Bioactive component analysis of seed coat hexane extract of Ardahan (Türkiye) walnut

Yıl 2024, , 89 - 94, 30.08.2024

Esra Palabıyık , Handan Uğuz , Bahri Avcı , Ayşe Nurseli Sulumer , Bilal Yılmaz , Hakan Aşkın

https://doi.org/10.51753/flsrt.1410006

Öz

The walnut seed coat (WSC), a significant waste product that is underappreciated compared to other walnut parts, is responsible for the emergence of biological potential, has a favorable and protective effect on health, and includes a wealth of bioactive phytochemicals. Considering this situation, the aim of the study was to clarify the bioactive components in the WSC hexane extract. A hexane WSC extract (H-WSC) was initially produced to conduct the analysis. Four chemical components in the walnut seed coat were identified using the gas chromatography-mass spectrometry (GC-MS) method. Accordingly, the main components in hexane extracts are β-sitosterol (%32.91) and ethyl iso-allocolate (%52.06); other components are 3-(octadecyloxy)propyl (9E)-9-octadecenoate (%8.41) and santa camphor (%4.45).

Anahtar Kelimeler

Gas chromatography-mass spectrometry, phytosterol, steroid, terpenoid, walnut seed coat

Destekleyen Kurum

Ataturk University

Teşekkür

We would like to thank Atatürk University Faculty of Pharmacy for the GC-MS analyzes of the study and the Department of Chemistry of the Faculty of Science for the plant extraction.

