Fruit extracts of Rosa canina L. and Rosa pimpinellifolia L.: Phytochemical profiles, in vitro antioxidant, anti-inflammatory, xanthine oxidase inhibitory effects, and in silico molecular dynamics studies

Yunus Başar; Semiha Yenigün; Mehmet Hakkı Alma; İbrahim Demirtas; Tevfik Ozen

doi:10.18016/ksutarimdoga.vi.1639294

TR EN

Rosa canina ve Rosa pimpinellifolia meyve özütleri: Fitokimyasal profilleri, in vitro antioksidan, anti-inflamatuar, ksantin oksidaz inhibitör etkileri ve in silico moleküler dinamik çalışmaları

Öz

Bu çalışmada, Rosa canina (RC) ve R. pimpinellifolia (RP) meyve metanol özütlerinin fitokimyasal ve biyolojik aktiviteleri araştırılmıştır. HPLC'de, RP ve RC özütleri ana bileşenler olarak büyük miktarlarda askorbik asit ve gallik asit içermektedir. GC-MS/MS'de, her özütte en yüksek miktarlarda oleik asit, linoleik asit ve palmitik asit metil esteri bulunmuştur. RP ve RC'nin toplam fenol içerikleri sırasıyla 17.28±0.10 ve 5.19±0,22 mg GAE/g özüt olarak bulunmuştur. Özütlerin DPPH˙ süpürücü aktivitesinin (RC için 13.45±0.21 µg/mL ve RP için 3.41±0.05 µg/mL), askorbik asitten (42.15±1.35 µg/mL) daha yüksek olduğu gözlenmiştir. RC ve askorbik asidin indirgeyici güç kapasiteleri sırasıyla 55,57±3,23 ve 87,24±2,44 µg/mL olarak bulundu. BSA denatürasyon deneyine göre, RP'nin anti-inflamatuar etkisinin DFS ile düşük dozlarda daha etkili olduğu ve yüksek dozlardaki etkiye benzer olduğu bulundu. RC özütü, 2,28±0,25 µg/mL'lik IC50 değeri ile yüksek ksantin oksidaz (XO) inhibisyonu gösterdi. Askorbik ve gallik asidin XO ile bağlanma afiniteleri sırasıyla -6,20 ve -6,60 kcal/mol olarak belirlendi. Ayrıca, komplekslerin moleküler dinamik simülasyonları 100 ns boyunca uygulandı ve kararlı oldukları gözlendi. Bağlanma enerjileri MM/PBSA yapılarak belirlendi ve gallik asidin yüksek değerinin -21,50 kcal/mol olarak bulunduğu kaydedildi. Bu şekilde iki farklı kuşburnu türünün fitokimyasal bileşenleri ve biyolojik aktiviteleri karşılaştırılmış ve gıda, kozmetik ve ilaç gibi alanlarda kullanımına yönelik fikirler sunulmuştur.

Anahtar Kelimeler

Fruit extracts of Rosa canina L. and Rosa pimpinellifolia L.: Phytochemical profiles, in vitro antioxidant, anti-inflammatory, xanthine oxidase inhibitory effects, and in silico molecular dynamics studies

