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Berberine - Wikipedia

From Wikipedia, the free encyclopedia

Quaternary ammonium cation

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-2

H

-7λ

5

-[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 CAS Number

3D model (

JSmol

)

Beilstein Reference 3570374 ChEBI ChEMBL ChemSpider DrugBank ECHA InfoCard 100.016.572 EC Number KEGG PubChem CID UNII CompTox Dashboard (EPA) InChI SMILES Properties Chemical formula C20H18NO4+ Molar mass 336.366 g·mol−1 Appearance Yellow solid Melting point 145 °C (293 °F; 418 K)[3] Solubility in water Slowly soluble[3]

Except where otherwise noted, data are given for materials in their

standard state

(at 25 °C [77 °F], 100 kPa).

N verify

(

what is YN

?)

Infobox references

Chemical compound

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids, occurring naturally as a secondary metabolite in some plants including species of Berberis, from which its name is derived.

Due to their yellow pigmentation, raw Berberis materials were once commonly used to dye wool, leather, and wood.[4] Under ultraviolet light, berberine shows a strong yellow fluorescence,[5] making it useful in histology for staining heparin in mast cells.[6] As a natural dye, berberine has a color index of 75160.

Biological sources[edit]

The following plants are biological sources of berberine:

Berberine is usually found in the roots, rhizomes, stems, and bark.[8]

Biosynthesis of berberine

The alkaloid berberine 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 the N-methyl group, supplied by S-adenosyl methionine (SAM), is oxidized to an iminium ion, and a cyclization to the aromatic ring occurs by virtue of the phenolic group.[9]

Reticuline is the immediate precursor of protoberberine alkaloids in plants.[10] 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 phenethylamine fragment of the tetrahydroisoquinoline ring system is formed via DOPA[definition needed]; the remaining carbon atoms come from tyrosine via 4-hydroxyphenylacetaldehyde.[11]

Studies on the pharmacological effects of berberine, including medical uses, are preliminary: some studies consider cell cultures or animal models, whereas clinical trials investigating the use of berberine in humans are limited.[12]

A 2023 review concluded that berberine may improve lipid concentrations.[13] High-quality, large clinical studies would be required to properly evaluate the effectiveness and safety of berberine in various health conditions.[12]

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. Studies linking berberine to health benefits are limited. The quality of berberine supplements can vary across brands. A 2017 study found that out of 15 different products sold in the U.S., only six contained at least 90% of the specified berberine quantity.[14][15]

Longer-term human clinical trials have reported flatulence and diarrhea as common issues. The problem can be replicated in rats, with disruption of the gut microbiome to blame.[16]

Berberine is known to inhibit the activity of CYP3A4, an important enzyme involved in drug metabolism and clearance of endogenous substances, including steroid hormones such as cortisol, progesterone and testosterone. Several studies have demonstrated that berberine can increase the concentrations of cyclosporine in renal transplant patients and midazolam in healthy adult volunteers, confirming its inhibitory effect on CYP3A4.[17][18][19]

It is approved in China as an over-the-counter (OTC) drug for diarrhea treatment. The package insert claims efficacy against E. coli and Shigella spp.[20]

The Chinese package insert contraindicates berberine for people with hemolytic anemia and with glucose-6-phosphate dehydrogenase deficiency (G6PD deficiency). The insert also specifically precautions its use in children with G6PD deficiency because it can produce hemolytic anemia and jaundice.[20]

  1. ^ a b c The 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. ISBN 978-0-85404-182-4.
  3. ^ a b The 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. Archived from the original on 2021-11-20. Retrieved 2017-12-28 – via NISCAIR Online Periodicals Repository.
  5. ^ Weiß D (2008). "Fluoreszenzfarbstoffe in der Natur" (in German). Archived from the original on 9 March 2007. Retrieved 17 July 2009.
  6. ^ "B3251 Berberine chloride form". Sigma-Aldrich. 2013. Archived from the original on 7 September 2012. Retrieved 2 Aug 2013.
  7. ^ 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. ISBN 978-3-319-41332-7. ISSN 0065-2598. PMID 27671811.
  8. ^ "Berberine". PubChem, National Library of Medicine, US National Institutes of Health. March 9, 2020. Archived from the original on March 5, 2016. Retrieved March 10, 2020.
  9. ^ Dewick P (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). West Sussex, England: Wiley. p. 357. ISBN 978-0-471-49641-0.
  10. ^ 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. PMID 10948228.
  11. ^ Dewick P (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). West Sussex, England: Wiley. p. 358. ISBN 978-0-471-49641-0.
  12. ^ a b Song 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. PMID 32335802. S2CID 216111561.
  13. ^ 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. PMID 37183391. S2CID 258687419. Archived from the original on 2023-06-01. Retrieved 2023-08-28.
  14. ^ 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. PMC 5807210. PMID 28792254.
  15. ^ Subbaraman N (14 June 2023). "The Cheaper Weight-Loss Alternative Riding the Ozempic Wave". Wall Street Journal. Archived from the original on 29 December 2023. Retrieved 29 December 2023.
  16. ^ Yue SJ, Liu J, Wang WX, Wang AT, Yang XY, Guan HS, Wang CY, Yan D (August 2019). "Berberine treatment-emergent mild diarrhea associated with gut microbiota dysbiosis". Biomedicine & Pharmacotherapy. 116: 109002. doi:10.1016/j.biopha.2019.109002. PMID 31154270.
  17. ^ Abushammala I (October 2021). "Tacrolimus and herbs interactions: a review". Pharmazie. 76 (10): 468–472. doi:10.1691/ph.2021.1684. PMID 34620272.
  18. ^ Hermann R, von Richter O (September 2012). "Clinical evidence of herbal drugs as perpetrators of pharmacokinetic drug interactions". Planta Med. 78 (13): 1458–77. doi:10.1055/s-0032-1315117. PMID 22855269.
  19. ^ Niwa T, Murayama N, Imagawa Y, Yamazaki H (May 2015). "Regioselective hydroxylation of steroid hormones by human cytochromes P450". Drug Metab Rev. 47 (2): 89–110. doi:10.3109/03602532.2015.1011658. PMID 25678418.
  20. ^ a b 精华制药集团股份有限公司. "盐酸小檗碱片说明书" [Package Insert: Berberine Hydrochloride Tablets]. ypk.39.net (in Chinese).
Muscarinic acetylcholine receptor modulators mAChRsTooltip Muscarinic acetylcholine receptors Agonists Antagonists Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators

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