Vobasine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.
History
Vobasine was first reported by Renner in 1959 after its isolation from
Voacanga africana.
The two structurally related compounds,
dregamine and tabernaemontanine, where its
alkene (=CHCH
3) sidechain was
redox to
in two configurations, had their relationship confirmed in the 1970s.
Vobasine has been found in many plants of the dogbane (
Apocynaceae) family including
Tabernaemontana dichotoma.
Synthesis
Biosynthesis
As with other
Indole alkaloids, the biosynthesis of vobasine starts from the
amino acid tryptophan. This is converted into
strictosidine 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 Tabernaemontana and
Voacanga, including the species
Ervatamia hirta,
Tabernaemontana elegans,
and
Voacanga africana.
Biochemistry
Plant
have been of interest for their possible biological activity and alkaloids in particular are major subjects for
ethnobotanical research.
Vobasine has been studied, for example as a potential anti-cancer agent
and for its
hypotensive 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.
See also
Further reading
