Delsoline and delcosine are two closely related naturally occurring

diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

s first isolated from ''

Delphinium consolida ''Consolida regalis'', known as forking larkspur, rocket-larkspur, and field larkspur, is an annual herbaceous plant belonging to the genus ''Consolida'' of the buttercup family (Ranunculaceae). Distribution ''Consolida regalis'' is native to: ...

''. They occur widely in the

Ranunculaceae Ranunculaceae (buttercup or crowfoot family; Latin "little frog", from "frog") is a family of over 2,000 known species of flowering plants in 43 genera, distributed worldwide. The largest genera are ''Ranunculus'' (600 species), ''Delphinium' ...

plant family. The polycyclic ring system containing nineteen carbon atoms and one nitrogen atom in these compounds is the same as in

aconitine Aconitine is an alkaloid toxin produced by various plant species belonging to the genus '' Aconitum'' (family Ranunculaceae), known also commonly by the names wolfsbane and monkshood. Monkshood is notorious for its toxic properties. Aconitine is ...

and this is reflected in their

preferred IUPAC name In chemical nomenclature, a preferred IUPAC name (PIN) is a unique name, assigned to a chemical substance and preferred among the possible names generated by IUPAC nomenclature. The "preferred IUPAC nomenclature" provides a set of rules for choo ...

History

Delsoline and delcosine were named in 1924 by Markwood, who isolated these alkaloids from

, but their structures were in doubt until established in 1963 and later confirmed by the

X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...

of delsoline. There are many other known diterpene alkaloids, some of which differ from these in only minor ways. Thus while delsoline (R=CH₃) is a

methylated In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These t ...

derivative of delcosine (R=H), it is also an isomeric methyl derivative of gigactonine.

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

The compounds co-occur in Aconitum variegatum and many species of

Delphinium ''Delphinium'' is a genus of about 300 species of annual and perennial flowering plants in the family (biology), family Ranunculaceae, native plant, native throughout the Northern Hemisphere and also on the high mountains of tropical Africa. Th ...

including

Delphinium ajacis ''Consolida ajacis'' (doubtful knight's spur or rocket larkspur) is an annual flowering plant of the family Ranunculaceae native to Eurasia. It is widespread in other areas, including much of North America, where it is an introduced species. It ...

and other ''

Consolida ''Consolida'' is a genus of about 40 species of annual flowering plants in the family Ranunculaceae, native to western Europe, the Mediterranean and Asia. Phylogenetic studies show that ''Consolida'' is actually an annual clade nested within the ...

'' 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, delsoline has been reported be one of the active components in traditional Chinese medicinal plants.

References

{{reflist

History

Synthesis

Natural occurrence

Biochemistry

References

See also