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Evodiamine

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-E2006

  • Specification : 98%

  • CAS number : 518-17-2

  • Formula : C19H17N3O

  • Molecular Weight : 303.36

  • PUBCHEM ID : 442088

  • Volume : 20mg

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Catalogue Number

BF-E2006

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

303.36

Appearance

White crystalline powder

Botanical Source

Tetradium ruticarpum

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3

Synonyms

EVODIAMINE PLANT EXTRACT/Indolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (13bS)-/Evodia rutaecarpa E.P./Indol(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (13bS)-/Indol(2',3':3,4)pyrido(2,1-b)quinazolin-5(7H)-one, 8,13,13b,14-tetrahydro-14-methyl-, (S)-/d-Evodiamine/(13bS)-14-Methyl-8,13,13b,14-tetrahydroindolo[2',3':3,4]pyrido[2,1-b]quinazolin-5(7H)-one

IUPAC Name

(1S)-21-methyl-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one

Density

1.4±0.1 g/cm3

Solubility

Methanol

Flash Point

301.6±30.1 °C

Boiling Point

575.1±50.0 °C at 760 mmHg

Melting Point

263 - 265ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2939800000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:518-17-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31894007

Abstract

Objective To observe the effect of evodiamine on the injury of human umbilical vein endothelial cells (HUVECs) induced by lipopolysaccharide (LPS) and investigate its impossible mechanism. Methods HUVECs were used to make the inflammatory injured cell model. The cultured cells in vitro were divided into a normal control group, LPS model group, DMSO control group, low- and high-dose evodiamine group. The cell survival rate was detected by CCK-8 assay. The content of nitric oxide (NO) in the medium serum was detected by ELISA. Nuclear factor-kappa Bp65 (NF-κBp65) mRNA was determined by reverse transcription polymerase chain reaction (RT-PCR). The protein expression of Toll-like receptor 4 (TLR4) and NF-κBp65 was detected by Western blotting. Results Compared with the control group, the cell survival rate and NO content obviously decreased, and the expression levels of TLR4 and NF-κBp65 increased in the LPS treated group. Compared with LPS group, the pre-treatment of evodiamine obviously improved the cell survival rate, promoted the secretion of NO, inhibited the expression of TLR4 and NF-κBp65 and down-regulated the mRNA expression of NF-κBp65. Conclusion Evodiamine can relieve the inflammatory injury of HUVECs induced by LPS and promote the synthesis of NO, which may be related to the regulation of TLR4/NF-κB signaling pathway.

Title

[Evodiamine inhibits injury of HUVECs induced by lipopolysaccharide through TLR4/NF-κB signaling pathway].

Author

Wang Y1, Yang W2, Peng F1, Chen T1, Fu Y1, Tian M1.

Publish date

2019 Dec

PMID

31328737

Abstract

Invasion and metastasis of colorectal cancer (CRC) are leading causes of death of CRC patients. Previous findings demonstrate that evodiamine (Evo), an indolequinone alkaloid, is effective in combating CRC; however, its poor aqueous solubility and low oral bioavailability limit its application in the prevention of invasion and metastasis of CRC. It is known that selectively targeting cancer-specific receptors highly expressed on the surface of cancer cells by nanocarriers loaded with cytotoxic drugs is a viable strategy in nanobiotechnology to enhance cancer cell killing and minimize side effects. In this study, we report the development of a new class of nanotherapeutics: EGFR-targeting Evo-encapsulated poly(amino acid) nanoparticles (GE11-Evo-NPs). These nanoparticles exhibited good aqueous solubility, slow release, and active targeting capability. Their inhibitory effect on human colon cancer cells and therapeutic efficacy against invasion and metastasis of CRC in nude mice were systematically investigated. Mechanisms of the GE11-Evo-NPs against EGFR mediated invasion and metastasis of CRC were also explored. Compared with free Evo, the GE11-Evo-NPs showed significantly increased cytotoxicity to colon cancer cells and potently inhibited CRC LoVo cell adhesion, invasion, and migration. The expression of EGFR, VEGF, and MMP proteins was dramatically down-regulated, which may partially account for their inhibition of invasion and metastasis of CRC. Moreover, in vivo studies show that the GE11-Evo-NPs exhibited much greater potency than other control groups in inhibiting CRC invasion and metastasis, tumor volume, and growth in nude mice, leading to a significantly prolonged tumor-bearing survival duration (P < 0.01).

Title

Development of EGFR-targeted evodiamine nanoparticles for the treatment of colorectal cancer.

Author

Li C 1, Cai G , Song D , Gao R , Teng P , Zhou L , Ji Q , Sui H , Cai J , Li Q , Wang Y .

Publish date

2019 Aug 20

PMID

31202495

Abstract

Evodiae Fructus is used as a traditional Chinese medicine for the treatment of several kinds of diseases with its bioactive constituents. In this study, a capillary electrochromatography-mass spectrometry (CEC-MS) method was developed to determine three bioactive compounds including evodiamine, rutaecarpine and limonin in Evodiae Fructus fruit. Home-developed monolithic columns with methyl-vinylimidazole functionalized organic polymer monolilth as stationary phases were used in CEC-MS with excellent separation selectivity and high efficiency. The CEC-MS methods provided 4-16 folds improvement of LODs when compared with CEC-UV method. The conditions, which could affect separation efficiency and detection sensitivity, were optimized. Under optimum conditions, baseline separation with high detection sensitivity was obtained. The method showed good linearity (R2 >0.99) of 0.8-160 μg mL-1 with low limits of detection of 0.15-0.31 μg mL-1. Relative standard deviations of migration time and relative peak areas were <13.89%. Recoveries of evodiamine, rutaecarpine and limonin in Evodiae Fructus fruit were tested and calculated, which ranged from 102% to 113%. Finally, the three bioactive compounds in Evodiae Fructus herb samples from different regions were analyzed and studied. It has been demonstrated that the developed method has great potential for quality control of Evodiae Fructus herb.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Bioactive components; Capillary electrochromatography-mass spectrometry; Evodiae Fructus; Methyl-vinylimidazole functionalized organic polymer monolilth; Monolithic column

Title

Analysis of Evodiae Fructus by capillary electrochromatography-mass spectrometry with methyl-vinylimidazole functionalized organic polymer monolilth as stationary phases.

Author

Liu Y1, Zhou W2, Mao Z2, Chen Z3.

Publish date

2019 Sep 27;


Description :

Evodiamine is an alkaloid isolated from the fruit of Evodia rutaecarpa Bentham with diverse biological activities including anti-inflammatory, anti-obesity, and antitumor