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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/09 00:10:13」(JST)

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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 was supposedly used in China as a broad-spectrum anti-microbial medicine by Shennong around 3000 BC. This first recorded use of Berberine is described in the ancient Chinese medical book The Divine Farmer's Herb-Root Classic.

Due to Berberine's strong yellow color, Berberis species were used to dye wool, leather, and wood. Wool is still dyed with berberine today in northern India.^{[citation needed]} 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.

1 Traditional use
2 Newer and experimental uses
- 2.1 Antiarrhythmia
- 2.2 Diabetes, dyslipidemias and cardiovascular conditions
  - 2.2.1 Diabetes mellitus
  - 2.2.2 Lipids
  - 2.2.3 Liver
  - 2.2.4 Congestive heart failure
  - 2.2.5 Transplants
- 2.3 Cancer
- 2.4 Mental health
- 2.5 Intestinal disorders
- 2.6 HIV/AIDS
3 Contraindications
4 Biosynthesis
5 See also
6 References

Traditional use

As a Chinese traditional medicine or dietary supplement, berberine has shown some activity against fungal infections, Candida albicans, yeast, parasites, and bacterial/viral infections.^[5]^[6] Berberine seems to exert synergistic effects with fluconazole even in drug-resistant C. albicans infections.^[7]

Some research has been undertaken into possible use against MRSA infection.^[8]

Berberine is considered antibiotic.^[9]^[10] When applied in vitro and in combination with methoxyhydnocarpin, an inhibitor of multidrug resistance pumps, berberine inhibits growth of Staphylococcus aureus^[11] and Microcystis aeruginosa,^[12] a toxic cyanobacterium.

Berberine is a component of some eye drop formulations. There is some evidence it is useful in the treatment of trachoma,^[13] and it has been a standard treatment for leishmaniasis.^[14]

Berberine prevents and suppresses proinflammatory cytokines, E-selectin,^[15] and genes, and increases adiponectin expression^[16] which partly explains its versatile health effects. Berberine is a nucleic acid-binding isoquinoline alkaloid with wide potential therapeutic properties.^[17]

Newer and experimental uses

Antiarrhythmia

The antiarrhythmic effect of Berberine has been demonstrated in animal models and clinical studies. Berberine increases the cardiac action potential duration by inhibiting potassium channels.^[18] Berberine can be grouped as class III antiarrhythmic drug.

Diabetes, dyslipidemias and cardiovascular conditions

During the last few decades, many studies have shown berberine has various beneficial effects on the cardiovascular system and significant anti-inflammatory activities.^[19] A Canadian report suggested berberine can effectively reduce intracellular superoxide levels in LPS-stimulated macrophages. Such a restoration of cellular redox by berberine is mediated by its selective inhibition of gp91phox expression and enhancement of SOD activity.^[20]

Berberine exerts up-regulating activity on both the low-density-lipoprotein receptor (LDLR) and the insulin receptor (InsR). This one-drug-multiple-target characteristic might be suitable for the treatment of metabolic syndrome.^[21]^[22]

Diabetes mellitus

Berberine has been tested and used successfully in experimental^[23]^[24] and human diabetes mellitus.^[25]^[26]^[27]^[28]

Berberine has been shown to lower elevated blood glucose as effectively as metformin.^[29] The mechanisms of action include inhibition of aldose reductase,^[30] inducing glycolysis,^[31] preventing insulin resistance^[32]^[33] through increasing insulin receptor expression^[26] and acting like incretins.^[34] A new study suggested berberine may overcome insulin resistance via modulating key molecules in insulin signaling pathway, leading to increased glucose uptake in insulin-resistant cells.^[35]

Berberine might exert its insulinotropic effect in isolated rat islets by up-regulating the expression of hepatocyte nuclear factor 4 alpha, which probably acts solely or together with other HNFs to modulate glucokinase activity, rendering β cells more sensitive to glucose fluctuation and to respond more effectively to glucose challenge.^[36]

Berberine seems to inhibit human dipeptidyl peptidase-4 (DPP4), as well as the prodiabetic target human protein tyrosine phosphatase 1B (h-PTP 1B), which explain at least some of its antihyperglycemic activities.^[37] Berberine suppresses intestinal disaccharidases with beneficial metabolic effects in diabetic states.^[38]

