Berberina

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Berberina
Berberin.svg
Nome IUPAC
umbellatine; 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
Nomi alternativi
Giallo naturale 18
Caratteristiche generali
Formula bruta o molecolare C20H18NO4+
Massa molecolare (u) 336,36122 g/mol
Aspetto solido giallo
Numero CAS 633-66-9
Numero EINECS 218-229-1
PubChem 2353
DrugBank DB04115
SMILES O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5
Proprietà chimico-fisiche
Solubilità in acqua solubile lentamente
Temperatura di ebollizione 145 °C (293 °F; 418 K)
Indicazioni di sicurezza
Frasi H 302​‐​312​‐​332
Consigli P 280 [1]

La berberina è un sale di ammonio quaternario appartenente al gruppo degli alcaloidi benzilisochinolinici. Si trova in alcune piante del genere Berberis (da cui il nome), di solito nelle radici, rizomi, fusti e corteccia.

Specie vegetali contenenti berberina[modifica | modifica wikitesto]

Farmacodinamica[modifica | modifica wikitesto]

La berberina è ligando agonista del recettore sigma-1 e 2 ed è anche un agonista del PPARγ (Peroxisome proliferator-activated receptor gamma).

Possiede attività antimicrobiche su batteri, virus, funghi, protozoi, elminti, e clamidia.[2][3][4][5][6][7][8] In vitro la berberina mostra di interferire con il DNA dei protozoi (forma promastigote) inibendo la maturazione del microrganismo parassita.[9]

Inoltre, ha anche proprietà inibenti la produzione di citochine proinfiammatorie.[10][11][12]

Clinica[modifica | modifica wikitesto]

Nella medicina tradizionale è usato per il trattamento della diarrea e delle infezioni intestinali da parassiti oltre che usato nel tracoma[2][13] e della leishmaniasi.[14][15][16]

Recentemente viene studiato per le sue documentate proprietà:

Effetti collaterali[modifica | modifica wikitesto]

Ai dosaggi comunemente usati nella medicina tradizionale la berberina è ben tollerata e sicura; a dosaggi più alti può determinare: disturbi gastrointestinali, dispnea, diminuzione pressoria, sintomi simil-influenzali e danno cardiaco. Va evitato l'uso in gravidanza e nei neonati.[2]

Note[modifica | modifica wikitesto]

