Erciyes Üniversitesi Fen Bilimleri Enstitüsü Fen Bilimleri Dergisi

1012-2354

Erciyes Üniversitesi

10.65520/erciyesfen.1886194

Natural Products and Bioactive Compounds

Doğal Ürünler ve Biyoaktif Bileşikler

Potansiyel Çoklu Enzim İnhibitörü Olarak Crataegus tanacetifolia ve Crataegus orientalis Meyve Ekstraktlarının Fitokimyasal ve Biyoaktif Değerlendirmesi

Phytochemical and Bioactive Assessment of Crataegus tanacetifolia and Crataegus orientalis Fruit Extracts as a Potential Multi-Enzyme Inhibitor

https://orcid.org/0000-0002-0030-4106

Fındık

Bahar

NEVSEHIR HACI BEKTAS VELI UNIVERSITY

https://orcid.org/0000-0002-7966-455X

Yıldız

Hilal

NEVSEHIR HACI BEKTAS VELI UNIVERSITY

03 26 2026

42 1 02 10 2026 03 23 2026

1985

Erciyes Üniversitesi Fen Bilimleri Enstitüsü Fen Bilimleri Dergisi

Bitkiler, biyoaktif bileşiklerin sonsuz kaynağı olup bitki kökenli ilaçlar ve besin takviyeleri geliştirmeye yönelik araştırmaların odağında yer almaktadır. Bu çalışmada, Crataegus tanacetifolia ve Crataegus orientalis'ten elde edilen polar ekstraktların fenolik profilleri, triterpenoid içeriği, enzim inhibisyon aktiviteleri, antioksidan kapasiteleri ve toplam fenolik içerikleri (TPC) değerlendirilmiştir. LCMS/MS ve GC-MS analizleri sonucunda, C. tanacetifolia'da 25 adet fenolik bileşik ve iki adet triterpenoid, C. orientalis'te ise 26 adet fenolik bileşik ve bir adet triterpenoid tespit edilmiştir. Her iki ekstrakta da baskın fenolik bileşiğin kinik asit olduğu belirlenmiştir. C. tanacetifolia ekstraktında oleanolik asit ve ursolik asit saptanırken, C. orientalis ekstraktında yalnızca ursolik asit tespit edilmiştir. Her iki ekstrakt da güçlü anjiyotensin dönüştürücü enzim inhibisyon aktivitesi (~%99) göstererek antihipertansif potansiyeli ve ayrıca dikkate değer üreaz inhibisyon aktivitesi (C. tanacetifolia: %87,08; C. orientalis: %91,66) göstermiştir. C. tanacetifolia ve C. orientalis ekstraktları, DPPH radikal süpürme aktivitesi için sırasıyla 123,38 ve 97,29 µg/mL IC₅₀ değerleri ile linoleik asit/β-karoten ağartma testinde %82,37 ve %92,34 oranlarında önemli antioksidan aktivite göstermiştir. Ekstraktların TPC değerleri sırasıyla 26,13 ve 76,80 mg GAE/g olarak belirlenmiştir. Sonuçlar, C. tanacetifolia ve C. orientalis'in farmasötik ve nutrasötik ürünlerin geliştirilmesinde kullanılabilecek değerli biyoaktif bileşik kaynakları olabileceğini ortaya koymuştur.

Plants are an endless source of bioactive compounds and have been at the centre of research investigating pivotal candidates for plant-derived drugs and dietary supplements. This study evaluated phenolic profiles, triterpenoid contents, enzyme inhibitory activities, antioxidant capacities, and total phenolic content (TPC) of the polar extracts from Crataegus tanacetifolia and Crataegus orientalis. LCMS/MS and GC-MS analyses revealed 25 phenolic compounds and two triterpenoids in C. tanacetifolia, and 26 phenolic compounds and one triterpenoid in C. orientalis, with quinic acid as the dominant phenolic compound in both extracts. Oleanolic acid and ursolic acid were detected in the C. tanacetifolia extract, whereas only ursolic acid was identified in the C. orientalis extract. Both extracts showed strong angiotensin-converting enzyme inhibition activity (~99%), indicating antihypertensive potential, as well as notable urease inhibition activity (C. tanacetifolia: 87.08%; C. orientalis: 91.66%). The C. tanacetifolia and C. orientalis extracts also exhibited significant antioxidant activity with an IC50 value of 123.38 and 97.29 µg/mL for DPPH radical scavenging activity and 82.37 and 92.34% for linoleic acid/β-carotene bleaching capacity. The TPC of the extracts was determined to be 26.13 and 76.80 mg GAE/g, respectively. The results showed that C. tanacetifolia and C. orientalis could be valuable sources of bioactive compounds for pharmaceutical and nutraceutical products.

