Natural sources for coumarins and their derivatives with relevance to health-promoting properties: A systematic review
Subject Areas : Phytochemistry: Isolation, Purification, CharacterizationNadia Sharif 1 , Hina Jabeen 2
1 - Department of Biotechnology, Women University Mardan, 23200, KPK, Pakistan
2 - Department of Biotechnology, Women University Mardan, 23200, KPK, Pakistan
Keywords: Anti-inflammatory, Coumarin, Furanocoumarin, Neurodegenerative disorders, Secondary metabolites, Pharmacological, Pyranocoumarins, Warfarin ,
Abstract :
Coumarins and their derivatives are bioactive compounds recognized for their diverse range of health-promoting properties. This systematic review aims to identify and summarize the natural sources of coumarins and their derivatives. Electronic databases, including PubMed, Scopus, and Web of Science, were thoroughly searched with precise keywords and inclusion/exclusion criteria. Studies published in English from 2000 to 2023 were considered for inclusion. Natural sources of coumarins and their derivatives were identified, including plants, fungi, and bacteria. Some common plant families known to contain coumarins and their derivatives were Asteraceae, Rutaceae, and Fabaceae. The health-promoting properties of coumarins and their derivatives were found to be extensive. Many studies have reported their antioxidant, anti-inflammatory, anticancer, antibacterial, and antifungal activities. The compounds have shown potential in protecting against cardiovascular diseases, neurodegenerative disorders, diabetes, and obesity. Understanding the structure-activity relationships of these compounds is crucial for further research and development in this area.
Abdul Khaliq, H., Alhouayek, M., Quetin-Leclercq, J., Muccioli, G.G., 2022. 5’AMP-activated protein kinase: An emerging target of phytochemicals to treat chronic inflammatory diseases. Crit. Rev. Food Sci. Nutr. 64(14), 1-26.
Aberoumandi, S.M., Mohammadhosseini, M., Abasi, E., Saghati, S., Nikzamir, N., Akbarzadeh, A., Panahi, Y., Davaran, S., 2017. An update on applications of nanostructured drug delivery systems in cancer therapy: A review. Artif. Cells Nanomed. Biotechnol. 45(6), 1058-1068.
Adimule, V.M., Nandi, S.S., Kerur, S., Khadapure, S.A., Chinnam, S., 2022. Recent advances in the one-pot synthesis of coumarin derivatives from different starting materials using nanoparticles: A review. Top. Catal. 12(1), 1-31.
Akki, M., Reddy, D.S., Katagi, K.S., Kumar, A., Devarajegowda, H.C., Kumari M, S., Babagond, V., Joshi, S.D., 2022. Coumarin hydrazone oxime scaffolds as potent anti-tubercular agents: Synthesis, X ray crystal and molecular docking studies. ChemistrySelect 7(46), e202203260.
Al-Zehouri, J., 2017. Determination of coumarin in methanol extract of cinnamon (Cinnamomum cassia Blume) using reversed-phase high performance liquid chromatography. J. Pharmacogn. Phytochem. 6(4), 726-729.
Al Aboody, M.S., Mickymaray, S., 2020. Anti-fungal efficacy and mechanisms of flavonoids. J. Antibiot. 9(2), 45.
Alamgir, A., 2017. Pharmacognostical botany: Classification of medicinal and aromatic plants (MAPs), botanical taxonomy, morphology, and anatomy of drug plants. Pharmacogn. J. 1, 177-293.
Ali, S.I., Sheikh, W.M., Rather, M.A., Venkatesalu, V., Muzamil Bashir, S., Nabi, S.U., 2021. Medicinal plants: Treasure for antiviral drug discovery. Phytother. Res. 35(7), 3447-3483.
Alm, T., 2015. Scented grasses in Norway—Identity and uses. J. Ethnobiol. 11(1), 1-18.
Anatheil, A.H., Hayal, M.Y., Abdulredhad, W.S., 2022. A review on heterocyclic and their application in chemistry of coumarin moiety. RJAI 3(10), 1-12.
Aprotosoaie, A.C., Gille, E., Trifan, A., Luca, V.S., Miron, A., 2017. Essential oils of Lavandula genus: A systematic review of their chemistry. Phytochem. Rev. 16, 761-799.
Aydın, T., Gümüştaş, M., Sancı, T.Ö., Çakır, A., 2024. Herniarin and skimmin coumarins in spice and edible plants and their benefits for health. Stud. Nat. Prod. Chem. 81, 339-365.
