Jatrorrhizine

Title: Jatrorrhizine
CAS Registry Number: 3621-38-3
CAS Name: 5,6-Dihydro-3-hydroxy-2,9,10-trimethoxydibenzo[a,g]quinolizinium
Additional Names: 7,8,13,13a-tetradehydro-3-hydroxy-2,9,10-trimethoxyberbinium; jateorrhizine; neprotin
Molecular Formula: [C20H20NO4]+
Literature References: From root of Jateorhiza palmata (DC.) Miers (J. columba Miers), Menispermaceae: Feist, Arch. Pharm. 245, 586 (1907); from Berberis asiatica Roxb. ex DC. and B. thunbergii DC., Berberidaceae: Chatterjee et al., J. Indian Chem. Soc. 31, 83 (1954); Tomita, Kikuchi, J. Pharm. Soc. Jpn. 76, 597 (1956); from Coptis teeta Wall., Ranunculaceae: Chatterjee et al., J. Indian Chem. Soc. 29, 97 (1952); from Mahonia acanthifolia Wall., M. borealis Takeda and M. simonsii Takeda, Berberidaceae: Chatterjee, Guha, J. Am. Pharm. Assoc. 39, 577 (1950); Chatterjee et al., ibid. 40, 36 (1951). Structure: Späth, Duschinsky, Ber. 58, 1939 (1925).
Derivative Type: Iodide
Molecular Formula: C20H20INO4
Molecular Weight: 465.28
Percent Composition: C 51.63%, H 4.33%, I 27.27%, N 3.01%, O 13.75%
Properties: Reddish-yellow needles, mp 208-210°. Sol in water and alcohol.
Melting point: mp 208-210°
Javanicin Jerusalem Artichoke Jesaconitine Jojoba Oil Josamycin

Jatrorrhizine
Jatrorrhizine.svg
Identifiers
PubChem 72323
Jmol-3D images Image 1
Properties
Molecular formula C20H20NO4
Molar mass 338.38 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Jatrorrhizine is a protoberberine alkaloid isolated from Enantia chlorantha (Annonaceae) and other species.[1] Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, or yatrorizine. It 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 micromolar for MAO-A and 62 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]