Peganine (Figure 107) is a quinazoline alkaloid
found in Peganum harmala (Zygophyllaceae),
where it co-occurs with the β-carboline alkaloid
harmine. It is also responsible for
the bronchodilator activity of Justicia adhatoda(Adhatoda vasica) (Acanthaceae), a plant used
in the treatment of respiratory ailments. As a
result, the alternative name vasicine is also sometimes
used for peganine. Studies in Peganum harmalahave clearly demonstrated peganine to be
derived from anthranilic acid, the remaining part
of the structure being a pyrrolidine ring supplied
by ornithine (compare Figure 1, page 292). The
peganine skeleton is readily rationalized as a result
of nucleophilic attack from the anthranilate nitrogen
on to the pyrrolinium cation, followed by
amide formation (Figure 107). Remarkably, this pathway is not operative in Justicia adhatoda, and a much less predictable sequence from Nacetylanthranilic acid and aspartic acid is observed (Figure 107). |
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