Strictosidine

Strictosidine

Names
IUPAC name Methyl (2S,3R,4S)-3-ethenyl-4-([(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
Other names Isovincoside
Identifiers
CAS Number	20824-29-7
3D model (Jmol)	Interactive image
ChemSpider	141721
PubChem	161336
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	530.57 g·mol^−1
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 terpene indole alkaloid formed by the condensation of tryptamine with secologanin by the enzyme strictosidine synthase.^[1][2] Strictosidine is the base molecule for numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine and vincristine.

Distribution

Strictosidine is found in the following plant families.

• Apocynaceae
• Loganiaceae
• Rubiaceae
• Icacinaceae
• Nyssaceae
• Alangiaceae

Recent efforts in metabolic engineering have permitted the synthesis of strictosidine by yeast (Saccharomyces cerevisiae).^[3] This was accomplished by adding 21 genes and 3 gene deletions.

References

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 / FEBS. 101 (1): 225–33. doi:10.1111/j.1432-1033.1979.tb04235.x. PMID 510306.
3. Brown, S; Clastre, M; Courdavault, V; O'Connor, S. E. (2015). "De novo production of the plant-derived alkaloid strictosidine in yeast". Proceedings of the National Academy of Sciences. 112: 201423555. doi:10.1073/pnas.1423555112. PMID 25675512.