| 词条 | Berberine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 457785306 | ImageFile1_Ref = {{chemboximage|correct|??}} | ImageFile1 =Berberin.svg | ImageSize1 = | ImageFile2_Ref = {{chemboximage|correct|??}} | ImageFile2 =Berberine 3D.png | ImageSize2 = | IUPACName = | OtherNames =Umbellatine; 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium |Section1={{Chembox Identifiers | 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 | InChIKey = YBHILYKTIRIUTE-UHFFFAOYAJ | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YBHILYKTIRIUTE-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo =2086-83-1 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2263 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 12089 | PubChem =2353 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 0I8Y3P32UF | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 16118 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB04115 | SMILES = O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5 }} |Section2={{Chembox Properties | C=20|H=18|N=1|O=4 | Formula_Charge =+ | Appearance =Yellow solid | Density = | MeltingPtC = 145 | MeltingPt_ref = [1] | BoilingPt = | Solubility =Slowly soluble[1] |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids found in such plants as Berberis (e.g. Berberis vulgaris – barberry, Berberis aristata – tree turmeric, Mahonia aquifolium – Oregon-grape, Hydrastis canadensis – goldenseal, Xanthorhiza simplicissima – yellowroot, Phellodendron amurense[2] – Amur cork tree, Coptis chinensis – Chinese goldthread, Tinospora cordifolia, Argemone mexicana – prickly poppy, and Eschscholzia californica – Californian poppy). Berberine is usually found in the roots, rhizomes, stems, and bark.{{citation needed|date=November 2011}} 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.[3] Under ultraviolet light, berberine shows a strong yellow fluorescence,[4] so it is useful in histology for staining heparin in mast cells.[5] As a natural dye, berberine has a color index of 75160. Folk medicineBerberine was supposedly used in China as a folk 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.[6] ResearchAlthough the clinical research has been low in quality, studies have been conducted to determine if berberine may affect diabetes[7] or blood lipids.[8][9] As of 2018, there is insufficient evidence to conclude that berberine is safe or effective for any condition.[10] BiosynthesisThe alkaloid berberine has a tetracyclic skeleton derived from a benzyltetrahydroisoquinoline system with the incorporation of an extra carbon atom provided by S-adenosyl methionine 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.[11] Reticuline is known as the immediate precursor of protoberberine alkaloids in plants.[12] Berberine is an alkaloid derived from tyrosine. L-DOPA and 4-hydroxypyruvic acid both come from L-tyrosine. 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-hydroxyphenylacetaldehyde 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.[13]See also
References1. ^1 The Merck Index, 10th Ed. (1983), p.165, Rahway: Merck & Co. {{Other antibacterials}}{{PPAR modulators}}{{Sigma receptor modulators}}2. ^{{cite journal | vauthors = Zhang Q, Cai L, Zhong G, Luo W | title = Simultaneous determination of jatrorrhizine, palmatine, berberine, and obacunone in Phellodendri Amurensis Cortex by RP-HPLC | journal = Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica | volume = 35 | issue = 16 | pages = 2061–4 | year = 2010 | pmid = 21046728 | doi = 10.4268/cjcmm20101603 }} 3. ^{{Cite journal|last=Gulrajani|first=ML|date=2001|title=Present status of natural dyes|url=http://nopr.niscair.res.in/handle/123456789/24928|journal=Indian Journal of Fibre & Textile Research|language=en-US|volume=26|pages=191–201|via=NISCAIR Online Periodicals Repository}} 4. ^{{cite web |title=Fluoreszenzfarbstoffe in der Natur |url=http://www.chemie.uni-jena.de/institute/oc/weiss/naturstoffe.htm |first=Dieter |last=Weiß |year=2008 |accessdate=17 July 2009 |language=German}} 5. ^{{cite web |title=B3251 Berberine chloride form |url=http://www.sigmaaldrich.com/catalog/product/sigma/b3251?lang=en®ion=US |publisher=Sigma-Aldrich |year=2013 |accessdate=2 Aug 2013}} 6. ^{{Cite book|url=https://www.worldcat.org/oclc/41048949|title=The divine farmer's materia medica : a translation of the Shen Nong Ben Cao Jing|date=1998|publisher=Blue Poppy Press|others=Yang, Shouzhong|isbn=9780936185965|edition=1st|location=Boulder, CO|oclc=41048949}} 7. ^{{cite journal |vauthors=Dong H, Wang N, Zhao L, Lu F |title=Berberine in the treatment of type 2 diabetes mellitus: a systemic review and meta-analysis |journal=Evid Based Complement Alternat Med |volume=2012 |issue= |pages=591654 |year=2012 |pmid=23118793 |pmc=3478874 |doi=10.1155/2012/591654 |url=}} 8. ^{{cite journal | last=Ju | first=Jianqing | last2=Li | first2=Jingen | last3=Lin | first3=Qian | last4=Xu | first4=Hao | title=Efficacy and safety of berberine for dyslipidaemias: A systematic review and meta-analysis of randomized clinical trials | journal=Phytomedicine | volume=50 | date=15 November 2018 | issn=0944-7113 | pmid=30466986 | doi=10.1016/j.phymed.2018.09.212 | pages=25–34}} 9. ^{{cite journal |vauthors=Dong H, Zhao Y, Zhao L, Lu F |title=The effects of berberine on blood lipids: a systemic review and meta-analysis of randomized controlled trials |journal=Planta Med. |volume=79 |issue=6 |pages=437–46 |year=2013 |pmid=23512497 |doi=10.1055/s-0032-1328321 |url=}} 10. ^{{cite web | title=Berberine: MedlinePlus Supplements | publisher=MedlinePlus, National Library of Medicine, US National Institutes of Health | date=19 January 2019 | url=https://medlineplus.gov/druginfo/natural/1126.html | access-date=15 February 2019}} 11. ^{{cite book |author=Dewick, P. |title=Medicinal Natural Products: A Biosynthetic Approach |edition=3rd |publisher=Wiley |location=West Sussex, England |year=2009 |page=357 |isbn=0-471-49641-3}} 12. ^{{cite journal | vauthors = Park SU, Facchini PJ | title = Agrobacterium rhizogenes-mediated transformation of opium poppy, Papaver somniferum l., and California poppy, Eschscholzia californica cham., root cultures | journal = Journal of Experimental Botany | volume = 51 | issue = 347 | pages = 1005–16 | date = June 2000 | pmid = 10948228 | doi = 10.1093/jexbot/51.347.1005 }} 13. ^{{cite book |author=Dewick, P. |title=Medicinal Natural Products: A Biosynthetic Approach |edition=3rd |publisher=Wiley |location=West Sussex, England |year=2009 |page=358 |isbn=0-471-49641-3}} 8 : Alkaloids|Aromatase inhibitors|Quaternary ammonium compounds|Phenol ethers|Nitrogen heterocycles|Benzodioxoles|Antibiotics|DNA-binding substances |
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