Affinisine

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Affinisine

Affinisine is a chemical compound found in the Tabernaemontana genus of plants, specifically in Tabernaemontana elegans. It is a member of the indole alkaloid family of natural products, which are known for their diverse biological activities and complex structures. Affinisine is a monoterpenoid indole alkaloid, a subclass characterized by a monoterpenoid unit attached to an indole nucleus.

Chemical Structure

The chemical structure of affinisine consists of a pentacyclic system, with a quinolizidine core fused to an indole ring. The indole ring is substituted at the 3-position with a hydroxy group, and the quinolizidine core is substituted at the 1-position with a methyl group. The stereochemistry of affinisine is characterized by five stereocenters.

Biosynthesis

The biosynthesis of affinisine, like other monoterpenoid indole alkaloids, is believed to originate from the condensation of tryptamine and secologanin to form strictosidine. Strictosidine then undergoes a series of transformations involving hydrolysis, rearrangement, and cyclization to form the affinisine skeleton.

Biological Activity

Affinisine has been reported to exhibit antiplasmodial activity, suggesting potential utility in the treatment of malaria. However, further studies are needed to fully understand its mechanism of action and potential therapeutic applications.

See Also

• Tabernaemontana
• Indole alkaloid
• Monoterpenoid indole alkaloid
• Biosynthesis
• Antiplasmodial