N-(p-Coumaroyl) serotonin | CAS:68573-24-0

N-(p-Coumaroyl) serotonin

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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:

J Interferon Cytokine Res. 1998 Jun;18(6):423-8.

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 ]

We have reported that N-(p-Coumaroyl) serotonin (CS) and its derivatives with antioxidative activity are present in safflower seeds.
METHODS AND RESULTS:
As reactive oxygen species (ROS) are implicated in the signaling of lipopolysaccharide (LPS), we examined whether CS has a suppressive effect on inflammatory cytokine generation from human monocytes in vitro. CS at 50-200 microM reduced tumor necrosis factor (TNF), interleukin-1 (IL-1), and IL-6 activities in the culture supernatants from LPS-stimulated human blood monocytes without cytotoxicity. ELISA assay revealed that the production of TNF-alpha, IL-1alpha, IL-1beta, and IL-6 was inhibited by CS. Northern blot analysis showed that LPS-induced expression of these cytokine mRNA in monocytes was suppressed by CS. NF-kappaB activation was also inhibited by CS.
CONCLUSIONS:
These findings indicate that CS 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.

J Neurooncol. 2017 May;132(3):373-381.

N-(p-coumaroyl) serotonin inhibits glioblastoma cells growth through triggering S-phase arrest and apoptosis.[Pubmed: 28365838 ]

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.
METHODS AND RESULTS:
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.
CONCLUSIONS:
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.

N-(p-Coumaroyl) serotonin Description

Source:	The seeds of Griffonia simplicifolia
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Animal Research:

Hypertens Res. 2009 Nov;32(11):944-9.

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 ]

Pulse wave velocity (PWV) has been used clinically as a direct measure of arterial stiffness.
METHODS AND RESULTS:
We investigated the inhibitory effects of defatted safflower seed extract (SSE) and serotonin derivatives ( N-(p-Coumaroyl) serotonin, N-feruloylserotonin; CS+FS), which are the active components in SSE, on hypercholesterolemia and atherosclerosis, using PWV in Kurosawa and Kusanagi-hypercholesterolemic (KHC) rabbits. SSE and CS+FS were supplemented with a commercial diet containing 0.5% cholesterol for 8 weeks in male KHC rabbits, aged 2 months. Pulse waves were recorded at different aortic positions using two catheters with micromanometers under pentobarbital anesthesia. The atherosclerotic lesioned area in the aorta was significantly reduced in the SSE and CS+FS groups, without significant changes in serum cholesterol and triglyceride levels among the three groups after supplementation. Local PWV (LPWV) in the middle thoracic and distal abdominal aortas was significantly smaller in the SSE and CS+FS groups than in the control group. PWV in the entire aorta was also significantly lower in the SSE and CS+FS groups, compared with that in the control group. Pressure-strain elastic modulus, an index of wall distensibility, was significantly lower in the middle thoracic and middle abdominal aortas in the SSE and CS+FS groups than in the control group. Wall thickness was also significantly smaller in the middle thoracic aorta in the SSE and CS+FS groups compared with that in the control group.
CONCLUSIONS:
Serotonin derivatives inhibited the progress of atherosclerosis and ameliorated wall distensibility, which contributed, in part, to the lowering of LPWV. Serotonin derivatives may be beneficial in improving vascular distensibility and in reducing cardiovascular risk.

Product Name	N-(p-Coumaroyl) serotonin
Price:	$268 / 5mg
CAS No.:	68573-24-0
Catalog No.:	CFN91127
Molecular Formula:	C₁₉H₁₈N₂O₃
Molecular Weight:	322.4 g/mol
Purity:	>=98%
Type of Compound:	Alkaloids
Physical Desc.:	Powder
Source:	The seeds of Griffonia simplicifolia
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Alkaloids Compound Library TNF-α Inhibitor Library ROS Inhibitor Library

	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

CFN91166	Cinobufotenine	60657-23-0	219.3	C₁₃H₁₉N₂O
CFN90037	Melatonin	73-31-4	232.28	C₁₃H₁₆N₂O₂
CFN90202	Abrine	526-31-8; 21339-55-9	218.25	C₁₂H₁₄N₂O₂
CFN90634	Hypaphorine	487-58-1	246.3	C₁₄H₁₈N₂O₂
CFN90473	Tryptophan	54-12-6	204.22	C₁₁H₁₂N₂O₂
CFN70337	N-Malonyl DL-tryptophan	3184-74-5	290.3	C₁₄H₁₄N₂O₅
CFN99742	5-Hydroxytryptophan	56-69-9	220.23	C₁₁H₁₂N₂O₃
CFN94005	Nb-Feruloyltryptamine	53905-13-8	336.39	C₂₀H₂₀N₂O₃
CFN94006	Moschamine	68573-23-9	352.39	C₂₀H₂₀N₂O₄
CFN94007	cis-Moschamine	193224-24-7	352.39	C₂₀H₂₀N₂O₄