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
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.844
EC Number
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
C 19 H 18 O 8
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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] analgesic , anti-inflammatory , antibacterial , antifungal , cytotoxic , antioxidant , antiviral , and immunomodulatory properties.[ 5] [ 4] [ 6] [ 7] allergic reaction to atranorin.[ 8]
References
^ a b "Atranorin (CAS 479-20-9)" . www.caymanchem.com .^ "479-20-9 | Atranorin | Atranorine; NSC 249980; NSC 685591; NSC 87512; Parmelin; Parmelin Acid; Usnarin; Usnarin Acid | C19 18 8 | TRC" . www.trc-canada.com .^ 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 . ^ a b Jaeck, Andreas. "Atranorin" . www.internetchemie.info . ^ a b 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 . ^ 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 . ^ 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 . ^ "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 .
