Atranorin

Last updated
Atranorin
Atranorin.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-527-7
PubChem CID
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).

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]

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<span class="mw-page-title-main">Stictic acid</span> Chemical compound

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Botryosphaeran is an exopolysaccharide (EPS) produced by the ascomyceteous fungus Botryosphaeria rhodina. Characterization of the chemical structure of botryosphaeran showed this EPS to be a (1→3)(1→6)-β-D-glucan. This particular β-glucan can be produced by several strains of Botryosphaeria rhodina that include: MAMB-05, DABAC-P82, and RCYU 30101. Botryosphaeran exhibits interesting rheological properties and novel biological functions including hypoglycaemia, hypocholesterolaemia, anti-atheroslerosis and anti-cancer activity, with potential commercial applications. Three cosmetic products formulated with botryosphaeran have been developed to promote skin health and treat skin conditions for future intended commercialization purposes.

<span class="mw-page-title-main">Lecanoric acid</span> Chemical compound

Lecanoric acid is a chemical produced by several species of lichen. Lecanoric acid is classified as a polyphenol and a didepside and it functions as an antioxidant. The acid is named after the lichen Lecanora. The acid has also been isolated from Usnea subvacata, Parmotrema stuppuem, Parmotrema tinctorum,Parmotrema grayana, Xanthoparmelia arida and Xanthoparmelia lecanorica. A related compound, 5-chlorolecanoric acid, is found in some species of Punctelia.

<i>Stereocaulon ramulosum</i> Species of lichen

Stereocaulon ramulosum, commonly known as snow lichen, is a terricolous fruticose lichen belonging to the family Stereocaulaceae. It has cosmopolitan distribution. In the Australasian region, it is common in eastern Australia, New Zealand and has also been recorded at Lord Howe Island and Macquarie Island.

<i>Punctelia borreri</i> Species of lichen

Punctelia borreri is a species of foliose lichen in the family Parmeliaceae. It is a common and widely distributed species, occurring in tropical, subtropical, and temperate regions of Africa, Asia, Europe, North America, Oceania, and South America. The lichen typically grows on bark of deciduous trees, and less commonly on rock. Some European countries have reported increases in the geographic range or regional frequency of the lichen in recent decades, attributed alternatively to a reduction of atmospheric sulphur dioxide levels or an increase in temperatures resulting from climate change.

<span class="mw-page-title-main">Salazinic acid</span> Chemical compound found in some lichens

Salazinic acid is a depsidone with a lactone ring. It is found in some lichens, and is especially prevalent in Parmotrema and Bulbothrix, where its presence or absence is often used to help classify species in those genera.

<span class="mw-page-title-main">Lichexanthone</span> Chemical compound found in some lichens

Lichexanthone is an organic compound in the structural class of chemicals known as xanthones. Lichexanthone was first isolated and identified by Japanese chemists from a species of leafy lichen in the 1940s. The compound is known to occur in many lichens, and it is important in the taxonomy of species in several genera, such as Pertusaria and Pyxine. More than a dozen lichen species have a variation of the word lichexanthone incorporated as part of their binomial name. The presence of lichexanthone in lichens causes them to fluoresce a greenish-yellow colour under long-wavelength UV light; this feature is used to help identify some species. Lichexanthone is also found in several plants, and some species of fungi that do not form lichens.

<i>Pulchrocladia retipora</i> Species of fruticose lichen

Pulchrocladia retipora, commonly known as the coral lichen, is a species of fruticose lichen in the family Cladoniaceae. Found predominantly in Australasia, its habitats range from the Australian Capital Territory to New Zealand's North and South Islands, and even the Pacific region of New Caledonia, where it grows in coastal and alpine heathlands. The lichen features coral-like branches and subbranches with numerous intricate, netlike perforations. It is known by multiple names, with some sources referring to it by its synonym Cladia retipora, or the common name lace lichen.

Lichen products, also known as lichen substances, are organic compounds produced by a lichen. Specifically, they are secondary metabolites. Lichen products are represented in several different chemical classes, including terpenoids, orcinol derivatives, chromones, xanthones, depsides, and depsidones. Over 800 lichen products of known chemical structure have been reported in the scientific literature, and most of these compound are exclusively found in lichens. Examples of lichen products include usnic acid, atranorin, lichexanthone, salazinic acid, and isolichenan, an α-glucan. Many lichen products have biological activity, and research into these effects is ongoing.

<span class="mw-page-title-main">Barbatic acid</span> Chemical compound found in some lichens

Barbatic acid is an organic compound that is made by some lichens. It is in the structural class known as depsides. It is particularly common in the genera Usnea and Cladonia.

References

  1. 1 2 "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. 1 2 Jaeck, Andreas. "Atranorin". www.internetchemie.info.
  5. 1 2 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