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N-trans-Feruloyltyramine Sale

(Synonyms: N-反式-阿魏酰酪胺,N-feruloyltyramine; Moupinamide) 目录号 : GC40686

A phenolic amide with diverse biological activities

N-trans-Feruloyltyramine Chemical Structure

Cas No.:66648-43-9

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产品描述

N-trans-Feruloyltyramine is a phenolic amide originally isolated from S. melongena that has diverse biological activities, including anti-inflammatory, antioxidative, and antiproliferative properties. It decreases nitric oxide (NO) production (IC50 = 17.36 µM) and inducible NO synthase (iNOS) activity and increases NO scavenging without inducing cytotoxicity in LPS-stimulated BV-2 cells. It also scavenges 2,2-diphenyl-1-picrylhydrazyl radicals in TLC autographic and spectrophotometric assays. N-trans-Feruloyltyramine inhibits proliferation of HeLa and L929 cells by 72.2 and 22%, respectively, when used at a concentration of 30 µg/ml.

Chemical Properties

Cas No. 66648-43-9 SDF
别名 N-反式-阿魏酰酪胺,N-feruloyltyramine; Moupinamide
Canonical SMILES OC1=CC=C(CCNC(/C=C/C2=CC(OC)=C(O)C=C2)=O)C=C1
分子式 C18H19NO4 分子量 313.4
溶解度 DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:3): 0.33 mg/ml,Ethanol: 25 mg/ml 储存条件 4°C, protect from light
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1 mM 3.1908 mL 15.9541 mL 31.9081 mL
5 mM 0.6382 mL 3.1908 mL 6.3816 mL
10 mM 0.3191 mL 1.5954 mL 3.1908 mL
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Research Update

N-trans-Feruloyltyramine as a melanin biosynthesis inhibitor

Biol Pharm Bull 2007 Oct;30(10):1972-4.PMID:17917275DOI:10.1248/bpb.30.1972.

In this study, we examined the effect of N-trans-Feruloyltyramine (FA) on melanogenesis in mouse B16 melanoma cells. Melanogenesis was inhibited by FA in a dose-dependent manner. FA exhibited a greater potency than kojic acid as a standard inhibitor of melanogenesis. Moreover, treatment of B16 melanoma cells with FA was found to cause marked decreases in the expression levels of tyrosinase. FA-induced downregulation of tyrosinase resulted in suppression of melanin biosynthesis in murine B16 melanoma cells.

N-trans-Feruloyltyramine inhibits LPS-induced NO and PGE2 production in RAW 264.7 macrophages: Involvement of AP-1 and MAP kinase signalling pathways

Chem Biol Interact 2015 Jun 25;235:56-62.PMID:25843058DOI:10.1016/j.cbi.2015.03.029.

Mitogen-activated protein kinase (MAPK) signalling pathway can regulate inflammatory and immune responses. N-trans-Feruloyltyramine (FLA) is an active phenylpropanoid compound. It possesses antioxidant, antimicrobial, anti-melanogenesis, and anticancer activities. However, the precise molecular mechanisms underlying FLA modulation of cytokine expression in LPS-stimulated RAW 264.7 macrophages have not been fully investigated. In this study, we examined the mechanisms underlying the immunomodulative effects of FLA isolated from Arcangelisia gusanlung. FLA strongly suppressed mRNA expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), but not tumor necrosis factor (TNF)-α, thereby inhibiting the production of nitric oxide (NO) and prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Furthermore, FLA also inhibited nuclear translocation of activation protein (AP)-1, and simultaneously decreased the expression and phosphorylation of the c-Jun N-terminal kinase (JNK) protein. These results suggest that the anti-inflammatory effects of FLA might be attributed to downregulation of COX-2 and iNOS via suppression of AP-1 and the JNK signalling pathway in RAW 264.7 macrophages.

Effects of N-trans-Feruloyltyramine isolated from laba garlic on antioxidant, cytotoxic activities and H2O2-induced oxidative damage in HepG2 and L02 cells

Food Chem Toxicol 2019 Aug;130:130-141.PMID:31103739DOI:10.1016/j.fct.2019.05.021.

