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
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.
29761161
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.
Anti-virulence; Natural compound; Salmonella; Sanguinarine chloride; Type III secretion
Natural compound sanguinarine chloride targets the type III secretion system of Salmonella enterica Serovar Typhimurium.
Zhang Y1,2, Liu Y2, Wang T2, Deng X1,2, Chu X1.
2018 May 9
29107809
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.
Benzophenanthridine alkaloids; Ene adduct; Hydride transfer; LC-MS; NADH; NADH depletion; Redox cycling; Sanguinarine
Sanguinarine is reduced by NADH through a covalent adduct.
Sandor R1, Slanina J1, Midlik A2, Sebrlova K1, Novotna L1, Carnecka M1, Slaninova I3, Taborsky P4, Taborska E1, Pes O5.
2018 Jan
18466423
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.
Sanguinarine.
Mackraj I1, Govender T, Gathiram P.
2008 Spring