Kaynakça

• Abubacker, M. N., & Devi, P. K. (2014). In vitro antifungal potentials of bioactive compound oleic acid, 3-(octadecyloxy) propyl ester isolated from Lepidagathis cristata Willd.(Acanthaceae) inflorescence. Asian Pacific Journal of Tropical Medicine, 7, S190-S193.
• Alawode, T. T., Lajide, L., Olaleye, M., & Owolabi, B. (2021). Stigmasterol and β-sitosterol: Antimicrobial compounds in the leaves of Icacina trichantha identified by GC-MS. Beni-Suef University Journal of Basic and Applied Sciences, 10, 1-8.
• Alkali, K., Dikwa, K. B., Ajibade, G. A., Magaji, Y., & Abdulhamid, M. B. (2024). Qualitative and quantitative phytochemicals screening of aqueous, methanol and hexane leaves extracts of Senna occidentalis. Asian Plant Research Journal, 12(3), 27-35.
• Arsana, I. N., Juliasih, N. K. A., Ayu Sauca Sunia Widyantari, A. A., Suriani, N. L., & Manto, A. (2022). GC-MS analysis of the active compound in ethanol extracts of white pepper (Piper nigrum L.) and pharmacological effects. Cellular, Molecular and Biomedical Reports, 2(3), 151-161.
• Askin, S., Askin, H., Dursun, E., Palabiyik, E., Uguz, H., Cakmak, O., & Koc, K. (2022b). The hepato-renal protective potential of walnut seed skin extract against acute renal ischemia/reperfusion damage. Cytokine, 153, 155861.
• Askin, H., Askın, S., & Palabiyik, E. (2022a). Walnut seed coat can attenuate renal ischemia reperfusion injury in distant organ by inhibiting apoptosis. Health Sciences in International Research (1st edition) (pp 93-104). New York: Eğitim Publishing Group, Inc.
• Bayrak, S., Ozturk, C., Demir, Y., Alim, Z., & Kufrevioglu, O. I. (2020). Purification of polyphenol oxidase from potato and investigation of the inhibitory effects of phenolic acids on enzyme activity. Protein and Peptide Letters, 27(3), 187-192.
• Bhosale, Y. K., Varghese, S. M., Thivya, P., Hema, V., & Sinija, V. R. (2021). Studies on assessment of safety and nutritional quality of shallot waste fractions. Journal of Food Processing and Preservation, 45(2), e15147.
• Boligon, A. A., Schwanz, T. G., Piana, M., Bandeira, R. V., Frohlich, J. K., Brum, T. F. D., ... & Athayde, M. L. (2013). Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves. Natural Product Research, 27(1), 68-71.
• Choi, N. H., Jang, J. Y., Choi, G. J., Choi, Y. H., Jang, K. S., Min, B. S., ... & Kim, J. C. (2017). Antifungal activity of sterols and Dipsacus saponins isolated from Dipsacus asper roots against phytopathogenic fungi. Pesticide Biochemistry and Physiology, 141, 103-108.
• Dardeer, H. M., Abbas, S. A., El-Sayyad, G. S., & Ali, M. F. (2022). Effect of titanium dioxide nanoparticles and β-cyclodextrin polymer on physicochemical, antimicrobial, and antibiofilm properties of a novel chitosan-camphor polymer. International Journal of Biological Macromolecules, 219, 1062-1079.
• Demir, Y., Durmaz, L., Taslimi, P., & Gulcin, I. (2019). Antidiabetic properties of dietary phenolic compounds: Inhibition effects on α‐amylase, aldose reductase, and α‐glycosidase. Biotechnology and Applied Biochemistry, 66(5), 781-786.
• Devaraj, E., Roy, A., Royapuram Veeraragavan, G., Magesh, A., Varikalam Sleeba, A., Arivarasu, L., & Marimuthu Parasuraman, B. (2020). β-Sitosterol attenuates carbon tetrachloride–induced oxidative stress and chronic liver injury in rats. Naunyn-Schmiedeberg’s Archives of Pharmacology, 393, 1067-1075.
• Diab, T. A., Donia, T., & Saad-Allah, K. M. (2021). Characterization, antioxidant, and cytotoxic effects of some Egyptian wild plant extracts. Beni-Suef University Journal of Basic and Applied Sciences, 10(1), 1-13.
• Dos Santos, E., Leitão, M. M., Ito, C. N. A., Silva-Filho, S. E., Arena, A. C., de Souza Silva-Comar, F. M., ... & Kassuya, C. A. L. (2021). Analgesic and anti-inflammatory articular effects of essential oil and camphor isolated from Ocimum kilimandscharicum Gürke leaves. Journal of Ethnopharmacology, 269, 113697.
