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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
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Preferred IUPAC name
Methyl (19E)-3-oxovobasan-17-oate | |
Identifiers | |
3D model (
JSmol)
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ChEBI | |
ChemSpider | |
KEGG | |
PubChem
CID
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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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Vobasine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata. [1]
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]
As with other Indole alkaloids, the biosynthesis of vobasine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration. [8]
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]
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]
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.
Very high dose of vobasine at around 300 mg/kg may cause death through CNS and respiratory depression. [19]
![]() | |
Names | |
---|---|
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)
|
|
ChEBI | |
ChemSpider | |
KEGG | |
PubChem
CID
|
|
| |
| |
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).
|
Vobasine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata. [1]
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]
As with other Indole alkaloids, the biosynthesis of vobasine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration. [8]
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]
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]
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.
Very high dose of vobasine at around 300 mg/kg may cause death through CNS and respiratory depression. [19]