User:WriterHound/Beberine

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|Section2= {{Chembox Properties

| Formula=C₁₉H₁₄NO₄+

| MolarMass=336.36122 g/mol

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Berberine is a plant alkaloid 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 and leather. Wool is still today died with berberine in Northern India. Under ultraviolet light, berberine shows a strong yellow fluorescence.[http://www.chemie.uni-jena.de/institute/oc/weiss/naturstoffe.htm Fluoreszenzfarbstoffe in der Natur] Because of this it is used in histology for staining heparin in mast cells.[http://www.sigmaaldrich.com/catalog/search/ProductDetail?ProdNo=B3251&Brand=SIGMA Anwendung als Cell Stain] As a natural dye berberin has a Colour Index (CI) of 75160. It is the only known natural dye which is basic rather than acidic or neutral.

==Occurrence in nature==

HusemannA. Husemann und T. Husemann, Die Pflanzenstoffe in chemischer, physiologischer, pharmakologischer und toxikologischer Hinsicht, Berlin, 1871 writes about the Berberin:

Image:Jeffersonia diphylla.jpg contains berberine]]

"Berberin is one of the few alkaloids, which is not only distributed across different genres of the same plant family, but also in the most diverse plant families. It is in the Jamaica niche worm bark, the bark of Geoffroya jamaicensis Mur. or Andria inermis Kuth. (Fam. Casealpineae) according to Gastell, in the bark of Xanthoxylum clava Herculis L. (Fam. Xanthoxyleae) to Perrins, Podophyllum peltatum. Leontice thalictroides and Jeffersonia diphylla (Fam. Papaveraceae) to FF Mayer (Amer. Journ. Pharm XXXV. 97), in the West African Abeocouta bark Coelocline polycarpa De C. (Fam. Anonaceae) according to Stenhouse, in the roots of Hydrastis canadensis L. Xanthorhiza Apiifolia Herit. and Coptis teeta (Family Ranunculaceae) according to Mahla and Perrins in Colombo root, the root of Cocculus palmatus De C. and the Ceylonian Colombo wood, the wood Coscinium fenestratum Colebr. (Fam. Menispermeae) to Bödeker and Perrins, in the root, bark, blossoms, unripe berries and leaves of Berberis vulgaris L. , as well as in the Indian and Mexican Berberis species (Fam. Berberideae) according to Buchner, Polex, Ferrein, Solley, Witt Stein and others, according Perrins finally also in the St. John's roots from the Rio Grande, in the bark of Pachnelo tree of Bogota, in one of the natives Woodunpar called yellow color wood from Upper Assam."

class="wikitable" style="margin: 1em auto 1em auto" style="background:white" |+ Some Plants Containing Berberine[http://www.ars-grin.gov/cgi-bin/duke/highchem.pl]
width="200pt"|{{center|Species}} |width="100pt"|{{center|Rhizome}} |width="100pt"|{{center|Root}} |width="100pt"|{{center|Bark}} |width="100pt"|{{center|Plant}}
Coptis chinensis Franch.	{{center|90,000 ppm}}			{{center| }}
Coptis japonica (Thunb.) Makino	{{center|70,000 ppm}}			{{center| }}
Hydrastis canadensis L.	{{center| }}	{{center|60,000 ppm}}
Berberis vulgaris L.	{{center| }}			{{center|30,000 ppm}}
Phellodendron amurense Rupr.	{{center| }}		{{center|10,000 ppm}}
Argemone mexicana L.	{{center| }}			{{center|410 ppm}}

== Discovery of berberine ==

After Husemann isolated hut Schmidt 1824 first from the Jamaica niche worm bark "Jamaicin". And berberine was 1835 by the German pharmacologist Johann Andreas Buchner first time from the root bark of Berberis vulgaris L. were isolated. Gastell but acknowledged 1866 that "Jamaicin" with Berberin identical.

