 | |
| Names | |
|---|---|
| IUPAC name Methyl (19S,20R)-19-(β-D-glucopyranosyloxy)-16,17,21,21a-tetradehydro-18-oxa-21a-homo-20,21-secoyohimban-16-carboxylate | |
| Systematic IUPAC name Methyl (4S,5R,6S)-5-ethenyl-4-{[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl}-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate | |
| Other names Isovincoside | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| |
| |
| Properties | |
| C27H34N2O9 | |
| Molar mass | 530.574 g·mol−1 |
| Melting point | 193-197 °C |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Strictosidine is a naturalchemical compound and is classified as aglucoalkaloid and avinca alkaloid. It is formed by thePictet–Spenglercondensation reaction oftryptamine withsecologanin, catalyzed by the enzymestrictosidine synthase. Thousands of strictosidinederivatives are sometimes referred to by the broad phrase ofmonoterpeneindole alkaloids.[1][2] Strictosidine is an intermediate in thebiosynthesis of numerous pharmaceutically valuable metabolites includingquinine,camptothecin,ajmalicine,serpentine,vinblastine,vincristine andmitragynine.
Biosynthetic pathways help to define the subgroups of strictosidine derivatives.[3][4]
Strictosidine is found in the following plant families:
Here especially inRhazya stricta andCatharanthus roseus.
Recent efforts in metabolic engineering have permitted the synthesis of strictosidine by yeast (Saccharomyces cerevisiae).[5] This was accomplished by adding 21 genes and 3 gene deletions.
The involvement of the glucoalkaloid strictosidine in the antimicrobial and antifeedant activity of Catharanthus roseus leaves was studied. Strictosidine and its deglucosylation product, specifically formed by the enzyme strictosidine glucosidase, were found to be active against several microorganisms.[6]
