Apiaceae) Essential Oils Toward Antidiabetic Enzymes

Yıl 2025, Cilt: 2 Sayı: 3, 130 - 147, 02.11.2025

Amine Sena Aydın , Temel Özek , Bilal Yılmaz , Hilal Özbek , Zuhal Güvenalp , Songül Karakaya

https://doi.org/10.62425/crihs.1790811

Öz

This study provides the first comprehensive comparative analysis of the essential oils of Ferula huber-morathii and F. longipedunculata. Yields varied markedly by plant part, with aerial parts of F. huber-morathii (0.943%) and fruits of F. longipedunculata (4.546%) showing the highest contents. GC–MS revealed distinct chemotypes: F. huber-morathii aerial oil was dominated by octyl butyrate, while its fruits were enriched in shyobunone derivatives; roots contained cadinane-type sesquiterpenes and nitrogenous compounds. In contrast, F. longipedunculata oils were characterized by α-pinene, bornyl acetate, and diverse sesquiterpenes, with fruits showing strong monoterpene dominance. Molecular docking highlighted favorable binding of major metabolites to α-amylase and α-glucosidase, with distinct hydrogen-bonding and hydrophobic anchoring profiles compared to acarbose. ADMET analysis indicated baseline oral drug-likeness but emphasized solubility and absorption as primary challenges, alongside potential CYP-mediated interactions. Overall, the findings underscore the phytochemical richness and pharmacological promise of these species for antidiabetic research.

Anahtar Kelimeler

Ferula huber-morathii , Ferula longipedunculata , Essential oils , GC–MS analysis , Molecular docking

Etik Beyan

No need

Destekleyen Kurum

Atatürk University

Proje Numarası

THD-2018-6812

Teşekkür

Atatürk University

Ferula huber-morathii ve Ferula longipedunculata (Apiaceae) Uçucu Yağlarının GC–MS Profillemesi ve Antidiyabetik Enzimlere Karşı Moleküler Docking Analizi

Öz

Bu çalışma, Ferula huber-morathii ve F. longipedunculata uçucu yağlarının ilk kapsamlı karşılaştırmalı analizini sunmaktadır. Verimler bitki kısımlarına göre önemli ölçüde değişmiş; F. huber-morathii’nin toprak üstü kısımları (%0,943) ve F. longipedunculata’nın meyveleri (%4,546) en yüksek içerik göstermiştir. GC–MS analizi farklı kemotipleri ortaya koymuştur: F. huber-morathii’nin toprak üstü yağı oktil bütiratça baskınken, meyveler şiyobunon türevlerince zengin; kökler ise kadinan tipi seskiterpenler ve azotlu bileşikler içermektedir. Buna karşılık F. longipedunculata yağları α-pinen, bornil asetat ve çeşitli seskiterpenlerle karakterize edilmiş; meyveler güçlü monoterpen baskınlığı sergilemiştir. Moleküler yerleştirme (docking) çalışmaları, başlıca metabolitlerin α-amilaz ve α-glukosidaz enzimlerine karşı elverişli bağlanmasını ve akarbos ile kıyaslandığında farklı hidrojen bağlanma ve hidrofobik etkileşim profilleri sunduğunu göstermiştir. ADMET analizi temel ağızdan alınabilir ilaç-benzeri özellikleri işaret etmiş, ancak çözünürlük ve emilim başlıca zorluklar olarak öne çıkmış, ayrıca olası CYP-aracılı etkileşimlere dikkat çekilmiştir. Genel olarak bulgular, bu türlerin fitokimyasal zenginliğini ve antidiyabetik araştırmalar için farmakolojik potansiyelini vurgulamaktadır.

Anahtar Kelimeler

Ferula huber-morathii , Ferula longipedunculata , Uçucu yağlar , GC–MS analizi , Moleküler docking

