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Isovalerylshikonin

$760

  • Brand : BIOFRON

  • Catalogue Number : BN-O1818

  • Specification : 98%(HPLC)

  • CAS number : 52387-14-1

  • Formula : C21H24O6

  • Molecular Weight : 372.41

  • Volume : 10mg

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Quantity
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Catalogue Number

BN-O1818

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

372.41

Appearance

Botanical Source

Structure Type

Category

SMILES

CC(C)CC(=O)OC(CC=C(C)C)C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O

Synonyms

ALKANNIN,ISOVALIRIC ACID ISVL/Alkannin isovalerate/(R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthyl)-4-methyl-3-pentenyl isovalerate/I0422/Isovalerylshikonin/UTOUNDHZJFIVPK-UHFFFAOYSA

IUPAC Name

Applications

Density

1.246g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

198.6ºC

Boiling Point

570.1ºC at 760 mmHg

Melting Point

107ºC

InChl

InChI=1S/C21H24O5/c1-7-20(3,4)15-9-13-8-14-10-18(21(5,6)26-12(2)22)24-16(14)11-17(13)25-19(15)23/h7-9,11,18H,1,10H2,2-6H3

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:52387-14-1) 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

30176356

Abstract

Antimicrobial resistance is the greatest threat to the treatment of bacterial infectious diseases. The development of resistance-modifying agents (RMAs) represents a promising strategy to mitigate the spread of bacterial antimicrobial resistance. In this study, a natural product, isovalerylshikonin (IVS), was isolated from Arnebia euchroma, a traditional Chinese medicine herb, that exhibited marginal antibacterial activity against drug-resistant Staphylococcus aureus RN4220, with a minimum inhibitory concentration (MIC) of 16 mg/L. In addition, a synergistic effect between IVS and streptomycin (STM) was detected by the microdilution antimicrobial chequerboard assay, with a reduction in the MIC of STM by up to 16-fold against strain RN4220. A bacterial ethidium bromide efflux assay and reverse transcription PCR were performed to investigate the synergistic mechanism. IVS significantly inhibited bacterial efflux and expression of msrA mRNA in vitro. A murine peritonitis/sepsis model was employed to test the in vivo synergistic activity of IVS and STM. IVS synergistically decreased bacterial counts with STM in peritoneal, spleen and liver tissue and increased mouse survival with STM in 7 days. The acute toxicity of IVS was tested and the 50% lethal dose (LD50) of IVS with a single exposure was 2.584 g/kg in mice. Overall, IVS, a low-toxicity RMA, exhibited synergistic antibacterial activities in vitro and in vivo against drug-resistant S. aureus. The effects were mediated by suppression of msrA mRNA expression and reduced bacterial efflux. In addition, these data support that IVS is a potential RMA against microbial resistance caused by the MsrA efflux pump.

Copyright © 2018 Elsevier Ltd. All rights reserved.

KEYWORDS

Arnebia euchroma; Drug-resistant Staphylococcus aureus; Isovalerylshikonin; Resistance-modifying agent; Synergistic effect

Title

Isovalerylshikonin, a new resistance-modifying agent from Arnebia euchroma, supresses antimicrobial resistance of drug-resistant Staphylococcus aureus.

Author

He JM1, Sun SC1, Sun ZL1, Chen JT1, Mu Q2.

Publish date

2019 Jan

PMID

19662625

Abstract

A new, fast and sensitive high-performance liquid chromatography/electrospray ionization tandem mass spectrometry (HPLC/ESI-MS/MS) method was developed and validated for isovalerylshikonin in rat plasma using emodin as internal standard (IS). The analyte was extracted from rat plasma with ethyl acetate, after 10% HCl treatment and protein precipitated by methanol. The compound was separated on an Ultimate XB-C(18) analytical column using a mobile phase of methanol-10 mM ammonium acetate in water-acetonitrile containing 0.05% formic acid (45 : 10 : 45, v/v/v) with isogradient elution. The analyte was detected in negative ion mode using multiple-reaction monitoring. The method was validated and the specificity, linearity, lower limit of quantitation (LLOQ), precision, accuracy, recoveries and stability were determined. LLOQ was 9 ng/mL for isovalerylshikonin. Correlation coefficient (r) value for the linear range of the analyte was greater than 0.99. The intra-day and inter-day precision and accuracy were better than 8.52%. The relative and absolute recovery was above 86% and no matrix effects were observed for isovalerylshikonin. This validated method provides a modern, rapid and robust procedure for the pharmacokinetic study of the two compounds in rats after intravenous administration to rats (n = 4).

Copyright (c) 2009 John Wiley & Sons, Ltd.

Title

A rapid HPLC/ESI-MS/MS method for quantitative analysis of isovalerylshikonin in rat plasma.

Author

Zhu M1, Gao Y, Wu Z, Zhao Y

Publish date

2010 Apr