  1. ^ Sigma Aldrich; rev. del 15.05.2012, riferita al cloruro
  2. ^ a b c Berberine, in Altern Med Rev, vol. 5, nº 2, 2000, pp. 175–7, PMID 10767672.
  3. ^ Yu HH, Kim KJ, Cha JD, Kim HK, Lee YE, Choi NY, You YO, Antimicrobial activity of berberine alone and in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus, in J Med Food, vol. 8, nº 4, 2005, pp. 454–61, DOI:10.1089/jmf.2005.8.454, PMID 16379555.
  4. ^ Poster Presentations, in FEBS Journal, vol. 277, 2010, pp. 37, DOI:10.1111/j.1742-4658.2010.07680.x.
  5. ^ Li Y., Zuo G.-Y. 'Advances in studies on antimicrobial activities of alkaloids" Chinese Traditional and Herbal Drugs 2010 41:6 (1006-1014)
  6. ^ Stermitz FR, Lorenz P, Tawara JN, Zenewicz LA, Lewis K, Synergy in a medicinal plant: antimicrobial action of berberine potentiated by 5'-methoxyhydnocarpin, a multidrug pump inhibitor, in Proceedings of the National Academy of Sciences of the United States of America, vol. 97, nº 4, February 2000, pp. 1433–7, Bibcode:2000PNAS...97.1433S, DOI:10.1073/pnas.030540597, PMC 26451, PMID 10677479.
  7. ^ Zhang S, Zhang B, Xing K, Zhang X, Tian X, Dai W, Inhibitory effects of golden thread (Coptis chinensis) and berberine on Microcystis aeruginosa, in Water Science & Technology, vol. 61, nº 3, 2010, pp. 763, DOI:10.2166/wst.2010.857, PMID 20150713.
  8. ^ Manosalva L, Mutis A, Urzúa A, Fajardo V, Quiroz A, Antibacterial Activity of Alkaloid Fractions from Berberis microphylla G. Forst and Study of Synergism with Ampicillin and Cephalothin, in Molecules, vol. 21, nº 1, 2016, DOI:10.3390/molecules21010076, PMID 26760994.
  9. ^ Ghosh AK, Bhattacharyya FK, Ghosh DK, Leishmania donovani: amastigote inhibition and mode of action of berberine, in Exp. Parasitol., vol. 60, nº 3, 1985, pp. 404–13, PMID 4076392.
  10. ^ Hu Y, Chen X, Duan H, Hu Y, Mu X, Chinese herbal medicinal ingredients inhibit secretion of IL-6, IL-8, E-selectin and TXB2 in LPS-induced rat intestinal microvascular endothelial cells, in Immunopharmacol Immunotoxicol, vol. 31, nº 4, 2009, pp. 550–5, DOI:10.3109/08923970902814129, PMID 19874221.
  11. ^ Niu X, Zhang H, Li W, Wang Y, Mu Q, Wang X, He Z, Yao H, Protective effect of cavidine on acetic acid-induced murine colitis via regulating antioxidant, cytokine profile and NF-κB signal transduction pathways, in Chem. Biol. Interact., vol. 239, 2015, pp. 34–45, DOI:10.1016/j.cbi.2015.06.026, PMID 26102009.
  12. ^ Ai F, Chen M, Yu B, Yang Y, Xu G, Gui F, Liu Z, Bai X, Chen Z, Berberine regulates proliferation, collagen synthesis and cytokine secretion of cardiac fibroblasts via AMPK-mTOR-p70S6K signaling pathway, in Int J Clin Exp Pathol, vol. 8, nº 10, 2015, pp. 12509–16, PMC 4680383, PMID 26722438.
  13. ^ Babbar OP, Chhatwal VK, Ray IB, Mehra MK, Effect of berberine chloride eye drops on clinically positive trachoma patients, in The Indian Journal of Medical Research, vol. 76, Suppl, December 1982, pp. 83–8, PMID 7185757.
  14. ^ Kalla, G. & Singhi, M.K., Cutaneous leishmaniasis in Jodhpur district, in Indian Journal of Dermatology, Venereology and Leprology, vol. 62, nº 3, 1996, pp. 149–51.
  15. ^ Mahmoudvand H, Ayatollahi Mousavi SA, Sepahvand A, Sharififar F, Ezatpour B, Gorohi F, Saedi Dezaki E, Jahanbakhsh S, Antifungal, Antileishmanial, and Cytotoxicity Activities of Various Extracts of Berberis vulgaris (Berberidaceae) and Its Active Principle Berberine, in ISRN Pharmacol, vol. 2014, 2014, pp. 602436, DOI:10.1155/2014/602436, PMC 3964876, PMID 24977052.
