1154. Berberine
Nomenclature
Description and references
Tautomeric alkaloid widely distributed in nine or more botanical familes but occurs most frequently in Berberidaceae. A component of many traditional medicines, first isolated in 1826. Structure: Perkin, Robinson, J. Chem. Soc. 97, 305 (1910). Biosynthesis: J. R. Gear, I. D. Spenser, Can. J. Chem. 41, 783 (1963). Pharmacology: Fukuda et al., Chem. Pharm. Bull. 18, 1299 (1970). Total synthesis: Kametani et al., J. Chem. Soc. C 1969, 2036. NMR: G. Blasko et al., Heterocycles 27, 911 (1988). HPLC determn in biological fluids: C.-M. Chen, H.-C. Chang, J. Chromatogr. B 665, 117 (1995). Clinical evaluation in malaria: W. D. Sheng et al., East Afr. Med. J. 74, 283 (1997). Review of biological activities: F. E. Hahn, J. Ciak, in Antibiotics vol. 3, D. Gottlieb et al., Eds. (Springer-Verlag, New York, 1975) pp 577-584; of chemistry, distribution and use: R. S. Thakur, S. K. Srivastava, Curr. Res. Med. Aromat. Plants 4, 249-272 (1982). Review of antidiarrheal action: A. W. Baird et al., Adv. Drug Delivery Rev. 23, 111-120 (1997).
Properties
Yellow needles from ether, mp 145°: Gadamer, Arch. Pharm. 243, 33 (1905). uv max: 265, 343 nm. pK 2.47.Derivative
Acid sulfate.Nomenclature
Berberine bisulfate.Properties
Yellow needles. Sol in about 100 parts water; slightly sol in alc.Derivative
Chloride dihydrate.Properties
Yellow crystals. Slightly sol in cold, freely in boiling water. Practically insol in cold alcohol, chloroform, ether.Derivative
Sulfate trihydrate.Properties
Yellow needles. Sol in about 30 parts water; sol in alcohol. Activity studies: Amin et al., Can. J. Microbiol. 15, 1067 (1969). Pharmacology: Sabir, Bhide, Indian J. Physiol. Pharmacol. 15, 111 (1971).Therapeutic Category
Antiprotozoal (Leishmania); antimalarial; antibacterial; antidiarrheal.
Keywords
Antimalarial; Antipyretic