N-(p-Coumaroyl) serotoninCAS# 68573-24-0 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 68573-24-0 | SDF | Download SDF |
| PubChem ID | 5458879 | Appearance | Powder |
| Formula | C19H18N2O3 | M.Wt | 322.4 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide | ||
| SMILES | C1=CC(=CC=C1C=CC(=O)NCCC2=CNC3=C2C=C(C=C3)O)O | ||
| Standard InChIKey | WLZPAFGVOWCVMG-FPYGCLRLSA-N | ||
| Standard InChI | InChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | N-(p-Coumaroyl) serotonin has antioxidant, cardioprotective effects after ischemia and antitumor activity, it may be beneficial in improving vascular distensibility and in reducing cardiovascular risk.N-(p-Coumaroyl) serotonin has a suppressive effect on proinflammatory cytokine production from monocytes, and this effect is based in part on the suppression of cytokine mRNA expression through inhibition of NF-kappaB activation. |
| Targets | ROS | IL Recepter | TNF-α | NF-κB |
| In vitro | Serotonin derivative, N-(p-coumaroyl) serotonin, inhibits the production of TNF-alpha, IL-1alpha, IL-1beta, and IL-6 by endotoxin-stimulated human blood monocytes.[Pubmed: 9660250 ]J Interferon Cytokine Res. 1998 Jun;18(6):423-8.We have reported that N-(p-Coumaroyl) serotonin (CS) and its derivatives with antioxidative activity are present in safflower seeds.
N-(p-coumaroyl) serotonin inhibits glioblastoma cells growth through triggering S-phase arrest and apoptosis.[Pubmed: 28365838 ]J Neurooncol. 2017 May;132(3):373-381.Glioblastoma is the most common and most malignant primary brain tumor with a median survival of 15 months. N-(p-Coumaroyl) serotonin (CS) is an indole alkaloid with antioxidant, cardioprotective effects after ischemia and antitumor activity. In the present study we sought to determine whether could exert cytotoxic and cytostatic effects in glioma cells in vitro.
|
| Animal Research | Safflower seed polyphenols (N-(p-coumaroyl)serotonin and N-feruloylserotonin) ameliorate atherosclerosis and distensibility of the aortic wall in Kurosawa and Kusanagi-hypercholesterolemic (KHC) rabbits.[Pubmed: 19763138 ]Hypertens Res. 2009 Nov;32(11):944-9.Pulse wave velocity (PWV) has been used clinically as a direct measure of arterial stiffness. |
N-(p-Coumaroyl) serotonin Dilution Calculator
N-(p-Coumaroyl) serotonin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.1017 mL | 15.5087 mL | 31.0174 mL | 62.0347 mL | 77.5434 mL |
| 5 mM | 0.6203 mL | 3.1017 mL | 6.2035 mL | 12.4069 mL | 15.5087 mL |
| 10 mM | 0.3102 mL | 1.5509 mL | 3.1017 mL | 6.2035 mL | 7.7543 mL |
| 50 mM | 0.062 mL | 0.3102 mL | 0.6203 mL | 1.2407 mL | 1.5509 mL |
| 100 mM | 0.031 mL | 0.1551 mL | 0.3102 mL | 0.6203 mL | 0.7754 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- Emodin-1-O-beta-gentiobioside
Catalog No.:BCN8869
CAS No.:849789-95-3
- Cassiaside B
Catalog No.:BCN8868
CAS No.:119170-51-3
- Piperlonguminine
Catalog No.:BCN8867
CAS No.:5950-12-9
- 7-Ethoxyrosmanol
Catalog No.:BCN8866
CAS No.:111200-01-2
- 5,7,3',4',5'-Pentamethoxyflavone
Catalog No.:BCN8865
CAS No.:53350-26-8
- Isorhamnetin 7-O-glucoside
Catalog No.:BCN8864
CAS No.:6743-96-0
- 7-Methylcoumarin
Catalog No.:BCN8863
CAS No.:2445-83-2
- Isoarnebin I
Catalog No.:BCN8862
CAS No.:24502-79-2
- Pangelin
Catalog No.:BCN8861
CAS No.:33783-80-1
- 3beta-Methoxy-2,3-dihydrowithaferin A
Catalog No.:BCN8859
CAS No.:73365-94-3
- Hellebrigenin
Catalog No.:BCN8857
CAS No.:465-90-7
- Rhaponticin 6''-O-gallate
Catalog No.:BCN8856
CAS No.:94356-23-7
- Quercetin 3-O-sophoroside-7-O-rhamnoside
Catalog No.:BCN8871
CAS No.:64828-40-6
- Hydroxy-alpha-sanshool
Catalog No.:BCN8872
CAS No.:83883-10-7
- Aegeline
