(''S'')-Canadine, also known as (''S'')-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

(BIA), of the protoberberine structural subgroup, and is present in many plants from the family

Papaveraceae The Papaveraceae are an economically important family of about 42 genera and approximately 775 known species of flowering plants in the order Ranunculales, informally known as the poppy family. The family is cosmopolitan, occurring in temperat ...

, such as '' Corydalis yanhusuo'' and '' C. turtschaninovii''.

Biosynthesis

Metabolically, (''S'')-canadine is derived from (''S'')-

reticuline Reticuline is a chemical compound found in a variety of plants including ''Lindera aggregata'', ''Annona squamosa'', and ''Ocotea fasciculata'' (also known as ''Ocotea duckei''). It is based on the benzylisoquinoline structure. Reticuline is one ...

, 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. (''S'')-Canadine is the immediate metabolic precursor of

berberine Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids found in such plants as ''Berberis vulgaris'' (barberry), '' Berberis aristata'' (tree turmeric), '' Mahonia aquifolium'' (Oregon grape), '' Hyd ...

, which is obtained through the action of the enzyme (''S'')-tetrahydroprotoberberine oxidase. It is also an intermediate in the complex biosynthesis of

noscapine Noscapine (also known as Narcotine, Nectodon, Nospen, Anarcotine and (archaic) Opiane) is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae ( ...

, which is likewise a benzylisoquinoline

, but of the phthalideisoquinoline structural subgroup. (''S'')-Canadine, berberine, palmatine, and

hydrastine Hydrastine is an isoquinoline alkaloid which was discovered in 1851 by Alfred P. Durand. Hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug during the 1910s. It is present in ''Hydrastis canadensis'' ...

are the major alkaloids present in

goldenseal ''For the magazine from West Virginia see Goldenseal (magazine)'' Goldenseal (''Hydrastis canadensis''), also called orangeroot or yellow puccoon, is a perennial herb in the buttercup family Ranunculaceae, native to North America. It may be di ...

Effects

A number of ''

in vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology ...

'' effects of (''S'')-canadine have been reported. It stimulates

myogenesis Myogenesis is the formation of skeletal muscular tissue, particularly during embryonic development. Muscle fibers generally form through the fusion of precursor myoblasts into multinucleated fibers called ''myotubes''. In the early development o ...

and inhibits muscle protein degradation. (''S'')-Canadine blocks K(ATP) channels in dopamine neurons. (''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. (''S'')-Canadine can block voltage-dependent calcium channels, but at a level significantly lower than that of

verapamil Verapamil, sold under various trade names, is a calcium channel blocker medication used for the treatment of high blood pressure, angina (chest pain from not enough blood flow to the heart), and supraventricular tachycardia. It may also be ...

References

{{Calcium channel blockers Calcium channel blockers Benzodioxoles Benzylisoquinoline alkaloids