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Phellodendrine

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-P2012

  • Specification : 98%

  • CAS number : 6873-13-8

  • Formula : C20H24NO4+

  • Molecular Weight : 342.413

  • PUBCHEM ID : 3081405

  • Volume : 20mg

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Catalogue Number

BF-P2012

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

342.413

Appearance

White crystalline powder

Botanical Source

Phellodendron chinense

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C[N+]12CCC3=CC(=C(C=C3C1CC4=CC(=C(C=C4C2)OC)O)O)OC

Synonyms

OB-5 Compound/Phellodendrin/2,11-dihydroxy-3,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolinium/6H-Dibenzo(a,g)quinolizinium,5,8,13,13a-tetrahydro-2,11-dihydroxy-3,10-dimethoxy-7-methyl-,(7S-cis)/6H-Dibenzo[a,g]quinolizinium, 5,8,13,13a-tetrahydro-2,11-dihydroxy-3,10-dimethoxy-7-methyl-, chloride, (13aS)- (1:1)/Phallodendrin/Phellodendrine/(13aS)-2,11-Dihydroxy-3,10-dimethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolinium chloride

IUPAC Name

(7S,13aS)-3,10-dimethoxy-7-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-7-ium-2,11-diol

Density

Solubility

Methanol

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C20H23NO4/c1-21-5-4-12-8-19(24-2)18(23)10-15(12)16(21)6-13-7-17(22)20(25-3)9-14(13)11-21/h7-10,16H,4-6,11H2,1-3H3,(H-,22,23)/p+1/t16-,21-/m0/s1

InChl Key

RBBVPNQTBKHOEQ-KKSFZXQISA-O

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:6873-13-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

27428451

Abstract

Phellodendrine, a quaternary ammonium alkaloid extracted from the dried bark of Phellodendrom chinensis Schneid and Phellodendrom amurense Rupr, has the effect of suppressing cellular immune response, reducing blood pressure and antinephritis. However, few investigations have been conducted for the pharmacokinetic study of phellodendrine. Thus, a rapid, simple and reliable ultra-high performance liquid chromatography-tandem quadrupole mass spectrometry (UHPLC-QQQ MS/MS) method has been established for quantification of phellodendrine in rat plasma and tissues by using magnoflorine as internal standard. The chromatographic separation was achieved on an Agilent ZORBAX SB-C18 column (4.6mm×50mm, 1.8μm) by gradient elution using 0.1% aqueous formic acid (A) and methanol (B). Triple quadrupole mass detection with multiple reaction monitoring mode was used to monitor the ion transitions, at m/z 342.20→192.20 for phellodendrine and m/z 342.20→58.20 for internal standard, respectively. The developed method was fully validated and successfully applied to the pharmacokinetics and tissue distribution study of phellodendrine after intravenous administration. The lower limits of quantification were 0.5ng/mL for plasma samples, 2.5ng/g for brain and 1ng/g for other tested tissues. Precisions and accuracy values were within the Food and Drug Administration acceptance criteria, the recovery and matrix effects were between 87.8-113.5%. The area under the curve (AUC0-t) ranged from 15.58 to 57.41mg/L min and Cmax were between 1.63-4.93mg/L. The results showed that phellodendrine was eliminated in 120min in plasma and most of tissues and the highest concentrations of phellodendrine were found in the kidney. This study may provide a basis for the further study of phellodendrine.

Copyright © 2016 Elsevier B.V. All rights reserved.

KEYWORDS

Cortex phellodendri; Pharmacokinetic; Phellodendrine; Tissue distribution; UHPLC-MS/MS

Title

Pharmacokinetic studies of phellodendrine in rat plasma and tissues after intravenous administration using ultra-high performance liquid chromatography-tandem mass spectrometry.

Author

Li Y1, Liu XG1, Wang HY1, Dong X1, Gao W1, Xu XJ1, Li P2, Yang H3.

