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Chemical Structure| 91-64-5 Chemical Structure| 91-64-5

Structure of Coumarin
CAS No.: 91-64-5

Chemical Structure| 91-64-5

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Coumarin is a secondary phytochemical isolated and purified from the herbs of Melilotus officinalis with hepatotoxic and carcinogenic properties.

4.5 *For Research Use Only !

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Product Citations

Product Citations      Show More

Aleksandra Grzelakowska ; Balaraman Kalyanaraman ; Jacek Zielonka ;

Abstract: Peroxynitrite (ONOO‒/ONOOH) is a short-lived but highly reactive species that is formed in the diffusion-controlled reaction between nitric oxide and the superoxide radical anion. It can oxidize certain biomolecules and has been considered as a key cellular oxidant formed under various pathophysiological conditions. It is crucial to selectively detect and quantify ONOO– to determine its role in biological processes. In this review, we discuss various approaches used to detect ONOO‒ in cell-free and cellular systems with the major emphasis on small-molecule chemical probes. We review the chemical principles and mechanisms responsible for the formation of the detectable products, and plausible limitations of the probes. We recommend the use of boronate-based chemical probes for ONOO‒, as they react directly and rapidly with ONOO–, they produce minor but ONOO‒‒specific products, and the reaction kinetics and mechanism have been rigorously characterized. Specific experimental approaches and protocols for the detection of ONOO– in cell-free, cellular, and in vivo systems using boronate-based molecular probes are provided (as shown in BOX 1, BOX 2, BOX 3, BOX 4, BOX 5, BOX 6).

Keywords: peroxynitrite ; molecular ; ; bioluminescence ; chromatography ; biomarkers

Purchased from AmBeed: ; ; ; ; ;

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski ; Michael Zimmermann ;

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

Scott, Jared Lee ;

Abstract: Breast cancer (BC) is the second greatest contributor to the death of women, second only to heart disease, and is the most common type of cancer. BC treatments involve the administration of adjuvant chemotherapies which often have side effects that prevent patients from completing the full course of drugs or the refusal to take these potentially lifesaving treatments. Many chemotherapy drugs are developed from plants, and some plant extracts can exhibit significant anticancer activities while also having less toxic side effects. However, these potential "plant therapeutics" suffer from poor oral bioavailability. The Apiaceae plant family consists of several species that are used as culinarily spices including anise, celery, cumin, and coriander, all of which have demonstrated antioxidant, chemopreventive, and anticancer activities. One method to improve the systemic distribution of anticancer phytochemicals is their encapsulation in naturally produced membrane bound nanoparticles known as exosomes. Exosomes are produced by most eukaryotic organisms, as well as some prokaryotes, and are involved in cell-to-cell communication through the delivery of proteins, nucleic acids, and small molecules from one cell to another. Exosomes are found in many extracellular fluids including blood, urine, and milk. Bovine milk exosomes represent a scalable source of exosomes that are already present in the human diet and have been explored as a drug delivery system that can increase effectiveness and improve bioavailability. To enhance the loading potential and anticancer bioactivity of Apiaceae phytochemicals, an acid hydrolysis (AH) of the glycoside compounds present in ethanolic spice extracts was performed on eight ethanolic spice extracts. The antiproliferative effects of AH extracts and exosomal formulations were assayed with three model types of BC cells. Cumin was characterized in greater detail as these extracts had the highest concentration of terpenoids and alkaloids while also having significant concentrations of phenolics and responded well to AH with increased antiproliferative activity and exosomal loading. Extracts and exosomal formulations exhibited broad antiproliferative effects with lower IC50s in the extracts delivered with exosomes. The phytochemical contents of AH-cumin extracts and exosomal formulations were assayed with HPLC-DAD, LC-MS/MS, and GC-MS, while the potential anticancer mechanisms of these treatments were investigated in triple negative BC (TNBC). AHcumin extracts were determined to have numerous phenolic compounds, many of which have known anticancer mechanisms, in addition to several alkaloids and lipid compounds, some of which have activities that could contribute to the anticancer effects observed. Mechanistically, AH-cumin extracts and exosomal formulations were shown to interact with multidrug resistance proteins and inhibit lipid metabolism in TNBC cells. These results indicate that acid hydrolyzed cumin extracts delivered through exosome nanoparticles represent a possible avenue towards the development of novel treatments for TNBC, the hardest type of BC to treat.

