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Veratramine

$143

  • Brand : BIOFRON

  • Catalogue Number : BF-V2012

  • Specification : 98%

  • CAS number : 60-70-8

  • Formula : C27H39NO2

  • Molecular Weight : 409.61

  • PUBCHEM ID : 6070

  • Volume : 20mg

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Catalogue Number

BF-V2012

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

409.61

Appearance

White needle crystal

Botanical Source

Veratrum nigrum

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CC1CC(C(NC1)C(C)C2=C(C3=C(C=C2)C4CC=C5CC(CCC5(C4C3)C)O)C)O

Synonyms

Veratramine/(3β,23R)-14,15,16,17-Tetradehydroveratraman-3,23-diol/Vreaframine/(3b,23b)-14,15,16,17-Tetradehydroveratraman-3,23-diol/3-Piperidinol, 5-methyl-2-[(1S)-1-[(3S,6aR,11aS,11bR)-2,3,4,6,6a,11,11a,11b-octahydro-3-hydroxy-10,11b-dimethyl-1H-benzo[a]fluoren-9-yl]ethyl]-, (2S,3R,5S)-/Veratraman-3,23-diol, 14,15,16,17-tetradehydro-, (3β,23β)-/veratraMin

IUPAC Name

(2S,3R,5S)-2-[(1S)-1-[(3S,6aR,11aS,11bR)-3-hydroxy-10,11b-dimethyl-1,2,3,4,6,6a,11,11a-octahydrobenzo[a]fluoren-9-yl]ethyl]-5-methylpiperidin-3-ol

Density

1.1±0.1 g/cm3

Solubility

Methanol; Ethanol; Chloroform

Flash Point

86.2±20.7 °C

Boiling Point

565.0±50.0 °C at 760 mmHg

Melting Point

122-124ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2933590000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:60-70-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29237043

Abstract

Because the transcription factor activator protein-1 (AP-1) regulates a variety of protein-encoding genes, it is a participant in many cellular functions, including proliferation, transformation, epithelial mesenchymal transition (EMT), and apoptosis. Inhibitors targeting AP-1 have potential use in the treatment of cancer and other inflammatory diseases. Here, we identify veratramine as a potent natural modulator of AP-1, which selectively binds to a specific site (TRE 5′-TGACTCA-3′) of the AP-1 target DNA sequence and regulates AP-1-dependent gene transcription without interfering with cystosolic signaling cascades that might lead to AP-1 activation. Moreover, RNA-seq experiments demonstrate that veratramine does not act on the Hedgehog signaling pathway in contrast to its analogue, cyclopamine, and likely does not harbor the same teratogenicity and toxicity. Additionally, veratramine effectively suppresses EGF-induced AP-1 transactivation and transformation of JB6 P+ cells. Finally, we demonstrate that veratramine inhibits solar-ultraviolet-induced AP-1 activation in mice. The identification of veratramine and new findings in its specific regulation of AP-1 down stream genes pave ways to discovering and designing regulators to regulate transcription factor.

© The Author(s) 2017. Published by Oxford University Press on behalf of Nucleic Acids Research.

Title

Veratramine modulates AP-1-dependent gene transcription by directly binding to programmable DNA.

Author

Bai F1,2,3, Liu K4,5,6,7, Li H8, Wang J2, Zhu J2,7, Hao P9, Zhu L2, Zhang S2, Shan L8, Ma W6, Bode AM6, Zhang W8, Li H2, Dong Z6,7.

Publish date

2018 Jan 25

PMID

26791530

Abstract

Veratramine, a major alkaloid from Veratrum nigrum L., has distinct anti-tumor and anti-hypertension effects. Our previous study indicated that veratramine had severe toxicity toward male rats. In order to elucidate the underling mechanism, in vivo pharmacokinetic experiments and in vitro mechanistic studies have been conducted. Veratramine was administrated to male and female rats intravenously via the jugular vein at a dose of 50 μg/kg or orally via gavage at 20 mg/kg. As a result, significant pharmacokinetic differences were observed between male and female rats after oral administration with much lower concentrations of veratramine and 7-hydroxyl-veratramine and higher concentrations of veratramine-3-O-sulfate found in the plasma and urine of female rats. The absolute bioavailability of veratramine was 0.9% in female rats and 22.5% in male rats. Further experiments of veratramine on Caco-2 cell monolayer model and in vitro incubation with GI content or rat intestinal subcellular fractions demonstrated that its efficient passive diffusion mediated absorption with minimal intestinal metabolism, suggesting no gender-related difference during its absorption process. When veratramine was incubated with male or female rat liver microsomes/cytosols, significant male-predominant formation of 7-hydroxyl-veratramine and female-predominant formation of veratramine-3-O-sulfate were observed. In conclusion, the significant gender-dependent hepatic metabolism of veratramine could be the major contributor to its gender-dependent pharmacokinetics.

KEYWORDS

7-hydroxyl-veratramine; enterohepatic recirculation; gender-dependent pharmacokinetics; veratramine; veratramine-3-O-sulfate

Title

Gender-Dependent Pharmacokinetics of Veratramine in Rats: In Vivo and In Vitro Evidence.

Author

Lyu C1,2, Zhang Y2, Zhou W3, Zhang S4, Kou F3, Wei H5, Zhang N6, Zuo Z7.

Publish date

2016 Mar

PMID

26972867

Abstract

A simple and sensitive high-performance liquid chromatography coupled with hybrid triple quadrupole-linear ion trap mass spectrometry (Q-trap-MS) method was developed and validated for the determination of veratramine, the major bioactive and neurotoxic component in Veratrum nigrum L. Veratramine and the internal standard (IS) were separated with a Waters Symmetry C18 column and eluted with a gradient mobile phase system containing acetonitrile and 0.1% aqueous formic acid. The analysis was performed by using positive electrospray ionization mode with multiple reaction monitoring (MRM). Transition ions of m/z 410.2 → 295.2 for veratramine and m/z 426.1 → 113.8 for the IS were monitored. The method was validated with a good linearity in the range of 1-1000 ng/mL and lower limit of quantification of 1 ng/mL. The precision (CV) of intra- and inter-day ranged from 3.92 to 7.29%, while the accuracy (bias) intra- and inter-day were between -4.78 and 1.65%. The recovery, stability and matrix effect were within the acceptable ranges. Five metabolites of veratramine, including four hydroxylated and one sulfated metabolites, were tentatively identified using predictive MRM-information dependent acquisition-enhanced product ion mode (predictive MRM-IDA-EPI). The developed method was successfully applied to the pharmacokinetic and metabolic study of veratramine in mice after oral administration of veratramine.

Copyright © 2016 John Wiley & Sons, Ltd.

KEYWORDS

Veratrum nigrum; metabolism; mouse; pharmacokinetics; veratramine

Title

Pharmacokinetics and metabolism study of veratramine in mice after oral administration using LC-MS/MS.

Author

Cong Y1, Zhang JL2, Li SS1, Shen S1, Wang JY1, Cai Z3.

Publish date

2016 Sep


Description :

Veratramine(NSC17821; NSC23880) is useful as a signal transduction inhibitor for treating tumors.