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

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

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

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

• Berberine
• Benzylisoquinoline
• Alkaloid

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