Badalamenti, N., Vaglica, A., Porrello, A., Maggio, A., Bruno, M., Lauricella, M., D’Anneo, A., 2023. Phytochemical investigation and antitumor activity of coumarins from Sicilian accession of Ferulago nodosa (L.) Boiss. roots. Nat. Prod. Res. 1-12.
Banikazemi, Z., Mirazimi, S.M., Dashti, F., Mazandaranian, M.R., Akbari, M., Morshedi, K., Aslanbeigi, F., Rashidian, A., Chamanara, M., Hamblin, M.R., 2021. Coumarins and gastrointestinal cancer: a new therapeutic option?. Front. Oncol. 11, 752784.
Berenbaum, M.R., 2002. Postgenomic chemical ecology: from genetic code to ecological interactions. J. Chem. Ecol. 28, 873-896.
Bhattarai, N., Kumbhar, A.A., Pokharel, Y.R., Yadav, P.N., 2021. Anticancer potential of coumarin and its derivatives. Mini Rev. Med. Chem. 21(19), 2996-3029.
Borges, M.F.M., Roleira, F.M.F., Milhazes, N., Villare, E., Penin, L.S., 2010. Simple coumarins: Privileged scaffolds in medicinal chemistry. Front. Med. Chem. 4, 23-85.
Bouhaoui, A., Eddahmi, M., Dib, M., Khouili, M., Aires, A., Catto, M., Bouissane, L., 2021. Synthesis and biological properties of coumarin derivatives. A review. ChemistrySelect 6(24), 5848-5870.
Chen, Y.-Q., Song, H.-Y., Zhou, Z.-Y., Ma, J., Luo, Z.-Y., Zhou, Y., Wang, J.-Y., Liu, S., Han, X.-H., 2022. Osthole inhibits the migration and invasion of highly metastatic breast cancer cells by suppressing ITGα3/ITGβ5 signaling. Acta Pharmacol. Sin. 43(6), 1544-1555.
Elmusa, F., Elmusa, M., 2024. Mini-Review on coumarins: Sources, biosynthesis, bioactivity, extraction and toxicology. J. Turk. Chem. Soc. A: Chem. 11(3), 933-944.
Ez zoubi, Y., Bousta, D., Farah, A., 2020. A phytopharmacological review of a Mediterranean plant: Lavandula stoechas L. Clin. Phytoscience 6, 1-9.
Fallico, M., Raciti, G., Longo, A., Reibaldi, M., Bonfiglio, V., Russo, A., Caltabiano, R., Gattuso, G., Falzone, L., Avitabile, T., 2021. Current molecular and clinical insights into uveal melanoma. Int. J. Oncol. 58(4), 1-1.
Fan, M., Zhu, M., Chen, G., Guo, M., 2022. Duchesnea genus: A comprehensive review of its phytochemistry, bioactivity, and pharmacology. Phytochem. Rev. 1-25.
Fathi Karkan, S., Mohammadhosseini, M., Panahi, Y., Milani, M., Zarghami, N., Akbarzadeh, A., Abasi, E., Hosseini, A., Davaran, S., 2017. Magnetic nanoparticles in cancer diagnosis and treatment: a review. Artif. Cells Nanomed. Biotechnol. 45(1), 1-5.
Fatima, S., Kumari, A., Dwivedi, V.P., 2021. Advances in adjunct therapy against tuberculosis: Deciphering the emerging role of phytochemicals. Med. Comm. 2(4), 494-513.
Feng, D., Zhang, A., Yang, Y., Yang, P., 2020. Coumarin‐containing hybrids and their antibacterial activities. Arch. Pharm. 353(6), 1900380.
Flores-Morales, V., Villasana-Ruíz, A.P., Garza-Veloz, I., González-Delgado, S., Martinez-Fierro, M.L., 2023. Therapeutic effects of coumarins with different substitution patterns. Molecules 28(5), 2413.
Gaio, P., Cramer, A., de Melo Oliveira, N.F., Porto, S., Kramer, L., Nonato Rabelo, R.A., Pereira, R.d.D., de Oliveira Santos, L.L., Nascimento Barbosa, C.L., Silva Oliveira, F.M., 2023. N-(coumarin-3-yl) cinnamamide promotes immunomodulatory, neuroprotective, and lung function-preserving effects during severe malaria. Pharmaceuticals 17(1), 46.
Ghosh, S., Sarkar, T., Pati, S., Kari, Z.A., Edinur, H.A., Chakraborty, R., 2022. Novel bioactive compounds from marine sources as a tool for functional food development. Front. Mar. Sci. 9, 832957.
Goncalves, G.A., Spillere, A.R., das Neves, G.M., Kagami, L.P., von Poser, G.L., Canto, R.F.S., Eifler-Lima, V., 2020. Natural and synthetic coumarins as antileishmanial agents: A review. Eur. J. Med. Chem. 203, 112514.