Abstract

In this study, the phytochemical and biological activities of Rosa canina (RC) and R. pimpinellifolia (RP) fruit methanol extracts were investigated. HPLC analysis revealed that RP and RC extracts contained high amounts of ascorbic acid and gallic acid as the major components. In GC-MS/MS analysis, oleic acid, linoleic acid, and palmitic acid methyl ester were the most abundant compounds in both extracts. The total phenolic contents of RP and RC were 17.28±0.10 and 5.19±0,22 mg GAE/g extract, respectively. DPPH˙ scavenging activities of the extracts (13.45±0.21 µg/mL for RC and 3.41±0.05 µg/mL for RP) were observed to be higher than ascorbic acid (42.15±1.35 µg/mL). The reducing power capacities of RC and ascorbic acid were 55.57±3.23 and 87.24±2.44 µg/mL, respectively. According to the BSA denaturation assay, the anti-inflammatory effect of RP was found to be more effective at low doses with DFS and similar to the effect at high doses. RC extract showed high xanthine oxidase (XO) inhibition with an IC50 value of 2.28±0.25 µg/mL. The binding affinities of ascorbic and gallic acid with XO were determined as 6.20 and 6.60 kcal/mol, respectively. In addition, molecular dynamics simulations of the complexes were applied for 100 ns and observed to be stable. Binding energies were determined by performing MM/PBSA, and it was recorded that a high level of gallic acid was found at 21.50 kcal/mol. In this way, the phytochemical constituents and biological activities of two different rosehip species were compared, and ideas for their use in food, cosmetics, and medicine were presented.

Keywords

Supporting Institution

Ondokuz Mayis University Iğdır University

Project Number

BAP01-2024-4682 ..... YİP0723İ01

Ethical Statement

yok

Thanks

Ondokuz Mayis University Iğdır University

References

Abraham, M. J., Murtola, T., Schulz, R., Páll, S., Smith, J. C., Hess, B., & Lindahl, E. (2015). GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX, 1, 19-25. https://doi.org/https://doi.org/10.1016/j.softx.2015.06.001
Akkoc, S., Karatas, H., Muhammed, M. T., Kökbudak, Z., Ceylan, A., Almalki, F., Laaroussi, H., & Ben Hadda, T. (2023). Drug design of new therapeutic agents: Molecular docking, molecular dynamics simulation, DFT and POM analyses of new Schiff base ligands and impact of substituents on bioactivity of their potential antifungal pharmacophore site. Journal of Biomolecular Structure and Dynamics, 41(14), 6695-6708. https://doi.org/https://doi.org/10.1080/07391102.2022.2111360
Atienza, S. G., Torres, A. M., Millan, T., & Cubero, J. I. (2005). Genetic diversity in Rosa as revealed by RAPDs. Agriculturae Conspectus Scientificus, 70(3), 75-85.
Başar, Y., Demirtaş, İ., Yenigün, S., İpek, Y., Özen, T., & Behçet, L. (2024a). Molecular docking, molecular dynamics, MM/PBSA approaches and bioactivity studies of nepetanudoside B isolated from endemic Nepeta aristata. Journal of Biomolecular Structure and Dynamics, 1-14.
Başar, Y., & Erenler, R. (2024). Phytochemical analysis of Silybum marianum flowers: Quantitative analysis of natural compounds and molecular docking application. Turkish Journal of Biodiversity, 7(1), 20-31. https://doi.org/https://doi.org/10.38059/biodiversity.1450643
Başar, Y., Gül, F., Nas, M. S., Alma, M. H., & Çalımlı, M. H. (2024b). Investigation of value-added compounds derived from oak wood using hydrothermal processing techniques and comprehensive analytical approaches (HPLC, GC-MS, FT-IR, and NMR). International Journal of Chemistry and Technology, 8(1), 53-61.
Başar, Y., Yenigün, S., Gül, F., Ozen, T., Demirtas, İ., Alma, M. H., & Temel, S. (2024c). Phytochemical profiling, molecular docking and ADMET prediction of crude extract of Atriplex nitens Schkuhr for the screening of antioxidant and urease inhibitory. International Journal of Chemistry and Technology, 8(1), 62-71.
Bjelkmar, P., Larsson, P., Cuendet, M. A., Hess, B., & Lindahl, E. (2010). Implementation of the CHARMM force field in GROMACS: analysis of protein stability effects from correction maps, virtual interaction sites, and water models. Journal of chemical theory and computation, 6(2), 459-466. https://doi.org/https://doi.org/10.1021/ct900549r

