Berberine

Title: Berberine
CAS Registry Number: 2086-83-1
CAS Name: 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
Additional Names: 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium; umbellatine
Molecular Formula: [C20H18NO4]+
Literature 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.
Melting point: mp 145°: Gadamer, Arch. Pharm. 243, 33 (1905)
pKa: pK 2.47
Absorption maximum: uv max: 265, 343 nm
Derivative Type: Acid sulfate
Additional Names: Berberine bisulfate
Molecular Formula: C20H19NO8S
Molecular Weight: 433.43
Percent Composition: C 55.42%, H 4.42%, N 3.23%, O 29.53%, S 7.40%
Properties: Yellow needles. Sol in about 100 parts water; slightly sol in alc.
Derivative Type: Chloride dihydrate
Molecular Formula: C20H18NO4.Cl.2H2O
Molecular Weight: 407.84
Percent Composition: C 58.90%, H 5.44%, N 3.43%, O 23.54%, Cl 8.69%
Properties: Yellow crystals. Slightly sol in cold, freely in boiling water. Practically insol in cold alcohol, chloroform, ether.
Derivative Type: 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).
Therap-Cat: Antiprotozoal (Leishmania); antimalarial; antibacterial; antidiarrheal.
Keywords: Antimalarial; Antipyretic.
Berberis Aristata Berbine Bergapten Bergenin Bermoprofen

Berberine
Berberin.svg
Identifiers
CAS number 2086-83-1 N
PubChem 2353
ChemSpider 2263 YesY
UNII 0I8Y3P32UF YesY
DrugBank DB04115
ChEBI CHEBI:16118 YesY
ChEMBL CHEMBL12089 N
Jmol-3D images Image 1
Properties
Molecular formula C20H18NO4+
Molar mass 336.36122 g/mol
Appearance yellow solid
Melting point 145°C[1]
Solubility in water slowly soluble[1]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in such plants as Berberis [e.g. Berberis aquifolium (Oregon grape), Berberis vulgaris (barberry), Berberis aristata (tree turmeric)], Hydrastis canadensis (goldenseal), Xanthorhiza simplicissima (yellowroot), Phellodendron amurense[2] (Amur cork tree), Coptis chinensis (Chinese goldthread 黄连素 or Huang Lian Su), Tinospora cordifolia, Argemone mexicana (prickly poppy), and Eschscholzia californica (Californian poppy). Berberine is usually found in the roots, rhizomes, stems, and bark.[citation needed]

Berberine is strongly yellow colored, which is why in earlier times Berberis species were used to dye wool, leather and wood. Wool is still today dyed with berberine in northern India. Under ultraviolet light, berberine shows a strong yellow fluorescence,[3] so it is used in histology for staining heparin in mast cells.[4] As a natural dye, berberine has a colour index of 75160.