Laba garlic is a kind of processed garlic products, it is the traditional Chinese food with a long history. In this study, the antitumor, antioxidant and cytotoxic properties of the blue pigment (BP) from Laba garlic were investigated. N-trans-Feruloyltyramine (FLA) was isolated and identified from BP. The protective effects of FLA against H2O2-induced oxidative damages in L02 cells were also assessed. The apoptotic effects of FLA were detected by using flow cytometry analysis. Results showed that the tumor growth was significantly suppressed by BP (P<0.05). BP and FLA exhibited remarkable antioxidant activities. L02 cells pretreatment with FLA could significantly fight against the oxidative damage induced by H2O2, inhibit the morphological changes of mitochondria and maintain the integrity of mitochondria. FLA showed proliferation inhibition on HepG2 cells with IC50 value of 194 ± 0.894 μM. After treatment of FLA (320 μM), the results of MTT assay on HepG2 and L02 cells indicated that FLA had selective cytotoxic effects. It suggested a new way of prevention and treatment of tumors and FLA might be a promising candidate in cancer therapy and functional foods.

Protective role of N-trans-Feruloyltyramine against β-amyloid peptide-induced neurotoxicity in rat cultured cortical neurons

Neurosci Lett 2012 Apr 4;513(2):229-32.PMID:22387154DOI:10.1016/j.neulet.2012.02.047.

Enhanced oxidative stress and inflammation play important roles in the pathogenesis of Alzheimer's disease (AD). Amyloid β-peptide (Aβ), a major component of amyloid plaques, is considered to have a causal role in the development and progress of AD by being the initiator of a pathological cascade leading to oxidative stress. The present study investigated the effect of N-trans-Feruloyltyramine (NTF) purified from Polyalthia suberosa, an alkaloid shown to protect against oxidative stress and cell death. Pre-treatment of rat primary cortical cell cultures with 25-250μM NTF significantly attenuated 10μM Aβ(1-42)-induced neuronal death in a dose-dependent manner. Apoptotic cell death was demonstrated morphologically as well as by detection of the presence of activated caspase-3 and Bax, levels of which could be reduced by NTF pre-treatment. NTF also reduced production of reactive oxygen species induced by Aβ(1-42). These findings suggest that the protective effect of NTF against Aβ(1-42)-induced neuronal death might be due to its antioxidative property.

Metabolites Identification of Bioactive Compounds Daturataturin A, Daturametelin I, N-trans-Feruloyltyramine, and Cannabisin F From the Seeds of Datura metel in Rats

Front Pharmacol 2018 Jul 9;9:731.PMID:30050436DOI:10.3389/fphar.2018.00731.

Datura metel L. is a widely used traditional herbal medicine, and withanolides and amides are the two groups of main bioactive constituents in Datura metel seeds. This study aimed to elucidate the metabolism of four representative bioactive compositions containing daturataturin A (1), daturametelin I (2), N-trans-Feruloyltyramine (3), and cannabisin F (4) in rats. After separately oral administration of 20 mg/kg withanolides (1, 2) and amides (3, 4) to rats, a total of 12, 24, and 21 metabolites were detected in the plasma, urine, and fecal samples, respectively. Among them, three hydroxylated metabolites, 1-M3, 2-M2, and 3-M5, were detected in plasma and rat liver microsome incubation system in high abundance. Two metabolites of 1 and 2 were unambiguously identified by comparing with reference standards. Particularly, the methylated metabolite 27α-methoxy-(22R)-22,26-epoxy-27-[(β-D-glucopyranosyl)oxy]ergosta-2,4,6,24-tetraene-1,26-dione (daturametelin L) is a new compound. The withanolides could readily get hydroxylation or methylation metabolism. Meanwhile, the phase II metabolism (glucuronidation or sulfation) was the major reaction for the amides. This is the first study on in vivo metabolism of these active compounds in seeds of Datura metel.