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Jatrorrhizine

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Jatrorrhizine
Names
IUPAC name 2,9,10-trimethoxy-5,6-dihydroisoquinolinoisoquinolin-7-ium-3-ol
Other names jateorrhizine, neprotin
Identifiers
3D model (JSmol)
ECHA InfoCard 100.020.744 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
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+1Key: MXTLAHSTUOXGQF-UHFFFAOYSA-O
SMILES
  • COC1=C(C2=C3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC
Properties
Chemical formula C20H20NO4
Molar mass 338.383 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

jatrorrhizine is a protoberberine alkaloid isolated from Enantia chlorantha (Annonaceae) 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 (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.

References

  1. "jatrorrhizine - Compound Summary (CID 72323)". PubChem.
  2. Arens, H; Fischer, H; Leyck, S; Römer, A; Ulbrich, B (1985). "Antiinflammatory Compounds from Plagiorhegma dubium Cell Culture1". Planta medica. 51 (1): 52–6. doi:10.1055/s-2007-969392. PMID 17340402.
  3. Virtanen, P; Lassila, V; Njimi, T; Mengata, DE (1988). "Natural protoberberine alkaloids from Enantia chlorantha, palmatine, columbamine and jatrorrhizine for thioacetamide-traumatized rat liver". Acta anatomica. 131 (2): 166–70. doi:10.1159/000146507. PMID 3369286.
  4. Moody, JO; Bloomfield, SF; Hylands, PJ (1995). "In-vitro evaluation of the antimicrobial activities of Enantia chlorantha Oliv. Extractives". African journal of medicine and medical sciences. 24 (3): 269–73. PMID 8798963.
  5. Volleková, A; Kost'álová, D; Kettmann, V; Tóth, J (2003). "Antifungal activity of Mahonia aquifolium extract and its major protoberberine alkaloids". Phytotherapy research : PTR. 17 (7): 834–7. doi:10.1002/ptr.1256. PMID 12916091.
  6. Kong, LD; Cheng, CH; Tan, RX (2001). "Monoamine oxidase inhibitors from rhizoma of Coptis chinensis". Planta medica. 67 (1): 74–6. doi:10.1055/s-2001-10874. PMID 11270727.
  7. Zhang, H; Yang, L; Liu, S; Ren, L (2001). "Study on active constituents of traditional Chinese medicine reversing multidrug resistance of tumor cells in vitro". Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 24 (9): 655–7. PMID 11799777.
  8. Wang, LJ; Ye, XL; Li, XG; Sun, QL; Yu, G; Cao, XG; Liang, YT; Zhang, HS; Zhou, JZ (2008). "Synthesis and antimicrobial activity of 3-alkoxyjatrorrhizine derivatives". Planta medica. 74 (3): 290–2. doi:10.1055/s-2008-1034312. PMID 18300191.
  9. Wang, LJ; Ye, XL; Chen, Z; Li, XG; Sun, QL; Zhang, BS; Cao, XG; Yu, G; Niu, XH (2009). "Synthesis and antimicrobial activity of 3-octyloxy-8-alkyljatrorrhizine derivatives". Journal of Asian natural products research. 11 (4): 365–70. doi:10.1080/10286020902727447. PMID 19431018.
  10. Bhadra, K; Kumar, GS (2010). "Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: Binding aspects and implications for drug design". Medicinal research reviews: n/a. doi:10.1002/med.20202. PMID 20077560.
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