Canadine

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Canadine
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(S)-(-)-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
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3D model (JSmol)
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  • 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 mass 339.391 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.

Biosynthesis

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]

Metabolism

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

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It is also an intermediate in the biosynthesis of noscapine, which is likewise a benzylisoquinoline alkaloid, but of the phthalideisoquinoline structural subgroup.[2][3]

(S)-Canadine, berberine, palmatine, and hydrastine are the major alkaloids present in goldenseal.[4] In Corydalis cava, the enzyme berberine reductase converts berberine back to canadine but as the (R) enantiomer of the product.[5]

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This type of inversion of stereochemistry allows both enantiomers of some alkaloids to be present in this species.[6]

The enzyme (S)-tetrahydroprotoberberine N-methyltransferase characterised from Eschscholtzia californica converts (S)-canadine to (S)-cis-N-methylcanadine. The methyl group comes from the cofactor, S-adenosyl methionine (SAM).[7]

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Effects

A number of in vitro effects of (S)-canadine have been reported. It stimulates myogenesis and inhibits muscle protein degradation.[8] (S)-Canadine blocks K(ATP) channels in dopamine neurons.[9][10] (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.[11][12] (S)-Canadine can block voltage-dependent calcium channels, but at a level significantly lower than that of verapamil.[13]

CPU 86017

File:CPU 86017.svg
CPU 86017 [149088-32-4]

Canadine is also used in the synthesis of CPU 86017 (a novel Class III antiarrhythmic agent with multiple actions at ion channels).[14]

References

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  1. ^ a b Page Module:Citation/CS1/styles.css has no content.Hagel, 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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.Weber HA, Zart MK, Hodges AE, et al. (December 2003). "Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers". Journal of Agricultural and Food Chemistry. 51 (25): 7352–8. Bibcode:2003JAFC...51.7352W. doi:10.1021/jf034339r. PMID 14640583.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Bauer W, Zenk MH (1991). "Formation of (R)-configurated tetrahydroprotoberberine alkaloids in vivo and in vitro". Tetrahedron Lett. 32 (4): 487–490. doi:10.1016/S0040-4039(00)79475-5.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Bitchagno, Gabin Thierry M.; Nchiozem-Ngnitedem, Vaderament-A.; Melchert, Dennis; Fobofou, Serge Alain (2022). "Demystifying racemic natural products in the homochiral world". Nature Reviews Chemistry. 6 (11): 806–822. doi:10.1038/s41570-022-00431-4. PMC 9562063.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Rueffer M, Zumstein G, Zenk MH (1990). "Partial purification and characterization of S-adenosyl-L-methionine:(S)-tetrahydroprotoberberine cis-N-methyltransferase from suspension-cultured cells of Eschscholtzia and Corydalis" (PDF). Phytochemistry. 29 (12): 3727–3733. doi:10.1016/0031-9422(90)85321-6.
  8. ^ Page Module:Citation/CS1/styles.css has no content.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.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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.
  10. ^ Page Module:Citation/CS1/styles.css has no content.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.
  11. ^ Page Module:Citation/CS1/styles.css has no content.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.
  12. ^ Page Module:Citation/CS1/styles.css has no content.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.
  13. ^ Page Module:Citation/CS1/styles.css has no content.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.
  14. ^ Page Module:Citation/CS1/styles.css has no content.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.

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