Strictosidine
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| Names | |
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| IUPAC name
Methyl (19S,20R)-19-(β-D-glucopyranosyloxy)-16,17,21,21a-tetradehydro-18-oxa-21a-homo-20,21-secoyohimban-16-carboxylate
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| 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
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| Identifiers | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C27H34N2O9 | |
| Molar mass | 530.574 g·mol−1 |
| Melting point | 193-197 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
Strictosidine is a natural chemical compound and is classified as a glucoalkaloid and a vinca alkaloid. It is formed by the Pictet–Spengler condensation reaction of tryptamine with secologanin, catalyzed by the enzyme strictosidine synthase. Thousands of strictosidine derivatives are sometimes referred to by the broad phrase of monoterpene indole alkaloids.[1][2] Strictosidine is an intermediate in the biosynthesis of numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine, vincristine and mitragynine.
Biosynthetic pathways help to define the subgroups of strictosidine derivatives.[3][4]
Distribution
Strictosidine is found in the following plant families:
Here especially in Rhazya stricta and Catharanthus 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.
Research
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]
References
Page Template:Reflist/styles.css has no content.
- ^ Page Module:Citation/CS1/styles.css has no content.Mizukami H, Nordlöv H, Lee SL, Scott AI (August 1979). "Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells". Biochemistry. 18 (17): 3760–3763. doi:10.1021/bi00584a018. PMID 476085.
- ^ Page Module:Citation/CS1/styles.css has no content.Treimer JF, Zenk MH (November 1979). "Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation". European Journal of Biochemistry. 101 (1): 225–233. doi:10.1111/j.1432-1033.1979.tb04235.x. PMID 510306.
- ^ Page Module:Citation/CS1/styles.css has no content.Seigler DS (1998). Plant Secondary Metabolism. Springer. ISBN 978-0-412-01981-4.
- ^ Page Module:Citation/CS1/styles.css has no content.Wink M (2010). Biochemistry of Plant Secondary Metabolism. Blackwell. ISBN 978-0-8493-4085-7.
- ^ Page Module:Citation/CS1/styles.css has no content.Brown S, Clastre M, Courdavault V, O'Connor SE (March 2015). "De novo production of the plant-derived alkaloid strictosidine in yeast". Proceedings of the National Academy of Sciences of the United States of America. 112 (11): 3205–3210. Bibcode:2015PNAS..112.3205B. doi:10.1073/pnas.1423555112. PMC 4371906. PMID 25675512.
- ^ Page Module:Citation/CS1/styles.css has no content.Luijendijk TJ, van der Meijden E, Verpoorte R (August 1996). "Involvement of strictosidine as a defensive chemical inCatharanthus roseus". Journal of Chemical Ecology. 22 (8): 1355–66. doi:10.1007/BF02027718. PMID 24226242.
