Therapeutic Effects of Coumarins with Different Substitution Patterns
Abstract
:1. Introduction
2. Coumarins
3. Coumarins and Their Pharmacological Activity
3.1. Therapeutic Use of Coumarins in Inflammatory Diseases
3.1.1. Coumarins in Inflammatory Bowel Disease
3.1.2. Coumarins in Idiopathic Pulmonary Fibrosis
3.1.3. Coumarins in Rheumatoid Arthritis and Osteoarthritis
3.2. Coumarins in Cardiovascular Disease
3.2.1. Coumarins with Antihypertensive Activity
3.2.2. Coumarins with Vasodilator Effect
3.2.3. Coumarins in Heart Failure
3.2.4. Coumarins for the Treatment of Thromboembolic Conditions
3.3. Coumarins in Infectious Diseases
3.3.1. Antibacterial Activities of Coumarins
3.3.2. Coumarins with Antifungal Activities
3.3.3. Coumarins with Antiviral Activity
3.4. Coumarins in Neurodegenerative Diseases
3.4.1. Coumarins with Neuroprotective Activity
3.4.2. Epilepsy
3.4.3. Multiple Sclerosis
3.4.4. Parkinson’s Disease
3.4.5. Amyotrophic Lateral Sclerosis
3.4.6. Alzheimer’s Disease
3.4.7. Huntington’s Disease
3.4.8. Peripheral Neuropathies
3.5. Coumarins in Chronic Degenerative Diseases
3.5.1. Obesity
3.5.2. Metabolic Syndrome
3.5.3. Coumarins with Antihyperglycemic Activity in Diabetes Mellitus
3.6. Coumarins in Liver Diseases
3.7. Coumarins with Antioxidant Activity
3.8. Coumarins as Phytoalexins
3.9. Main Biological Targets of Coumarin Derivatives According to In Vitro, In Vivo, and Structure-Activity Relationship Analyses
4. Cancer
4.1. Molecular Aspects of Cancer and Therapies
4.2. Coumarins with Antineoplastic Activity
Synthetic Derivatives of Coumarin with Antineoplastic Activity
4.3. Coumarin Derivatives and Their Effect on Cell Signaling Pathways in Cancer
4.4. Usefulness of Structure–Activity (SAR) Analyses of Coumarin Derivatives to Identify Molecular Targets against Cancer
4.5. Adjuvant Cancer Therapy: Potential Role of Coumarins
5. Concluding Remarks
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Acknowledgments
Conflicts of Interest
References
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Type of Coumarin | Structure | Examples of Coumarins | Reference |
---|---|---|---|
Single coumarin | Umbelliferone (7-hydroxycoumarin) | Esculetin | [15] |
Ostrutin | [16] | ||
Osthole | [17] | ||
Novobiocin | [18] | ||
Coumermycin | [19] | ||
Umbelliferone | [20] | ||
Fraxidine | [21] | ||
Ferudenol | [22] | ||
Furanocoumarin | Imperatorin | Isopimpinellin | [23] |
Psoralen | [24] | ||
Bergaptene | [25] | ||
Methoxsalene | [26] | ||
Marmelosin | [27] | ||
Pyranocoumarin | Nordentatin | 1. Linear type: | [28] |
Grandivitin | [29] | ||
Agasyllin | [30] | ||
Aegelinol de Benzonatate | |||
Xanthylethine | [31] | ||
2. Angular type: | |||
Inophyllum A, B, C, E, P, G1 and G2 | [32] | ||
Calanolide A, B and F | [33] | ||
(+)-Dihydrocalanolide A and B | |||
Pseudocordatolide | [34] | ||
Biscoumarin | Dicoumarol | Biscoumarin | [35] |
Dihydrofuranocoumarin | Felamidine | Anthogenol | [36] |
Marmesin | [37] | ||
Rutaretin | [38] | ||
Phenycoumarins | Isodispare B | Dispardiol B | [39] |
Mammea A/AB | [40] | ||
Disparinol D | [41] | ||
Disparpropylinol B | [42] |
Type of Cancer | Pharmacological Function | Structure | Substitute | Reference |
---|---|---|---|---|
Melanoma B16-F10 | In an in vitro study, 4-hydroxycoumarin demonstrated its therapeutic effect as an antineoplastic. By inhibiting the stability of the cytoskeleton, adhesion, and motility of the melanoma cell line B16-F10. | 4-Hydroxycoumarin | An OH group at position 4 of the basic coumarin core | [153] |
Lung | It was shown that 7-hydroxycoumarin exhibits an antiproliferative effect towards lung cancer cells (SK-LU-1, 1.3.15 and 3A5A). | 7-Hydroxycumarin | OH at position 7 of the coumarin (7-hydroxycoumarin Umbelliferone Basic nucleus) | [154] |
Breast/ Ovarian/ Prostate/ Kidney | The synthesis of new 4,7-disubstituted coumarin derivatives as apoptosis-inducing agents targeting galectin-1 was performed by evaluating the cytotoxic effect on cancer cell lines: MCF7, SKOV3, PC-3, DU145, and HEK293T. Compound 7q* conjugate showed a potential antiproliferative effect against PC-3 prostate cancer cell lines by inhibiting the G1 phase of the cell cycle, reducing Gal-1 protein levels in a dose-dependent manner. | R1=COOC2H5 R2=4-NO2-C6H4-CH2 | Compound: 7q* substituent R2 (4-NO2-C6H4-CH2). | [155] |
Prostate | Overexpression of 1-lipoxygenase-1 (15-LOX-1) is considered a malignancy factor for prostate cancer. Synthetic derivatives of farnesyloxycoumarin (3f, 4f, 7f)** are potential inhibitors of 15-LOX-1, especially 7-farnesyloxycoumarin exerting cytotoxic and anticancer effects against prostate cancer PC-3 cells. | 7-Farnesyloxycoumarin | Prenylated coumarins derived from farnesyloxycoumarins | [156] |