Crataegus tanacetifolia Crataegus orientalis Phenolic Profile Triterpenoid Content Enzyme Inhibition Antioxidant Capacity

Crataegus tanacetifolia Crataegus orientalis Fenolik Profil Triterpenoid İçerik Enzim İnhibisyonu Antioksidan Kapasite

Verma, G., Bhushan, B., Singh, G., Singh, K., Kumar, S., Garg, A., et al., 2024. Pharmacological Strategies for Enzyme Inhibition in Disease Therapeutics: A Comprehensive Review. Current Enzyme Inhibition 20(2): 96–108, Doi: 10.2174/0115734080273835231127045336.

Pan, C., Kakeya, H., 2025. Recent progress in chemistry and bioactivity of novel enzyme inhibitors from natural products: A comprehensive review. European Journal of Medicinal Chemistry 289(9): 117481, Doi: 10.1016/j.ejmech.2025.117481.

Yin, J., Yang, J., Ma, H., Liang, T., Li, Y., Xiao, J., et al., 2020. Expression characteristics and function of CAS and a new beta-amyrin synthase in triterpenoid synthesis in birch (Betula platyphylla Suk.). Plant Science 294: 110433, Doi: 10.1016/j.plantsci.2020.110433.

Sahoo, N., Manchikanti, P., Dey, S., 2010. Herbal drugs: Standards and regulation. Fitoterapia 81(6): 462–71, Doi: 10.1016/j.fitote.2010.02.001.

Newman, D.J., Cragg, G.M., 2020. Natural Products as Sources of New Drugs over the Nearly Four Decades from 01/1981 to 09/2019. Journal of Natural Products 83(3): 770–803, Doi: 10.1021/acs.jnatprod.9b01285.

Martel, F., Monteiro, R., Calhau, C., 2010. Effect of polyphenols on the intestinal and placental transport of some bioactive compounds. Nutrition Research Reviews 23(1): 47–64, Doi: DOI: 10.1017/S0954422410000053.

Del Prete, S., Pagano, M., 2024. Enzyme Inhibitors as Multifaceted Tools in Medicine and Agriculture. Molecules 29(18), Doi: 10.3390/molecules29184314.

Rocchetti, G., Senizza, B., Zengin, G., Mahomodally, M.F., Senkardes, I., Lobine, D., et al., 2020. Untargeted metabolomic profiling of three Crataegus species (hawthorn) and their in vitro biological activities. Journal of the Science of Food and Agriculture 100(5): 1998–2006, Doi: https://doi.org/10.1002/jsfa.10216.

Moustafa, A., Zaghloul, M., Mansour, S., Alotaibi, M., 2019. Conservation Strategy for protecting Crataegus x sinaica against climate change and anthropologic activities in South Sinai Mountains, Egypt. Catrina: The International Journal of Environmental Sciences 18(1): 1–6, Doi: 10.21608/cat.2019.28577.

Chang, Q., Zuo, Z., Harrison, F., Chow, M.S.S., 2002. Hawthorn. The Journal of Clinical Pharmacology 42(6): 605–12, Doi: https://doi.org/10.1177/00970002042006003.

Güney, M., Kafkas, S., Keles, H., Aras, S., Ercişli, S., 2018. Characterization of hawthorn (Crataegus spp.) genotypes by SSR markers. Physiology and Molecular Biology of Plants 24(6): 1221–30, Doi: 10.1007/s12298-018-0604-6.

