Vobasine is a naturally occurring

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 func ...

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 differ ...

found in several species in the

genus Genus (; : genera ) is a taxonomic rank above species and below family (taxonomy), family as used in the biological classification of extant taxon, living and fossil organisms as well as Virus classification#ICTV classification, viruses. In bino ...

Tabernaemontana ''Tabernaemontana'' is a genus of flowering plants in the family Apocynaceae. It has a pan-tropical distribution, found in Asia, Africa, Australia, North America, South America, and islands of the Indian and Pacific Oceans. These plants are everg ...

'' including ''

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 ...

''.

History

Vobasine was first reported by Renner in 1959 after its isolation from ''

Voacanga africana ''Voacanga'' is a genus of plants in the family Apocynaceae found in Africa, Southeast Asia, New Guinea, and Australia. the World Checklist of Selected Plant Families recognises 13 species:Search for "Voacanga", ;Species # ''Voacanga africana' ...

''. The two structurally related compounds, dregamine and tabernaemontanine, where its

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

(=CHCH₃) sidechain was

reduced Reduction, reduced, or reduce may refer to: Science and technology Chemistry * Reduction (chemistry), part of a reduction-oxidation (redox) reaction in which atoms have their oxidation state changed. ** Organic redox reaction, a redox reacti ...

ethyl group In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry The International Union of Pure and Applied ...

s in two configurations, had their relationship confirmed in the 1970s. Vobasine has been found in many plants of the dogbane (

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. Notable mem ...

) family including '' Tabernaemontana dichotoma''.

Synthesis

Biosynthesis

As with other

Indole alkaloids Indole alkaloids are a class of alkaloids containing a Moiety (chemistry), structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than ...

, the biosynthesis of vobasine starts from the

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...

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 aromat ...

. This is converted into

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. ...

before further elaboration.

Chemical synthesis

The synthesis of alkaloids with the same carbon skeleton as vobasine began in the 1960s and has continued, with some work providing enantiospecific approaches to closely related compounds.

Natural occurrence

Vobasine is found commonly in the

genera Genus (; : genera ) is a taxonomic rank above species and below family as used in the biological classification of living and fossil organisms as well as viruses. In binomial nomenclature, the genus name forms the first part of the binomial s ...

'' and ''

Voacanga ''Voacanga'' is a genus of plants in the family Apocynaceae found in Africa, Southeast Asia, New Guinea, and Australia. the World Checklist of Selected Plant Families recognises 13 species:Search for "Voacanga", ;Species # ''Voacanga africana' ...

'', including the species '' Ervatamia hirta'',

Tabernaemontana elegans ''Tabernaemontana elegans'', the toad tree, is a shrub or small tree in the family Apocynaceae. It is native to eastern Africa. Description ''Tabernaemontana elegans'' grows up to tall, with a trunk diameter of up to . Its fragrant flowers feat ...

, ''

'' and ''Voacanga africana''.

Biochemistry

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 been of interest for their possible

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 an interdisciplinary field at the interface of natural and social sciences that studies the relationships between humans and plants. It focuses on traditional knowledge of how plants are used, managed, and perceived in human societi ...

research. Vobasine has been studied, for example as a potential anti-cancer agent and for its

hypotensive Hypotension, also known as low blood pressure, is a cardiovascular condition characterized by abnormally reduced blood pressure. Blood pressure is the force of blood pushing against the walls of the arteries as the heart pumps out blood and is ...

activity. However, the alkaloid itself has not been developed as a drug.

Toxicity

Very high dose of vobasine at around 300 mg/kg may cause death through CNS and respiratory depression.