Canadine Explained

(S)-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]

(S)-Canadine is the immediate metabolic precursor of berberine, which is obtained through the action of the enzyme (S)-tetrahydroprotoberberine oxidase. It is also an intermediate in the complex 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.

Effects

A number of in vitro effects of (S)-canadine have been reported. It stimulates myogenesis and inhibits muscle protein degradation.[4] (S)-Canadine blocks K(ATP) channels in dopamine 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-dependent calcium channels, but at a level significantly lower than that of verapamil.[9]

Notes and References

  1. 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. 227. 10.1186/s12870-015-0596-0. 26384972. 4575454 . free .
  2. Dang. Thu-Thuy T.. Facchini. Peter J.. 2014. CYP82Y1 is N-Methylcanadine 1-Hydroxylase, a Key Noscapine Biosynthetic Enzyme in Opium Poppy. The Journal of Biological Chemistry. 289. 4. 2013–2026. 10.1074/jbc.M113.505099. 24324259. 3900951. free.
  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. 10.1111/tpj.12379. 24708518. free.
  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. 10.3390/ijms18122748. 29258243. 5751347. free.
  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. 10.1016/j.neuropharm.2010.08.018. 20804776. 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. 10.1016/s0006-8993(97)00960-8. 9439847. 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. 10.1016/j.bmc.2008.02.015. 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. 10.1016/j.bmc.2018.08.038. 30196978. 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. 8237399.

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