Berberine
| Berberine | |
|---|---|
 | |
| Identifiers | |
| CAS number | 633-66-9 |
| PubChem | |
| SMILES |
COC1=C(C2=C[N+]3= C(C=C2C=C1)C4= CC5=C(C=C4CC3)OCO5)OC |
| ChemSpider ID | |
| Properties | |
| Molecular formula | C20H18NO4+ |
| Molar mass | 336.36122 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references | |
Berberine is a quaternary ammonium salt from the group of isoquinoline alkaloids. It is found in such plants as Berberis, goldenseal (Hydrastis canadensis), and Coptis chinensis, usually in the roots, rhizomes, stems, and bark. 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.[1] Because of this it is used in histology for staining heparin in mast cells.[2] As a natural dye berberin has a Colour Index (CI) of 75160.
As a drug, berberine has showed some activity against fungal infections, candida, yeast, parasites, and bacterial/viral infections.[3][4] Some research has been undertaken into possible use against MRSA infection.[5] Although berberine has been tested and used in diabetes, prostate cancer cell lines,[6] liver and leukaemia cancers,[7] cardiac arrhythmia,[8] and leukemia,[9] it has not been researched thoroughly with humans. Berberine is considered an ineffective antibiotic, but a minority claim that when not tested in isolation but in conjunction with the other biochemical substances from the barberry plant, berberine might then be effective.[10]
Berberine is a component of some eye drops formulations[11]. There is some evidence that it is useful in the treatment of trachoma, [12] and it has been a standard treatment for leishmaniasis [13].
See also
- Sanguinarine; a plant based compound with very similar chemical classification as berberine
- Coptisine for a related pharmacological discussion.
- Goldenseal for a related pharmacological discussion.
Footnotes
- Fluoreszenzfarbstoffe in der Natur
- Anwendung als Cell Stain
- Birdsall TC, Kelly GS (1997). "Berberine: Therapeutic potential of an alkaloid found in several medicinal plants" (PDF). Altern Med Rev 2 (2): 94–103. http://www.thorne.com/media/berberine.pdf.
- "Berberine" (PDF). Altern Med Rev 5 (2): 175–7. 2000. PMID 10767672. http://www.thorne.com/media/berberine_monograph.pdf.
- Yu HH, Kim KJ, Cha JD, et al (2005). "Antimicrobial activity of berberine alone and in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus". J Med Food 8 (4): 454–61. doi:. PMID 16379555.
- Mantena SK, Sharma SD, Katiyar SK (2006). "Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells". Mol. Cancer Ther. 5 (2): 296–308. doi:. PMID 16505103. http://mct.aacrjournals.org/cgi/content/full/5/2/296.
- Lin CC, Ng LT, Hsu FF, Shieh DE, Chiang LC (2004). "Cytotoxic effects of Coptis chinensis and Epimedium sagittatum extracts and their major constituents (berberine, coptisine and icariin) on hepatoma and leukaemia cell growth". Clin. Exp. Pharmacol. Physiol. 31 (1-2): 65–9. PMID 14756686.
- Lau CW, Yao XQ, Chen ZY, Ko WH, Huang Y (2001). "Cardiovascular actions of berberine". Cardiovasc Drug Rev 19 (3): 234–44. PMID 11607041.
- Lin CC, Lin SY, Chung JG, Lin JP, Chen GW, Kao ST (2006). "Down-regulation of cyclin B1 and up-regulation of Wee1 by berberine promotes entry of leukemia cells into the G2/M-phase of the cell cycle". Anticancer Res. 26 (2A): 1097–104. PMID 16619512.
- Kim Lewis. "Research Description -- 3) Natural inhibitors of microbial resistance from medicinal plants". Northeastern University. Retrieved on 2008-02-10.
- "Drugs (Listed by Trade Name) > Murine Eye Drops". Bigpond.com. Retrieved on 2009-01-01.
- Babbar OP, Chatwal VK, Ray IB, et al. (1982). "Effect of berberine chloride eye drops on clinically positive trachoma patients.". Indian Journal of Medical Research 76: 83–8.
- Kalla G; Singhi MK; Gyaneshwar Kalla. (1996). "Cutaneous leishmaniasis in Jodhpur district.". Indian Journal of Dermatology, Venereology and Leprology. 62(3): 149-51.
Source: adapted by the editor from Wikipedia, the free encyclopedia; from the article "Berberine". Image Credit.