Purchased from AmBeed: ; ; ; ; ; ; ; ; 117-39-5 ; ; ; ;

Alternative Products

Product Details of Coumarin

CAS No. :91-64-5
Formula : C9H6O2
M.W : 146.14
SMILES Code : O=C1OC2=CC=CC=C2C=C1
MDL No. :MFCD00006850
InChI Key :ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Pubchem ID :323

Safety of Coumarin

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301
Precautionary Statements:P501-P270-P264-P301+P310+P330-P405
Class:6.1
UN#:2811
Packing Group:

Related Pathways of Coumarin

RTK

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
MC3T3-E1 cells 1–20 μM 21 days High glucose diminished alkaline phosphatase activity and collagen type 1 induction of osteoblasts, which was strongly enhanced by submicromolar levels of coumarin to diabetic cells. Furthermore, coumarin restored the induction of RANK and osteoprotegerin in osteoclasts and osteoblasts under glucotoxic condition, indicating a tight coupling of osteoclastogenesis and osteoblastogenesis. Biomolecules. 2020 Jul 15;10(7):1052
Raw 264.7 cells 1–20 μM 5 days High glucose diminished tartrate-resistant acid phosphatase activity and bone resorption in RANKL-differentiated osteoclasts, accompanying a reduction of cathepsin K induction and actin ring formation. In contrast, coumarin reversed the defective osteoclastogenesis in diabetic osteoclasts. Biomolecules. 2020 Jul 15;10(7):1052
Hepatocytes 25–400 µg/mL 1 hour To evaluate the inhibitory effect of coumarin on lipid peroxidation in hepatocytes. Results showed coumarin inhibited 25% of lipid peroxidation at 248.5 µg/mL. Biomolecules. 2020 Jan 31;10(2):207
Candida albicans SC5314 0.5, 1.0, 2.0 mg/mL 4 h To evaluate the effects of coumarin on the growth and viability of Candida albicans. Results showed that coumarin significantly inhibited strain growth and reduced survival rate. Front Cell Infect Microbiol. 2019 Jan 4;8:445
Rice seeds 0.1, 0.5, 1, 2, 5, 10, 20 mM 6, 12, 18, 24, 36, 48, 72 h To investigate the inhibitory effect of coumarin on rice seed germination and its impact on ABA content and ROS accumulation. Results showed that coumarin significantly inhibited rice seed germination, increased ABA content, and suppressed ROS accumulation. Front Plant Sci. 2019 Jun 27;10:828
Pseudomonas aeruginosa PAO1 and clinical strains 2 mM 24 h Evaluate the effect of coumarin on the production of virulence factors (pyocyanin and protease) in P. aeruginosa, results showed significant reduction in pyocyanin and protease production. Front Microbiol. 2018 Aug 21;9:1952
Pseudomonas aeruginosa QSIS2 reporter strain 1.5, 2, 2.5, 3 mM 10 h Evaluate the QS inhibitory effect of coumarin on the QSIS2 reporter strain, results showed significant QS inhibition at 1.5-3 mM coumarin. Front Microbiol. 2018 Aug 21;9:1952
Porphyromonas gingivalis ATCC33277 25, 50, 100, 200 μM 48 h To investigate the effect of coumarin on P. gingivalis biofilm formation. Results showed that coumarin significantly inhibited biofilm formation after 48 h, with 200 μM coumarin reducing biofilm metabolic activity by approximately 40.4%. J Oral Microbiol. 2022 Mar 29;14(1):2055523
Porphyromonas gingivalis ATCC33277 0, 25, 50, 100, 200, 400, 800, 1,600, 3,200 μM 4 h To evaluate the antibacterial activity of coumarin on P. gingivalis planktonic cell growth. Results showed that 400 μM coumarin led to a 50% reduction in growth rate, and 800 μM completely inhibited bacterial growth (MIC). J Oral Microbiol. 2022 Mar 29;14(1):2055523

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Apple trees Apple branches Exogenous application 200 μg/g Single application Exogenous coumarin improved resistance in low-K apple branches Plant Physiol. 2023 May 31;192(2):1396-1419
C57BL/6 mice Candida albicans infection model Oral gavage 20 mg/kg, 40 mg/kg Once daily for 3 days To evaluate the therapeutic effect of coumarin on Candida albicans-infected mice. Results showed that 40 mg/kg coumarin significantly prolonged the survival of infected mice. Front Cell Infect Microbiol. 2019 Jan 4;8:445
Rice Spray 10 mM Single treatment, lasting 15 days To investigate the inhibitory effect of coumarin on pre-harvest sprouting in rice. Results showed that coumarin significantly inhibited pre-harvest sprouting in rice. Front Plant Sci. 2019 Jun 27;10:828

