Berberine - Wikipedia, the free encyclopedia

http://en.wikipedia.org/wiki/Berberine

Berberine
From Wikipedia, the free encyclopedia

Berberine

Identiers 633-66-9

0I8Y3P32UF DB04115 CHEBI:16118 CHEMBL12089 Image 1 (http://chemapps.stolaf.edu /jmol/jmol.php?model=O1c2c%28OC1%29cc5c%28c2%29c4cc3ccc%28OC%29c%28OC%29c3c%5Bn %2B%5D4CC5)

SMILES InChI

Properties
18NO 4+

336.36122 g/mol (verify) (what is: / ?)

pt 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 protoberberine group of isoquinoline alkaloids. It is found in such plants as Berberis (e.g. Berberis aquifolium (Oregon grape), Berberis vulgaris (Barberry), and Berberis aristata (Tree Turmeric)), Hydrastis canadensis (Goldenseal), Phellodendron amurense[1] (Amur Cork Tree, Huang Bai, Huang Po, Po Mu) and Coptis chinensis (Chinese Goldthread, Huang-Lian, Huang-Lien), and Tinospora cordifolia, and to a smaller extent in Argemone mexicana (Prickly Poppy) and Eschscholzia californica (Californian Poppy). Berberine is usually [citation needed] found in the roots, rhizomes, stems, and bark.

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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 [2] northern India. Under ultraviolet light, berberine shows a strong yellow uorescence. Because of this it is used in histology for staining heparin in mast cells. [3] As a natural dye, berberine has a Colour Index (CI) of 75160.

Contents
1 Traditional use 2 Newer and experimental uses 2.1 Diabetes, dyslipidemias and cardiovascular conditions 2.1.1 Diabetes mellitus 2.1.2 Lipids 2.1.3 Liver 2.1.4 Congestive heart failure 2.1.5 Transplants 2.2 Cancer 2.3 Mental health 2.4 Intestinal disorders 2.5 HIV 3 Biosynthesis 4 See also 5 References

Traditional use
As a traditional medicine or dietary supplement, berberine has shown some activity against fungal infections, Candida albicans, yeast, parasites, and bacterial/viral [4][5] Berberine seems to exert synergistic eects with uconazole even in infections. [6] drug-resistant Candida albicans infections. Some research has been undertaken into possible use against MRSA infection. [7] Berberine is considered antibiotic.[8][9] When applied in vitro and in combination with methoxyhydnocarpin, an inhibitor of multidrug resistance pumps, berberine inhibits [10] and Microcystis aeruginosa [11], a toxic growth of Staphylococcus aureus cyanobacterium.
[citation needed] There is some Berberine is a component of some eye drop formulations. [12] and it has been a standard evidence it is useful in the treatment of trachoma, [13] treatment for leishmaniasis.

Berberine prevents and suppresses proinammatory cytokines, E-selectin, [14] and [15] which partly explains its versatile genes, and increases adiponectin expression

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health eects. Berberine is a nucleic acid-binding isoquinolone alkaloid with wide [16] potential therapeutic properties.

Newer and experimental uses

Diabetes, dyslipidemias and cardiovascular conditions
During the last few decades, many studies have shown berberine has various benecial [17] A eects on the cardiovascular system and signicant anti-inammatory activities. Canadian report suggested berberine can eectively 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 [18] activity. Berberine exerts up-regulating activity on both the low-density-lipoprotein receptor (LDLR) and the insulin receptor (InsR). This one-drug-multiple-target characteristic [19][20] might be suitable for the treatment of metabolic syndrome. Diabetes mellitus Berberine has been tested and used successfully in experimental[21][22] and human [23][24][25][26] diabetes mellitus. Berberine has been shown to lower elevated blood glucose as eectively as [27] The mechanisms of action include inhibition of aldose reductase,[28] metformin. inducing glycolysis,[29] preventing insulin resistance[30][31] through increasing insulin [24] and acting like incretins.[32] A new study suggested berberine receptor expression may overcome insulin resistance via modulating key molecules in insulin signaling [33] pathway, leading to increased glucose uptake in insulin-resistant cells. Berberine might exert its insulinotropic eect 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 cells more sensitive to [34] glucose uctuation and to respond more eectively to glucose challenge. Berberine seems to inhibit human dipeptidyl peptidase-4 (DPP IV), as well as the pro-diabetic target human protein tyrosine phosphatase 1B (h-PTP 1B), which explain at [35] Berberine suppresses intestinal least some of its anti-hyperglycemic activities. [36] disaccharidases with benecial metabolic eects in diabetic states. A recent comprehensive metabonomics 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, [23] concluded the authors. Berberine has been shown to boost the eects of metformin and 2,4-thiazolidinedione
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(THZ), and can partly replace the commercial drugs, which could lead to a reduction in [37] toxicity and side eects of the latter. Berberine inhibits Foxo1,[38] which integrates insulin signaling with mitochondrial function. Inhibition of Foxo1 can improve hepatic metabolism during insulin resistance [39] and the metabolic syndrome. Lipids Berberine lowers elevated blood total cholesterol, LDL cholesterol, triglycerides and [40] but the mechanism of action is distinct atherogenic apolipoproteins (apo B) (Apo B), [41][42][43] Berberine reduces LDL cholesterol by upregulating LDLR mRNA from statins. expression posttranscriptionally while downregulating the transcription of proprotein convertase subtilisin/kexin type 9 (PCSK9), a natural inhibitor of LDL receptor [44] and increasing in the liver the expression of LDL receptors through (LDLR), [45] while statins inhibit extracellular signal-regulated kinase (ERK) signaling pathway, cholesterol synthesis in the liver by blocking HMG-CoA-reductase. This explains why berberine does not cause side eects typical to statins. Berberine and plant stanols [46] synergistically inhibit cholesterol absorption in hamsters. Berberine seems to improve the arterial endothelial function in humans. [25][47] Berberine activates AMP-activated protein kinase (AMPK),[48] specically extracellular [49] which plays a central role in glucose and lipid signal-regulated kinases (ERK), [50][51] suppresses proinammatory cytokines,[52] and reduces MMP-9 and metabolism, [53] which are all benecial changes for heart health. EMMPRIN expression, Liver Morevover, berberine reduces hepatic fat content in the rats of non-alcoholic fatty liver [54] Berberine also prevents proliferation of hepatic stellate cells disease (NAFLD). [38] (HSCs), which are central for the development of brosis during liver injury. Congestive heart failure Experimental[55][56][57] and clinical studies[58][59] suggest berberine may be useful for patients with severe congestive heart failure. Anti-atherosclerosis properties.[60] Transplants According to a Chinese report, combined use of berberine with ciclosporin 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 [61] heart-transplant recipients.