Catalog No.:BCN8873
CAS No.:456-12-2
- Caulophyllogenin
Catalog No.:BCN8874
CAS No.:52936-64-8
- N-trans-Sinapoyltyramine
Catalog No.:BCN8875
CAS No.:200125-11-7
- Sanguisorbigenin
Catalog No.:BCN8876
CAS No.:6812-98-2
- Benzoylgomisin P
Catalog No.:BCN8803
CAS No.:129445-43-8
- Silyamandin
Catalog No.:BCN8804
CAS No.:1009565-36-9
- (+)-δ-Tocopherol
Catalog No.:BCN8805
CAS No.:119-13-1
- 6-Hydroxykaempferol 3-beta-rutinoside
Catalog No.:BCN8807
CAS No.:205527-00-0
- Syringetin-3-O-rutinoside
Catalog No.:BCN8819
CAS No.:53430-50-5
- Quercetin 3-O-rutinoside-1-2-O-rhamnoside
Catalog No.:BCN8820
CAS No.:55696-57-6
Protective Effects of Serotonin and its Derivatives, N-Feruloylserotonin and N-(p-Coumaroyl) Serotonin, Against Cisplatin-Induced Renal Damage in Mice.[Pubmed:30827154]
Am J Chin Med. 2019;47(2):369-383.
This study examined whether serotonin and two of its derivatives, N -feruloylserotonin and N -( p -coumaroyl) serotonin, have a renoprotective effect in a mouse model of cisplatin-induced acute renal failure. Cisplatin (20 mg/kg body weight) was administered by intraperitoneal injection to male BALB/c mice that had received oral serotonin, N -feruloylserotonin or N -( p -coumaroyl) serotonin (7.5 mg/kg body weight per day) during the preceding 2 days. At 3 days after the cisplatin injection, serum and renal biochemical factors, oxidative stress, inflammation and apoptosis-related protein expression were evaluated, and histological examinations were performed. Cisplatin caused reduction in body weight and an increase in kidney weight; however, N -( p -coumaroyl) serotonin and N -feruloylserotonin attenuated these effects. Moreover, the serotonin derivatives significantly decreased serum urea nitrogen and creatinine levels. They also significantly reduced the level of reactive oxygen species and upregulated the expression of glutathione peroxidase in the kidney. Furthermore, the serotonin derivatives improved the abnormal expression of mitogen-activated protein kinases activation-dependent inflammation- and apoptosis-related protein and caused less renal damage. These results provide important evidence that N -( p -coumaroyl) serotonin and N -feruloylserotonin exert a pleiotropic effect on several parameters related to oxidative stress, inflammation and apoptosis. The derivatives also have a renoprotective effect in cisplatin-treated mice; however, this effect is higher with N -( p -coumaroyl) serotonin.
Antiproliferative and cytotoxic action of N-(p-coumaroyl) serotonin in lung cancer cells.[Pubmed:30610796]
J BUON. 2018 Nov-Dec;23(6):1693-1698.
PURPOSE: Lung cancer is among the leading causes of cancer-related cases and cancer-associated deaths. Tumor cells frequently acquire chemoresistance and, due to that, new therapies are always needed in the fight against cancer. Pharmaceutical plants continue to offer novel compounds as anticancer therapies. METHODS: We studied the action of N-p-coumaroyl-serotonin (CS), a natural compound from Centaurea seed and safflower on a lung adenocarcinoma cell line. Cytotoxic or antiproliferative effect was studied using the MTT assay. Cell cycle, caspase-8 activation, mitochondrial membrane potential (MMP) and expression of CD15/CD56/CD24/CD44/CD58/CD71 were studied by flow cytometry. RESULTS: CS exterted antiproliferative and cytotoxic activity, independent of mitochondrial membrane disruption. This compound caused S phase arrest and a decrease in the expression of CD24/CD44/CD58/CD71. CONCLUSION: This is the first report on the in vitro action of CS against lung cancer, necessitating further studies towards its use as a potential anticancer agent.