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT01837758 - Completed - Germany ... More >> Johann Wolfgang Goethe-University Frankfurt, Hessen, Germany, 60590 Less <<
NCT02017197 Atrial Fibrillation Phase 4 Completed - Brazil ... More >> Hospital São Paulo/Hospital Universitário da UNIFESP (University Hospital of UNIFESP) São Paulo, Brazil, 04024-002 Less <<
NCT02066662 Atrial Fibrillation or Pulmona... More >>ry Embolism Need of Long Term Oral Anticoagulation Therapy (OAT) Existent Coronary or Valvular Calcification, or Both and Agatston Score > 50 in at Least One Location Less << Phase 4 Active, not recruiting December 2019 Germany ... More >> Hospital Coburg, Med. Clinic II for Internal Medicine and Cardiology Coburg, Bavaria, Germany, 96450 University Hospital Aachen, Department of Cardiology Aachen, North Rhine Westphalia, Germany, 52074 St.-Antonius-Hospital Eschweiler, Internal Medicine Eschweiler, North Rhine Westphalia, Germany, 52249 Less <<
NCT00803101 Reversal of Coagulopathy Phase 3 Completed - -
NCT02238470 - Completed - Italy ... More >> Arcispedale Santa Maria Nuova IRCCS Reggio Emilia, Italy Spain Hospital Germans Trias i Pujol Badalona, Barcelona, Spain Fundació Hospital Asil Granollers Granollers, Barcelona, Spain Hospital de Mataró Mataró, Barcelona, Spain Hospital Parc Taulí Sabadell, Barcelona, Spain Hospital Moisés Broggi Sant Joan Despí, Barcelona, Spain Mutua de Terrassa Terrassa, Barcelona, Spain Hospital de la Cinta Tortosa, Tarragona, Spain Hospital de Albacete Albacete, Spain Hospital de la Santa Creu i Sant Pau Barcelona, Spain, 08025 Hospital Clínic Barcelona, Spain Hospital del Mar Barcelona, Spain Hospital de Basurto Bilbao, Spain Hospital CA de Burgos Burgos, Spain Hospital San Pedro de Alcántara Cáceres, Spain Hospital de Donostia Donostia, Spain Hospital Virgen de las Nieves Granada, Spain Hospital de León León, Spain Hospital Arnau de Vilanova Lleida, Spain Hospital La Rioja Logroño, Spain Hospital Gregorio Marañón Madrid, Spain Hospital Ramón y Cajal Madrid, Spain Hospital Universitario La Paz Madrid, Spain Centro Médico Asturias Oviedo, Spain Hospital Son Espases Palma de Mallorca, Spain Hospital de Navarra Pamplona, Spain CHU Santiago de Compostela Santiago de Compostela, Spain Hospital Virgen del Rocío Sevilla, Spain Hospital La Fe Valencia, Spain Hospital CU de Valladolid Valladolid, Spain Less <<
NCT00803101 - Completed - -
NCT00180674 Liver Fibrosis Phase 2 Completed - United Kingdom ... More >> St Mary's Hospital NHS Trust London, United Kingdom, W2 1NY Less <<
NCT01122147 Recurrent Aphthous Stomatitis Phase 1 Completed - Iran, Islamic Republic of ... More >> Mashhad University of Madical Science,Research Center of Mashhad Dental School Mashhad, Khorasan Razavi, Iran, Islamic Republic of, 91735 Less <<
NCT00732927 Retinal Vein Occlusion Phase 3 Terminated(slow recruitment ra... More >>te) Less << - Italy ... More >> University Of Insubria Varese, Italy, 21100 Less <<
NCT01155765 Hemodialysis ... More >>Chronic Renal Failure Less << Phase 3 Completed - Greece ... More >> Patras University Hospital Patras, Achaia, Greece, 26500 Less <<
NCT01492777 - Completed - Switzerland ... More >> University Hospitals Geneva 14, Switzerland, 1211 Less <<
NCT01431690 Hypertriglyceridemia Phase 1 Completed - United States, Arizona ... More >> Tempe, Arizona, United States, 85283 Less <<
NCT03015025 - Completed - Spain ... More >> Hospital Universitario La Paz Madrid, Spain, 28046 Less <<
NCT02872649 Thrombosis Bl... More >>eeding Less << Phase 2 Terminated(safety reasons) - Austria ... More >> Medical Univerity Vienna Vienna, Austria, 1090 Less <<
