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

alkaloid Alkaloids are a class of basic BASIC (Beginners' All-purpose Symbolic Instruction Code) is a family of general-purpose, high-level programming languages designed for ease of use. The original version was created by John G. Kemeny and Th ...

(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 tempera ...

, such as ''

Corydalis yanhusuo ''Corydalis yanhusuo'' is a plant species in the genus ''Corydalis''. The Chinese name for ''Corydalis yanhusuo'' is ''yan hu suo'' (). The Japanese common name is engosaku (エンゴサク) and the Korean common name is hyeonhosaek (현호색). ...

'' 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 o ...

, a pivotal intermediate in the biosynthesis of numerous BIA structural subgroups, through three enzymatic steps: 1)

Berberine bridge enzyme 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), ''Hydras ...

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, 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

, but of the phthalideisoquinoline structural subgroup. (''S'')-Canadine, berberine, palmatine, and hydrastine are the major alkaloids present in goldenseal.

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 and ...

'' 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 ...

and inhibits muscle protein degradation. (''S'')-Canadine blocks K(ATP) channels in

dopamine neurons Dopaminergic pathways (dopamine pathways, dopaminergic projections) in the human brain are involved in both physiological and behavioral processes including movement, cognition, executive functions, reward, motivation, and neuroendocrine control. ...

. (''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 A calcium channel is an ion channel which shows selective permeability to calcium ions. It is sometimes synonymous with voltage-gated calcium channel, although there are also ligand-gated calcium channels. Comparison tables The following tables ex ...

, 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