Vobasine
Chemical compound
From Wikipedia, the free encyclopedia
Vobasine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.[1]
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| Names | |
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| IUPAC name
Methyl (1S,14R,15E,18S)-15-ethylidene-17-methyl-12-oxo-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraene-18-carboxylate | |
| Preferred IUPAC name
Methyl (19E)-3-oxovobasan-17-oate | |
| Identifiers | |
3D model (JSmol) |
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| Properties | |
| C21H24N2O3 | |
| Molar mass | 352.434 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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]
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]