Blois, M. S. (1958). Antioxidant determinations by the use of a stable free radical. Nature, 181(4617), 1199-1200. https://doi.org/ https://doi.org/10.1038/1811199a0
Chrubasik, C., Roufogalis, B. D., Müller‐Ladner, U., & Chrubasik, S. (2008). A systematic review on the Rosa canina effect and efficacy profiles. Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives, 22(6), 725-733.
Çınar, İ., & Çolakoğlu, A. S. (2004). Potential health benefits of rose hip products. I International Rose Hip Conference 690, 253-258.
Çolak, A., Dönmez, A., Bulduk, İ., Torunoğlu, E. İ., & Aytar, E. C. (2025). Determination of Pomological and Chemical Properties and Molecular Docking Analysis of Crataegus orientalis and Crataegus orientalis subsp. orientalis Species and Subspecies in Sandıklı (Afyonkarahisar). Kahramanmaraş Sütçü İmam Üniversitesi Tarım ve Doğa Dergisi, 28(2), 446-458.
Doğan, A., Kazankaya, A., Çelik, F., & Uyak, C. (2006). Kuşburnunun halk hekimliğindeki yeri ve bünyesindeki bileşenler açısından yararları. II. Ulusal Üzümsü Meyveler Sempozyumu, Tokat, Türkiye, 14 - 16 Eylül 2006,, 47-53.
Encü, T. (2015). Doğu Anadolu bölgesinin bazı lokasyonlarından (Van-Hakkari-Şırnak) alınan kuşburnu (Rosa canina L.) meyvelerinin pomolojik ve bazı biyokimyasal özelliklerinin belirlenmesi. Yüzüncü Yıl Üniversitesi Fen Bilimleri Enstitüsü Bahçe Bitkileri Anabilim Dalı Yüksek lisans Tezi, Van.
Ercisli, S., Orhan, E., & Esitken, A. (2007). Fatty acid composition of Rosa species seeds in Turkey. Chemistry of Natural Compounds, 43(5), 605-606.
Fattahi, S., Jamei, R., & Hosseini, S. S. (2012). Antioxidant and antiradical activities of Rosa canina and Rosa pimpinellifolia fruits from West Azerbaijan. Iranian Journal of Plant Physiology, 2(4), 523-529.
Fetni, S., Bertella, N., Ouahab, A., Zapater, J. M. M., & Fernandez, S. D. P.-T. (2020). Composition and biological activity of the Algerian plant Rosa canina L. by HPLC-UV-MS. Arabian Journal of Chemistry, 13(1), 1105-1119.
Gautam, V., Nimmanpipug, P., Zain, S. M., Rahman, N. A., & Lee, V. S. (2021). Molecular dynamics simulations in designing DARPins as phosphorylation-specific protein binders of ERK2. Molecules, 26(15), 4540. https://doi.org/https://doi.org/10.3390/molecules26154540
Golmakani, E., Mohammadi, A., Sani, T. A., & Kamali, H. (2014). Phenolic and flavonoid content and antioxidants capacity of pressurized liquid extraction and perculation method from roots of Scutellaria pinnatifida A. Hamilt. subsp alpina (Bornm) Rech. f. The Journal of Supercritical Fluids, 95, 318-324. https://doi.org/ https://doi.org/10.1016/j.supflu.2014.09.020
Gostner, J. M., Becker, K., Ueberall, F., & Fuchs, D. (2015). The good and bad of antioxidant foods: an immunological perspective. Food and Chemical Toxicology, 80, 72-79.
Guven, L., Ozgen, U., Seçen, H., Sener, S., Badem, M., Celik, G., & Yayli, N. (2021). Phytochemical studies on the seeds, pseudofruits, and roots of Rosa pimpinellifolia. J. Res. Pharm, 25(2), 153-163.
Güneş, M., & Şen, S. M. (2001). Tokat Yöresinde Doğal Olarak Yetişen Kuşburnuların (Rosa spp.) Seleksiyon Yoluyla Islahı Üzerinde Bir Araştırma. Bahçe, 30(1), 9-16.
Güneş, S. (2011). Ümitvar bir kuşburnu (Rosa canina) genotipinin farklı iki lokasyondaki fenolojik, morfolojik ve pomolojik özellikleri Gaziosmanpaşa Üniversitesi, Fen Bilimleri Enstitüsü.
İlisulu, K. (1992). İlaç ve baharat bitkileri. Ankara Üniversitesi Ziraat Fakültesi.
Kandikattu, K., Kumar, P. B. R., Priya, R. V., Kumar, K. S., & Rathore, R. S. B. (2013). Evaluation of anti-inflammatory activity of Canthium parviflorum by in-vitro method. Indian Journal of Research in Pharmacy and Biotechnology, 1(5), 729-731.
Keleş, F., & Kökosmanlı, M. (1996). Kuşburnu ve kuşburnu çayında C vitamini. Kuşburnu sempozyumu, 5-6. Kutbay, H., & Kılınç, M. (1996). Kuşburnu (Rosa L.) Türlerinin Taksonomik Özellikleri ve Türkiye’deki Yayılışı. Kuşburnu sempozyumu, 5(6), 75-83.