NCT00224757 Atrial Fibrillation ... More >> Stroke Less << Not Applicable Completed - Netherlands ... More >> Twenteborg Almelo, Netherlands VUMC Amsterdam, Netherlands Rijnstate Ziekenhuis Arnhem, Netherlands Amphia Ziekenhuis Breda, Netherlands Jeroen Bosch Ziekenhuis Den Bosch, Netherlands Atrium Medisch Centrum Heerlen Heerlen, Netherlands Academisch Ziekenhuis Maastricht Maastricht, Netherlands Diaconessenhuis Meppel Meppel, Netherlands UMCN Nijmegen, Netherlands Viecuri Venlo, Netherlands Less <<
NCT00885950 - Completed - Netherlands ... More >> Department of Surgery; Maastricht University Medical Centre Maastricht, Netherlands Less <<
NCT00157118 Protein C Deficiency Phase 2 Phase 3 Completed - United States, California ... More >> Los Angeles, California, United States United States, Colorado Denver, Colorado, United States United States, Georgia Atlanta, Georgia, United States United States, Indiana Indianapolis, Indiana, United States United States, Kentucky Lexington, Kentucky, United States United States, Massachusetts Boston, Massachusetts, United States United States, Ohio Cincinnati, Ohio, United States Cleveland, Ohio, United States Dayton, Ohio, United States United States, Texas Fort Worth, Texas, United States Galveston, Texas, United States Houston, Texas, United States Less <<
NCT01006486 Cardiopathy C... More >>hagas Disease Hemorrhage Thrombosis Less << Phase 4 Completed - Brazil ... More >> Federal University of Minas Gerais Belo Horizonte, Minas Gerais, Brazil, 30130-100 Less <<
NCT01586702 Mini-Stroke Not Applicable Active, not recruiting February 2019 Germany ... More >> Dept. of Neurology, Charité Universitätsmedizin Berlin Berlin, Germany, 12200 Less <<
NCT01119274 Venous Thromboembolism (VTE) ... More >> Atrial Fibrillation (AF) Less << Phase 4 Completed - Austria ... More >> Elisabethinen Hospital Linz Linz, Austria Germany University of Ulm Ulm, Germany Netherlands Utrecht University Utrecht, Netherlands Less <<
NCT01569035 Oligohydramnios Phase 4 Completed - Egypt ... More >> Women Health Hospital Assiut, Egypt Less <<
NCT00264277 Deep Vein Thrombosis ... More >> Pulmonary Embolism Less << Phase 4 Completed - Italy ... More >> Dept. of Angiology & Blood Coagulation, University Hospital S. Orsola-Malpighi Bologna, BO, Italy, 40138 Less <<
NCT01119261 Venous Thromboembolism ... More >> Atrial Fibrillation Less << Phase 4 Completed - Greece ... More >> Democritus University of Thrace Medical School Alexandropoulis, Greece Netherlands Utrecht University Utrecht, Netherlands Less <<
NCT00708435 Blood Coagulation Disorders ... More >> Acute Major Bleeding Less << Phase 3 Completed - -
NCT00708435 - Completed - -
NCT01848210 Chronic Venous Insufficiency Phase 4 Completed - -
NCT03154489 Anticoagulant ... More >> Pharmacogenetics Community Pharmacy Services Drug Utilization Review Medication Therapy Management Less << Not Applicable Recruiting September 22, 2018 Spain ... More >> Centro de Salud Arrabal Recruiting Zaragoza, Spain, 50015 Contact: Ana Sáez-Benito, Pharmacist    +34 667 83 52 77    inim@usj.es Less <<
NCT01119300 Venous Thromboembolism ... More >> Atrial Fibrillation Less << Phase 4 Completed - Sweden ... More >> Uppsala University Uppsala, Sweden United Kingdom University of Liverpool Liverpool, United Kingdom University of Newcastle Newcastle, United Kingdom Less <<
NCT01848210 - Completed - -

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

6.84mL

1.37mL

0.68mL

34.21mL

6.84mL

3.42mL

68.43mL

13.69mL

6.84mL

References

 

Historical Records

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