Jatrorrhizine

Jatrorrhizine

Names
IUPAC name 2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol
Other names jateorrhizine, neprotin
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	65269 N
ECHA InfoCard	100.020.744
EC Number	222-817-3
KEGG	C09553 N
PubChem CID	72323
InChI 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
SMILES COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC
Properties
Chemical formula	C20H20NO4
Molar mass	338.38 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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

Jatrorrhizine has been reported to have antiinflammatory effect, and to improve blood flow and mitotic activity in thioacetamide-traumatized rat livers. It was found to have antimicrobial and antifungal activity. It binds and noncompetitively inhibits monoamine oxidase (IC₅₀ 4 micromolar for MAO-A and 62 for MAO-B) It interferes with multidrug resistance by cancer cells in vitro when exposed to a chemotherapeutic agent. 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.