A recent comprehensive metabolomics method, applied to 60 type 2 diabetics, suggested administration of berberine down-regulates the high level of free fatty acids which are known to be toxic to the pancreas and cause insulin resistance. These results suggest berberine might play a pivotal role in the treatment of type 2 diabetes, concluded the authors.^[25]

Berberine has been shown to boost the effects of metformin and 2,4-thiazolidinedione (TZD), and can partly replace the commercial drugs, which could lead to a reduction in toxicity and side effects of the latter.^[39]

Berberine inhibits FOXO1,^[40] which integrates insulin signaling with mitochondrial function. Inhibition of Foxo1 can improve hepatic metabolism during insulin resistance and the metabolic syndrome.^[41]

Lipids

Berberine lowers elevated blood total cholesterol, LDL cholesterol, triglycerides and atherogenic apolipoproteins (apo B) (Apo B),^[42] but the mechanism of action is distinct from that of statins.^[43]^[44]^[45] Berberine reduces LDL cholesterol by upregulating LDLR mRNA expression posttranscriptionally while downregulating the transcription of proprotein convertase subtilisin/kexin type 9 (PCSK9), a natural inhibitor of LDL receptor (LDLR),^[46] and increasing in the liver the expression of LDL receptors through extracellular signal-regulated kinase (ERK) signaling pathway,^[47] while statins inhibit cholesterol synthesis in the liver by blocking HMG-CoA-reductase. This explains why berberine does not cause side effects typical of statins. Berberine and plant stanols synergistically inhibit cholesterol absorption in hamsters.^[48]

Berberine seems to improve the arterial endothelial function in humans.^[27]^[49] Berberine activates AMP-activated protein kinase (AMPK),^[50] specifically extracellular signal-regulated kinases (ERK),^[51] which plays a central role in glucose and lipid metabolism,^[52]^[53] suppresses proinflammatory cytokines,^[54] and reduces MMP-9 and EMMPRIN expression,^[55] which are all beneficial changes for heart health.

Liver

Berberine reduces hepatic fat content in rats with nonalcoholic fatty liver disease.^[56] Berberine also prevents proliferation of hepatic stellate cells (HSCs), which are central for the development of fibrosis during liver injury.^[40]

Congestive heart failure

Experimental^[57]^[58]^[59] and clinical studies^[60]^[61] suggest berberine may be useful for patients with severe congestive heart failure.^[62]

Transplants

According to a Chinese report, combined use of berberine with cyclosporin A (CsA) could markedly increase the blood concentration of CsA and reduce the dosage of CsA required, save the cost for medical service, and shows no obvious adverse reaction in heart-transplant recipients.^[63]

Cancer

Berberine has drawn extensive attention towards its antineoplastic effects.^[64]^[65] It seems to suppress the growth of a wide variety of tumor cells, including breast cancer,^[66] leukemia, melanoma,^[67] epidermoid carcinoma, hepatoma, pancreatic cancer,^[68] oral carcinoma, tongue carcinoma,^[69] glioblastoma, prostate carcinoma and gastric carcinoma.^[70]^[71] Animal studies have shown that berberine can suppress chemical-induced carcinogenesis, clastogenesis,^[72] tumor promotion, tumor invasion,^[73]^[74]^[75]^[76]^[77] prostate cancer,^[78]^[79]^[80]^[81] neuroblastoma,^[82]^[83] and leukemia.^[49]^[84]

