3621-36-1

Basic information

• Product Name: columbamine
• Synonyms: 5,6-Dihydro-2-hydroxy-3,9,10-trimethoxydibenzo[a,g]quinolizinium;5,6-Dihydro-3,9,10-trimethoxydibenzo[a,g]quinolizinium-2-ol;Dehydroisocorypalmine
• CAS NO: 3621-36-1
• Molecular Formula: C₂₀H₂₀NO₄
• Molecular Weight: 0
• Mol File: 3621-36-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 280-282℃ (methanol )
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: columbamine(CAS DataBase Reference)
• NIST Chemistry Reference: columbamine(3621-36-1)
• EPA Substance Registry System: columbamine(3621-36-1)

Safety Data

• Hazardous Substances Data: 3621-36-1(Hazardous Substances Data)

Usage

General Description

Columbamine is a chemical compound found in several plant species, including the stem of the Magnolia and Tinospora cordifolia. It possesses various biological activities, including anti-inflammatory, antioxidant, and anti-cancer properties. Columbamine has been used in traditional medicine to treat various ailments, such as fever, diarrhea, and gastrointestinal disorders. Its potential as a therapeutic agent has also been investigated in modern research, showing promise in the treatment of inflammatory diseases and certain types of cancer. Additionally, columbamine has been studied for its ability to modulate the immune system and protect against oxidative stress, making it a compound of interest in the development of new pharmaceuticals and nutraceuticals.

InChI:InChI=1/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1

Upstream product

• 6487-33-8 (-)-isocorypalmine 
• 483-34-1 isocorypalmine 
• 485-19-8 (+)-(S)-reticuline 
• 605-34-5 (S)-scoulerine 

Downstream Products

• 483-34-1 isocorypalmine 

Relevant articles and documents

BERBERINE SYNTHASE, THE METHYLENEDIOXY GROUP FORMING ENZYME IN BERBERINE SYNTHESIS

An Fe(2+) containing enzyme responsible for the formation of the methylenedioxy group in berberine was discovered, purified to homogeneity and characterized; it acts on columbamine as a substrate rather than on (S)-tetrahydrocolumbamine as previously assumed.

Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis

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.