Gupta, P.D., Birdi, T.J., 2017. Development of botanicals to combat antibiotic resistance. J-AIM 8(4), 266-275.
Gupta, V., Ambatwar, R., Bhanwala, N., Khatik, G.L., 2023. Coumarin as a privileged and medicinally important Scaffold in the treatment of tuberculosis. Curr. Top. Med. Chem. 23(16), 1489-1502.
Hassanein, E.H., Sayed, A.M., Hussein, O.E., Mahmoud, A.M., 2020. Coumarins as modulators of the Keap1/Nrf2/ARE signaling pathway. Oxid. Med. Cell. Longev. 2020.
He, L., He, T., Farrar, S., Ji, L., Liu, T., Ma, X., 2017. Antioxidants maintain cellular redox homeostasis by elimination of reactive oxygen species. Cell. Physiol. Biochem. 44(2), 532-553.
Hsieh, C.J., Sun, M., Osborne, G., Ricker, K., Tsai, F.C., Li, K., Tomar, R., Phuong, J., Schmitz, R., Sandy, M.S., 2019. Cancer hazard identification integrating human variability: The case of coumarin. Int. J. Toxicol. 38(6), 501-552.
Hussain, M.I., Syed, Q.A., Khattak, M.N.K., Hafez, B., Reigosa, M.J., El-Keblawy, A., 2019. Natural product coumarins: Biological and pharmacological perspectives. Biologia 74, 863-888.
Jebir, R.M., Mustafa, Y.F., 2022. Natural coumarin-lead compounds: A review of their medicinal potentials. Iraqi J. Pharm. Sci. 18(2), 139-161.
Jha, Y., Mohamed, H.I., 2022. Plant secondary metabolites as a tool to investigate biotic stress tolerance in plants: A review. Gesunde Pflanzen 74(4), 771-790.
Kasperkiewicz, K., Ponczek, M.B., Owczarek, J., Guga, P., Budzisz, E., 2020. Antagonists of vitamin K—popular coumarin drugs and new synthetic and natural coumarin derivatives. Molecules 25(6), 1465.
Küpeli Akkol, E., Genç, Y., Karpuz, B., Sobarzo-Sánchez, E., Capasso, R., 2020. Coumarins and coumarin-related compounds in pharmacotherapy of cancer. Cancers 12(7), 1959.
Kurzawa, M., Wilczyńska, E., Brudzyńska, P., Sionkowska, A., 2022. Total phenolic content, antioxidant capacity and UV radiation protection properties of marigold (Calendula officinalis), carrot (Daucus carota), tomato (Solanum lycopersicum) and hop (Humulus lupulus) extracts. Cosmetics 9(6), 134.
Leal, L.E., Moreira, E.S., Correia, B.L., Bueno, P.S.A., Comar, J.F., de Sá-Nakanishi, A.B., Cuman, R.K.N., Bracht, A., Bersani-Amado, C.A., Bracht, L., 2024. Comparative study of the antioxidant and anti-inflammatory effects of the natural coumarins 1, 2-benzopyrone, umbelliferone and esculetin: In Silico, in vitro and in vivo analyses. Naunyn Schmiedebergs Arch. 397(1), 173-187.
Lončar, M., Gašo-Sokač, D., Molnar, M., 2023. Coumarin derivatives as antifungal agents--A review. Czech J. Food Sci. 41(2).
Lončar, M., Jakovljević, M., Šubarić, D., Pavlić, M., Buzjak Služek, V., Cindrić, I., Molnar, M., 2020. Coumarins in food and methods of their determination. Foods 9(5), 645.
Luo, B., Ning, Y., Rao, B., 2022. Comprehensive overview of β-methoxyacrylate derivatives as cytochrome BC1 inhibitors for novel pesticide discovery. J. Agric. Food Chem. 70(50), 15615-15630.
Mahdavi, B., Mohammadhosseini, M., 2022. Antioxidant, antimicrobial and anti-prostate cancer activity of the extracts from different parts of Etlingera velutina (Ridl.) R. M. Sm (Zingiberaceae). Trends Phytochem. Res. 6(4), 353-362.
Mahmoud, A.M., Hozayen, W.G., Hasan, I.H., Shaban, E., Bin-Jumah, M., 2019. Umbelliferone ameliorates CCl4-induced liver fibrosis in rats by upregulating PPARγ and attenuating oxidative stress, inflammation, and TGF-β1/Smad3 signaling. Inflammation 42, 1103-1116.