It is a radiosensitizer of tumor cells, but not of normal cells. How berberine mediates these effects is not fully understood, but its ability to inhibit angiogenesis and to modulate Mcl-1, Bcl-xL, cyclooxygenase (COX)-2, MDR, tumor necrosis factor (TNF)- and IL-6, iNOS, IL-12, intercellular adhesion molecule-1 and ELAM-1 expression, MCP-1 and CINC-1, cyclin D1,^[85] activator protein (AP-1), HIF-1, PPAR-, and topoisomerase II has been shown. By using yeast mutants, berberine was found to bind and inhibit stress-induced mitogen-activated protein kinase kinase activation. Because apoptotic, carcinogenic, and inflammatory effects and various gene products (such as TNF-α, IL-6, COX-2, adhesion molecules, cyclin D1, and MDR) modulated by berberine are regulated by the transcription factor nuclear factor- B (NF- B), it is postulated this pathway plays a major role in the action of berberine.^[86] Berberine suppressed NF-κB activation induced by various inflammatory agents and carcinogens. This alkaloid also suppressed constitutive NF-κB activation found in certain tumor cells. It seems to protect against side effects of radiation therapy in lung cancer.^[87] However, new studies suggest that while berberine decreases cell growth, it increases the side population (stem cell) fraction of H460 lung cancer cells.^[88] In lung cancer it can also act through suppression of TGF-β1-induced epithelial-to-mesenchymal transition.^[89] Berberine enhances chemosensitivity to some chemotherapeutic agents like irinotecan .^[90]

Berberine, 300 mg three times a day orally, also seems to inhibit complication of abdominal or pelvic radiation, called radiation-induced acute intestinal symptoms.^[91] The studies suggest its use in clinical development may be more as a cytostatic agent than a cytotoxic compound.

Mental health

Berberine seems to act as an herbal antidepressant and a neuroprotector against neurodegenerative disorders.^[92]^[93]^[94]^[95] Berberine inhibits prolyl oligopeptidase (POP) in a dose-dependent manner. Berberine is also known to bind to sigma receptors like many synthetic antidepressant drugs. As berberine is a natural compound that has been safely administered to humans, preliminary results suggest the initiation of clinical trials in patients with depression, bipolar affective disorder, schizophrenia, or related diseases in which cognitive capabilities are affected, with either the extract or pure berberine. New experimental results suggest berberine may have a potential for inhibition and prevention of Alzheimer's disease (AD), mainly through both cholinesterase (ChEs) inhibitory and β-amyloids pathways,^[96]^[97] and additionally through antioxidant capacities.^[98]

Other studies have shown berberine to increase noradrenaline and serotonin levels in the brain (rats) while inhibiting dopaminergic activity.^[99]^[100] The half-life of berberine in vivo seems to be three to four hours, thus suggesting administration three times a day if steady levels are to be achieved.^[101]

Intestinal disorders

Berberine can ameliorate proinflammatory cytokines-induced intestinal epithelial tight junction damage in vitro, and berberine may be one of the targeted therapeutic agents that can restore barrier function in intestinal disease states.^[102]^[103]

HIV/AIDS

A new study identified a key cellular mechanism underlying the protective effect of berberine on HIV PI-induced inflammatory response in macrophages. Modulation of the endoplasmic reticulum stress response represents a potential therapeutic target for various inflammatory diseases and metabolic syndromes, including HIV PI-associated atherosclerosis. The report shows the potential application of berberine as a complementary therapeutic agent for HIV/AIDS.^[104]

Contraindications

Berberine use in newborns has been associated with kernicterus, a bilirubin-induced brain dysfunction.^[105] Also, at dosages about 60-100 times as large as a human pharmacological dose, a small dose-response teratogenic effect was observed in rodents.^[106] For these reasons, berberine is not usually recommended for use during pregnancy, although there are some reason to believe that this may not be harmful.^[107]

Biosynthesis

Biosynthesis of berberine

The alkaloid berberine has a tetracyclic skeleton derived from a benzyltetrahydroisoquinoline system with the incorporation of an extra carbon atom provided by S-adenosyl methionine (SAM) via an N-methyl group. Formation of the berberine bridge is readily rationalized as an oxidative process in which the N-methyl group is oxidized to an iminium ion, and a cyclization to the aromatic ring occurs by virtue of the phenolic group.^[108]

