Gigactonine

Gigactonine is a naturally occurring diterpene alkaloid first isolated from Aconitum gigas. It occurs widely in the Ranunculaceae plant family. The polycyclic ring system of this chemical compound contains nineteen carbon atoms and one nitrogen atom, which is the same as in aconitine and this is reflected in its preferred IUPAC name.

History
Gigactonine was reported in 1978 after its isolation from Aconitum gigas. Although a novel structure at that time, it was recognised to be related to known diterpene alkaloids including delsoline, which is methylated on its 4-hydroxymethyl primary alcohol sidechain.

Synthesis
Although individual members of this class of alkaloids have been extensively studied, their chemical complexity has limited the number which have been individually synthesised. Similarly, their full biosynthetic pathway is only known in outline in most cases.

Natural occurrence
Gigactonine has been reported as the main alkaloid in the flowers of Aconitum lycoctonum and has been isolated from Delphinium including Delphinium ajacis and other Consolida species in the Ranunculaceae plant family.

Biochemistry
Compounds related to aconitine are widely studied for their properties in biological systems and these have been reviewed. For example, gigactonine has been reported to have hERG-inhibiting activity.