User:WriterHound/Beberine

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WriterHound/Beberine
Identifiers
CAS number [633-66-9]
PubChem 2353
SMILES COC1=C(C2=C[N+]3= C(C=C2C=C1)C4= CC5=C(C=C4CC3)OCO5)OC
Properties
Molecular formula C19H14NO4+
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 disclaimer and references

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.[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. It is the only known natural dye which is basic rather than acidic or neutral.

Contents

[edit] Occurrence in nature

Husemann[3] writes about the Berberin:

Jeffersonia diphylla contains berberine
Jeffersonia diphylla 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."


Some Plants Containing Berberine[4]
Species
Rhizome
Root
Bark
Plant
Coptis chinensis Franch.
90,000 ppm
Coptis japonica (Thunb.) Makino
70,000 ppm
Hydrastis canadensis L.
60,000 ppm
Berberis vulgaris L.
30,000 ppm
Phellodendron amurense Rupr.
10,000 ppm
Argemone mexicana L.
410 ppm

[edit] Discovery of berberine

After Husemann [3] 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.

[edit] Physiological effects

Counterparts bacteria[5] 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[6][7][8][9]. 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:

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)[20], 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.[21] In vitro, could mean a Telomerase -Inhibierung determine[22] Also, in vitro the ability of the Beberins than radical be.[23]

It is nutritionally helpful against fungal infections, candida, yeast, parasites, and bacterial/viral infections.[24][25] Although berberine has been tested and used in diabetes, prostate cancer cell lines,[26] cardiac arrhythmia, and leukemia,[27] 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.[28] 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."

[edit] See also

  • See Goldenseal also for a related pharmacological discussion.

[edit] External links

[edit] References

[edit] Footnotes

  1. ^ Fluoreszenzfarbstoffe in der Natur
  2. ^ Anwendung als Cell Stain
  3. ^ a b A. Husemann und T. Husemann, Die Pflanzenstoffe in chemischer, physiologischer, pharmakologischer und toxikologischer Hinsicht, Berlin, 1871
  4. ^ [1]
  5. ^ 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
  6. ^ R. Verpoorte, PLANTS AS SOURCE OF MEDICINES, 2006, S. 266
  7. ^ 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.2032-2035
  8. ^ F.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
  9. ^ Dissertation Andreas Gärtner, Entwicklung und Charakterisierung von Enzymimmuntests für den Nachweis von Fluorchinolonen, 2006, S. 8
  10. ^ Focus-Artikel: Chinesische Medizin bremst Zucker
  11. ^ Zhou, L. et. al., Berberine stimulates glucose transport through a mechanism distinct from insulin, Metabolism. 2007 Mar;56(3):405-12
  12. ^ 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
  13. ^ 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.
  14. ^ 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
  15. ^ 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.
  16. ^ 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
  17. ^ 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.
  18. ^ 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
  19. ^ 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
  20. ^ Kuo, C.L. et al., "The anti-inflammatory potential of berberine in vitro and in vivo", Cancer Lett. 203, 127 (2004)
  21. ^ "TRADITIONELLE CHINESISCHE MEDIZIN", J KARDIOL, 1999; 6 (4), S. 215
  22. ^ 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
  23. ^ Shirwaikar, A. et. al. "In vitro antioxidant studies on the benzyl tetra isoquinoline alkaloid berberine.", Biol Pharm Bull. 2006 Sep;29(9):1906-10.
  24. ^ 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. free fulltext article
  25. ^ "Berberine.". Altern Med Rev, jrg.5 (nr.2) (2000) : pp. 175-177. PMID 10767672 free fulltext article
  26. ^ 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, jrg.5 (nr.2): pp. 296-308. PMID 16505103 free fulltext article
  27. ^ 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.
  28. ^ [http://www.biology.neu.edu/faculty03/lewis03.html Biofilms; Multidrug resistance; co-antibioitcs, Kim Lewis

[edit] General references

  • "Antimicrobial activity of berberine alone and in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus.", J Med Food. 2005 Winter;8(4):454-61.
  • "Cytotoxic effects of Coptis chinensis and Epimedium sagittatum extracts and their major constituents (berberine, coptisine and icariin) on hepatoma and leukemia cell growth.", Clin Exp Pharmacol Physiol. 2004 Jan-Feb;31(1-2):65-9.
  • "Cardiovascular actions of berberine.", Cardiovasc Drug Rev. 2001 Fall;19(3):234-44.
  • Web Site of Dr. Kim Lewis: http://www.biology.neu.edu/faculty03/lewis03.html