Reticuline is known as the immediate precursor of protoberberine alkaloids in plants.^[109] Berberine is an alkaloid derived from tyrosine. L-DOPA and 4-hydroxypyruvic acid both come from L-Tyr. Although two tyrosine molecules are used in the biosynthetic pathway, only the phenylethylamine fragment of the tetrahydroisoquinoline ring system is formed via DOPA, the remaining carbon atoms come from tyrosine via 4-hydroxyphenylacetaldehyde. L-DOPA loses carbon dioxide to form dopamine 1. Likewise, 4-hydroxypyruvic acid also loses carbon dioxide to form 4-hydroxyphenyl-acetaldehyde 2. Dopamine 1 then reacts with 4-hydroxy-phenylacetaldehyde 2 to form (S)-norcolaurine 3 in a reaction similar to the Mannich reaction. After oxidation and methylation by SAM, (S)-reticuline 4 is formed. (S)-reticuline serves as a pivotal intermediate to other alkaloids. Oxidation of the tertiary amine then occurs and an iminium ion is formed 5. In a Mannich-like reaction the ortho position to the phenol is nucleophilic, and electrons are pushed to form 6. Product 6 then undergoes keto-enol tautomerism to form (S)-scoulerine, which is then methylated by SAM to form (S)-tetrahydrocolumbamine 7. Product 7 is then oxidized to form the methylenedioxy ring from the ortho-methoxyphenol, via an O₂-, NADPH- and cytochrome P-450-dependent enzyme, giving (S)-canadine 8. (S)-canadine is then oxidized to give the quaternary isoquinolinium system of berberine. This happens in two separate oxidation steps, both requiring molecular oxygen, with H₂O₂ and H₂O produced in the successive processes.^[110]

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UpToDate Contents

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1. 癌に対する補完代替療法 complementary and alternative therapies for cancer
2. アレルギー疾患の治療のための漢方薬 chinese herbal medicine for the treatment of allergic diseases

English Journal

Berberine activates Nrf2 nuclear translocation and protects against oxidative damage via a phosphatidylinositol 3-kinase/Akt-dependent mechanism in NSC34 motor neuron-like cells.

Hsu YY, Chen CS, Wu SN, Jong YJ, Lo YC.SourceGraduate Institute of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2012 Aug 15;46(5):415-25. Epub 2012 Mar 24.
Berberine (BBR) is a well-known anti-diabetic herbal medicine in Asia due to its beneficial effects on insulin sensitivity, glucose metabolism and glycolysis. Here, we identified the critical role of phosphatidylinositol 3-kinase (PI3K)/Akt involved BBR cellular defense mechanisms and first revealed
PMID 22469516

Effect of berberine hydrochloride on grass carp Ctenopharyngodon idella serum bactericidal activity against Edwardsiella ictaluri.

Ji C, Zhang de F, Li AH, Gong XN.SourceState Key Laboratory of Freshwater Ecology and Biotechnology, Institute of Hydrobiology, Chinese Academy of Sciences, Donghu road 7#, Wuhan 430072, PR China; Graduate University of Chinese Academy of Sciences, Beijing 100049, PR China.
Fish & shellfish immunology.Fish Shellfish Immunol.2012 Jul;33(1):143-5. Epub 2012 Apr 12.
Bactericidal activity of grass carp (Ctenopharyngodon idella) serum was significantly enhanced when pre-treated with 15 mg l(-1) or 3 mg l(-1) of berberine hydrochloride, an effective component of several commonly used herbal medicines in aquaculture. The complement consumption experiment demons
PMID 22521421

Japanese Journal

Berberine Inhibits Growth and Induces G1 Arrest and Apoptosis in Human Cholangiocarcinoma QBC939 Cells

He Wei,Wang Bin,Zhuang Yun [他]
Journal of pharmacological sciences 119(4), 341-348, 2012-08
NAID 40019386623

Formation and Conformation of Baicalin–Berberine and Wogonoside–Berberine Complexes

Wang Jing-Rong,Tanaka Takashi,Zhang Hong [他]
Chemical and Pharmaceutical Bulletin 60(6), 706-711, 2012-06
… It is well-known that baicalin–berberine complex (1) precipitates in the water decoction of numerous Chinese Medicinal formulae containing Radix Scutellariae and Rhizoma Coptidis or Cortex Phellodendri. … In the current study, ionic interaction between the carboxylate ion of baicalin and the quaternary ammonium ion of berberine was revealed to be responsible for the formation of 1 and wogonoside–berberine (2) by using FAB-MS and NMR titration experiments. …
NAID 40019278366