• El-Naggar, H. M., Shehata, A. M., & Morsi, M. A. A. (2023). Micropropagation and GC-MS analysis of bioactive compounds in bulbs and callus of white squill. In Vitro Cellular & Developmental Biology-Plant, 59(1), 154-166.
• Fachriyah, E., Ayu, T., & Kusrini, D. (2019). Identification of phenolic acid from ethanol extract leaves binahong (Anredera cordifolia (ten) stennis) and antioxidant activity test. Journal of Physics: Conference Series, 1217(1), 012051.
• FAO, (2024). Food and Agriculture Organization of the United Nations, http://www.fao.org/faostat/en/#search/walnut/, Last accessed on August 25, 2024.
• Gaanapriya, V., Sivakumar, V. M., & Thirumarimurugan, M. (2024). In-vitro studies of bioactive nanoemulgel from agro-waste and mathematical modeling of drug release. Indian Journal of Chemical Technology (IJCT), 31(1), 135-142.
• Geng, S., Ning, D., Ma, T., Chen, H., Zhang, Y., & Sun, X. (2021). Comprehensive analysis of the components of walnut kernel (Juglans regia L.) in China. Journal of Food Quality, 2021, 1-11.
• Guz, L., Wawrzykowski, J., & Adaszek, Ł. (2021). Anti-babesial potential and chemical composition of essential oil from yarrow Achillea millefolium. Polish Journal of Veterinary Sciences, 24(1), 79-84.
• Ivanov, M., Kannan, A., Stojković, D. S., Glamočlija, J., Calhelha, R. C., Ferreira, I. C., ... & Soković, M. (2021). Camphor and eucalyptol—Anticandidal spectrum, antivirulence effect, efflux pumps interference and cytotoxicity. International Journal of Molecular Sciences, 22(2), 483.
• Johnson, T. O., Odoh, K. D., Nwonuma, C. O., Akinsanmi, A. O., & Adegboyega, A. E. (2020). Biochemical evaluation and molecular docking assessment of the anti-inflammatory potential of Phyllanthus nivosus leaf against ulcerative colitis. Heliyon, 6(5), 1-10.
• Karahan, F., Ozyigit, I. I., Saracoglu, I. A., Yalcin, I. E., Ozyigit, A. H., & Ilcim, A. (2020). Heavy metal levels and mineral nutrient status in different parts of various medicinal plants collected from eastern Mediterranean region of Turkey. Biological Trace Element Research, 197, 316-329.
• Karakose, M. (2022). Vascular plant diversity of Esenli (Giresun) forest planning unit. Forestist, 72(2), 156-164.
• Khongthaw, B., Chauhan, P. K., Dulta, K., Kumar, V., & Ighalo, J. O. (2023). A comparison of conventional and novel phytonutrient extraction techniques from various sources and their potential applications. Journal of Food Measurement and Characterization, 17(2), 1317-1342.
• Komaki, A., Kordali, S., Bozhuyuk, A. U., & Bostan, H. (2019). Microbial organisms detected on Juglans regia in Eastern Anatolia, Turkey. Fresenius Environmental Bulletin, 28(9), 6432-6434.
• Kumar, R., Ramachaandra, S. K., Kaushik, S., Austin, H., & Rajesh, T. (2024). Bioprospecting of wild botanicals against Alternaria leaf blight of radish and their phytochemical profiling by GC-MS. Research Square.
• Lin, F., Xu, L., Huang, M., Deng, B., Zhang, W., Zeng, Z., & Yinzhi, S. (2020). β-Sitosterol protects against myocardial ischemia/reperfusion injury via targeting PPARγ/NF-κB signalling. Evidence-Based Complementary and Alternative Medicine, 2020(1), 2679409.
• Liu, R., Hao, D., Xu, W., Li, J., Li, X., Shen, D., ... & Zhang, Y. (2019). β-Sitosterol modulates macrophage polarization and attenuates rheumatoid inflammation in mice. Pharmaceutical Biology, 57(1), 161-168.
• Malathi, K., & Ramaiah, S. (2017). Ethyl iso-allocholate from a medicinal rice Karungkavuni inhibits dihydropteroate synthase in Escherichia coli: A molecular docking and dynamics study. Indian Journal of Pharmaceutical Sciences, 78(6), 780-788.
• Martínez, M. L., Labuckas, D. O., Lamarque, A. L., & Maestri, D. M. (2010). Walnut (Juglans regia L.): genetic resources, chemistry, by‐products. Journal of the Science of Food and Agriculture, 90(12), 1959-1967.
• Mates, L., Rusu, M. E., & Popa, D. S. (2023). Phytochemicals and biological activities of walnut septum: A systematic review. Antioxidants, 12(3), 604.