Çaliskan, O., Gündüz, K., Serçe, S., Toplu, C., Kamiloglu, Ö., Sengül, M., et al., 2012. Phytochemical characterization of several hawthorn (Crataegus spp.) species sampled from the Eastern Mediterranean region of Turkey. Pharmacognosy Magazine 8(29): 16–21, Doi: 10.4103/0973-1296.93305.

Ng, Z.X., Soh, E.Y.W., Yong, P.H., 2022. The influence of fermentation and drying methods on the functional activities and sensory quality of Artemisia argyi H.Lév. & Vaniot herbal tea. Journal of Applied Research on Medicinal and Aromatic Plants 30: 100393, Doi: 10.1016/J.JARMAP.2022.100393.

Meng, J., Fang, Y., Zhang, A., Chen, S., Xu, T., Ren, Z., et al., 2011. Phenolic content and antioxidant capacity of Chinese raisins produced in Xinjiang Province. Food Research International 44(9): 2830–6, Doi: https://doi.org/10.1016/j.foodres.2011.06.032.

Yilmaz, M.A., 2020. Simultaneous quantitative screening of 53 phytochemicals in 33 species of medicinal and aromatic plants: A detailed, robust and comprehensive LC–MS/MS method validation. Industrial Crops and Products 149: 112347, Doi: https://doi.org/10.1016/j.indcrop.2020.112347.

Yilmaz, M.A., Ertas, A., Yener, I., Akdeniz, M., Cakir, O., Altun, M., et al., 2018. A comprehensive LC–MS/MS method validation for the quantitative investigation of 37 fingerprint phytochemicals in Achillea species: A detailed examination of A. coarctata and A. monocephala. Journal of Pharmaceutical and Biomedical Analysis 154: 413–24, Doi: 10.1016/J.JPBA.2018.02.059.

Bakir, D., Akdeniz, M., Ertas, A., Yilmaz, M.A., Yener, I., Firat, M., et al., 2020. A GC–MS method validation for quantitative investigation of some chemical markers in Salvia hypargeia Fisch. & C.A. Mey. of Turkey: Enzyme inhibitory potential of ferruginol. Journal of Food Biochemistry 44(9): e13350, Doi: https://doi.org/10.1111/jfbc.13350.

Findik, B.T., Yildiz, H., Akdeniz, M., Yener, I., Yilmaz, M.A., Cakir, O., et al., 2024. Phytochemical profile, enzyme inhibition, antioxidant, and antibacterial activity of Rosa pimpinellifolia L.: A comprehensive study to investigate the bioactivity of different parts (whole fruit, pulp, and seed part) of the fruit. Food Chemistry 455: 139921, Doi: 10.1016/j.foodchem.2024.139921.

Ciniviz, M., Yildiz, H., 2020. Determination of phenolic acid profiles by HPLC in lacto-fermented fruits and vegetables (pickle): Effect of pulp and juice portions. Journal of Food Processing and Preservation 44(7): 1–11, Doi: 10.1111/jfpp.14542.

Albuquerque, B.R., Heleno, S.A., Oliveira, M.B.P.P., Barros, L., Ferreira, I.C.F.R., 2021. Phenolic compounds: current industrial applications, limitations and future challenges. Food Funct. 12(1): 14–29, Doi: 10.1039/D0FO02324H.

Benali, T., Bakrim, S., Ghchime, R., Benkhaira, N., El Omari, N., Balahbib, A., et al., 2024. Pharmacological insights into the multifaceted biological properties of quinic acid. Biotechnology and Genetic Engineering Reviews 40(4): 3408–37, Doi: 10.1080/02648725.2022.2122303.

Goudjil, S., Boussekine, S., Goudjil, S., Goudjil, H., Yilmaz, M.A., Ola, M.S., et al., 2024. Investigation of Algerian Crataegus monogyna Jacq Phenolic Compounds (Using LC-ESI-MS/MS Analysis, Antioxidant Activity, and Enzyme Inhibition) and Their Potential Implications for Food and Nutraceutical Applications. Antioxidants 13(11), Doi: 10.3390/antiox13111350.

