Jatrorrhizine

Jatrorrhizine

Jatrorrhizine

Chemical compound

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.

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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]

References

  1. [1]
    "jatrorrhizine - Compound Summary (CID 72323)". PubChem.
  2. [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. [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. [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. [5]
    Volleková, A; Kost'álová, D; Kettmann, V; Tóth, J (2003). "Antifungal activity of Mahonia aquifolium extract and its major protoberberine alkaloids". Phytotherapy Research. 17 (7): 834–7. doi:10.1002/ptr.1256. PMID 12916091. S2CID 33470505.
  6. [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. [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. 24 (9): 655–7. PMID 11799777.
  8. [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. [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. S2CID 29474375.
  10. [10]
    Bhadra, K; Kumar, GS (2010). "Therapeutic potential of nucleic acid-binding isoquinoline alkaloids: Binding aspects and implications for drug design". Medicinal Research Reviews. 31 (6): 821–862. doi:10.1002/med.20202. PMID 20077560. S2CID 206250975.
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