Jatrorrhizine
Encyclopedia
Jatrorrhizine is a protoberberine
Berberine
Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in such plants as Berberis Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in such plants as Berberis Berberine is a quaternary...

 alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

 isolated from Enantia chlorantha (Annonaceae
Annonaceae
Annonaceae, also called the custard apple familyis a family of flowering plants consisting of trees, shrubs or rarely lianas.With about 2300 to 2500 species and more than 130 genera,...

) and other species. Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, or yatrorizine. It 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
Monoamine oxidase
L-Monoamine oxidases are a family of enzymes that catalyze the oxidation of monoamines. They are found bound to the outer membrane of mitochondria in most cell types in the body. The enzyme was originally discovered by Mary Bernheim in the liver and was named tyramine oxidase...

 (IC50 4 micromolar for MAO-A and 62 for MAO-B) It interferes with multidrug resistance
Multidrug resistance
Multiple drug resistance or Multidrug resistance is a condition enabling a disease-causing organism to resist distinct drugs or chemicals of a wide variety of structure and function targeted at eradicating the organism...

 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
Glycolysis
Glycolysis is the metabolic pathway that converts glucose C6H12O6, into pyruvate, CH3COCOO− + H+...

.

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.
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