Li, Z., Zhang, W., Abubaker, M. A., Shu, Q., & Liu, Y. (2025). In silico identification and experimental validation of two types of angiotensin-converting enzyme (ACE) and xanthine oxidase (XO) milk inhibitory peptides. Food Chemistry, 464, 141864. https://doi.org/https://doi.org/10.1016/j.foodchem.2024.141864
Liu, X., Shi, D., Zhou, S., Liu, H., Liu, H., & Yao, X. (2018). Molecular dynamics simulations and novel drug discovery. Expert Opinion on Drug Discovery, 13(1), 23-37. https://doi.org/https://doi.org/10.1080/17460441.2018.1403419
Macit, M. G., & Köse, Y. B. (2015). Medicinal plants used for folk medicine in Oltu (Erzurum/Turkey). Biological Diversity and Conservation, 8(2), 74-80.
Majewski, M., Ruiz-Carmona, S., & Barril, X. (2019). An investigation of structural stability in protein-ligand complexes reveals the balance between order and disorder. Communications Chemistry, 2(1), 110, 1-8. https://doi.org/https://doi.org/10.1038/s42004-019-0205-5
Orhan, N., Aslan, M., Hosbas, S., & Deliorman, O. D. (2009). Antidiabetic effect and antioxidant potential of Rosa canina fruits. Pharmacognosy Magazine, 5(20), 309-319.
Oyaizu, M. (1986). Studies on products of browning reaction. The Japanese Journal of Nutrition and Dietetics, 44(6), 307-315. https://doi.org/https://doi.org/10.5264/eiyogakuzashi.44.307
Rahman, H., Eswaraiah, M. C., & Dutta, A. (2015). In-vitro anti-inflammatory and anti-arthritic activity of Oryza Sativa Var. joha rice (an aromatic indigenous rice of Assam). Am. Eurasian J. Agric. Environ. Sci, 15(1), 115-121. https://doi.org/https://doi.org/10.13188/2328-1723.1000005
Sarkar, F. H., Li, Y., Wang, Z., & Kong, D. (2009). Cellular signaling perturbation by natural products. Cellular signalling, 21(11), 1541-1547.
Schmidt, B. M., Ribnicky, D. M., Lipsky, P. E., & Raskin, I. (2007). Revisiting the ancient concept of botanical therapeutics. Nature chemical biology, 3(7), 360-366.
Sen, S., & Gunes, M. (1996). Some chemical and physical properties of roses are grown in Tokat provinces in Turkey. Proceedings of 1st National Roseship Conference, 4-7.
Shakibaei, M., Allaway, D., Nebrich, S., & Mobasheri, A. (2012). Botanical extracts from Rosehip (Rosa canina), Willow Bark (Salix alba), and Nettle Leaf (Urtica dioica) suppress IL‐1β‐induced NF‐κB activation in canine articular chondrocytes. Evidence‐Based Complementary and Alternative Medicine, 2012(1), 509383.
Singh, J. V., Bedi, P. M. S., Singh, H., & Sharma, S. (2020). Xanthine oxidase inhibitors: patent landscape and clinical development (2015–2020). Expert Opinion on Therapeutic Patents, 30(10), 769-780.
Su, L., Yin, J.-J., Charles, D., Zhou, K., Moore, J., & Yu, L. L. (2007). Total phenolic contents, chelating capacities, and radical-scavenging properties of black peppercorn, nutmeg, rosehip, cinnamon and oregano leaf. Food Chemistry, 100(3), 990-997.
Tanker, N., Koyuncu, M., & Coşkun, M. (1993). Farmasötik botanik ders kitabı. Ankara Üniversitesi Eczacılık Fakültesi yayınları, Yayın(70), 449.
Valdés-Tresanco, M. S., Valdés-Tresanco, M. E., Valiente, P. A., & Moreno, E. (2021). gmx_MMPBSA: a new tool to perform end-state free energy calculations with GROMACS. Journal of chemical theory and computation, 17(10), 6281-6291. https://doi.org/https://doi.org/10.1021/acs.jctc.1c00645
Wissemann, V. (2017). Conventional taxonomy (wild roses).
Xue, H., Xu, M., Gong, D., & Zhang, G. (2023). Mechanism of flavonoids inhibiting xanthine oxidase and alleviating hyperuricemia from structure–activity relationship and animal experiments: A review. Food Frontiers, 4(4), 1643-1665.
Yamankaradeniz, R. (1983). Kuşburnu (Rosa sp) değerlendirme olanakları. Gıda, 8(4), 157-162.
Yenigun, S., Basar, Y., Ipek, Y., Gok, M., Behcet, L., Ozen, T., & Demirtas, I. (2024). A potential DNA protector, enzyme inhibitor and in silico studies of daucosterol isolated from six Nepeta species. Process Biochemistry, 143, 234-247. https://doi.org/https://doi.org/10.1016/j.procbio.2024.04.039
Yılmaz, S. (1996). Kuşburnu bitkisinin erozyon kontrolündeki yeri ve önemi. Kuşburnu Sempozyumu Bildiriler Kitabı, 167-168.