==Physiological effects==

Counterparts bacteria[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=retrieve&db=pubmed&list_uids=1796883&dopt=Abstract Y. Kaneda u.a.: In vitro effects of berberine sulphate on the growth and structure of Entamoeba histolytica, Giardia lamblia, and Trichomonas vaginalis. In: Annals of Tropical Medicine and Parasitology. 85(4)/1991, S. 417-425] and amoeba shows Berberin antiseptic. It shows weak antibotische effects. The effect can be estimated by the MDR -Inhibitor 5'-Methoxyhydnocarpin (5'-MHC) exponentiation be[http://library.wur.nl/frontis/medicinal_aromatic_plants/19_verpoorte.pdf R. Verpoorte, PLANTS AS SOURCE OF MEDICINES, 2006, S. 266]N.P. Brenwald u.a., Prevalence of a Putative Efflux Mechanism among Fluoroquinolone-Resistant Clinical Isolates of Streptococcus pneumoniae, in Antimicrob. Agents Chemother. 42/1998, S.2032-2035F.R. Stermitz u.a., Synergy in a medicinal plant: Antimicrobial action of berberine potentiated by 5´-methoxyhydnocarpin, a multidrug pump inhibitor, in PNAS 97/2000, S. 1433-1437[http://deposit.ddb.de/cgi-bin/dokserv?idn=981942334&dok_var=d1&dok_ext=pdf&filename=981942334.pdf Dissertation Andreas Gärtner, Entwicklung und Charakterisierung von Enzymimmuntests für den Nachweis von Fluorchinolonen, 2006, S. 8]. Moreover effect Berberin sedative on the central nervous system. In a number of medical applications seems Berberin ongoing pharmakologisches potential. So it is, or was tested against:

• Diabetes mellitus[http://www.focus.de/gesundheit/news/diabetes_nid_32887.html Focus-Artikel: Chinesische Medizin bremst Zucker][http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=17292731 Zhou, L. et. al., Berberine stimulates glucose transport through a mechanism distinct from insulin, Metabolism. 2007 Mar;56(3):405-12]

• Alzheimer's disease[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=17125739 Asai, M. et. al.,Berberine alters the processing of Alzheimer's amyloid precursor protein to decrease Abeta secretion, Biochem Biophys Res Commun. 2007 Jan 12;352(2):498-502. Epub 2006 Nov 15][http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1693919 Zhu, F. et. al.,Berberine chloride can ameliorate the spatial memory impairment and increase the expression of interleukin-1beta and inducible nitric oxide synthase in the rat model of Alzheimer's disease, BMC Neurosci. 2006; 7: 78.]
• Prostate cancer[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16505103 Mantena, S.K. et. al., Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells, Mol Cancer Ther. 2006 Feb;5(2):296-308.Click here to read]

• Breast cancer[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=17089049 Issat, T., et. al., Berberine, a natural cholesterol reducing product, exerts antitumor cytostatic/cytotoxic effects independently from the mevalonate pathway, Oncol Rep. 2006 Dec;16(6):1273-6.]
• Heart rhythm disorders[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=retrieve&db=pubmed&list_uids=8730735&dopt=Abstract J. Sanchez-Chapula J. in Increase in action potential duration and inhibition of the delayed rectifier outward current IK by berberine in cat ventricular myocytes, In: Br J Pharmacol. 117(7)/1996, S. 1427-1434]
• Leukemia [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16619512 Lin, C.C. et. al., 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. 2006 Mar-Apr;26(2A):1097-104.]
• Skin cancer[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16621886 Mantena, S.K., et. al., Berberine inhibits growth, induces G1 arrest and apoptosis in human epidermoid carcinoma A431 cells by regulating Cdki-Cdk-cyclin cascade, disruption of mitochondrial membrane potential and cleavage of caspase 3 and PARP, Carcinogenesis. 2006 Oct; 27(10):2018-27. Epub 2006 Apr 18]
• Lung cancer[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16621886 Peng, P.L. et. al., Inhibitory effect of berberine on the invasion of human lung cancer cells via decreased productions of urokinase-plasminogen activator and matrix metalloproteinase-2, Toxicol Appl Pharmacol. 2006 Jul 1;214(1):8-15. Epub 2006 Jan 4]

