 | |
| Names | |
|---|---|
| IUPAC name (1α,6β,14α,16β)-20-Ethyl-4-(hydroxymethyl)-6,14,16-trimethoxyaconitane-1,7,8-triol | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| |
| |
| Properties[1] | |
| C24H39NO7 | |
| Molar mass | 453.576 g·mol−1 |
| Melting point | 168 °C (334 °F; 441 K) |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Gigactonine is a naturally occurringditerpenealkaloid first isolated fromAconitum gigas. It occurs widely in theRanunculaceae plant family. Thepolycyclic ring system of thischemical compound contains nineteen carbon atoms and one nitrogen atom, which is the same as inaconitine and this is reflected in itspreferred IUPAC name.
Gigactonine was reported in 1978 after its isolation fromAconitum gigas. Although a novel structure at that time, it was recognised to be related to known diterpene alkaloids includingdelsoline, which ismethylated on its 4-hydroxymethylprimary alcohol sidechain.[1]
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.[2]
Gigactonine has been reported as the main alkaloid in the flowers ofAconitum lycoctonum[3] and has been isolated fromDelphinium[4] includingDelphinium ajacis[5] and otherConsolida species in the Ranunculaceae plant family.[6]
Compounds related to aconitine are widely studied for their properties in biological systems and these have been reviewed.[6] For example, gigactonine has been reported to havehERG-inhibiting activity.[7]
