Strictosidine information

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]

^ Mizukami, H; Nordlöv, H; Lee, S. L.; Scott, A. I. (1979). "Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells". Biochemistry. 18 (17): 3760–3. doi:10.1021/bi00584a018. PMID 476085.
^ Treimer, J. F.; Zenk, M. H. (1979). "Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation". European Journal of Biochemistry. 101 (1): 225–33. doi:10.1111/j.1432-1033.1979.tb04235.x. PMID 510306.
^ David S Seigler (1998). Plant Secondary Metabolism. Springer.
^ Michael Wink (2010). Biochemistry of Plant Secondary Metabolism. Blackwell.

[1] Mizukami, H; Nordlöv, H; Lee, S. L.; Scott, A. I. (1979). "Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cells". Biochemistry. 18 (17): 3760–3. doi:10.1021/bi00584a018. PMID 476085.

[2] Treimer, J. F.; Zenk, M. H. (1979). "Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation". European Journal of Biochemistry. 101 (1): 225–33. doi:10.1111/j.1432-1033.1979.tb04235.x. PMID 510306.

[3] David S Seigler (1998). Plant Secondary Metabolism. Springer.

[4] Michael Wink (2010). Biochemistry of Plant Secondary Metabolism. Blackwell.

Strictosidine information

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Strictosidine

Strictosidine synthase

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