Vinervine is a

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...

indole alkaloid Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known differe ...

of the

Vinca ''Vinca'' (; Latin: ''vincire'' "to bind, fetter") is a genus of flowering plants in the family Apocynaceae, native to Europe, northwest Africa and southwest Asia. The English name periwinkle is shared with the related genus ''Catharanthus'' (an ...

sub-group. It is a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

akuammicine Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including ''Picralima nitida'', ''Vinca minor'' and the ''Aspidosperma''. History The alkaloids are a large group of natural pr ...

, with one additional hydroxy (OH) group in the indole portion, hence it is also known as 12-hydroxyakuammicine.

History

The

alkaloids 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 st ...

are a large group of

natural products A natural product is a natural Chemical compound, compound or chemical substance, substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural product ...

which are classified according to the part-structure which members of a particular group contain. Vinervine is a monoterpene indole alkaloid of the Vinca sub-group which shares a common

biosynthesis Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules. ...

with other members, namely that they are derived from

strictosidine Strictosidine is a natural chemical compound and is classified as a glucoalkaloid and a vinca alkaloid. It is formed by the Pictet–Spengler condensation reaction of tryptamine with secologanin, catalyzed by the enzyme strictosidine synthase. ...

. It was first characterised in 1964 and the structures of closely related materials including akuammicine were confirmed in 1983.

Natural occurrence

Vinervine is found in a variety of plants of the

Apocynaceae Apocynaceae (from ''Apocynum'', Greek for "dog-away") is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison Members of the ...

family, including ''

Vinca erecta ''Vinca'' (; Latin: ''vincire'' "to bind, fetter") is a genus of flowering plants in the family Apocynaceae, native to Europe, northwest Africa and southwest Asia. The English name periwinkle is shared with the related genus ''Catharanthus'' (an ...

'', ''

Tabernaemontana divaricata ''Tabernaemontana divaricata'', commonly called pinwheel flower, crape jasmine, East India rosebay, and Nero's crown, is an evergreen shrub or small tree native to South Asia, Southeast Asia and China. In zones where it is not hardy it is grown a ...

'' and several other flowering plants species that are native to Africa, Asia, and Europe.

Biosynthesis

As with other indole alkaloids, the biosynthesis of vinervine starts from the

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha am ...

tryptophan Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α- carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic ...

. This is converted into strictosidine before further elaboration.

Research

Plant

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

s have long been studied for their

biological activity In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or ...

and alkaloids in particular are major subjects for

ethnobotanical Ethnobotany is the study of a region's plants and their practical uses through the traditional knowledge of a local culture and people. An ethnobotanist thus strives to document the local customs involving the practical uses of local flora for m ...

research. However, vinervine has had little reported utility.

History

Natural occurrence

Biosynthesis

Research

See also

References

Further reading