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Strictosidine - Wikipedia

From Wikipedia, the free encyclopedia

Strictosidine
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
CAS Number	20824-29-7
3D model (JSmol)	Interactive image
ChemSpider	141721
PubChem CID	161336
CompTox Dashboard (EPA)	DTXSID40943068
InChI InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16+,19+,20-,22-,23+,24-,26+,27+/m1/s1 Key: XBAMJZTXGWPTRM-NTXHKPOFSA-N
SMILES COC(=O)C1=CO[C@H]([C@@H]([C@@H]1C[C@H]2C3=C(CCN2)C4=CC=CC=C4N3)C=C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
Properties
Chemical formula	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). Infobox references

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:

Apocynaceae

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

^ 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.
^ 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.
^ Seigler DS (1998). Plant Secondary Metabolism. Springer. ISBN 978-0-412-01981-4.
^ Wink M (2010). Biochemistry of Plant Secondary Metabolism. Blackwell. ISBN 978-0-8493-4085-7.
^ 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.
^ 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.

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