Canadine: Difference between revisions

Latest revision as of 10:46, 15 February 2025

Overview[edit]

Canadine is an isoquinoline alkaloid found in several plant species, most notably in the Berberis genus. It is a secondary metabolite that plays a role in the plant's defense mechanisms against herbivores and pathogens. Canadine is chemically related to other alkaloids such as berberine and palmatine.

Chemical Structure[edit]

Canadine is characterized by its isoquinoline structure, which is a common feature among alkaloids in the Berberidaceae family. The chemical structure of canadine includes a tetracyclic ring system with methoxy groups that contribute to its biological activity.

Biological Activity[edit]

Canadine exhibits a range of biological activities, including antimicrobial, anti-inflammatory, and potential anticancer properties. These activities are attributed to its ability to interact with various biological targets, including enzymes and receptors involved in cellular processes.

Sources[edit]

Canadine is primarily extracted from plants in the Berberis genus, such as Berberis vulgaris (common barberry) and Berberis aquifolium (Oregon grape). These plants have been used in traditional medicine for their therapeutic properties, which are partly due to the presence of canadine and other alkaloids.

Pharmacology[edit]

The pharmacological effects of canadine are being studied for their potential therapeutic applications. Its antimicrobial properties make it a candidate for treating infections, while its anti-inflammatory effects could be beneficial in managing inflammatory conditions.

Related Compounds[edit]

Canadine is structurally and functionally related to other isoquinoline alkaloids such as:

These compounds share similar biosynthetic pathways and biological activities.

Related Pages[edit]

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-'''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]].
+{{DISPLAYTITLE:Canadine}}
-== Biosynthesis ==
+== Overview ==
-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.
+[[File:Canadine_structure.svg|thumb|right|Chemical structure of Canadine]]
+'''Canadine''' is an isoquinoline alkaloid found in several plant species, most notably in the [[Berberis]] genus. It is a secondary metabolite that plays a role in the plant's defense mechanisms against herbivores and pathogens. Canadine is chemically related to other alkaloids such as [[berberine]] and [[palmatine]].
-== Occurrence ==
+== Chemical Structure ==
-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).
+Canadine is characterized by its isoquinoline structure, which is a common feature among alkaloids in the Berberidaceae family. The chemical structure of canadine includes a tetracyclic ring system with methoxy groups that contribute to its biological activity.
+== Biological Activity ==
+Canadine exhibits a range of biological activities, including antimicrobial, anti-inflammatory, and potential anticancer properties. These activities are attributed to its ability to interact with various biological targets, including enzymes and receptors involved in cellular processes.
+== Sources ==
+Canadine is primarily extracted from plants in the Berberis genus, such as [[Berberis vulgaris]] (common barberry) and [[Berberis aquifolium]] (Oregon grape). These plants have been used in traditional medicine for their therapeutic properties, which are partly due to the presence of canadine and other alkaloids.
 == 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.
+The pharmacological effects of canadine are being studied for their potential therapeutic applications. Its antimicrobial properties make it a candidate for treating infections, while its anti-inflammatory effects could be beneficial in managing inflammatory conditions.
-== See also ==
+== Related Compounds ==
+Canadine is structurally and functionally related to other isoquinoline alkaloids such as:
 * [[Berberine]]
-* [[Benzylisoquinoline]]
+* [[Palmatine]]
+* [[Jatrorrhizine]]
+These compounds share similar biosynthetic pathways and biological activities.
+== Related Pages ==
 * [[Alkaloid]]
+* [[Isoquinoline]]
+* [[Berberis]]
+* [[Traditional medicine]]
 [[Category:Alkaloids]]
-[[Category:Benzylisoquinoline alkaloids]]
+[[Category:Isoquinoline alkaloids]]
 [[Category:Phytochemicals]]
-{{stub}}
-{{No image}}