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Cancer
Berberine has drawn extensive attention towards its antineoplastic eects. [62][63] It seems to suppress the growth of a wide variety of tumor cells, including breast [64] leukemia, melanoma,[65] epidermoid carcinoma, hepatoma, pancreatic cancer, [66] oral carcinoma, tongue carcinoma,[67] glioblastoma, prostate carcinoma and cancer, [68][69] Animal studies have shown that berberine can suppress gastric carcinoma. [70] tumor promotion, tumor invasion, chemical-induced carcinogenesis, clastogenesis , [71][72][73][74][75] [76][77][78][79] prostate cancer, neuroblastoma,[80][81] and leukemia. [47][82] It is a radiosensitizer of tumor cells but not of normal cells. How berberine mediates these eects 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 [83] activator protein (AP-1), HIF-1 , ELAM-1 expression, MCP-1 and CINC-1, cyclin D1, 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 inammatory eects and various gene products (such as TNF-, IL-6, COX-2, adhesion molecules, cyclin D1, and MDR) modulated by berberine are regulated by the transcription factor nuclear factor- B (NF[84] B), it is postulated this pathway plays a major role in the action of berberine. Berberine suppressed NF-B activation induced by various inammatory agents and carcinogens. This alkaloid also suppressed constitutive NF-B activation found in certain tumor cells. It seems to protect against side eects of radiation therapy in lung [85] cancer. Berberine, 300 mg three times a day orally, also seems to inhibit complication of abdominal or pelvic radiation, called radiation-induced acute intestinal symptoms [86] The studies suggest its use in clinical development may be more as a (RIAISs). cytostatic agent than a cytotoxic compound.

Mental health
Berberine seems to act as an herbal antidepressant and a neuroprotector against [87][88][89][90] Berberine inhibits prolyl oligopeptidase neurodegenerative disorders. (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 aective disorder, schizophrenia, or related diseases in which cognitive capabilities are aected, 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 [91][92] and additionally cholinesterase (ChEs)inhibitory and -amyloids pathways, [93] through antioxidant capacities. Other studies have shown berberine to increase noradrenaline and serotonin levels in [94][95] The half-life of berberine the brain (rats) while inhibiting dopaminergic activity.
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in vivo seems to be three to four hours, thus suggesting administration three times a [96] day if steady levels are to be achieved. Berberine seems to be able to antagonize orexin receptors, which may partly explain its metabolic, anti-Alzheimer and neurotransmitter modulating properties. [1] (http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=12456) Berberine may also act in a manner comparable to Tianeptine by increasing the number [97] of serotonin transporters available in the brain, enhacing the reuptake of serotonin.

Intestinal disorders
Berberine can ameliorate proinammatory cytokines-induced intestinal epithelial tight junction damage in vitro, and berberine may be one of the targeted therapeutic agents [98][99] that can restore barrier function in intestinal disease states.

HIV
A new study identied a key cellular mechanism underlying the protective eect of berberine on HIV PI-induced inammatory response in macrophages. Modulation of the endoplasmic reticulum (ER) stress response represents a potential therapeutic target for various inammatory diseases and metabolic syndromes, including HIV PI-associated atherosclerosis. The report shows the potential application of berberine [100] as a complementary therapeutic agent for HIV infection.

Biosynthesis
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 [101] group. (S)-reticuline is known as the immediate precursor of [102] Berberine is an protoberberine alkaloids in plants. 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-

Biosynthesis of Berberine

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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-450dependent 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 [103] processes.

See also
Sanguinarine, a plant based compound with very similar chemical classication as berberine Coptisine for a related pharmacological discussion Goldenseal for a related pharmacological discussion Jatrorrhizine another protoberberine alkaloid

References
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