Related Pictures

★リンクテーブル★

リンク元	「ベルベリン」
拡張検索	「berberine tannate」「berberine sulfate」「berberine alkaloid」

「ベルベリン」

Berberine
Names
	Other names umbellatine; 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
Identifiers
CAS Registry Number	2086-83-1
ChEBI	CHEBI:16118
ChEMBL	ChEMBL12089
ChemSpider	2263
DrugBank	DB04115
	InChI InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1 ; Key: YBHILYKTIRIUTE-UHFFFAOYSA-N ; InChI=1/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1; Key: YBHILYKTIRIUTE-UHFFFAOYAJ ;
Jmol-3D images	Image
PubChem	2353
	SMILES O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5 ;
UNII	0I8Y3P32UF
Properties
Chemical formula	C20H18NO4+
Molar mass	336.36122 g/mol
Appearance	yellow solid
Melting point	145 °C (293 °F; 418 K)
Solubility in water	slowly soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	Infobox references

　　[★]

英: berberine
ラ: berberinum
商: エルベン、キョウベリン、フェロベリン、リーダイ
関: 塩化ベルベリン berberine chloride; 塩酸ベルベリン berberine hydrochloride、berberine sulfate、タンニン酸ベルベリン berberine tannate

GOO. 998

止瀉薬

殺菌剤

薬理作用

殺菌作用など

「berberine tannate」

　　[★]

タンニン酸ベルベリン

関: berberine、berberine chloride、berberine sulfate

「berberine sulfate」

　　[★]

硫酸ベルベリン

関: berberine、berberine chloride、berberine tannate

「berberine alkaloid」

　　[★]

ベルベリン型アルカロイド

[Merck-1] The Merck Index, 10th Ed. (1983), p.165, Rahway: Merck & Co.

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[unijena-3] Weiß, Dieter (2008). "Fluoreszenzfarbstoffe in der Natur" (in German). Retrieved 17 July 2009.

[sigma2-4] "B3251 Berberine chloride form". Sigma-Aldrich. 2013. Retrieved 2 Aug 2013.

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[8] Yu HH, Kim KJ, Cha JD, Kim HK, Lee YE, Choi NY, You YO (2005). "Antimicrobial activity of berberine alone and in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus". Journal of Medicinal Food 8 (4): 454–61. doi:10.1089/jmf.2005.8.454. PMID 16379555.

[9] "Poster Presentations". FEBS Journal 277: 37. 2010. doi:10.1111/j.1742-4658.2010.07680.x.

[10] Li Y., Zuo G.-Y. 'Advances in studies on antimicrobial activities of alkaloids" Chinese Traditional and Herbal Drugs 2010 41:6 (1006-1014)

[11] Stermitz FR, Lorenz P, Tawara JN, Zenewicz LA, Lewis K (February 2000). "Synergy in a medicinal plant: antimicrobial action of berberine potentiated by 5'-methoxyhydnocarpin, a multidrug pump inhibitor". Proceedings of the National Academy of Sciences of the United States of America 97 (4): 1433–7. Bibcode:2000PNAS...97.1433S. doi:10.1073/pnas.030540597. PMC 26451. PMID 10677479.

[12] Zhang S, Zhang B, Xing K, Zhang X, Tian X, Dai W (2010). "Inhibitory effects of golden thread (Coptis chinensis) and berberine on Microcystis aeruginosa". Water Science & Technology 61 (3): 763. doi:10.2166/wst.2010.857. PMID 20150713.

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[15] Hu Y, Chen X, Duan H, Hu Y, Mu X (2009). "Chinese herbal medicinal ingredients inhibit secretion of IL-6, IL-8, E-selectin and TXB2in LPS-induced rat intestinal microvascular endothelial cells". Immunopharmacology and Immunotoxicology 31 (4): 550–5. doi:10.3109/08923970902814129. PMID 19874221.

[16] Choi BH, Kim YH, Ahn IS, Ha JH, Byun JM, Do MS (2009). "The inhibition of inflammatory molecule expression on 3T3-L1 adipocytes by berberine is not mediated by leptin signaling". Nutrition Research and Practice 3 (2): 84–8. doi:10.4162/nrp.2009.3.2.84. PMC 2788178. PMID 20016706.

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berberine