Etik Beyan

Gerek yok

Destekleyen Kurum

Atatürk Üniversitesi

Proje Numarası

THD-2018-6812

Teşekkür

Atatürk Üniversitesi

Kaynakça

• Akın. M. (1996). Konya'da doğal olarak yetişen bazı bitkilerde uçucu yağ miktarları ve uçucu yağların antimikrobiyal etkileri (Tez No: 57164). [Doktora Tezi, Selçuk Üniversitesi]. YÖK Tez Merkezi.
• Akshatha, J. V., SantoshKumar, H. S., Prakash, H. S., & Nalini, M. S. (2021). In silico docking studies of α-amylase inhibitors from the anti-diabetic plant Leucas ciliata Benth. and an endophyte, Streptomyces longisporoflavus. Biotech, 11(2), 51. https://doi.org/10.1007/s13205-020-02547-0
• Assaggaf, H., El Hachlafi, N., El Fadili, M., Elbouzidi, A., Ouassou, H., Jeddi, M., ... & Mrabti, H. N. (2023). GC/MS profiling, in vitro antidiabetic efficacy of origanum compactum benth. Essential oil and in silico molecular docking of its major bioactive compounds. Catalysts, 13(11), 1429. https://doi.org/10.3390/catal13111429
• Aydın, B., Aydın, A. S., Çeçen, Ö., Yuca, H., Bona, G. E., Demirci, B., ... & Karakaya, S. (2025). From Herbal Tea to Science: Phytochemical and Biological Investigation of Ajuga chamaepitys subsp. chia (Lamiaceae) With Molecular Docking Analysis. Food Science & Nutrition, 13(8), e70749. https://doi.org/10.1002/fsn3.70749
• Bahrami, G., Soltani, R., Sajjadi, S. E., Kanani, M. R., Naderi, R., Ghiasvand, N., & Shokoohinia, Y. (2013). Essential oil composition of Ferula assafoetida L. fruits from Western Iran. Journal of Reports in Pharmaceutical Sciences, 2(2), 90-97. https://doi.org/10.4103/2322-1232.22253
• Barnes, J., Anderson, L.A., & Phillipson J.D. (2007). Herbal Medicines, (3. baskı). pp.30, UK: Pharmaceutical Press Başer, K. H. C., Demirci, B., Sağıroğlu, M., & Duman, H. (2007, September). Essential oils of ferula species of turkey. in proceedings of the 38th international symposium on essential oils, Graz, Austria (pp. 9-12).
• Başer, K. H. C., & Kırımer, N. Essential Oils of Anatolian Apiaceae ‐ A Profile. Natural Volatiles and Essential Oils, 1(1), 1-50 (2014).
• Burcul, F., Blazevic, I., Radan, M., & Politeo. O. (2018). Terpenes, phenylpropanoids, sulfur and other essential oil constituents as inhibitors of cholinesterases. Current Medicinal Chemistry. 27(26), 4297-4343. https://doi.org/10.2174/0929867325666180330092607.
• Burt, S. (2004). Essential oils: their antimicrobial properties and potential applications in foods: a review. International Journal of Food Microbiology, 94, 223–253. https://doi.org/10.1016/j.ijfoodmicro.2004.03.022. Çağın, H. K. (2005). Bitkilerin gizli dünyası IV Maydanozgiller (Apiaceae), İstanbul.
• Dalli, M., Daoudi, N. E., Abrigach, F., Azizi, S. E., Bnouham, M., Kim, B., & Gseyra, N. (2022). In vitro α-amylase and hemoglobin glycation inhibitory potential of Nigella sativa essential oil, and molecular docking studies of its principal components. Frontiers in Pharmacology, 13, 1036129. https://doi.org/10.3389/fphar.2022.1036129
• Eberhardt, J., Santos-Martins, D., Tillack, A. F., & Forli, S. (2021). AutoDock Vina 1.2.0: New docking methods, expanded force field, and Python bindings. Journal of Chemical Information and Modeling, 61(8), 3891–3898.
• Elibol Z. (2009). Türkiye’deki Bazı Ferula L. (Apiaceae) Türlerinin Moleküler Teknikler Kullanarak Taksonomik Olarak İncelenmesi (Tez No: 259627). [Yüksek Lisans Tezi, Kırıkkale Üniversitesi]. YÖK Tez Merkezi.
• Eruçar, F. M., Kuran, F. K., Altıparmak Ülbegi, G., Özbey, S., Karavuş, Ş. N., Arcan, G. G., ... & Miski, M. (2023). Sesquiterpene coumarin ethers with selective cytotoxic activities from the roots of ferula huber-morathii Peşmen (Apiaceae) and unequivocal determination of the absolute stereochemistry of samarcandin. Pharmaceuticals, 16(6), 792. https://doi.org/10.3390/ph16060792
• Etsassala, N. G., Badmus, J. A., Marnewick, J. L., Iwuoha, E. I., Nchu, F., & Hussein, A. A. (2020). Alphaglucosidase and alphaamylase inhibitory activities, molecular docking, and antioxidant capacities of Salvia aurita constituents. Antioxidants, 9(11), 1149. https://doi.org/10.3390/antiox9111149
