# Argopsin

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{{Short description|Chemical compound}}
{{Chembox
<!-- Images -->
| ImageFile = Argopsin.svg
| ImageSize = 200px
<!-- Names -->
| IUPACName = 2,8-Dichloro-9-hydroxy-3-methoxy-1,4,7-trimethyl-6-oxobenzo[''b''][1,4]benzodioxepine-10-carbaldehyde
| OtherNames = 1-Chloropannarin
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 52809-10-6
| CASNo_Ref = {{Cascite|changed|EPA}}
| ChEBI = 144113
| ChEMBL = 1982613
| ChemSpiderID = 142840
| PubChem = 162698
| InChI = 1S/C18H14Cl2O6/c1-6-10-17(9(5-21)13(22)11(6)19)25-15-7(2)12(20)14(24-4)8(3)16(15)26-18(10)23/h5,22H,1-4H3
| InChIKey = SNNDIPJEAQAKTJ-UHFFFAOYSA-N
| SMILES = CC1=C2C(=C(C(=C1Cl)O)C=O)OC3=C(C(=C(C(=C3OC2=O)C)OC)Cl)C
  }}
| Section2 = {{Chembox Properties
| C=18 | H=14 | Cl=2 | O=6
| Appearance = 
| Density = 
| MeltingPtC = 
| Solubility = 
  }}
| Section3 = {{Chembox Hazards
 
  }}
}}

'''Argopsin''', also known as '''1-chloropannarin''', is a [secondary metabolite](/source/secondary_metabolite) produced by many [lichen](/source/lichen) species, such as ''[Biatora cuprea](/source/Biatora_cuprea)''<ref>Hörður Kristinsson (2016). ''Íslenskar fléttur''. Reykjavík: Hið íslenska bókmenntafélag. ISBN 978-9979-66-347-8</ref> and ''[Micarea lignaria](/source/Micarea_lignaria)''.<ref>Flóra Íslands. [http://www.floraislands.is/FLETTUR/micarlig.html Viðarkúpa - ''Micarea lignaria'']. Sótt 4. mars 2017.</ref>

Argopsin (also known as 1'-chloropannarin) is a chlorinated [depsidone](/source/depsidone) compound first isolated from the lichen ''[Argopsis friesiana](/source/Argopsis_friesiana)'' by [Siegfried Huneck](/source/Siegfried_Huneck) and [Elke Mackenzie](/source/Elke_Mackenzie) in 1975. It was independently discovered by both Huneck and Mackenzie's team and by Bodo and Molho in the same year. The structure was confirmed through multiple analytical methods including [mass spectrometry](/source/mass_spectrometry), which showed characteristic isotope peaks at [mass-to-charge ratio](/source/mass-to-charge_ratio)s (m/z) of 396, 398, and 400 in a 9:6:1 ratio, indicating the presence of two [chlorine](/source/chlorine) atoms. Its [UV spectrum](/source/Ultraviolet%E2%80%93visible_spectroscopy) matched that of [pannarin](/source/pannarin), and [infrared spectroscopy](/source/infrared_spectroscopy) revealed characteristic [aldehyde](/source/aldehyde) (1725&nbsp;cm⁻¹) and [hydroxyl](/source/hydroxyl) (3500&nbsp;cm⁻¹) bands. The researchers [synthesized](/source/chemical_synthesis) argopsin by [chlorinating](/source/Chlorination_reaction) pannarin in [acetic acid](/source/acetic_acid), which produced a compound identical to the naturally occurring substance. This synthesis also helped confirm a recently revised chemical structure of pannarin, correcting an earlier proposed structure from 1941.<ref name="Huneck & Lamb 1975"/>

In the lichen ''A.&nbsp;friesiana'', argopsin occurs alongside [atranorin](/source/atranorin), though its presence is described as "inconstant". The related species ''[A.&nbsp;megalospora](/source/Argopsis_megalospora)'' does not contain argopsin but instead contains various combinations of other lichen substances including atranorin, [fumarprotocetraric acid](/source/fumarprotocetraric_acid), [psoromic acid](/source/psoromic_acid), and [perlatolic acid](/source/perlatolic_acid).<ref name="Huneck & Lamb 1975"/>
The compound produces a red color when treated with [ferric chloride](/source/ferric_chloride) in ethanol and an orange color with [''p''-phenylenediamine](/source/p-Phenylenediamine) in ethanol, characteristics useful for its identification.<ref name="Huneck & Lamb 1975">{{cite journal |doi=10.1016/0031-9422(75)85363-5 |title = 1'-Chloropannarin, a new depsidone from ''Argopsis friesiana'': Notes on the structure of pannarin and on the chemistry of the lichen genus ''Argopsis'' |year=1975 |last1=Huneck |first1=Siegfried |last2=Lamb |first2 = I. Mackenzie |journal = Phytochemistry |volume=14 |issue=7 |pages=1625–1628}}</ref>

== Uses ==
Argopsin can have [photohemolytic effect](/source/photohemolytic_effect) when activated under [ultraviolet light](/source/Ultraviolet) with a wavelength of 366&nbsp;nm.<ref>{{cite journal | pmid = 8289110| year = 1993| last1 = Hidalgo| first1 = M. E.| last2 = Fernández| first2 = E.| last3 = Quilhot| first3 = W.| last4 = Lissi| first4 = E. A.| title = Photohemolytic activity of lichen metabolites| journal = Journal of Photochemistry and Photobiology B: Biology| volume = 21| issue = 1| pages = 37–40| doi = 10.1016/1011-1344(93)80161-2| bibcode = 1993JPPB...21...37H}}</ref>

Argopsin has been shown to have an ''[in vitro](/source/in_vitro)'' effect on ''[Leishmania](/source/Leishmania)'' at a concentration of 50 μg/ml.<ref>{{cite journal | doi = 10.1016/S0742-8413(96)00127-2 | title = Activity of compounds isolated from chilean lichens against experimental cutaneous leishmaniasis | year = 1997 | last1 = Fournet | first1 = Alain | last2 = Ferreira | first2 = Maria-Elena | last3 = De Arias | first3 = Antonieta Rojas | last4 = De Ortiz | first4 = Susana Torres | last5 = Inchausti | first5 = Alba | last6 = Yalaff | first6 = Gloria | last7 = Quilhot | first7 = Wanda | last8 = Fernandez | first8 = Ernesto | last9 = Hidalgo | first9 = Maria Elena | journal = Comparative Biochemistry and Physiology Part C: Pharmacology, Toxicology and Endocrinology | volume = 116 | issue = 1 | pages = 51–54 | pmid = 9080673 }}</ref>

== References ==
{{Reflist}}

Category:Secondary metabolites
Category:Lichen products
Category:Chloroarenes
Category:Heterocyclic compounds with 3 rings
Category:Lactones
Category:Cyclic ethers
Category:Methoxy compounds
Category:Benzodioxepines
Category:Chlorine-containing natural products

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Adapted from the Wikipedia article [Argopsin](https://en.wikipedia.org/wiki/Argopsin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Argopsin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.