Jatrorrhizine Explained

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.

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]

Notes and References

  1. Web site: jatrorrhizine - Compound Summary (CID 72323). PubChem.
  2. Arens . H . Fischer . H . Leyck . S . Römer . A . Ulbrich . B . Antiinflammatory Compounds from Plagiorhegma dubium Cell Culture1 . Planta Medica . 51 . 1 . 52–6 . 1985 . 17340402 . 10.1055/s-2007-969392 .
  3. Virtanen . P . Lassila . V . Njimi . T . Mengata . DE . Natural protoberberine alkaloids from Enantia chlorantha, palmatine, columbamine and jatrorrhizine for thioacetamide-traumatized rat liver . Acta Anatomica . 131 . 2 . 166–70 . 1988 . 3369286 . 10.1159/000146507 .
  4. Moody . JO . Bloomfield . SF . Hylands . PJ . In-vitro evaluation of the antimicrobial activities of Enantia chlorantha Oliv. Extractives . African Journal of Medicine and Medical Sciences . 24 . 3 . 269–73 . 1995 . 8798963 .
  5. Volleková . A . Kost'álová . D . Kettmann . V . Tóth . J . Antifungal activity of Mahonia aquifolium extract and its major protoberberine alkaloids . Phytotherapy Research . 17 . 7 . 834–7 . 2003 . 12916091 . 10.1002/ptr.1256 . 33470505 .
  6. Kong . LD . Cheng . CH . Tan . RX . Monoamine oxidase inhibitors from rhizoma of Coptis chinensis . Planta Medica . 67 . 1 . 74–6 . 2001 . 11270727 . 10.1055/s-2001-10874 .
  7. Zhang . H . Yang . L . Liu . S . Ren . L . Study on active constituents of traditional Chinese medicine reversing multidrug resistance of tumor cells in vitro . Zhong Yao Cai . 24 . 9 . 655–7 . 2001 . 11799777 .
  8. Wang . LJ . Ye . XL . Li . XG . Sun . QL . Yu . G . Cao . XG . Liang . YT . Zhang . HS . Zhou . JZ . Synthesis and antimicrobial activity of 3-alkoxyjatrorrhizine derivatives . Planta Medica . 74 . 3 . 290–2 . 2008 . 18300191 . 10.1055/s-2008-1034312 .
  9. Wang . LJ . Ye . XL . Chen . Z . Li . XG . Sun . QL . Zhang . BS . Cao . XG . Yu . G . Niu . XH . Synthesis and antimicrobial activity of 3-octyloxy-8-alkyljatrorrhizine derivatives . Journal of Asian Natural Products Research . 11 . 4 . 365–70 . 2009 . 19431018 . 10.1080/10286020902727447 . 29474375 .
  10. Bhadra . K . Kumar . GS . Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: Binding aspects and implications for drug design . Medicinal Research Reviews . 821–862. 2010 . 20077560 . 10.1002/med.20202 . 31 . 6 . 206250975 . free .

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