Atranorin

Atranorin is a chemical substance produced by some species of lichen. It is a secondary metabolite belonging to a group of compounds known as depsides.[3][4][5] Atranorin has analgesic, anti-inflammatory, antibacterial, antifungal, cytotoxic, antioxidant, antiviral, and immunomodulatory properties.[5][4][6][7] In rare cases, people can have an allergic reaction to atranorin.[8]

Atranorin
Names
IUPAC name
(3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 3-formyl-2,4-dihydroxy-6-methylbenzoate
Other names
NSC 87512, NSC 249980, NSC 685591[1]Atranorine, Parmelin, Parmelin Acid, Usnarin, Usnarin Acid[2]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.844
EC Number
  • 207-527-7
UNII
  • InChI=1S/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3
    Key: YLOYKYXNDHOHHT-UHFFFAOYSA-N[1]
  • CC1=CC(OC(C2=C(O)C(C=O)=C(O)C=C2C)=O)=C(C)C(O)=C1C(OC)=O
Properties
C19H18O8
Molar mass 374.345 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. "Atranorin (CAS 479-20-9)". www.caymanchem.com.
  2. "479-20-9 | Atranorin | Atranorine; NSC 249980; NSC 685591; NSC 87512; Parmelin; Parmelin Acid; Usnarin; Usnarin Acid | C
    19    G
    18    O
    8     | TRC"    . www.trc-canada.com.
  3. Melo, Marcelia Garcez Dória; dos Santos, João Paulo Almeida; Serafini, Mairim Russo; Caregnato, Fernanda Freitas; de Bittencourt Pasquali, Matheus Augusto; Rabelo, Thallita Kelly; da Rocha, Ricardo Fagundes; Quintans Jr., Lucindo; de Souza Araújo, Adriano Antunes; da Silva, Francilene Amaral; Moreira, José Cláudio Fonseca & Gelain, Daniel Pens (March 2011). "Redox properties and cytoprotective actions of atranorin, a lichen secondary metabolite". Toxicology in Vitro. 25 (2): 462–468. doi:10.1016/j.tiv.2010.11.014. PMID 21111802.
  4. Jaeck, Andreas. "Atranorin". www.internetchemie.info.
  5. Studzinska-Sroka, Elzbieta; Galanty, Agnieszka; Bylka, Wieslawa (7 November 2017). "Atranorin - An Interesting Lichen Secondary Metabolite". Mini-Reviews in Medicinal Chemistry. 17 (17): 1633–1645. doi:10.2174/1389557517666170425105727. PMID 28443519.
  6. Zhou, Rui; Yang, Yi; Park, So-Yeon; Nguyen, Thanh Thi; Seo, Young-Woo; Lee, Kyung Hwa; Lee, Jae Hyuk; Kim, Kyung Keun; Hur, Jae-Seoun; Kim, Hangun (15 August 2017). "The lichen secondary metabolite atranorin suppresses lung cancer cell motility and tumorigenesis". Scientific Reports. 7 (1): 8136. Bibcode:2017NatSR...7.8136Z. doi:10.1038/s41598-017-08225-1. ISSN 2045-2322. PMC 5557893. PMID 28811522.
  7. Melo, Marcelia Garcez Dória; dos Santos, João Paulo Almeida; Serafini, Mairim Russo; Caregnato, Fernanda Freitas; de Bittencourt Pasquali, Matheus Augusto; Rabelo, Thallita Kelly; da Rocha, Ricardo Fagundes; Quintans, Lucindo; de Souza Araújo, Adriano Antunes; da Silva, Francilene Amaral; Moreira, José Cláudio Fonseca; Gelain, Daniel Pens (March 2011). "Redox properties and cytoprotective actions of atranorin, a lichen secondary metabolite". Toxicology in Vitro. 25 (2): 462–468. doi:10.1016/j.tiv.2010.11.014. PMID 21111802.
  8. "Allergen Atranorin Allergie Allergologie". www.alles-zur-allergologie.de.

Further reading
  • Zeitschrift Für Naturforschung: A journal of chemical sciences. B (in German). Verlag der Zeitschrift für Naturforschung.
  • Jahresbericht über die Fortschritte der Chemie und verwandter Theile anderer Wissenschaften (in German). Friedrich Vieweg Und Sohn.
  • Vos, Carlo; Mckinney, Phillip; Pearson, Colby; Heiny, Erik; Gunawardena, Gamini; Holt, Emily A. (2018). "The optimal extraction and stability of atranorin from lichens, in relation to solvent and pH". The Lichenologist. 50 (4): 499–512. doi:10.1017/S0024282918000075. ISSN 0024-2829. S2CID 91786583.
  • Harikrishnan, Adhikesavan; Veena, V.; Lakshmi, B.; Shanmugavalli, R.; Theres, Sonia; Prashantha, C. N.; Shah, Tanya; Oshin, K.; Togam, Ringu; Nandi, Sisir (4 March 2021). "Atranorin, an antimicrobial metabolite from lichen Parmotrema rampoddense exhibited in vitro anti-breast cancer activity through interaction with Akt activity". Journal of Biomolecular Structure and Dynamics. 39 (4): 1248–1258. doi:10.1080/07391102.2020.1734482. ISSN 0739-1102. PMID 32096436. S2CID 211475842.
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