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Canadine

From Wikipedia, the free encyclopedia
Canadine
Names
IUPAC name
9,10-Dimethoxy-2′H-[1,3]dioxolo[4′,5′:2,3]berbine
Systematic IUPAC name
(13aS)-9,10-Dimethoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline
Other names
(S)-Tetrahydroberberine; Xanthopuccine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.023.468Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3/t16-/m0/s1
    Key: VZTUIEROBZXUFA-INIZCTEOSA-N
  • O1c2c(OC1)cc3c(c2)CCN5[C@H]3Cc4ccc(OC)c(OC)c4C5
Properties
C20H21NO4
Molar mass339.391 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

(S)-Canadine, also known as(S)-tetrahydroberberine andxanthopuccine, is abenzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the familyPapaveraceae, such asCorydalis yanhusuo andC. turtschaninovii.

Biosynthesis

[edit]

Metabolically, (S)-canadine is derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIA structural subgroups, through three enzymatic steps: 1)Berberine bridge enzyme to(S)-scoulerine; 2)(S)-scoulerine 9-O-methyltransferase to (S)-tetrahydrocolumbamine; and 3)(S)-canadine synthase/CYP719A21 to (S)-canadine.[1]

(S)-Canadine is the immediate metabolic precursor of berberine, which is produced through the action of the enzymetetrahydroberberine oxidase.[1]

2D representation of the chemical structure of canadine .
+H+
 
 
2 O2
2 H2O2
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
2 O2
2 H2O2
 
2D representation of the chemical structure of berberine .

It is also an intermediate in the biosynthesis ofnoscapine, which is likewise abenzylisoquinolinealkaloid, but of the phthalideisoquinoline structural subgroup.[2][3]

(S)-Canadine, berberine,palmatine, andhydrastine are the major alkaloids present ingoldenseal.

Effects

[edit]

A number ofin vitro effects of (S)-canadine have been reported. It stimulatesmyogenesis and inhibits muscle protein degradation.[4] (S)-Canadine blocksK(ATP) channels indopamine neurons.[5][6] (S)-Canadine has displayed antioxidant activity: though it lacked any demonstrable cytotoxic effect in three unique cell cultures, it was observed to possess antioxidant activity against free radical-induced oxidative injury.[7][8] (S)-Canadine can block voltage-dependentcalcium channels, but at a level significantly lower than that ofverapamil.[9]

CPU 86017

[edit]
CPU 86017 [149088-32-4]

Canadine is also used in the synthesis ofCPU 86017 (a novel Class III antiarrhythmic agent with multiple actions at ion channels).[10]

References

[edit]
  1. ^abHagel, Jillian M.; Morris, Jeremy S.; Lee, Eun-Jeong; Desgagne-Penix, Isabel; Bross, Crystal D.; Chang, Limei; Chen, Xue; Farrow, Scott C.; Zhang, Ye (2015)."Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants".BMC Plant Biology.15 (1): 227.Bibcode:2015BMCPB..15..227H.doi:10.1186/s12870-015-0596-0.PMC 4575454.PMID 26384972.
  2. ^Dang, Thu-Thuy T.; Facchini, Peter J. (2014)."CYP82Y1 is N-Methylcanadine 1-Hydroxylase, a Key Noscapine Biosynthetic Enzyme in Opium Poppy"(PDF).The Journal of Biological Chemistry.289 (4):2013–2026.doi:10.1074/jbc.M113.505099.PMC 3900951.PMID 24324259.
  3. ^Chen, Xue; Facchini, Peter J. (2014)."Short-chain dehydrogenase/reductase catalyzing the final step of noscapine biosynthesis is localized to laticifers in opium poppy".The Plant Journal.77 (2):173–184.Bibcode:2014PlJ....77..173C.doi:10.1111/tpj.12379.PMID 24708518.
  4. ^Lee, Hyejin; Lee, Sang-Jin; Bae, Gyu-Un; Baek, Nam-In; Ryu, Jae-Ha (2017)."Canadine from Corydalis turtschaninovii Stimulates Myoblast Differentiation and Protects against Myotube Atrophy".International Journal of Molecular Sciences.18 (12): 2748.doi:10.3390/ijms18122748.PMC 5751347.PMID 29258243.
  5. ^Wu, Chen; Yang, Kechun; Liu, Qiang; Wakui, Matoko; Jin, Guo-zhang; Zhen, Xuechu; Wu, Jie (2010). "Tetrahydroberberine blocks ATP-sensitive potassium channels in dopamine neurons acutely-dissociated from rat substantia nigra pars compacta".Neuropharmacology.59 (7–8):567–72.doi:10.1016/j.neuropharm.2010.08.018.PMID 20804776.S2CID 27386799.
  6. ^Wu, Jie; Jin, Guo Zhang (1997). "Tetrahydroberberine blocks membrane K+ channels underlying its inhibition of intracellular message-mediated outward currents in acutely dissociated CA1 neurons from rat hippocampus".Brain Research.775 (1–2):214–8.doi:10.1016/s0006-8993(97)00960-8.PMID 9439847.S2CID 42250453.
  7. ^Correché, Estela R.; Andujar, Sebastian A.; Kurdelas, Rita R.; Lechón, María J. Gómez; Freile, Mónica L.; Enriz, Ricardo D. (2008). "Antioxidant and cytotoxic activities of canadine: Biological effects and structural aspects".Bioorganic & Medicinal Chemistry.16 (7):3641–51.doi:10.1016/j.bmc.2008.02.015.PMID 18295494.
  8. ^Mari, Giacomo; Catalani, Simona; Antonini, Elena; De Crescentini, Lucia; Mantellini, Fabio; Santeusanio, Stefania; Lombardi, Paolo; Amicucci, Antonella; Battistelli, Serafina (2018). "Synthesis and biological evaluation of novel heteroring-annulated pyrrolino-tetrahydroberberine analogues as antioxidant agents".Bioorganic & Medicinal Chemistry.26 (18):5037–44.doi:10.1016/j.bmc.2018.08.038.PMID 30196978.S2CID 52177815.
  9. ^Yang, S; Miao, Y.S.; Han, Q; Jiang, M.H.; Jin, G.Z. (1993)."Effects of (-)-stepholidine and tetrahydroberberine on high potassium-evoked contraction and calcium influx in rat artery".Zhongguo Yao Li Xue Bao.14 (3):235–7.PMID 8237399.
  10. ^Dai, De-Zai (2006). "CPU86017: a novel Class III antiarrhythmic agent with multiple actions at ion channels".Cardiovascular Drug Reviews.24 (2):101–115.doi:10.1111/j.1527-3466.2006.00101.x.ISSN 0897-5957.PMID 16961724.
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
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