Isostrychnine

Chemical compound From Wikipedia, the free encyclopedia

Isostrychnine is a monoterpenoid indole alkaloid and a structural isomer of strychnine. It is a secondary plant metabolite and may have antitumor activity.

Quick facts Names, Identifiers ...
Isostrychnine
Names
IUPAC name
(1R,13S,14E,19S,21S)-14-(2-Hydroxyethylidene)-8,16-diazahexacyclo[11.5.2.11,8.02,7.016,19.012,21]henicosa-2,4,6,11-tetraen-9-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C21H22N2O2/c24-10-7-13-12-22-9-8-21-16-3-1-2-4-17(16)23-19(25)6-5-14(20(21)23)15(13)11-18(21)22/h1-5,7,15,18,20,24H,6,8-12H2/b13-7-/t15-,18-,20-,21+/m0/s1 checkY
    Key: PNYOGGAOQVIZDM-JQNVFVSUSA-N checkY
  • С1CN2C/C(=C/CO)/[C@@H]3C[C@H]2[C@@]14[C@@H]5C3=CCC(=O)N5C6=CC=CC=C46
Properties
C21H22N2O2
Molar mass 334.419 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Occurrence

Isostrychnine has been isolated from plant extracts of Strychnos species (e.g the seeds of Strychnos nux-vomica (strychnine tree) or the roots of Strychnos icaja).[1][2] It is also present in Strychnos ignatii.[2]

Pharmacology

One study observed inhibitory effects against Hep G2 cell proliferation.[3] Another study found isostrychnine arrested the growth of the human hepatocarcinoma cell line SMMC 7721.[4]

References

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