N-(p-coumaroyl) serotonin induces cell cycle arrest and apoptosis in breast cancer cells.[Pubmed:29552772]
J BUON. 2018 Jan-Feb;23(1):129-133.
PURPOSE: Breast cancer is the most commonly diagnosed malignancy among women. Breast cancer cells may develop resistance to current chemotherapy, thus new chemotherapeutic agents are urgently needed. METHODS: A major number of drugs with anticancer activity have been isolated from plants. Herewith, we investigated for the first time the effect of N-(p-Coumaroyl) serotonin (CS), isolated from Centaurea seed on a drug-resistant breast carcinoma (MCF-7) cells. Viability and proliferation of the cells were examined with trypan blue exclusion assay and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Caspace-8, cell cycle, and CD24/CD44/CD56/ CD58/CD71/CD15 expression were tested with flow cytometry. RESULTS: Treatment with CS significantly reduced cell viability. Induction of cell death and cell cycle arrest was confirmed with flow cytometry. After treatment with CS, there was a dose-dependent decrease in CD24/CD44/CD58/CD71 expression, whereas there was no change in CD56 and CD15 expression. CONCLUSION: The treatment of breast cancer cells with CS may represent a novel therapeutic strategy and requires further investigation.
Engineering of Escherichia coli for the synthesis of N-hydroxycinnamoyl tryptamine and serotonin.[Pubmed:28819877]
J Ind Microbiol Biotechnol. 2017 Nov;44(11):1551-1560.
Plants synthesize various phenol amides. Among them, hydroxycinnamoyl (HC) tryptamines and serotonins exhibit antioxidant, anti-inflammatory, and anti-atherogenic activities. We synthesized HC-tryptamines and HC-serotonin from several HCs and either tryptamine or serotonin using Escherichia coli harboring the 4CL (4-coumaroyl CoA ligase) and CaHCTT [hydroxycinnamoyl-coenzyme A:serotonin N-(hydroxycinnamoyl)transferase] genes. E. coli was engineered to synthesize N-cinnamoyl tryptamine from glucose. TDC (tryptophan decarboxylase) and PAL (phenylalanine ammonia lyase) along with 4CL and CaHCTT were introduced into E. coli and the phenylalanine biosynthetic pathway of E. coli was engineered. Using this strategy, approximately 110.6 mg/L of N-cinnamoyl tryptamine was synthesized. By feeding 100 muM serotonin into the E. coli culture, which could induce the synthesis of cinnamic acid or p-coumaric acid, more than 99 muM of N-cinnamoyl serotonin and N-(p-Coumaroyl) serotonin were synthesized.
N-(p-coumaroyl) serotonin inhibits glioblastoma cells growth through triggering S-phase arrest and apoptosis.[Pubmed:28365838]
J Neurooncol. 2017 May;132(3):373-381.
Glioblastoma is the most common and most malignant primary brain tumor with a median survival of 15 months. N-(p-Coumaroyl) serotonin (CS) is an indole alkaloid with antioxidant, cardioprotective effects after ischemia and antitumor activity. In the present study we sought to determine whether could exert cytotoxic and cytostatic effects in glioma cells in vitro. CS was tested for toxicity in zebrafish. We investigated the effect of CS in U251MG and T98G glioblastoma cell lines. Viability and proliferation of the cells were examined with trypan blue exclusion assay and the xCELLigence system. Cell cycle, activation of caspase-8, mitochondrial membrane potential and CD24/CD44/CD56/CD15/CD71 expression were tested with flow cytometry. Treatment with CS significantly reduced cell viability in both cell lines tested. Induction of cell death and cell cycle arrest at G2/M and S-phase was confirmed with flow cytometry in both cell lines. CS produced significant higher activity of caspase-8 compared to control. After treatment with CS there was a dose-dependent increase in CD15 and CD71 expression, whereas there was no change in CD24/CD44/CD56 expression in both cell lines. The zebrafish mortality on the fifth post fertilization day was zero for even 1 mM of CS concentration. The treatment of glioblastoma cell lines with CS may represent a novel strategy for targeting glioblastoma. Further studies are obviously needed to elucidate the complete mechanism of its antitumor activity.
Lignans and indole alkaloids from the seeds of Centaurea vlachorum Hartvig (Asteraceae), growing wild in Albania and their biological activity.[Pubmed:27609488]
Nat Prod Res. 2017 May;31(10):1195-1200.
