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Sanguinarine chloride

$64

  • Brand : BIOFRON

  • Catalogue Number : BD-P0394

  • Specification : 98.0%(HPLC)

  • CAS number : 5578-73-4

  • PUBCHEM ID : 68635

  • Volume : 25mg

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Catalogue Number

BD-P0394

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

Appearance

Red needle crystal

Botanical Source

Macleaya cordata (Willd.) R. Br.

Structure Type

Quinolines/Isoquinolines

Category

Standards;Natural Pytochemical;API

SMILES

C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6.[Cl-]

Synonyms

Sanguinarine chloride/Sanguinarine chloride hydrate/13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-13-ium chloride/13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride/13-Methyl[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium chloride/[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-, chloride (1:1)/sanguinarine/13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium chloride (1:1)/chlorure de sanguinarium/sanguinarium chloride/13-Methyl[1,3]dioxolo[4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-iumchlorid/Sanguinarine (chloride)

IUPAC Name

24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene;chloride

Applications

Sanguinarine chloride, a benzophenanthridine alkaloid derived from the root of Sanguinaria Canadensis, can stimulate apoptosis via activating the production of reactive oxygen species (ROS). Sanguinarine-induced apoptosis is associated with the activation of JNK and NF-κB.

Density

Solubility

Methanol

Flash Point

Boiling Point

Melting Point

287-289 ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2934990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:5578-73-4) 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

29761161

Abstract

The type III secretion system (T3SS) is a key virulence mechanism of many Gram-negative bacterial pathogens. Upon contact between bacteria and host cells, T3SS transfers a series of effectors from the bacterial cytosol to host cells. It is widely known that a mutation in T3SS does not impair bacterial growth, thereby avoiding any subsequent development of resistance. Thus, T3SS is expected to be a candidate therapeutic target. While developing the T3SS screening method, we discovered that sanguinarine chloride, a natural compound, could decrease the production of the SPI-1 type III secretion system main virulence proteins SipA and SipB and prevent the invasion of HeLa cells by Salmonella enterica serovar Typhimurium without affecting the growth of Salmonella. Furthermore, sanguinarine chloride downregulated the transcription of HilA and consequently regulated the expression of the SPI-1 apparatus and effector genes. In summary, our study directly demonstrated that this putative SPI-1 inhibitor belongs to a novel class of anti-Salmonella compounds.

KEYWORDS

Anti-virulence; Natural compound; Salmonella; Sanguinarine chloride; Type III secretion

Title

Natural compound sanguinarine chloride targets the type III secretion system of Salmonella enterica Serovar Typhimurium.

Author

Zhang Y1,2, Liu Y2, Wang T2, Deng X1,2, Chu X1.

Publish date

2018 May 9

PMID

29107809

Abstract

Sanguinarine is a benzo[c]phenanthridine alkaloid with interesting cytotoxic properties, such as induction of oxidative DNA damage and very rapid apoptosis, which is not mediated by p53-dependent signaling. It has been previously documented that sanguinarine is reduced with NADH even in absence of any enzymes while being converted to its dihydro form. We found that the dark blue fluorescent species, observed during sanguinarine reduction with NADH and misinterpreted by Matkar et al. (Arch. Biochem. Biophys. 2008, 477, 43-52) as an anionic form of the alkaloid, is a covalent adduct formed by the interaction of NADH and sanguinarine. The covalent adduct is then converted slowly to the products, dihydrosanguinarine and NAD+, in the second step of reduction. The product of the reduction, dihydrosanguinarine, was continually re-oxidized by the atmospheric oxygen back to sanguinarine, resulting in further reacting with NADH and eventually depleting all NADH molecules. The ability of sanguinarine to diminish the pool of NADH and NADPH is further considered when explaining the sanguinarine-induced apoptosis in living cells.

Copyright © 2017 Elsevier Ltd. All rights reserved.

KEYWORDS

Benzophenanthridine alkaloids; Ene adduct; Hydride transfer; LC-MS; NADH; NADH depletion; Redox cycling; Sanguinarine

Title

Sanguinarine is reduced by NADH through a covalent adduct.

Author

Sandor R1, Slanina J1, Midlik A2, Sebrlova K1, Novotna L1, Carnecka M1, Slaninova I3, Taborsky P4, Taborska E1, Pes O5.

Publish date

2018 Jan

PMID

18466423

Abstract

Sanguinarine is an alkaloid found in many medicinal plants. It has diverse biological activities, including modulation of nuclear factor-kappaB and of several enzymes. It is also known to induce apoptosis, perturb microtubules, and to have antimicrobial effects. This article reviews its cardiovascular properties, including hypotensive, antiplatelet, and positive inotropic effects. Its pharmacokinetics, and toxicology, including its carcinogenic potential, are also discussed. Further pharmacological and toxicological studies with sanguinarine are needed before its therapeutic use can be considered.

Title

Sanguinarine.

Author

Mackraj I1, Govender T, Gathiram P.

Publish date

2008 Spring