Chanoclavine II

Chanoclavine II

Chanoclavine II is a type of ergoline alkaloid that is found in various species of fungi, including those in the Claviceps genus. It is one of the many compounds that are derived from the amino acid tryptophan.

Chemistry

Chanoclavine II is a tetracyclic compound that is part of the larger ergoline family of alkaloids. It is structurally similar to other ergolines, with the main difference being the presence of a double bond between the 9 and 10 positions of the ergoline ring system. This double bond is not present in other ergolines, such as ergotamine and lysergic acid.

Biosynthesis

The biosynthesis of Chanoclavine II involves several steps. The first step is the condensation of tryptophan and dimethylallyl pyrophosphate (DMAPP) to form 4-dimethylallyltryptophan (4-DMAT). This reaction is catalyzed by the enzyme dimethylallyltryptophan synthase (DMATS). The 4-DMAT is then converted to Chanoclavine I aldehyde by the enzymes chanoclavine-I dehydrogenase and chanoclavine-I synthase. Finally, the Chanoclavine I aldehyde is converted to Chanoclavine II by the enzyme chanoclavine-II synthase.

Biological Activity

The biological activity of Chanoclavine II is not well-studied. However, it is known that it has a high affinity for serotonin receptors, similar to other ergoline alkaloids. This suggests that it may have psychoactive properties, although this has not been confirmed in humans.

See Also

• Ergoline
• Claviceps
• Tryptophan
• Ergotamine
• Lysergic acid