Strictosidine
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Chembox
| ImageFile = Strictosidine skeletal.svg
| ImageAlt =Structure of strictosidine
| IUPACName = Methyl (19S,20R)-19-(β-D-glucopyranosyloxy)-16,17,21,21a-tetradehydro-18-oxa-21a-homo-20,21-secoyohimban-16-carboxylate
| SystematicName = 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
| OtherNames = Isovincoside
|Section1={{Chembox Identifiers
| CASNo = 20824-29-7
| EINECS =
| PubChem = 161336
| ChemSpiderID = 141721
| 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
| 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
| InChIKey = XBAMJZTXGWPTRM-NTXHKPOFSA-N
| StdInChI =
| StdInChIKey = }}
|Section2={{Chembox Properties
| C=27 | H=34 | N=2 | O=9
| Appearance =
| Density =
| MeltingPt = 193-197 °C
| BoilingPt =
| Solubility = }}
}}
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.{{cite journal | vauthors = Mizukami H, Nordlöv H, Lee SL, Scott AI | title = Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells | journal = Biochemistry | volume = 18 | issue = 17 | pages = 3760–3763 | date = August 1979 | pmid = 476085 | doi = 10.1021/bi00584a018 }}{{cite journal | vauthors = Treimer JF, Zenk MH | title = Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation | journal = European Journal of Biochemistry | volume = 101 | issue = 1 | pages = 225–233 | date = November 1979 | pmid = 510306 | doi = 10.1111/j.1432-1033.1979.tb04235.x | doi-access = free }} 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.{{cite book | title = Plant Secondary Metabolism | vauthors = Seigler DS | publisher = Springer | date = 1998 | isbn = 978-0-412-01981-4 }}{{cite book | title = Biochemistry of Plant Secondary Metabolism | vauthors = Wink M | publisher = Blackwell | date = 2010 | isbn = 978-0-8493-4085-7 }}
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).{{cite journal | vauthors = Brown S, Clastre M, Courdavault V, O'Connor SE | title = De novo production of the plant-derived alkaloid strictosidine in yeast | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 112 | issue = 11 | pages = 3205–3210 | date = March 2015 | pmid = 25675512 | pmc = 4371906 | doi = 10.1073/pnas.1423555112 | doi-access = free | bibcode = 2015PNAS..112.3205B }} 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.{{cite journal | vauthors = Luijendijk TJ, van der Meijden E, Verpoorte R | title = Involvement of strictosidine as a defensive chemical inCatharanthus roseus | journal = Journal of Chemical Ecology | volume = 22 | issue = 8 | pages = 1355–66 | date = August 1996 | pmid = 24226242 | doi = 10.1007/BF02027718 }}