Mazreku, I., Rudhani, I., Lajqi, L., Hadergjonaj, M., Ibrahimi, H., Haziri, A., 2022. Some experimental studies on the anticoagulant activity of the synthetic coumarin derivatives. Jordan J. Biol. Sci. 15(4).
Menezes, J.C., Diederich, M., 2019. Translational role of natural coumarins and their derivatives as anticancer agents. Future Med. Chem. 11(09), 1057-1082.
Mujeeb, S., Singh, K., Yogi, B., Ansari, V., Sinha, S., 2022. A review on coumarin derivatives as potent anti-tuberculosis agents. Mini Rev. Med. Chem. 22(7), 1064-1080.
Mustafa, Y.F., 2024. Coumarins from carcinogenic phenol: Synthesis, characterization, in silico, biosafety, anticancer, antioxidant, and anti-inflammatory assessments. Chem. Pap. 78(1), 493-504.
Nawrot-Chorabik, K., Sułkowska, M., Gumulak, N., 2022. Secondary metabolites produced by trees and fungi: Achievements so far and challenges remaining. Forests 13(8), 1338.
Nazari‐Khanamiri, F., Ghasemnejad‐Berenji, M., 2021. Cellular and molecular mechanisms of genistein in prevention and treatment of diseases: An overview. J. Food Biochem. 45(11), e13972.
Nekoei, M., Mohammadhosseini, M., Pourbasheer, E., 2021. A quantitative structure–activity relationship study on CXL017 derivatives as effective drugs for cancer treatment. J. Chin. Chem. Soc. 68(10), 1972-1986.
Nibin Joy, M., Guda, M.R., Zyryanov, G.V., 2023. Evaluation of anti-inflammatory and anti-tubercular activity of 4-methyl-7-substituted coumarin hybrids and their structure activity relationships. Pharmaceuticals 16(9), 1326.
Niederberger, E., Parnham, M.J., 2021. The impact of diet and exercise on drug responses. Int. J. Mol. Sci. 22(14), 7692.
Niknejad, A., Razavi, S.M., Hosseini, Y., Arab, Z.N., Abdolghaffari, A.H., Momtaz, S., 2024. Cinnamon modulates toll-like receptors: A new therapeutic approach for diabetes. Rev. Bras. Farmacogn. 34(2), 223-235.
Nisha, H., Dheeraj, B., Rupali, B., K DP, R.B., 2021. A review of coumarin derivatives and its biological activities. World J. Pharm. Res. 10(2), 234-246.
Olennikov, D.N., 2022. Coumarins of lovage roots (Levisticum officinale): LC-MS profile, quantification, and stability during postharvest storage. Metabolites 13(1), 3.
Önder, A., 2020. Anticancer activity of natural coumarins for biological targets. Stud. Nat. Prod. Chem. 64, 85-109.
Pangal, A., Mujahid, Y., Desai, B., Shaikh, J., Ahmed, K., 2022. Synthesis of 3-(2-(subsituted-(trifluoromethyl) phenylamino) acetyl)-2H-chromen-2-one derivatives as new anticancer agents. Curr. Chem. Lett. 11(1), 105-112.
Pangal, A., Tambe, P., Ahmed, K., 2023. Screening of 3-acetylcoumarin derivatives as multifunctional biological agents. Curr. Chem. Lett. 12(2), 343-352.
Peng, X.-M., LV Damu, G., Zhou, H., 2013. Current developments of coumarin compounds in medicinal chemistry. Curr. Pharm. Des. 19(21), 3884-3930.
Perumalsamy, H., Sankarapandian, K., Veerappan, K., Natarajan, S., Kandaswamy, N., Thangavelu, L., Balusamy, S.R., 2018. In silico and in vitro analysis of coumarin derivative induced anticancer effects by undergoing intrinsic pathway mediated apoptosis in human stomach cancer. Phytomedicine 46, 119-130.
Pourbagher-Shahri, A.M., Schimmel, J., Shirazi, F.M., Nakhaee, S., Mehrpour, O., 2022. Use of fomepizole (4-methylpyrazole) for acetaminophen poisoning: A scoping review. Toxicol. Lett. 355, 47-61.
Razak, A.M., Tan, J.K., Mohd Said, M., Makpol, S., 2023. Modulating effects of Zingiberaceae phenolic compounds on neurotrophic factors and their potential as neuroprotectants in brain disorders and age-associated neurodegenerative disorders: A review. Nutrients 15(11), 2564.
Robe, K., Izquierdo, E., Vignols, F., Rouached, H., Dubos, C., 2021. The coumarins: Secondary metabolites playing a primary role in plant nutrition and health. Trends Plant Sci. 26(3), 248-259.