  16. ^ Mahmoudvand H, Sharififar F, Sharifi I, Ezatpour B, Fasihi Harandi M, Makki MS, Zia-Ali N, Jahanbakhsh S, In Vitro Inhibitory Effect of Berberis vulgaris (Berberidaceae) and Its Main Component, Berberine against Different Leishmania Species, in Iran J Parasitol, vol. 9, nº 1, 2014, pp. 28–36, PMC 4289877, PMID 25642257.
  17. ^ Sun Y, Xun K, Wang Y, Chen X, A systematic review of the anticancer properties of berberine, a natural product from Chinese herbs, in Anticancer Drugs, vol. 20, nº 9, October 2009, pp. 757–69, DOI:10.1097/CAD.0b013e328330d95b, PMID 19704371.
  18. ^ Berberine and Coptidis Rhizoma as novel antineoplastic agents: a review of traditional use and biomedical investigations, in Journal of Ethnopharmacology, vol. 126, nº 1, August 2009, pp. 5–17, DOI:10.1016/j.jep.2009.08.009, PMID 19686830.
  19. ^ Serafim TL, Oliveira PJ, Sardao VA, Perkins E, Parke D, Holy J, Different concentrations of berberine result in distinct cellular localization patterns and cell cycle effects in a melanoma cell line, in Cancer Chemotherapy and Pharmacology, vol. 61, nº 6, May 2008, pp. 1007–18, DOI:10.1007/s00280-007-0558-9, PMID 17661039.
  20. ^ Pinto-Garcia L, Efferth T, Torres A, Hoheisel JD, Youns M, Berberine Inhibits Cell Growth and Mediates Caspase-Independent Cell Death in Human Pancreatic Cancer Cells, in Planta Medica, vol. 76, nº 11, May 2010, pp. 1155–61, DOI:10.1055/s-0030-1249931, PMID 20455200.
  21. ^ Ho YT, Lu CC, Yang JS, Chiang JH, Li TC, Ip SW, Hsia TC, Liao CL, Lin JG, Wood WG, Chung JG, Berberine induced apoptosis via promoting the expression of caspase-8, -9 and -3, apoptosis-inducing factor and endonuclease G in SCC-4 human tongue squamous carcinoma cancer cells, in Anticancer Research, vol. 29, nº 10, October 2009, pp. 4063–70, PMID 19846952.
  22. ^ Ho YT, Lu CC, Yang JS, Chiang JH, Li TC, Ip SW, Hsia TC, Liao CL, Lin JG, Wood WG, Chung JG, Berberine induced apoptosis via promoting the expression of caspase-8, -9 and -3, apoptosis-inducing factor and endonuclease G in SCC-4 human tongue squamous carcinoma cancer cells, in Anticancer Research, vol. 29, nº 10, October 2009, pp. 4063–70, PMID 19846952.
  23. ^ Coptis chinensis inhibits hepatocellular carcinoma cell growth through nonsteroidal anti-inflammatory drug-activated gene activation, in International journal of molecular medicine, vol. 24, nº 4, October 2009, pp. 571–7, DOI:10.3892/ijmm_00000267, PMID 19724899.
  24. ^ Tang F, Wang D, Duan C, Huang D, Wu Y, Chen Y, Wang W, Xie C, Meng J, Wang L, Wu B, Liu S, Tian D, Zhu F, He Z, Deng F, Cao Y, Berberine inhibits metastasis of nasopharyngeal carcinoma 5-8F cells by targeting Rho kinase-mediated Ezrin phosphorylation at threonine 567, in The Journal of Biological Chemistry, vol. 284, nº 40, October 2009, pp. 27456–66, DOI:10.1074/jbc.M109.033795, PMC 2785675, PMID 19651779.
  25. ^ Qi MY, Feng Y, Dai DZ, Li N, Cheng YS, Dai Y, CPU86017, a berberine derivative, attenuates cardiac failure through normalizing calcium leakage and downregulated phospholamban and exerting antioxidant activity, in Acta Pharmacol Sin, vol. 31, nº 2, February 2010, pp. 165–74, DOI:10.1038/aps.2009.180, PMC 4002834, PMID 20139899.
  26. ^ Huang WM, Yan H, Jin JM, Yu C, Zhang H, Beneficial effects of berberine on hemodynamics during acute ischemic left ventricular failure in dogs, in Chinese Medical Journal, vol. 105, nº 12, December 1992, pp. 1014–9, PMID 1299549.