Meinhart, A.D., Damin, F.M., Caldeirão, L., de Jesus Filho, M., da Silva, L.C., da Silva Constant, L., et al., 2019. Study of new sources of six chlorogenic acids and caffeic acid. Journal of Food Composition and Analysis 82: 103244, Doi: 10.1016/j.jfca.2019.103244.

Takó, M., Tunali, F., Zambrano, C., Kovács, T., Varga, M., Szekeres, A., et al., 2024. Phenolic Content, Antioxidant and Antimicrobial Properties of Hawthorn (Crataegus orientalis) Fruit Extracts Obtained via Carbohydrase-Assisted Extraction. Applied Sciences 14(21), Doi: 10.3390/app14219790.

Yang, Y.H., Dai, S.Y., Deng, F.H., Peng, L.H., Li, C., Pei, Y.H., 2022. Recent advances in medicinal chemistry of oleanolic acid derivatives. Phytochemistry 203: 113397, Doi: 10.1016/J.phytochem.2022.113397.

Tohtahon, Z., Zhang, L., Han, J., Xie, X., Tu, Z., Yuan, T., 2017. Extraction optimization, structural characterization and bioactivity evaluation of triterpenoids from hawthorn (Crataegus cuneata) fruits. Journal of Food Biochemistry 41(4): e12377, Doi: https://doi.org/10.1111/jfbc.12377.

Simaratanamongkol, A., Umehara, K., Noguchi, H., Panichayupakaranant, P., 2014. Identification of a new angiotensin-converting enzyme (ACE) inhibitor from Thai edible plants. Food Chemistry 165(48): 92–7, Doi: 10.1016/j.foodchem.2014.05.080.

Al Shukor, N., Van Camp, J., Gonzales, G.B., Staljanssens, D., Struijs, K., Zotti, M.J., et al., 2013. Angiotensin-Converting Enzyme Inhibitory Effects by Plant Phenolic Compounds: A Study of Structure Activity Relationships. Journal of Agricultural and Food Chemistry 61(48): 11832–9, Doi: 10.1021/jf404641v.

Szikora, Z., Mátyus, R.O., Szabó, B.V., Csupor, D., Tóth, B., 2025. Hawthorn (Crataegus spp.) Clinically Significantly Reduces Blood Pressure in Hypertension: A Meta-Analysis of Randomized Placebo-Controlled Clinical Trials. Pharmaceuticals 18(7), Doi: 10.3390/ph18071027.

Yavuz, M., Çelikezen, F.Ç., Firat, M., Baş, Z., Türkoğlu, V., 2025. The investigation of hawthorn (Crataegus orientalis) plant’s inhibition effect on angiotensin converting enzyme and in silico studies. Natural Product Research 39(11): 3079–85, Doi: 10.1080/14786419.2024.2324467.

Khan, M., Zhang, B., Zhang, H., Wu, J., Gao, P., Li, J., 2025. Ureases in nature: Multifaceted roles and implications for plant and human health - A review. International Journal of Biological Macromolecules 306(8): 141702, Doi: 10.1016/j.ijbiomac.2025.141702.

Golbabaei, S., Bazl, R., Golestanian, S., Nabati, F., Omrany, Z.B., Yousefi, B., et al., 2013. Urease inhibitory activities of β-boswellic acid derivatives. DARU Journal of Pharmaceutical Sciences 21(1): 2, Doi: 10.1186/2008-2231-21-2.

Li, Y., Zou, H., Sun-Waterhouse, D., Chen, Y., 2024. Chlorogenic acid, caffeic acid and luteolin from dandelion as urease inhibitors: insights into the molecular interactions and inhibition mechanism. Journal of the Science of Food and Agriculture 104(13): 8079–88, Doi: https://doi.org/10.1002/jsfa.13637.

Lin, L., Yao, H., Fu, J., Zhang, W., Li, Y., Wang, Y., et al., 2025. Elastase inhibition by natural flavonoids: mechanistic insights and potential therapeutic applications. Frontiers in Nutrition Volume 12-2025, Doi: 10.3389/fnut.2025.1693869.