1153. Berbamine

Nomenclature

CAS number: 478-61-5
(4aS,16aR)-3,4,4a,5,16a,17,18,19-Octahydro-21,22,26-trimethoxy-4,17-dimethyl-16H-1,24:6,9-dietheno-11,15-metheno-2H-pyrido[2′,3′:17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolin-12-ol; 6,6′,7-trimethoxy-2,2′-dimethylberbaman-12-ol; berbenine.
C37H40N2O6; mol wt 608.72.
C 73.00%, H 6.62%, N 4.60%, O 15.77%.

Description and references

Alkaloid found in various members of Berberis family. Used as a traditional medicine in China as antipyretic, antidiarrheoa and as a tonic. Identification in Berberis vulgaris: C. Rüdel, Arch. Pharm. 229, 631 (1895); isoln from Atherosperma moschatum Labill., Monimiaceae: I. R. C. Bick et al., Aust. J. Chem. 9, 111 (1956). Structure: F. von Bruchhausen et al., Ann. 507, 144 (1933); configuration: Y. Inubishi, J. Pharm. Soc. Jpn. 72, 220 (1952), C.A. 47, 6429e (1953). Immunopharmacology and toxicology: C. W. Wong et al., Int. J. Immunopharmacol. 13, 579 (1991). Brief review: C.-X. Liu et al., Phytother. Res. 5, 228-230 (1991).

Chemical structure

Properties

Colorless plates from aq ethanol as the monohydrate, sinters 147°. pKa (20°): 7.33 in aq methanol. [α]D20 +114.6° (c = 1.0 in chloroform). uv max (ethanol): 282 nm (log ε 3.89; E 1cm1% 126).