Jatrorrhizine
| Jatrorrhizine | ||
|---|---|---|
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| IUPAC name 2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol | ||
| Other names jateorrhizine, neprotin | ||
| Identifiers | ||
| PubChem | 72323 | |
| Jmol-3D images | {{#if:COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC|Image 1 | |
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| Properties | ||
| Molecular formula | C20H20NO4 | |
| Molar mass | 338.38 g mol−1 | |
 (verify) (what is: / ?)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]
References
- ↑ "jatrorrhizine - Compound Summary (CID 72323)". PubChem.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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): n/a. doi:10.1002/med.20202. PMID 20077560.