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Daurisoline

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-D2032

  • Specification : 98%

  • CAS number : 70553-76-3

  • Formula : C37H42N2O6

  • Molecular Weight : 610.747

  • PUBCHEM ID : 51106

  • Volume : 20mg

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Catalogue Number

BF-D2032

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

610.747

Appearance

White crystalline powder

Botanical Source

roots of Menispermum dauricum

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)OC4=C(C=CC(=C4)CC5C6=CC(=C(C=C6CCN5C)OC)O)O)OC)OC

Synonyms

7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[[4-hydroxy-3-[4-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]phenoxy]phenyl]methyl]-6-methoxy-2-methyl-, (1R)-/(1R)-1-[3-(4-{[(1R)-6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl]methyl}phenoxy)-4-hydroxybenzyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydro-7-isoquinolinol/(1R)-1-[3-(4-{[(1R)-6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)-4-hydroxybenzyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

IUPAC Name

(1R)-1-[[3-[4-[[(1R)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]phenoxy]-4-hydroxyphenyl]methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol

Density

1.2±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate; Petroleum ether; Acetone

Flash Point

392.0±32.9 °C

Boiling Point

724.5±60.0 °C at 760 mmHg

Melting Point

96-102ºC

InChl

InChI=1S/C37H42N2O6/c1-38-15-13-26-20-36(43-4)37(44-5)22-29(26)30(38)16-23-6-9-27(10-7-23)45-35-18-24(8-11-32(35)40)17-31-28-21-33(41)34(42-3)19-25(28)12-14-39(31)2/h6-11,18-22,30-31,40-41H,12-17H2,1-5H3/t30-,31-/m1/s1

InChl Key

BURJAQFYNVMZDV-FIRIVFDPSA-N

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#:70553-76-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29100416

Abstract

Autophagy is a cellular bulk degradation pathway implicated in various diseases. Inhibition of autophagy has been regarded as a new therapeutic strategy for cancer treatment, especially in combination with chemotherapy. In our study, we identified two natural compounds, dauricine (DAC) and daurisoline (DAS), as two potent autophagy blockers through a high-content screening. DAC and DAS are alkaloids isolated from traditional Chinese medicine Rhizoma Menispermi. We systematically examined the effects of DAC and DAS on autophagy function in HeLa cells and found that DAC and DAS induced massive formation of autophagic vacuoles and lipidation of LC3. The accumulation of autophagic vacuoles and LC3 lipidation are due to blockage of autophagosome maturation as evidenced by interrupted colocalization of autophagsosome and lysosome, increased GFP-LC3/RFP-LC3 ratio and accumulation of autophagic substrate p62. Moreover, DAC and DAS impaired lysosomal function, as indicated by reduced lysosomal protease activity and increased lysosomal pH values. Importantly, we showed that DAC and DAS strongly inhibited the lysosome V-type ATPase activity. For the therapeutic potential, we found that DAC and DAS blocked the campothecin (CPT)-induced protective autophagy in HeLa cells, and dramatically sensitized the multiple cancer cells to CPT-induced cell death. In conclusion, our result shows that DAC and DAS are autophagy inhibitors which inhibit the lysosomal degradation of auophagic vacuoles, and sensitize the CPT-induced cancer cell death. The study implies the therapeutic potential of DAC and DAS in the treatment of cancers in combination of chemotherapy by inhibiting autophagy.

KEYWORDS

autophagy blocker; cancer cells; cell toxicity; dauricine; daurisoline

Title

Natural autophagy blockers, dauricine (DAC) and daurisoline (DAS), sensitize cancer cells to camptothecin-induced toxicity.

Author

Wu MY1, Wang SF1, Cai CZ1, Tan JQ2, Li M3, Lu JJ1, Chen XP1, Wang YT1, Zheng W4, Lu JH1.

Publish date

2017 Sep 8

PMID

9812749

Abstract

AIM:
To explain the effect of daurisoline (DS) on delayed afterdepolarization (DAD).

METHODS:
Ca(2+)-sensitive microelectrode technic was used to record intracellular Ca2+ activity (alpha Cai) and triggered activity (TA) arising from DAD in myocardium.

RESULTS:
Strophantin G 3 mumol.L-1 yielded an increase in resting myocardial alpha Cai by 0.19 +/- 0.11 mumol.L-1 and transient elevations of alpha Cai by 1.48 +/- 0.55 and 4.96 +/- 1.81 mumol.L-1, respectively during the development of DAD and TA. By pretreatment with DS or verapamil, strophantin G-caused elevations of the alpha Cai in resting and provoked myocardia were eliminated and TA disappeared. DS 50 mumol.L-1 reduced Na(+)-free medium-induced elevation of dog Purkinje fibrous alpha Cai and abolished caffeine-induced increase of dog myocardial alpha Cai.

CONCLUSIONS:
DS inhibited DAD and TA by preventing an increase of alpha Cai via transmembrane Ca2+ entry and Ca2+ release from the reticulum.

Title

Effects of daurisoline on intracellular Ca2+ activity in myocardium.

Author

Wang ZX1, Zhu JQ, Zeng FD, Hu CJ, Ma YL, Zhong SM.

Publish date

1996 May

PMID

22974355

Abstract

Daurisoline (1) is a bis-benzylisoquinoline alkaloid isolated from the rhizomes of Menispermum dauricum. The antiarrhythmic effect of 1 has been demonstrated in different experimental animals. In previous studies, daurisoline (1) prolonged action potential duration (APD) in a normal use-dependent manner. However, the electrophysiological mechanisms for 1-induced prolongation of APD have not been documented. In the present study, the direct effect of 1 was investigated on the hERG current and the expression of mRNA and protein in human embryonic kidney 293 (HEK293) cells stably expressing the hERG channel. It was shown that 1 inhibits hERG current in a concentration- and voltage-dependent manner. In the presence of 10 μM 1, steady-state inactivation of V(1/2) was shifted negatively by 15.9 mV, and 1 accelerated the onset of inactivation. Blockade of hERG channels was dependent on channel opening. The expression and function of hERG were unchanged by 1 at 1 and 10 μM, while hERG expression and the hERG current were decreased significantly by 1 at 30 μM. These results indicate that 1, at concentrations below 30 μM, exerts a blocking effect on hERG, but does not affect the expression and function of the hERG channel. This may explain the relatively lower risk of long QT syndrome after long-term usage.

Title

Effect of daurisoline on HERG channel electrophysiological function and protein expression.

Author

Liu Q1, Mao X, Zeng F, Jin S, Yang X.

Publish date

2012 Sep 28


Description :

Daurisoline is a hERG inhibitor and also an autophagy blocker.