Jatrorrhizine

Jatrorrhizine

Names
IUPAC name 3-Hydroxy-2,9,10-trimethoxy-7,8,13,13a-tetradehydroberbin-7-ium
Systematic IUPAC name 3-Hydroxy-2,9,10-trimethoxy-5,6-dihydro-7λ^5-isoquinolino[3,2-a]isoquinolin-7-ylium
Other names Jateorrhizine Neprotin Jatrochizine Jatrorhizine Yatrorizine
Identifiers
CAS Number	3621-38-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6087
ChEMBL	ChEMBL251055
ChemSpider	65269^Y
ECHA InfoCard	100.020.744
EC Number	222-817-3
KEGG	C09553^Y
PubChem CID	72323
UNII	091S1F8V5Q
CompTox Dashboard (EPA)	DTXSID40189767
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+1^N Key: MXTLAHSTUOXGQF-UHFFFAOYSA-O^N 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+1 Key: MXTLAHSTUOXGQF-UHFFFAOYSA-O InChI=1/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+1 Key: MXTLAHSTUOXGQF-IKLDFBCSAC
SMILES COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC
Properties
Chemical formula	C20H20NO4^+1
Molar mass	338.382 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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]

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. 17 (7): 834–7. doi:10.1002/ptr.1256. PMID 12916091. S2CID 33470505.
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. 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. S2CID 29474375.
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.