Description
An alkaloid from Sophora angustifolia var. flavescens S. and Z., the bas'e crystal_x0002_lizes as the monohydrate having the lower melting point given above. It is
dextrorotatory with [α]19D + 47.7° (EtOH) and yields crystalline salts and
derivatives: hydrobromide, m.p. 21SoC; aurichloride, m.p. 207°C (dec.); perchlorate, m.p. 240°C (dec.); picrate, m.p. 21SoC and the methochloride aurichloride, m.p. 18SoC (dec.). Ochiai and Ito have shown that it is formed by the
action of hydrogen peroxide on Matrine (q.v.), indicating that its structure is
matrine-N-oxide.
Chemical Properties
Colorless block crystals, easily soluble in chloroform and methanol, insoluble in petroleum ether and acetone, derived from Sophora flavescens and Radix Sophorae flavescentis.
Uses
antifungal, hepatoprotectant
Definition
ChEBI: Ammothamnine is an alkaloid and a tertiary amine oxide.
Enzyme inhibitor
This quinolizidine alkaloid (FW = 264.37 g/mol), also known as matrine
oxide, matrine N-oxide, matrine 1-oxide, and (7aS,13aR,13bR,3cS)
dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one
4-oxide, from the root of the traditional Chinese herb Sophora flavescens
inhibits/suppresses ulceration (e.g., experimental gastric ulcer, pylorus
ligation ulcer and indomethacin), most likely by decreasing acid secretion
and inhibiting gastric motility. Oxymatrine induces mitochondria dependent
apoptosis in human osteosarcoma MNNG and HOS cells through the
inhibition of PI3K/Akt pathway. Oxymatrine also prevents NF-κB
nuclear translocation, thereby ameliorating acute intestinal inflammation
.
References
Kondo et al., Arch. Pharm., 275,493 (1937)
Ochiai, Ito., Ber., 81,938 (1938)
