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Berberine

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Berberine
Names
IUPAC name
9,10-Dimethoxy-7,8,13,13a-tetradehydro-2′H-[1,3]dioxolo[4′,5′:2,3]berbin-7-ium
Systematic IUPAC name
9,10-Dimethoxy-5,6-dihydro-2H-7λ5-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ylium[2]
Other names
Umbellatine;[1]
5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;[1]
7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium[1]
Identifiers
3D model (JSmol)
3570374
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.016.572Edit this at Wikidata
EC Number
  • 218-229-1
KEGG
UNII
  • 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+1checkY
    Key: YBHILYKTIRIUTE-UHFFFAOYSA-NcheckY
  • 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
  • O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5
Properties
C20H18NO4+
Molar mass 336.366g·mol−1
Appearance Yellow solid
Melting point 145 °C (293 °F; 418 K)[3]
Slowly soluble[3]
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Berberineis aquaternary ammoniumsalt from the protoberberine group ofbenzylisoquinoline alkaloids,occurring naturally as asecondary metabolitein some plants including species ofBerberis,from which its name is derived.

Due to their yellowpigmentation,rawBerberismaterials were once commonly used to dye wool, leather, and wood.[4]Underultraviolet light,berberine shows a strong yellowfluorescence,[5]making it useful inhistologyforstainingheparininmast cells.[6]As a natural dye, berberine has acolor indexof 75160.

Research

[edit]

Studies on the pharmacological effects of berberine, including its potential use as a medicine, are preliminarybasic research:some studies are conducted on cell cultures or animal models, whereasclinical trialsinvestigating the use of berberine in humans are limited.[7]A 2023 review study stated that berberine may improve lipid concentrations.[8]High-quality, large clinical studies are needed to properly evaluate the effectiveness and safety of berberine in various health conditions, because existing studies are insufficient to draw reliable conclusions.[7]

Berberine supplements are widely available in the U.S. but have not been approved by the U.S.Food and Drug Administration(FDA) for any specific medical use. Researchers publicly warn that studies linking berberine to supposed health benefits are limited. Furthermore, the quality of berberine supplements can vary between different brands. A study conducted in 2017 found that out of 15 different products sold in the U.S., only six contained at least 90% berberine content.[9][10]

Biological sources

[edit]

Berberine is usually found in the roots,rhizomes,stems, and bark.[12]

Biosynthesis

[edit]
Biosynthesis of berberine

Thealkaloidberberine has a tetracyclic skeleton derived from a benzyltetrahydroisoquinoline system with the incorporation of an extra carbon atom as a bridge. Formation of the berberine bridge is rationalized as an oxidative process in which theN-methyl group,supplied byS-adenosyl methionine(SAM), is oxidized to animinium ion,and a cyclization to the aromatic ring occurs by virtue of the phenolic group.[13]

Reticulineis the immediate precursor of protoberberine alkaloids in plants.[14]Berberine is an alkaloid derived fromtyrosine.L-DOPAand 4-hydroxypyruvic acid both come fromL-tyrosine. Although two tyrosine molecules are used in the biosynthetic pathway, only thephenethylaminefragment of thetetrahydroisoquinolinering system is formed via DOPA; the remaining carbon atoms come from tyrosine via 4-hydroxyphenylacetaldehyde.[15]

References

[edit]
  1. ^abcThe Merck Index, 14th ed., 1154. Berberine
  2. ^IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-73.3.1". In Favre HA, Powell WH (eds.).Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013.IUPAC–RSC.ISBN978-0-85404-182-4.
  3. ^abThe Merck Index,10th Ed. (1983), p.165, Rahway: Merck & Co.
  4. ^Gulrajani ML (2001)."Present status of natural dyes".Indian Journal of Fibre & Textile Research.26:191–201.Archivedfrom the original on 2021-11-20.Retrieved2017-12-28– via NISCAIR Online Periodicals Repository.
  5. ^Weiß D (2008)."Fluoreszenzfarbstoffe in der Natur"(in German).Archivedfrom the original on 9 March 2007.Retrieved17 July2009.
  6. ^"B3251 Berberine chloride form".Sigma-Aldrich.2013.Archivedfrom the original on 7 September 2012.Retrieved2 Aug2013.
  7. ^abSong D, Hao J, Fan D (October 2020). "Biological properties and clinical applications of berberine".Front Med.14(5): 564–582.doi:10.1007/s11684-019-0724-6.PMID32335802.S2CID216111561.
  8. ^Hernandez AV, Hwang J, Nasreen I, et al. (2023)."Impact of Berberine or Berberine Combination Products on Lipoprotein, Triglyceride and Biological Safety Marker Concentrations in Patients with Hyperlipidemia: A Systematic Review and Meta-Analysis".J Diet Suppl.21(2): 242–259.doi:10.1080/19390211.2023.2212762.PMID37183391.S2CID258687419.Archivedfrom the original on 2023-06-01.Retrieved2023-08-28.
  9. ^Funk RS, Singh RK, Winefield RD, Kandel SE, Ruisinger JF, Moriarty PM, Backes JM (May 2018)."Variability in Potency Among Commercial Preparations of Berberine".J Diet Suppl.15(3): 343–351.doi:10.1080/19390211.2017.1347227.PMC5807210.PMID28792254.
  10. ^Subbaraman N (14 June 2023)."The Cheaper Weight-Loss Alternative Riding the Ozempic Wave".Wall Street Journal.Archivedfrom the original on 29 December 2023.Retrieved29 December2023.
  11. ^Cicero AF, Baggioni A (2016). "Berberine and Its Role in Chronic Disease".Anti-inflammatory Nutraceuticals and Chronic Diseases.Advances in Experimental Medicine and Biology. Vol. 928. Cham: Springer International Publishing. pp. 27–45.doi:10.1007/978-3-319-41334-1_2.ISBN978-3-319-41332-7.ISSN0065-2598.PMID27671811.
  12. ^"Berberine".PubChem, National Library of Medicine, US National Institutes of Health. March 9, 2020.Archivedfrom the original on March 5, 2016.RetrievedMarch 10,2020.
  13. ^Dewick P (2009).Medicinal Natural Products: A Biosynthetic Approach(3rd ed.). West Sussex, England: Wiley. p.357.ISBN978-0-471-49641-0.
  14. ^Park SU, Facchini PJ (June 2000). "Agrobacterium rhizogenes-mediated transformation of opium poppy,Papaver somniferum l.,and California poppy,Eschscholzia californica cham.,root cultures ".Journal of Experimental Botany.51(347): 1005–16.doi:10.1093/jexbot/51.347.1005.PMID10948228.
  15. ^Dewick P (2009).Medicinal Natural Products: A Biosynthetic Approach(3rd ed.). West Sussex, England: Wiley. p.358.ISBN978-0-471-49641-0.
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