Publish date

2016 Sep 1

PMID

31020909

Abstract

1. Phellodendrine possesses numerous pharmacological activities. However, whether phellodendrine affects the activity of human liver cytochrome P450 (CYP) enzymes remains unclear.2. In this study, the inhibitory effects of phellodendrine on eight human liver CYP isoforms (i.e. 1A2, 3A4, 2A6, 2E1, 2D6, 2C9, 2C19 and 2C8) were investigated in vitro using human liver microsomes (HLMs).3. The results showed that phellodendrine inhibited the activity of CYP1A2, 3A4 and 2C9, with IC50 values of 20.56, 14.98 and 16.30 μM, respectively, but that other CYP isoforms were not affected. Enzyme kinetic studies showed that phellodendrine was not only a non-competitive inhibitor of CYP3A4, but also a competitive inhibitor of CYP1A2 and 2C9, with Ki values of 7.15, 10.52 and 7.98 μM, respectively. In addition, phellodendrine is a time-dependent inhibitor for CYP3A4 with Kinact/KI value of 0.046/11.57 μM-1 min-1.4. The in vitro studies of phellodendrine with CYP isoforms indicate that phellodendrine could inhibit the activities of CYP1A2, 3A4 and 2C9. Further clinical studies are needed to evaluate the significance of this interaction.

KEYWORDS

CYP1A2; CYP2C9; CYP3A4; phellodendrine

Title

In vitro inhibitory effects of phellodendrine on human liver cytochrome P450 enzymes.

Author

Li J1, Wen H2, Gao Z3.

Publish date

2020 Feb

PMID

27234894

Abstract

AIMS:
This study is to investigate the effect of phellodendrine (PHE) against AAPH-induced oxidative stress and find out the biological mechanism of PHE by using the zebrafish embryo model.

MAIN METHODS:
After treatments by AAPH or PHE, the mortality and heartbeat of zebrafish embryos were recorded and the production of reactive oxygen species (ROS), lipid-peroxidation and the rate of cell death were detected by fluorescence spectrophotometry respectively. Whereafter, the pathways of PHE against AAPH-induced oxidative stress were screened by inhibitors to explore its biological mechanism. The related genes and proteins expressions were analyzed by real-time quantitative reverse-transcription polymerase-chain-reaction (qRT-PCR) and western blotting.

KEY FINDINGS:
The PHE obviously improved the decreased survival rate and abnormally elevated heart-beating rate of zebrafish embryos caused by AAPH. Especially 200μg/mL of PHE make the survival rate increased to 90.26±1.40% at 72hfp and the heartbeat back to normal. Besides, AAPH caused a significant increase in the production of reactive oxygen species (ROS), lipid-peroxidation and cell death rate, all of which could be decreased after PHE treatment dose-dependently. And PHE exerted the protective activity against AAPH-induced oxidative stress through down-regulating AKT phosphorylation and NF-kB3 expression, which associate with modulation of IKK phosphorylation in zebrafish embryos.

SIGNIFICANCE:
The PHE showed a good antioxidant effect in vivo, and the mechanism has been stated that the PHE can down-regulating AKT, IKK, NF-kB phosphorylation and COX-2 expression induced by AAPH. Moreover, the PHE also ameliorated the ROS-mediated inflammatory response.

Copyright © 2016 Elsevier Inc. All rights reserved.

KEYWORDS

AAPH; AKT/NF-κB; Oxidative stress; Phellodendrine; Zebrafish embryo

Title

The defensive effect of phellodendrine against AAPH-induced oxidative stress through regulating the AKT/NF-κB pathway in zebrafish embryos.

Author

Li L1, Huang T1, Tian C1, Xiao Y1, Kou S2, Zhou X1, Liu S1, Ye X3, Li X4.

Publish date

2016 Jul 15


Description :

Phellodendrine, a isoquinoline alkaloid, is one of important characteristic ingredients in the Phellodendri chinensis cortex. phellodendrine is against AAPH-induced oxidative stress through regulating the AKT/NF-κB pathway. Phellodendrine has good antioxidant, and anti-inflammatory effect [1].