The present phytochemical investigation of the seeds of Centaurea vlachorum led to the isolation and characterisation of four compounds including two indole alkaloids N-(p-Coumaroyl) serotonin (1) and moschamine (2) and two dibenzylbutyrolactone lignans matairesinol (3) and arctiin (4). This is the first report on the isolation of non-volatile secondary metabolites from C. vlachorum. The chemataxonomic significance of these compounds was summarised. Moreover, the isolated compounds were tested for their free radical scavenging activity using the following in vitro assays: (i) interaction with the free stable radical of DPPH (1,1-diphenyl-2-picrylhydrazyl), (ii) inhibition of linoleic acid peroxidation with the dihydrochloric acid of 2,2-Azobis-2-amidinopropane (AAPH). Finally, their inhibitory activity towards soybean lipoxygenase was evaluated, using linoleic acid as substrate.
Preparative Separation of N-Feruloyl Serotonin and N-(p-Coumaroyl) Serotonin from Safflower Seed Meal Using High-Speed Counter-Current Chromatography.[Pubmed:25744248]
J Chromatogr Sci. 2015 Sep;53(8):1341-5.
High-speed counter-current chromatography (HSCCC) was successfully applied for the preparative separation and purification of N-feruloyl serotonin (NF) and N-(p-Coumaroyl) serotonin (NP) from safflower seed meal. After the measurement of partition coefficient of the two target compounds in the two-phase solvent systems, the HSCCC was performed well with a two-phase solvent system composed of CHCl3-methanol-0.1 M HCl at a volume ratio of 1 : 1 : 1, v/v. The upper phase was used as stationary phase and the lower phase was used as mobile phase. Under the optimized condition, 7.5 mg NF and 6.9 mg NP were separated from 40 mg crude sample with the purity of 98.8 and 97.3%, respectively. The structures of the isolated compounds were identified by (1)H NMR and (13)C NMR.
Antimicrobial and selected in vitro enzyme inhibitory effects of leaf extracts, flavonols and indole alkaloids isolated from Croton menyharthii.[Pubmed:24126380]
Molecules. 2013 Oct 11;18(10):12633-44.
Croton species are used in folk medicine in the management of infections, inflammation and oxidative stress-related diseases. In order to isolate, characterize and evaluate the bioactive constituents of Croton menyharthii Pax leaf extracts, repeated column fractionation of the ethyl acetate fraction from a 20% aqueous methanol crude extract afforded three flavonols identified by NMR (1D and 2D) spectroscopic methods as myricetrin-3-O-rhamnoside (myricetrin, 1), quercetin-3-O-rhamnoside (2) and quercetin (3) along with an indole alkaloid, (E)-N-(4-hydroxycinnamoyl)-5-hydroxytryptamine, [trans-N-(p-Coumaroyl) serotonin, 4]. All the compounds are reported from the leaf extract of this plant for the first time. The crude extracts, four solvent fractions (hexane, DCM, ethyl acetate and butanol) and isolated compounds obtained from the leaves were evaluated for their inhibitory effects on selected bacteria, a fungus (Candida albicans), cyclooxygenase (COX-2), alpha-glucosidase and acetylcholinesterase (AChE). Amongst the compounds, quercetin (3) was the most active against Bacillus subtilis and Candida albicans while myricetrin-3-O-rhamnoside (1) and trans-N-(p-Coumaroyl) serotonin (4) were the most active compounds against Escherichia coli, Klebsiella pneumonia and Staphylococcus aureus. The inhibitory activity of myricetrin-3-O-rhamnoside (1) against COX-2 was insignificant while that of the other three compounds 2-4 was low. The AChE inhibitory activity of the alkaloid, trans-N-(p-Coumaroyl) serotonin was high, with a percentage inhibitory activity of 72.6% and an IC50 value of 15.0 microg/mL. The rest of the compounds only had moderate activity. Croton menyharthii leaf extracts and isolated compounds inhibit alpha-glucosidase at very low IC50 values compared to the synthetic drug acarbose. Structure activity relationship of the isolated flavonols 1-3 is briefly outlined. Compounds 1-4 and the leaf extracts exhibited a broad spectrum of activities. This validates the ethnomedicinal use of the plant in folk medicine.