Details

Primary Language

English

Subjects

Pharmaceutical Botany

Journal Section

Research Article

Authors

Yunus Başar
0000-0002-7785-3242
Türkiye

Semiha Yenigün
0000-0002-1979-5427
Türkiye

Mehmet Hakkı Alma
0000-0001-6323-7230
Türkiye

İbrahim Demirtas
0000-0001-8946-647X
Türkiye

Tevfik Ozen ^*
0000-0003-0133-5630
Türkiye

Early Pub Date

May 1, 2025

Publication Date

June 9, 2025

Submission Date

February 13, 2025

Acceptance Date

April 11, 2025

Published in Issue

Year 2025 Volume: 28 Number: 3

DOI

https://doi.org/10.18016/ksutarimdoga.vi.1639294

IZ

https://izlik.org/JA47UK93NK

Cite

RIS / Bibtex

APA

Başar, Y., Yenigün, S., Alma, M. H., Demirtas, İ., & Ozen, T. (2025). Fruit extracts of Rosa canina L. and Rosa pimpinellifolia L.: Phytochemical profiles, in vitro antioxidant, anti-inflammatory, xanthine oxidase inhibitory effects, and in silico molecular dynamics studies. Kahramanmaraş Sütçü İmam Üniversitesi Tarım Ve Doğa Dergisi, 28(3), 636-649. https://doi.org/10.18016/ksutarimdoga.vi.1639294