• Mawlid, O. A., Abdelhady, H. H., & El-Deab, M. S. (2023). Highly active novel K2CO3 supported on MgFe2O4 magnetic nanocatalyst for low-temperature conversion of waste cooking oil to biodiesel: RSM optimization, kinetic, and thermodynamic studies. Journal of Environmental Chemical Engineering, 11(5), 110623.
• Mekarunothai, A., Bacher, M., Buathong, R., Intarasam, S., Tayana, N., Kongkiatpaiboon, S., ... & Napiroon, T. (2024). β-sitosterol isolated from the leaves of Trema orientalis (Cannabaceae) promotes viability and proliferation of BF-2 cells. PeerJ, 12, e16774.
• Nasution, R., Bahi, M., Saidi, N., & Junina, I. (2015). β-sitosterol from bark of Artocarpus camansi and its antidiabetic activity. Proceedings of The Annual International Conference, Syiah Kuala University-Life Sciences & Engineering Chapter, Banda Aceh, Indonesia. 118-124.
• Nikolić, B., Vasilijević, B., Mitić-Ćulafić, D., Vuković-Gačić, B., & Knežević-Vukćević, J. (2015). Comparative study of genotoxic, antigenotoxic and cytotoxic activities of monoterpenes camphor, eucalyptol and thujone in bacteria and mammalian cells. Chemico-Biological Interactions, 242, 263-271.
• Novotny, J. A., Chen, T. Y., Terekhov, A. I., Gebauer, S. K., Baer, D. J., Ho, L., ... & Ferruzzi, M. G. (2017). The effect of obesity and repeated exposure on pharmacokinetic response to grape polyphenols in humans. Molecular Nutrition & Food Research, 61(11), 1700043.
• Nweze, C., Ibrahim, H., & Ndukwe, G. I. (2019). Beta-sitosterol with antimicrobial property from the stem bark of pomegranate (Punica granatum Linn). Journal of Applied Sciences and Environmental Management, 23(6), 1045-1049.
• Okasha, N. I., Rahman, M. A., Nafie, M. S., Shama, N. M. A., Mostafa, A., El-Ebeedy, D. A., & Azeiz, A. Z. A. (2024). Identification of potential antiviral compounds from Egyptian sea stars against seasonal influenza A/H1N1 virus. Journal of Genetic Engineering and Biotechnology, 22(1), 100334.
• Okoye, F. B. C., Osadebe, P. O., Nworu, C. S., Okoye, N. N., Omeje, E. O., & Esimone, C. O. (2011). Topical anti-inflammatory constituents of lipophilic leaf fractions of Alchornea floribunda and Alchornea cordifolia. Natural Product Research, 25(20), 1941-1949.
• Palabiyik, E. (2022). Triton WR-1339 ile indüklenen hiperlipidemik sıçanlarda ceviz tohum kabuğu ekstresinin hipolipidemik, antiinflamatuar ve antioksidan özelliklerinin değerlendirilmesi, Doktora Tezi, (pp. 1-153). Ataturk University, Erzurum.
• Palabiyik, E., Sulumer, A. N., Uguz, H., Avcı, B., Askın, S., Askın, H., & Demir, Y. (2023). Assessment of hypolipidemic and anti‐inflammatory properties of walnut (Juglans regia) seed coat extract and modulates some metabolic enzymes activity in triton WR‐1339‐induced hyperlipidemia in rat kidney, liver, and heart. Journal of Molecular Recognition, 36(3), e3004.
• Palabiyik, E., Askin, S., & Askin, H. (2022). Effect of walnut seed skin against main organ damage caused by Hyperlipidemia. Avrupa Bilim ve Teknoloji Dergisi, (34), 652-656.
• Pan, Z., Wang, S. K., Cheng, X. L., Tian, X. W., & Wang, J. (2016). Caryophyllene oxide exhibits anti-cancer effects in MG-63 human osteosarcoma cells via the inhibition of cell migration, generation of reactive oxygen species and induction of apoptosis. Bangladesh Journal of Pharmacology, 11(4), 817-823.
• Paniagua-Pérez, R., Madrigal-Bujaidar, E., Reyes-Cadena, S., Molina-Jasso, D., Gallaga, J. P., Silva-Miranda, A., ... & Chamorro, G. (2005). Genotoxic and cytotoxic studies of beta-sitosterol and pteropodine in mouse. Journal of Biomedicine and Biotechnology, 2005(3), 242-247.
• Paniagua-Pérez, R., Madrigal-Bujaidar, E., Reyes-Cadena, S., Alvarez-González, I., Sánchez-Chapul, L., Pérez-Gallaga, J., ... & Velasco, O. (2008). Cell protection induced by beta-sitosterol: inhibition of genotoxic damage, stimulation of lymphocyte production, and determination of its antioxidant capacity. Archives of toxicology, 82, 615-622.
