Historically, Zanthoxylum (Prickly ash) bark was used in traditional medicine.[1]

Def. any "of many organic (often[2] heterocyclic) bases that occur in nature and often have medicinal properties"[3] is called an alkaloid.

Species identified in Nigeria contains several types of alkaloids including benzophenanthridines (nitidine, dihydronitidine, oxynitidine, fagaronine, dihydroavicine, chelerythrine, dihydrochelerythrine, methoxychelerythrine, norchelerythrine, oxychelerythrine, decarine and fagaridine), furoquinolines (dictamine, 8-methoxydictamine, skimmianine, 3-dimethylallyl-4-methoxy-2-quinolone), carbazoles (3-methoxycarbazole, glycozoline), aporphines (berberine, tembetarine,[4] magnoflorine, M-methyl-corydine), canthinones (6-canthinone), acridones (1-hydroxy-3-methoxy-10-methylacridon-9-one, 1-hydroxy-10-methylacridon-9-one, zanthozolin), and aromatic and aliphatic amides.[5] Hydroxy-alpha sanshool is a bioactive component of plants from the genus Zanthoxylum, including the Sichuan pepper.

Aporphines edit

Aporphines include berberine and tembetarine found in Prickly ash bark.[4]

Benzophenanthridines edit

Benzophenanthridines incude nitidine, dihydronitidine, oxynitidine, fagaronine, dihydroavicine, chelerythrine, dihydrochelerythrine, methoxychelerythrine, norchelerythrine, oxychelerythrine, decarine and fagaridine found in Prickly ash bark.[4]

Berberine edit

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids found in such plants as Berberis, such as Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape), Hydrastis canadensis (goldenseal), Xanthorhiza simplicissima (yellowroot), Phellodendron amurense (Amur cork tree),[6] 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.[7]

The safety of using berberine for any condition is not adequately defined by evidence-based medicine, high-quality clinical research.[8]

Its potential for causing adverse effects is high, including untoward interactions with prescription drugs, reducing the intended effect of established therapies.[8] Berberine inhibits the CYP2D6 and CYP3A4 enzymes which are involved in metabolism of endogenous substances and xenobiotics, including many prescription drugs.[9][10]

It is particularly unsafe for use in children.[8] On the other hand, in May 2021, a comprehensive review article was published that highlighted the efficacy of berberine as a promising anti-oncogenic herpesvirus drug.[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 phenethylamine 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 S-Adenosyl methionine (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 P450-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]

Carbazoles edit

Carbazoles include 3-methoxycarbazole and glycozoline found in Prickly ash bark.[4]

Furoquinolines edit

Furoquinolines include dictamine, 8-methoxydictamine, skimmianine, and 3-dimethylallyl-4-methoxy-2-quinolone found in Prickly ash bark.[4]

Valerian alkaloids edit

Actinidine,[14] chatinine,[14][15] shyanthine,[14] valerianine,[14] and valerine[14]

See also edit

References edit

  1. Wilbur, C. Keith, MD. Revolutionary Medicine 1700-1800. The Globe Pequot Press. Page 23. 1980.
  2. Alchemist peter (27 August 2021). "alkaloid". San Francisco, California: Wikimedia Foundation, Inc. Retrieved 10 September 2021. {{cite web}}: |author= has generic name (help)
  3. SemperBlotto (15 March 2005). "alkaloid". San Francisco, California: Wikimedia Foundation, Inc. Retrieved 2017-08-11. {{cite web}}: |author= has generic name (help)
  4. 4.0 4.1 4.2 4.3 4.4 "{title}". Retrieved 2017-05-18.
  5. S. K. Adesina (2005). "The Nigerian Zanthoxylum; Chemical and biological values". Afr. J. Trad. CAM 2 (3): 282-301. https://web.archive.org/web/20160303183649/https://tspace.library.utoronto.ca/bitstream/1807/9214/1/tc05032.pdf. Retrieved 2016-03-03. 
  6. Zhang Q, Cai L, Zhong G, Luo W (2010). "Simultaneous determination of jatrorrhizine, palmatine, berberine, and obacunone in Phellodendri Amurensis Cortex by RP-HPLC". Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica 35 (16): 2061–4. doi:10.4268/cjcmm20101603. PMID 21046728. 
  7. "Berberine". PubChem, National Library of Medicine, US National Institutes of Health. March 9, 2020. Retrieved March 10, 2020.
  8. 8.0 8.1 8.2 "Berberine: MedlinePlus Supplements". MedlinePlus, National Library of Medicine, US National Institutes of Health. 19 January 2019. Retrieved 15 February 2019.
  9. Hermann R, von Richter O (September 2012). "Clinical evidence of herbal drugs as perpetrators of pharmacokinetic drug interactions". Planta Medica 78 (13): 1458–77. doi:10.1055/s-0032-1315117. PMID 22855269. 
  10. Feng P, Zhao L, Guo F, Zhang B, Fang L, Zhan G, Xu X, Fang Q, Liang Z, Li B (September 2018). "The enhancement of cardiotoxicity that results from inhibiton of CYP 3A4 activity and hERG channel by berberine in combination with statins". Chemico-biological Interactions 293: 115–123. doi:10.1016/j.cbi.2018.07.022. PMID 30086269. 
  11. Šudomová, M.; Berchová-Bímová, K.; Marzocco, S.; Liskova, A.; Kubatka, P.; Hassan, S.T.S. Berberine in Human Oncogenic Herpesvirus Infections and Their Linked Cancers. Viruses 2021, 13, 1014. https://doi.org/10.3390/v13061014
  12. "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. June 2000. doi:10.1093/jexbot/51.347.1005. PMID 10948228. 
  13. Dewick, P. (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). West Sussex, England: Wiley. p. 358. ISBN 978-0-471-49641-0. https://archive.org/details/medicinalnatural00dewi_347. 
  14. 14.0 14.1 14.2 14.3 14.4 Fereidoon Shahidi and Marian Naczk (2013-06-24). Phenolics in food and nutraceuticals. Boca Raton, Florida, USA: CRC Press. ISBN 1-58716-138-9. https://web.archive.org/web/20130624105109/http://books.google.com/books?id=vHOJKw4umikC&pg=PA313. 
  15. S. Waliszewski (April 10, 1891). "Chatinine, alcaloïde de la racine de valériane". American Journal of Pharmacy 66. https://web.archive.org/web/20130619055528/http://books.google.com/books?id=aPkKAAAAYAAJ&pg=PA166. 

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