Berberine and its compounds berberine sulfate and phosphate were often in the Orient intestinal antiseptic oral form. Other systemic effects, such as hypertensive, the secretion of bilirubin - raising, inotrop, sedativ, antiinflammatorisch (inflammatory) Kuo, C.L. et al., "The anti-inflammatory potential of berberine in vitro and in vivo", Cancer Lett. 203, 127 (2004), dilatierende effect on coronary arteries, antikoagulatorisch, moderate reduction in heart rate, acceleration repairing the Pankreas-ß-Zellen, Low Density Lipoprotein -Cholesterin (LDL-C) lowering, described.[http://www.kup.at/kup/pdf/366.pdf "TRADITIONELLE CHINESISCHE MEDIZIN", J KARDIOL, 1999; 6 (4), S. 215] In vitro, could mean a Telomerase -Inhibierung determine[http://cancerres.aacrjournals.org/cgi/reprint/59/16/4004?maxtoshow=&HITS=10&hits=10&RESULTFORMAT=&titleabstract=Telomerase+Inhibitor&searchid=1&FIRSTINDEX=0&resourcetype=HWCIT Naasani, I. et. al. "FJ5002: A Potent Telomerase Inhibitor Identified by Exploiting the Disease-oriented Screening Program with COMPARE Analysis", CANCER RESEARCH 59, S. 4004–4011, 1999] Also, in vitro the ability of the Beberins than radical be.[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16946507 Shirwaikar, A. et. al. "In vitro antioxidant studies on the benzyl tetra isoquinoline alkaloid berberine.", Biol Pharm Bull. 2006 Sep;29(9):1906-10.]

It is nutritionally helpful against fungal infections, candida, yeast, parasites, and bacterial/viral infections.Birdsall TC, Kelly GS. (1997) "Berberine: Therapeutic potential of an alkaloid found in several medicinal plants". Altern Med Rev, jrg.2 (nr.2): pp. 94-103. [http://www.thorne.com/back_issues.wss free fulltext article]"Berberine.". Altern Med Rev, jrg.5 (nr.2) (2000) : pp. 175-177. PMID 10767672 [http://www.thorne.com/back_issues.wss free fulltext article] Although berberine has been tested and used in diabetes, prostate cancer cell lines,Mantena SK, Sharma SD, Katiyar SK. (2006) [http://dx.doi.org/10.1158/1535-7163.MCT-05-0448 "Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells.".] Mol Cancer Ther, jrg.5 (nr.2): pp. 296-308. PMID 16505103 [http://mct.aacrjournals.org/cgi/content/full/5/2/296 free fulltext article] cardiac arrhythmia, and leukemia,[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16619512 Lin, C.C. et. al., 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. 2006 Mar-Apr;26(2A):1097-104.] it has not been researched thoroughly with humans. Berberine is considered an ineffective antibiotic, but this perception is due to observations of its activity as an isolated compound; when tested in conjunction with other biochemical substances simultaneously as elaborated by the barberry plant, then berberine is indeed an effective antibiotic - promoted by the substances that are responsible for deactivating multidrug resistance pumps in bacteria and restoring the activity of the berberine.[http://www.biology.neu.edu/faculty03/lewis03.html Biofilms; Multidrug resistance; co-antibioitcs, Kim Lewis As Lewis puts it: "Plants have faced the problem of microbial multidrug resistance for far longer than we have, and their solution is apparently to use a combination of an antibiotic with an MDR inhibitor. Emulating Nature's strategy and potentiating antibiotics with MDR inhibitors can be an effective strategy against drug-resistant microorganisms."