Elaeagnine-obtained from the bark of Elaeagnus angustifolia

D. Elaeagnine


Biological Source It is obtained from the bark of Elaeagnus angustifolia Linn., (Synonyms: E. hortensis Bieb.) (Elaeagnaceae).
Chemical Structure

Elaeagnine
Biosynthesis of Elaeagnine, Harman, Harmaline and Harmine The various steps involved in the biosynthesis of the above mentioned four alkaloids are briefly summarized as under:
1. Tryptamine and acetyl carboxylic acid (i.e., keto acid) undergoes a Mannich-like reaction to yield a β-carboline carboxylic acid, which on oxidative decarboxylation gives rise to 1-methyl β-carboline.
2. The resulting product on subsequent reduction gives rise to the alkaloid elaeagnine.
3. The 1-methyl β-carboline upon mild oxidation yields the alkaloids harman with the elimination of a mole of water from the 6-membered heterocyclic nucleus.
4. The 1-methyl β-carboline upon hydroxylation followed by methylation produces harmaline.
5. Harmaline on further oxidation generates harmine by the loss of a mole of water from the 6-membered pyridine ring at C-3 and C-4 positions.
The these steps are sequentially arranged in the following course of reactions:

Biosynthesis of Elaeagnine, Harman, Harmaline and Harmine

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