Colon | Coumarin derivatives were tested in HCT116 colorectal cancer cell line, reducing its viability in a time- and concentration-dependent manner. Coumarin polysulfides accumulate in the G2-M phase of the cell cycle inducing apoptosis, decreasing balc-2, increased bax, cytochrome release, and inhibition of caspases 3-7 and cdc25C. They are considered potent antineoplastic agents. | 7-Mercapto-4-methyl-2H-chromen-2-one | Coumarin derivatives diallyl polysulfides (di-coumarin polysulfides) (di-coumarin polysulfides) | [157] |
Lung/ Skin/ Kidney/ | Several of these compounds showed antiproliferative activity. Compounds 14 and 17*** showed higher apoptotic activity. They became promising candidates for cancer treatment. | Several of these compounds showed antiproliferative activity. Compounds 14 and 17*** showed higher apoptotic activity. They became promising candidates for cancer treatment. | [158] | |
Breast/ Human oral epidermoid carcinoma | The cytotoxic effect of compound 9c was tested against breast cancer (MDA-MB-231) and human oral epidermoid carcinoma cell line (KB) cell lines. This compound showed antiproliferative, apoptotic activity, regulating ROS and caspase-3 levels. | (7-(Diethylamino)-N-(4-methoxyphenyl)-2-oxo-2H-chromene-3-sulfonamide) | Coumarin derivatives with sulfonamide and amide substituents | [159] |
Breast and Lung | This triad was shown to have a cytotoxic effect and a selective inhibition towards CDK4. These compounds were tested in breast cancer cell lines (MCF-7) and human lung carcinoma (A-549) and the IC50 was evaluated with good results. | thiazole-hydrazono-coumarin | 6-bromo-3-(substituted thiazolidine-2-ylidene) hydrazineylidene)-coumarin derivatives with different substituents at the 3-position of the coumarin nucleus | [160] |
Bone marrow (myeloma) | This compound showed an inhibitory effect against two enzymes, carbonic anhydrase, and lipoxygenase, which are involved in the development of cancer, so this compound is considered a promising target for inhibiting these enzymes. | 2-(2-(2-Oxo-2H-chromen-7-yl) oxy)-N-phenethylacetamide | 6,7-substituted coumarins derived from 7-hydroxycoumarins | [161] |
Prostate/ Melanoma/ Kidney | A coumarinic derivative 3,3’-methylenebis(4-hydroxycoumarin) “Dicoumarol” was shown to have an antineoplastic effect when tested in vitro in prostate, kidney, and melanoma cancer cell lines, as it inhibits cell proliferation by affecting mitotic spindle microtubules in the cell cycle phases. | 3,3’-methylenebis(4-hydroxycoumarin) | In position 3 there is a methylene bond | [162] |
Bladder | 7-isopentenyloxycoumarin was shown to have anticancer effects by demonstrating a cytotoxic effect against bladder cancer cell lines (5673 cells) by inducing apoptosis and inhibition of the G2/M phases of the cell cycle. | 7-isopentenyloxycoumarin | Isopentenyl group | [163] |
Small cell lung | 7,8-Dihydroxy-4-methylcoumarin was shown to induce apoptosis tested in A549 lung cancer cell lines by activating the mitochondria-mediated caspase-dependent pathway. | 7,8-Dihydroxy-4-methylcoumarin | Methyl group at position 4 and 7,8 Hydroxy. | [164] |
Breast and Colon | A new coumarinic derivative containing [3,4-d] imidazole-4(1H)-one was synthesized and its biological effect, named “compound 35”, was evaluated. It showed anticancer activity against colon cancer cell lines HCT116 and breast cancer MCF-7, affecting apoptosis and inhibiting the G0/G1 phases of the cell cycle. | 2-(4-(2-(tert-butoxy)-2,3-dimethyl-4-oxo-8-(quinolin-3-yl)-2,3-dihydrochromeno [3,4-d] imidazol-1 490 (4H)-yl) phenyl)-2-methylpropanenitrile (Compound 35) | [3,4-d] imidazole-4(1H)-one derivatives | [165] |
Lung | Isofraxidin was shown to possess apoptosis-inducing activity against A549 lung cancer cell lines demonstrating its effectiveness as a potential anticancer agent. | 7-hydroxy-6, 8-dimethoxy coumarin (Isofraxidin) | OH group at position 7 and methoxy at positions 6 and 8 | [166] |
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Flores-Morales, V.; Villasana-Ruíz, A.P.; Garza-Veloz, I.; González-Delgado, S.; Martinez-Fierro, M.L. Therapeutic Effects of Coumarins with Different Substitution Patterns. Molecules 2023, 28, 2413. https://doi.org/10.3390/molecules28052413
Flores-Morales V, Villasana-Ruíz AP, Garza-Veloz I, González-Delgado S, Martinez-Fierro ML. Therapeutic Effects of Coumarins with Different Substitution Patterns. Molecules. 2023; 28(5):2413. https://doi.org/10.3390/molecules28052413
Chicago/Turabian StyleFlores-Morales, Virginia, Ana P. Villasana-Ruíz, Idalia Garza-Veloz, Samantha González-Delgado, and Margarita L. Martinez-Fierro. 2023. "Therapeutic Effects of Coumarins with Different Substitution Patterns" Molecules 28, no. 5: 2413. https://doi.org/10.3390/molecules28052413