2447-54-3 Usage
Description
Different sources of media describe the Description of 2447-54-3 differently. You can refer to the following data:
1. Sanguinarine, a DNA intercalator extracted from the bloodroot plant of the poppy family, was used by Native Americans for warts and as a blood purifier. In modern use, although banned by the FDA for its association with epidemic dropsy and other toxic effects, it has shown potential as a treatment for cancer, with modes of action including inhibition of metastasis and angiogenesis, and promotion of apoptosis. It also has anti-inflammatory, anti-oxidant, and anti-microbial properties, and several applications in veterinary medicine.
2. A naphthoisoquinoline alkaloid, this base occurs in the roots of Chelidonium majus L., Glaucium fimbrilligerum and Sanguinaria canadensis L. The alkaloid was stated by Schmidt, Konig and Tietz to crystallize from EtOH or AcOEt as colourless needles, m.p. 213°C but this low melting point was found to be due to the presence of chelerythrine as an impurity. Once this is removed as the pseudocyanide, the base crystallizes from Et20 and has the above melting point or 242-3°C on slow heating. Obtained from EtOH it forms the alcoholate, m.p. 195-7°C. The hydrochloride forms long, slender, bloodred needles. On distillation with Zn dust, the alkaloid furnishes a-naphthaphenanthridine and the structure given above has been further confirmed by synthesis.
Sources
https://en.wikipedia.org/wiki/Sanguinarine
https://pubchem.ncbi.nlm.nih.gov/compound/sanguinarine#section=Human-Metabolite-Information
https://www.essense-of-life.com/healthtopics/A-513/Sanguinarine-Health-Topic.html
https://www.caymanchem.com/product/16951
https://www.sciencedirect.com/topics/nursing-and-health-professions/sanguinarine
Uses
Sanguinarium induces HO-1 expression thus inhibiting MMP-9 and COX-2 expression in TPA-induced breast cancer cells.
Definition
Sanguinarine is a benzophenanthridine alkaloid derived from the root of Sanguinaria canadendid. Limited available evidence indicates that it may be used to prevent and treat UV-induced
skin damage. Specifically, topical application of sanguinarine on the skin of SKH-1 hairless mice before or after UVB irradiation resulted in significantly lower UVB-mediated skin edema, skin hyperplasia and
infiltration of leukocytes, and markers of oxidative stress (e.g., H2O2).
References
Dana., Mag. Pharm., 23, 125 (1829) Bruchhausen, Bersch., Ber., 63, 2520 (1930) Spath, Kuffner., ibid, 64, 370, 1123, 2034 (1931) Synthesis: Dyke, Moon, Sainsbury., Tetrahedron Lett., 3933 (1968)
Check Digit Verification of cas no
The CAS Registry Mumber 2447-54-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,4 and 7 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2447-54:
(6*2)+(5*4)+(4*4)+(3*7)+(2*5)+(1*4)=83
83 % 10 = 3
So 2447-54-3 is a valid CAS Registry Number.
InChI:InChI=1/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
2447-54-3Relevant articles and documents
One step enzymatic synthesis of dihydrosanguinarine from protopine
Tanahashi,Zenk
, p. 5625 - 5628 (1988)
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A novel C-C radical-radical coupling reaction promoted by visible light: Facile synthesis of 6-substituted: N -methyl 5,6-dihydrobenzophenanthridine alkaloids
Liu, Zhaoying,Huang, Yajun,Xie, Hongqi,Liu, Wei,Zeng, Jianguo,Cheng, Pi
, p. 50500 - 50505 (2016/06/09)
A novel photoredox-mediated direct intermolecular C-H functionalization of N-methyl 5,6-dihydrobenzophenanthridine is developed utilizing the visible light-induced reductive quenching pathway of photocatalyst Ir(ppy)3. In the proposed coupling mechanism, an α-amino C-radical is generated at the 6-position of N-methyl 5,6-dihydrobenzophenanthridine which is capable of coupling with α-EWG (electron withdrawing group) substituted C-radicals. The utility of this methodology has been demonstrated via rapid access to the analogue of natural 6-substituted N-methyl 5,6-dihydrobenzophenanthridine alkaloids.
Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis
Hagel, Jillian M.,Beaudoin, Guillaume A. W.,Fossati, Elena,Ekins, Andrew,Martin, Vincent J. J.,Facchini, Peter J.
, p. 42972 - 42983 (2013/03/13)
Benzylisoquinoline alkaloids are a diverse class of plant specialized metabolites that includes the analgesic morphine, the antimicrobials sanguinarine and berberine, and the vasodilator papaverine. The two-electron oxidation of dihydrosanguinarine catalyzed by dihydrobenzophenanthridine oxidase (DBOX) is the final step in sanguinarine biosynthesis. The formation of the fully conjugated ring system in sanguinarine is similar to the four-electron oxidations of (S)-canadine to berberine and (S)-tetrahydropapaverine to papaverine. We report the isolation and functional characterization of an opium poppy (Papaver somniferum) cDNA encoding DBOX, a flavoprotein oxidase with homology to ( S)-tetrahydroprotoberberine oxidase and the berberine bridge enzyme. A query of translated opium poppy stem transcriptome databases using berberine bridge enzyme yielded several candidate genes, including an (S)-tetrahydroprotoberberine oxidase-like sequence selected for heterologous expression in Pichia pastoris. The recombinant enzyme preferentially catalyzed the oxidation of dihydrosanguinarine to sanguinarine but also converted (RS)-tetrahydropapaverine to papaverine and several protoberberine alkaloids to oxidized forms, including (RS)-canadine to berberine. The Km values of 201 and 146 μM for dihydrosanguinarine and the protoberberine alkaloid (S)-scoulerine, respectively, suggested high concentrations of these substrates in the plant. Virus-induced gene silencing to reduce DBOX transcript levels resulted in a corresponding reduction in sanguinarine, dihydrosanguinarine, and papaverine accumulation in opium poppy roots in support of DBOX as a multifunctional oxidative enzyme in BIA metabolism.