Ruiz, H., Lacasta, D., Ramos, J.J., Quintas, H., Ruiz de Arcaute, M., Ramo, M.Á., Villanueva-Saz, S., Ferrer, L.M., 2022. Anaemia in ruminants caused by plant consumption. Animals 12(18), 2373.
Senevirathne, B.S., Jayasinghe, M.A., Pavalakumar, D., Siriwardhana, C.G., 2022. Ceylon cinnamon: A versatile ingredient for futuristic diabetes management. J. Future Foods 2(2), 125-142.
Shaheen, H.M., Nyemb, J.N., Segueni, N., George, J., Patil, V.R., Batiha, G.E.-S., 2022. Anticancer properties and clinical trials of coumarins: A review. Free Radic. Antioxid. 12(2), 41-48.
Shaik, B.F., Gandhodi, G., Kondupalli, D., Payyala, R., Nelson, V.K., 2019. Coumarin modulates the pharmacological activity via structural modification. Int. J. Innov. Pharm. Sci. Res. 7(4), 31-46.
Sharapov, A.D., Fatykhov, R.F., Khalymbadzha, I.A., Zyryanov, G.V., Chupakhin, O.N., Tsurkan, M.V., 2023. Plant coumarins with anti-HIV activity: Isolation and mechanisms of action. Int. J. Mol. Sci. 24(3), 2839.
Sharifi-Rad, J., Cruz-Martins, N., López-Jornet, P., Lopez, E.P.-F., Harun, N., Yeskaliyeva, B., Beyatli, A., Sytar, O., Shaheen, S., Sharopov, F., 2021. Natural coumarins: Exploring the pharmacological complexity and underlying molecular mechanisms. Oxid. Med. Cell. Longev. 2021.
Sharifi-Rad, J., Seidel, V., Izabela, M., Monserrat-Mequida, M., Sureda, A., Ormazabal, V., Zuniga, F.A., Mangalpady, S.S., Pezzani, R., Ydyrys, A., 2023. Phenolic compounds as Nrf2 inhibitors: Potential applications in cancer therapy. J. Cell Commun. Signal. 21(1), 1-18.
Singla, R.K., Sharma, P., Dubey, A.K., Gundamaraju, R., Kumar, D., Kumar, S., Madaan, R., Shri, R., Tsagkaris, C., Parisi, S., 2021. Natural product-based studies for the management of castration-resistant prostate cancer: Computational to clinical studies. Front. Pharmacol. 12, 732266.
Soleimanjahi, H., Habibian, A., 2020. Novel anti-angiogenic strategies in cancer drug development. Anti-Angiogenesis Drug Discov. Dev. 5, 125.
Sun, C., Zhao, W., Wang, X., Sun, Y., Chen, X., 2020. A pharmacological review of dicoumarol: An old natural anticoagulant agent. Pharmacol. Res. 160, 105193.
Sun, Y., Ren, G., Shi, Q., Zhu, H., Zhou, N., Kong, X., Jiang, D., Liu, C., 2023. Identification of a novel coumarins biosynthetic pathway in the endophytic fungus Fusarium oxysporum GU-7 with antioxidant activity. Appl. Environ. Microbiol. 89(1), e01601-01622.
Thawabteh, A.M., Swaileh, Z., Ammar, M., Jaghama, W., Yousef, M., Karaman, R., A. Bufo, S., Scrano, L., 2023. Antifungal and antibacterial activities of isolated marine compounds. Toxins 15(2), 93.
Todorov, L., Saso, L., Kostova, I., 2023. Antioxidant activity of coumarins and their metal complexes. Pharmaceuticals 16(5), 651.
Tsivileva, O.M., Koftin, O.V., Evseeva, N.V., 2022. Coumarins as fungal metabolites with potential medicinal properties. Antibiotics 11(9), 1156.
Wang, L., Yao, W., 2022. A Cohort study on the safety and efficacy of warfarin and rivaroxaban in anticoagulant therapy in patients with atrial fibrillation study. Biomed Res. Int. 2022.
Wu, L., Wang, X., Xu, W., Farzaneh, F., Xu, R., 2009. The structure and pharmacological functions of coumarins and their derivatives. Curr. Med. Chem. 16(32), 4236-4260.
Wu, Y., Xu, J., Liu, Y., Zeng, Y., Wu, G., 2020. A review on anti-tumor mechanisms of coumarins. Front. Oncol. 10, 592853.
Yadav, A.K., Shrestha, R.M., Yadav, P.N., 2024. Anticancer mechanism of coumarin-based derivatives. Eur. J. Med. Chem. 267, 116179.