Canadine

Canadine is a benzylisoquinoline alkaloid. It is a structural isomer of berberine and is often found in plants alongside it. Canadine is a precursor in the biosynthesis of berberine.

Biosynthesis[edit | edit source]

The biosynthesis of canadine begins with the condensation of dopamine and 4-hydroxyphenylacetaldehyde (4-HPAA) to form (S)-norcoclaurine. This is followed by a series of methylation, hydroxylation, and methylenedioxy bridge formation to form (S)-reticuline. (S)-reticuline is then converted to (S)-scoulerine by the enzyme berberine bridge enzyme (BBE). (S)-scoulerine is then converted to (S)-tetrahydrocolumbamine by the enzyme tetrahydroprotoberberine cis-N-methyltransferase (TNMT). Finally, (S)-tetrahydrocolumbamine is converted to canadine by the enzyme cytochrome P450 enzyme CYP719A21.

Occurrence[edit | edit source]

Canadine is found in a variety of plants including Hydrastis canadensis (goldenseal), Coptis chinensis (Chinese goldthread), Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Argemone mexicana (Mexican prickly poppy), and Eschscholzia californica (California poppy).

Pharmacology[edit | edit source]

The pharmacological effects of canadine are not well studied. However, it is known to have anti-inflammatory and anti-tumor properties. It has also been shown to inhibit the growth of Staphylococcus aureus and Escherichia coli in vitro.

See also[edit | edit source]

Canadine Resources
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