  27. ^ Riccioppo Neto F, Electropharmacological effects of berberine on canine cardiac Purkinje fibres and ventricular muscle and atrial muscle of the rabbit, in British Journal of Pharmacology, vol. 108, nº 2, February 1993, pp. 534–7, DOI:10.1111/j.1476-5381.1993.tb12836.x, PMC 1908004, PMID 8448600.
  28. ^ Marin-Neto JA, Maciel BC, Secches AL, Gallo Júnior L, Cardiovascular effects of berberine in patients with severe congestive heart failure, in Clinical Cardiology, vol. 11, nº 4, April 1988, pp. 253–60, DOI:10.1002/clc.4960110411, PMID 3365876.
  29. ^ Zeng XH, Zeng XJ, Li YY, Efficacy and safety of berberine for congestive heart failure secondary to ischemic or idiopathic dilated cardiomyopathy, in The American Journal of Cardiology, vol. 92, nº 2, July 2003, pp. 173–6, DOI:10.1016/S0002-9149(03)00533-2, PMID 12860219.
  30. ^ Wu M., Wang J., Liu L.-T. "Advance of studies on anti-atherosclerosis mechanism of berberine", Chinese Journal of Integrative Medicine 2010 16:2 (188-192)
  31. ^ Kim JB, Yu JH, Ko E, Lee KW, Song AK, Park SY, Shin I, Han W, Noh DY, The alkaloid Berberine inhibits the growth of Anoikis-resistant MCF-7 and MDA-MB-231 breast cancer cell lines by inducing cell cycle arrest, in Phytomedicine, vol. 17, nº 6, October 2009, pp. 436–40, DOI:10.1016/j.phymed.2009.08.012, PMID 19800775.
  32. ^ Zhou JY, Zhou SW, Zhang KB, Tang JL, Guang LX, Ying Y, Xu Y, Zhang L, Li DD, Chronic effects of berberine on blood, liver glucolipid metabolism and liver PPARs expression in diabetic hyperlipidemic rats, in Biological & Pharmaceutical Bulletin, vol. 31, nº 6, June 2008, pp. 1169–76, DOI:10.1248/bpb.31.1169, PMID 18520050.
  33. ^ Holy EW, Akhmedov A, Lüscher TF, Tanner FC, Berberine, a natural lipid-lowering drug, exerts prothrombotic effects on vascular cells, in Journal of Molecular and Cellular Cardiology, vol. 46, nº 2, February 2009, pp. 234–40, DOI:10.1016/j.yjmcc.2008.10.011, PMID 19014947.
  34. ^ Kong W, Wei J, Abidi P, Lin M, Inaba S, Li C, Wang Y, Wang Z, Si S, Pan H, Wang S, Wu J, Wang Y, Li Z, Liu J, Jiang JD, Berberine is a novel cholesterol-lowering drug working through a unique mechanism distinct from statins, in Nature Medicine, vol. 10, nº 12, December 2004, pp. 1344–51, DOI:10.1038/nm1135, PMID 15531889.
  35. ^ Kim WS, Lee YS, Cha SH, Jeong HW, Choe SS, Lee MR, Oh GT, Park HS, Lee KU, Lane MD, Kim JB, Berberine improves lipid dysregulation in obesity by controlling central and peripheral AMPK activity, in American Journal of Physiology– Endocrinology and Metabolism, vol. 296, nº 4, April 2009, pp. E812–9, DOI:10.1152/ajpendo.90710.2008, PMID 19176354.
  36. ^ Li H, Dong B, Park SW, Lee HS, Chen W, Liu J, HNF1α plays a critical role in PCSK9 gene transcription and regulation by a natural hypocholesterolemic compound berberine, in The Journal of Biological Chemistry, vol. 284, nº 42, August 2009, pp. 28885–95, DOI:10.1074/jbc.M109.052407, PMC 2781434, PMID 19687008.
  37. ^ Abidi P, Zhou Y, Jiang JD, Liu J, Extracellular signal-regulated kinase-dependent stabilization of hepatic low-density lipoprotein receptor mRNA by herbal medicine berberine, in Arteriosclerosis, Thrombosis, and Vascular Biology, vol. 25, nº 10, October 2005, pp. 2170–6, DOI:10.1161/01.ATV.0000181761.16341.2b, PMID 16100034.
  38. ^ Wang Y, Jia X, Ghanam K, Beaurepaire C, Zidichouski J, Miller L, Berberine and plant stanols synergistically inhibit cholesterol absorption in hamsters, in Atherosclerosis, vol. 209, nº 1, 2009, pp. 111–7, DOI:10.1016/j.atherosclerosis.2009.08.050, PMID 19782362.

Altri progetti[modifica | modifica wikitesto]