Jatrorrhizine

Chemical compound From Wikipedia, the free encyclopedia

Jatrorrhizine is a protoberberine alkaloid found in some plant species, such as Enantia chlorantha (Annonaceae).[1] Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, and yatrorizine.

Quick facts Names, Identifiers ...
Jatrorrhizine
Names
IUPAC name
3-Hydroxy-2,9,10-trimethoxy-7,8,13,13a-tetradehydroberbin-7-ium
Systematic IUPAC name
3-Hydroxy-2,9,10-trimethoxy-5,6-dihydro-7λ5-isoquinolino[3,2-a]isoquinolin-7-ylium
Other names
  • Jateorrhizine
  • Neprotin
  • Jatrochizine
  • Jatrorhizine
  • Yatrorizine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.744 Edit this at Wikidata
EC Number
  • 222-817-3
KEGG
UNII
  • InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1 ☒N
    Key: MXTLAHSTUOXGQF-UHFFFAOYSA-O ☒N
  • InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7- 21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1
    Key: MXTLAHSTUOXGQF-UHFFFAOYSA-O
  • InChI=1/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1
    Key: MXTLAHSTUOXGQF-IKLDFBCSAC
  • COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC
Properties
C20H20NO4+1
Molar mass 338.382 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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Bioactive effects

Jatrorrhizine has been reported to have antiinflammatory effect,[2] and to improve blood flow and mitotic activity in thioacetamide-traumatized rat livers.[3] It was found to have antimicrobial[4] and antifungal[5] activity. It binds and noncompetitively inhibits monoamine oxidase (IC50 = 4 μM for MAO-A and 62 μM for MAO-B)[6] It interferes with multidrug resistance by cancer cells in vitro when exposed to a chemotherapeutic agent.[7] Large doses (50–100 mg/kg) reduced blood sugar levels in mice by increasing aerobic glycolysis.

Derivatives of jatrorrhizine (notably 3-alkoxy derivatives, and specifically 3-octyloxy 8-alkyljatrorrhizine derivatives such as 3-octyloxy 8-butyljatrorrhizine) have been synthesized and found to have much stronger antimicrobial effects.[8][9][10]

References

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