• Park, C., Moon, D. O., Rhu, C. H., Choi, B. T., Lee, W. H., Kim, G. Y., & Choi, Y. H. (2007). β-Sitosterol induces anti-proliferation and apoptosis in human leukemic U937 cells through activation of caspase-3 and induction of Bax/Bcl-2 ratio. Biological and Pharmaceutical Bulletin, 30(7), 1317-1323.
• Poochi, S. P., Easwaran, M., Balasubramanian, B., Anbuselvam, M., Meyyazhagan, A., Park, S., ... & Kaul, T. (2020). Employing bioactive compounds derived from Ipomoea obscura (L.) to evaluate potential inhibitor for SARS‐CoV‐2 main protease and ACE2 protein. Food frontiers, 1(2), 168-179.
• Prakash, N. K. U., Sripriya, N. S., Raj, D. D., Deepa, S., & Bhuvaneswari, S. (2019). Antioxidant potency and GC-MS composition of Origanum majorana Linn. Pakistan Journal of Pharmaceutical Sciences, 32(5), 2117-2122.
• Rashed, K. (2020). Beta-sitosterol medicinal properties: A review article. European Journal of Science, Innovation and Technology, 9, 208-212.
• Ravi, L., Girish, S., D’Souza, S. R., Sreenivas BK, A., Kumari GR, S., O, A., ... & Manjunathan, R. (2023). β-Sitosterol, a phytocompound from Parthenium hysterophorus, reveals anti-diabetic properties through α-Amylase inhibition: an in-silico and in-vitro analysis. Journal of Biomolecular Structure and Dynamics, 1-12.
• Rech, S. B., Batista, C. V., Schripsema, J., Verpoorte, R., & Henriques, A. T. (1998). Cell cultures of Rauwolfia sellowii: growth and alkaloid production. Plant Cell, Tissue and Organ Culture, 54, 61-63.
• Rutkowska, E., Wołejko, E., Kaczyński, P., Łuniewski, S., & Łozowicka, B. (2023). High and low temperature processing: Effective tool reducing pesticides in/on apple used in a risk assessment of dietary intake protocol. Chemosphere, 313, 137498.
• Sampathkumar, Y., Elumali, S., & Halith, A. M. (2020). GCMS determination of anticancer, anti-inflammatory and anti-bacterial compounds from salt tolerance microalgae (Lyngbya sp. Nostoc sp. and Phormidium sp.) Isolated from Marakkanam Salt Pan, Tamil Nadu, India. Engineering Sciences, 11, 1139-1152.
• Shah, S. I. A., Tipu, M. Y., Aslam, A., Khan, A. U., Shafee, M., Khan, S. A., ... & Akbar, A. (2021). Research article elucidating antiviral activity of Curcuma longa against H9 N2 influenza virus using embryonated chicken egg model. Tropical Biomedicine, 38(3), 353-359.
• Sokolova, A. S., Yarovaya, О. I., Baev, D. S., Shernyukov, А. V., Shtro, A. A., Zarubaev, V. V., & Salakhutdinov, N. F. (2017). Aliphatic and alicyclic camphor imines as effective inhibitors of influenza virus H1N1. European Journal of Medicinal Chemistry, 127, 661-670.
• Sujila, S. R., Rajadurai, M., & Shairibha, S. R. (2014). Hepatoprotective effect of β-sitosterol on lipid peroxidation and antioxidant status in ethanol-induced hepatotoxic rats. International Journal of Integrated Science and Technology, 3, 1-11.
• Suzen, A., & Atamov, V. (2022). Endemic and rare plant diversity of Ambarlik highland-case study from Çamlihemşin, Türkiye. Plant & Fungal Research, 5(1), 29-33.
• Thakur, R. S., & Ahirwar, B. (2019). A steroidal derivative from Trigonella foenum graecum L. that induces apoptosis in vitro and in vivo. Journal of Food and Drug Analysis, 27(1), 231-239.
• Uguz, H., Palabiyik, E. and Askin, H. (2022). Free radicals, oxidative stress and biological effects of oxidative stress, antioxidant defense system. In: Onay Derin, D. (ed) International Research in Health Sciences III (1st edition) (pp 7-24). New York: Eğitim Publishing Group, Inc.
• von Holtz, R. L., Fink, C. S., & Awad, A. B. (1998). β‐sitosterol activates the sphingomyelin cycle and induces apoptosis in LNCaP human prostate cancer cells. Nutrition and Cancer, 52(1), 8-12.
• Yang, H., Xiao, X., Li, J., Wang, F., Mi, J., Shi, Y., ... & Wan, X. (2022). Chemical compositions of walnut (Juglans spp.) oil: Combined effects of genetic and climatic factors. Forests, 13(6), 962.
• Zhu, Y., Wang, K., Jia, X., Fu, C., Yu, H., & Wang, Y. (2024). Antioxidant peptides, the guardian of life from oxidative stress. Medicinal Research Reviews, 44(1), 275-364.