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Dimethyl lithospermate B

$360

  • Brand : BIOFRON

  • Catalogue Number : BD-D1303

  • Specification : 98%(HPLC)

  • CAS number : 875313-64-7

  • Formula : C38H34O16

  • Molecular Weight : 746.674

  • PUBCHEM ID : 73349618

  • Volume : 20mg

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Catalogue Number

BD-D1303

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8?

Molecular Weight

746.674

Appearance

White crystalline powder

Botanical Source

Salvia miltiorrhiza Bge.

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

COC(=O)C(CC1=CC(=C(C=C1)O)O)OC(=O)C=CC2=C3C(C(OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)OC(CC5=CC(=C(C=C5)O)O)C(=O)OC

Synonyms

3-Benzofurancarboxylic acid, 2-(3,4-dihydroxyphenyl)-4-[(1E)-3-[(1R)-1-[(3,4-dihydroxyphenyl)methyl]-2-methoxy-2-oxoethoxy]-3-oxo-1-propen-1-yl]-2,3-dihydro-7-hydroxy-, (1R)-1-[(3,4-dihydroxyphenyl)methyl]-2-methoxy-2-oxoethyl ester, (2R,3R)-/(2R)-3-(3,4-Dihydroxyphenyl)-1-methoxy-1-oxo-2-propanyl (2R,3R)-2-(3,4-dihydroxyphenyl)-4-[(1E)-3-{[(2R)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxo-2-propanyl]oxy}-3-oxo-1-propen-1-yl]-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylate/Dimethyl lithospermate B

IUPAC Name

[(2R)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl] (2R,3R)-2-(3,4-dihydroxyphenyl)-4-[(E)-3-[(2R)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy-3-oxoprop-1-enyl]-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylate

Applications

Dimethyl lithospermate B (dmLSB) is a selective Na+ channel agonist. Dimethyl lithospermate B slows inactivation of sodium current (INa), leading to increased inward current during the early phases of the action potential (AP)[1][2].

Density

1.5±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate; Water

Flash Point

300.5±27.8 °C

Boiling Point

968.3±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C38H34O16/c1-50-36(47)29(15-18-3-8-22(39)26(43)13-18)52-31(46)12-7-20-5-11-25(42)35-32(20)33(34(54-35)21-6-10-24(41)28(45)17-21)38(49)53-30(37(48)51-2)16-19-4-9-23(40)27(44)14-19/h3-14,17,29-30,33-34,39-45H,15-16H2,1-2H3/b12-7+/t29-,30-,33-,34+/m1/s1

InChl Key

DHYLGBJCEGEBGQ-QIBPRZLVSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:875313-64-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

22124203

Abstract

Dimethyl lithosermate B (DLB) is a highly potent natural antioxidant and antidiabetic polyphenol with unknown mode of action. To determine its cellular targets, a photochemical and fluorescent dimethyl lithopermate B probe was designed and efficiently synthesized. The dual-labeled chemical probe for biological application was evaluated by UV and fluorescence to determine its electrochemical absorption and emission properties. This probe could be valuable for investigating ligand-protein interactions and subcellular localization.

© 2011 by the authors; licensee MDPI, Basel, Switzerland.

Title

Synthesis of a dual-labeled probe of dimethyl lithospermate B with photochemical and fluorescent properties.

Author

Lim E1, Ricci J, Jung M.

Publish date

2011 Nov 28

PMID

16534004

Abstract

BACKGROUND:
Dimethyl lithospermate B (dmLSB) is an extract of Danshen, a traditional Chinese herbal remedy, which slows inactivation of INa, leading to increased inward current during the early phases of the action potential (AP). We hypothesized that this action would be antiarrhythmic in the setting of Brugada syndrome.

METHODS AND RESULTS:
The Brugada syndrome phenotype was created in canine arterially perfused right ventricular wedge preparations with the use of either terfenadine or verapamil to inhibit INa and ICa or pinacidil to activate IK-ATP. AP recordings were simultaneously recorded from epicardial and endocardial sites together with an ECG. Terfenadine, verapamil, and pinacidil each induced all-or-none repolarization at some epicardial sites but not others, leading to ST-segment elevation as well as an increase in both epicardial and transmural dispersions of repolarization (EDR and TDR, respectively) from 12.9+/-9.6 to 107.0+/-54.8 ms and from 22.4+/-8.1 to 82.2+/-37.4 ms, respectively (P<0.05; n=9). Under these conditions, phase 2 reentry developed as the epicardial AP dome propagated from sites where it was maintained to sites at which it was lost, generating closely coupled extrasystoles and ventricular tachycardia and fibrillation. Addition of dmLSB (10 micromol/L) to the coronary perfusate restored the epicardial AP dome, reduced EDR and TDR to 12.4+/-18.1 and 24.4+/-26.7 ms, respectively (P<0.05; n=9), and abolished phase 2 reentry-induced extrasystoles and ventricular tachycardia and fibrillation in 9 of 9 preparations. CONCLUSIONS: Our data suggest that dmLSB is effective in eliminating the arrhythmogenic substrate responsible for the Brugada syndrome and that it deserves further study as a pharmacological adjunct to implanted cardioverter/defibrillator usage.

Title

Dimethyl lithospermate B, an extract of Danshen, suppresses arrhythmogenesis associated with the Brugada syndrome.

Author

Fish JM1, Welchons DR, Kim YS, Lee SH, Ho WK, Antzelevitch C.

Publish date

2006 Mar 21

PMID

15504759

Abstract

Voltage-gated Na(+) channel blockers have been widely used as local anaesthetics and antiarrhythmic agents. It has recently been proposed that Na(+) channel agonists can be used as inotropic agents. Here, we report the identification of a natural substance that acts as a Na(+) channel agonist. Using the patch-clamp technique in isolated rat ventricular myocytes, we investigated the electrophysiological effects of the substances isolated from the root extract of Salvia miltiorrhiza, which is known as ‘Danshen’ in Asian traditional medicine. By the intensive activity-guided fractionation, we identified dimethyl lithospermate B (dmLSB) as the most active component, while LSB, which is the major component of the extract, showed negligible electrophysiological effect. Action potential duration (APD(90)) was increased by 20 microM dmLSB from 58.8 +/- 12.1 to 202.3 +/- 9.5 ms. In spite of the prolonged APD, no early after-depolarization (EAD) was observed. dmLSB had no noticeable effect on K(+) or Ca(2+) currents, but selectively affected Na(+) currents (I(Na)). dmLSB slowed the inactivation kinetics of I(Na) by increasing the proportion of slowly inactivating component without inducing any persistent I(Na). The relative amplitude of slow component compared to the peak fast I(Na) was increased dose dependently by dmLSB (EC(50) = 20 microM). Voltage dependence of inactivation was not affected by dmLSB, while voltage dependence of activation shifted by 5 mV to the depolarised direction. Since the APD prolongation by dmLSB did not provoke EAD, which is thought as a possible mechanism for the proarrhythmia seen in other Na(+) channel agonists, dmLSB might be an excellent candidate for a Na(+) channel agonist.

British Journal of Pharmacology (2004).

Title

A novel Na+ channel agonist, dimethyl lithospermate B, slows Na+ current inactivation and increases action potential duration in isolated rat ventricular myocytes.

Author

Yoon JY1, Ahn SH, Oh H, Kim YS, Ryu SY, Ho WK, Lee SH.

Publish date

2004 Nov