Delsoline and delcosine are two closely related naturally occurring

diterpene alkaloids Diterpene alkaloids are natural products of the terpene alkaloid type. Occurrence Veatchine is found in the bark of '' Garrya veatchii'', a member of the Cup Catkins family. Aconitine is the main alkaloid in aconite Aconite may refer to: *' ...

first isolated from '' Delphinium consolida''. They occur widely in the

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

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), commonly known by the names wolfsbane and monkshood. Aconitine is notorious for its toxic properties. Structure and rea ...

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 all 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 '' Delphinium consolida'', 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 of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...

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 Methylation, in the chemical sciences, is 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 term ...

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

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 nitro ...

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 ''Aconitum variegatum'' is a species of flowering plant belonging to the family Ranunculaceae Ranunculaceae (, buttercup or crowfoot family; Latin "little frog", from "frog") is a family (biology), family of over 2,000 known species of flowe ...

'' 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 species, native throughout the Northern Hemisphere and also on the high mountains of tropical Africa. T ...

'' 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

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 Diterpene alkaloids

History

Synthesis

Natural occurrence

Biochemistry

See also

References