• Göçeri, A., Demirtaş, İ., Alma, M. H., Adem, Ş., Kasra, Z. A., Gül, F., & Uzun, A. (2022). Investigation on chemical composition, antioxidant activity and SARS-CoV-2 nucleocapsid protein of endemic Ferula longipedunculata Peşmen. Grasasy Aceites, 73(1), e450-e450. https://doi.org/10.3989/gya.0107211
• Jianu, C., Rusu, L. C., Muntean, I., Cocan, I., Lukinich-Gruia, A. T., Goleț, I., & Muntean, D. (2022). In vitro and in Silico evaluation of the antimicrobial and antioxidant potential of Thymus pulegioides essential oil. Antioxidants, 11(12), 2472. https://doi.org/10.3390/antiox11122472
• Karakaya, S. (2016). Ferulago trachycarpa Boiss., F. blancheana Post, F. pachyloba (Fenzl) Boiss. ve F. bracteata Boiss. & Haussk. (Apiaceae) Türleri üzerinde araştırmalar (Tez No: 431850). [Doktora Tezi, Ankara Üniversitesi]. YÖK Tez Merkezi.
• Karakaya, S., Göger, G., Bostanlik, F.D., Demirci, B., Duman, H., & Kilic, C. S. (2018). Comparison of the essential oils of Ferula orientalis L., Ferulago sandrasica Peşmen and Quézel, and Hippomarathrum microcarpum Petrov and their antimicrobial activity. Turkish Journal of Pharmaceutical Sciences, 16(1), 69. https://doi.org/10.4274/tjps.77200
• Karakaya, S., Koca, M., Sytar, O., & Duman, H. (2021). Determination of natural phenolic compounds of Ferula longipedunculata Peşmen and assessment their antioxidant and anticholinesterase potentials. Natural Product Research, 35(10), 1654-1656.
• Kartal, N., Sokmen Tepe, M., B., Daferer, Polissiou, D., & Sokmen, A. (2007). Investigation of the antioxidant properties of Ferula orientalis L. using a suitable extraction procedure. Food Chemistry 100, 584-589. https://doi.org/10.1016/j.foodchem.2005.09.084
• Kaya D., & Ergönül, P.G. (2015). Uçucu yağ elde etme yöntemleri. Celal Bayar Üniversitesi, Mühendislik Fakültesi Gıda Dergisi, 40, 1-3. https://doi.org/10.15237/gida.GD15014
• Keser, A. M., & Demir, İ. (2025). Assessment of conservation status of Ferula huber‐morathii: association with population genetic structure and regional climate. Nordic Journal of Botany, 2025(2), e04257. https://doi.org/10.1111/njb.04257
• Kose, E.O., Aktas, O., Deniz, I.G., & Sarikurkcu, C. (2010). Chemical composition, antimicrobial and antioxidant activity of essential oil of endemic Ferula lycia Boiss. Journal of Medicinal Plants Research, 4(17), 1698-1703. https://doi.org/10.5897/JMPR09.439
• Talebi Kouyakhi, E., Naghavi, M. R., & Alayhs, M. (2008). Study of the essential oil variation of Ferula gummosa samples from Iran. Chemistry of Natural Compounds, 44(1), 124-126.
• Tisserand R., & Balacs, T. (1995). Ess.Oil Safety A Guide for Health Care Professionals (2. baskı), pp. 14-18, 72, UK: Churchill Livingstone Elsevier.
• Trott, O., & Olson, A. J. (2010). AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry, 31(2), 455–461. https://doi.org/10.1002/jcc.21334
• Youssef, F. S., Mamatkhanova, M. A., Mamadalieva, N. Z., Zengin, G., Aripova, S. F., Alshammari, E., & Ashour, M. L. (2020). Chemical profiling and discrimination of essential oils from six Ferula species using GC analyses coupled with chemometrics and evaluation of their antioxidant and enzyme inhibitory potential. Antibiotics, 9(8), 518. https://doi.org/10.3390/antibiotics9080518
• Yusufoglu, H. S., Soliman, G. A., Abdel-Rahman, R. F., Abdel-Kader, M. S., Genaie, M. A., Bedir, E., ... & Öztürk, B. (2015). Antioxidant and antihyperglycemic effects of Ferula durdeana and Ferula huber-morathii in experimental diabetic rats. International Journal of Pharmacology, 11(7), 738-748. https://doi.org/10.3923/ijp.2015.738.748
• Zhang, Y., Wu, F., He, Z., Fang, X., & Liu, X. (2023). Optimization and molecular mechanism of novel α-glucosidase inhibitory peptides derived from camellia seed cake through enzymatic hydrolysis. Foods, 12(2), 39. https://doi.org/10.3390/foods12020393