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Vobasine
Chemical compound From Wikipedia, the free encyclopedia
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Vobasine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.[1]
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History
Vobasine was first reported by Renner in 1959 after its isolation from Voacanga africana.[2] The two structurally related compounds, dregamine and tabernaemontanine, where its alkene (=CHCH3) sidechain was reduced to ethyl groups in two configurations, had their relationship confirmed in the 1970s.[3][4][5] Vobasine has been found in many plants of the dogbane (Apocynaceae) family including Tabernaemontana dichotoma.[6][7]
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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.[8]
Chemical synthesis
The synthesis of alkaloids with the same carbon skeleton as vobasine began in the 1960s[9] and has continued, with some work providing enantiospecific approaches to closely related compounds.[10]
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Natural occurrence
Vobasine is found commonly in the genera Tabernaemontana and Voacanga, including the species Ervatamia hirta,[11] Tabernaemontana elegans,[12] Tabernaemontana divaricata[13][14] and Voacanga africana.[2]
Biochemistry
Plant metabolites have been of interest for their possible biological activity and alkaloids in particular are major subjects for ethnobotanical research.[15][16] Vobasine has been studied, for example as a potential anti-cancer agent[17] and for its hypotensive activity.[18] 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.[19]
See also
References
Further reading
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