Strictosidine

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{{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 = }}

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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 }}