Argopsin

Argopsin, also known as 1-chloropannarin, is a secondary metabolite produced by many lichen species, such as Biatora cuprea[1] and Micarea lignaria.[2] Argopsin was first isolated from the lichen Argopsis friesiana.[3] The chemical composition of argopsin is 2,7-Dichloro-3-hydroxy-8-methoxy-1,6,9-trimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-4-carbaldehyde.

Argopsin
Names
IUPAC name
2,8-Dichloro-9-hydroxy-3-methoxy-1,4,7-trimethyl-6-oxobenzo[b][1,4]benzodioxepine-10-carbaldehyde
Other names
1-Chloropannarin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • 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
    Key: SNNDIPJEAQAKTJ-UHFFFAOYSA-N
  • CC1=C2C(=C(C(=C1Cl)O)C=O)OC3=C(C(=C(C(=C3OC2=O)C)OC)Cl)C
Properties
C18H14Cl2O6
Molar mass 397.20 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

Uses

Argopsin can have photohemolytic effect when activated under ultraviolet light with a wavelength of 366 nm.[4]

Argopsin has been shown to have in vitro effect on Leishmania at a concentration of 50 µg/ml.[5]

References
  1. Hörður Kristinsson (2016). Íslenskar fléttur. Reykjavík: Hið íslenska bókmenntafélag. ISBN 978-9979-66-347-8
  2. Flóra Íslands. Viðarkúpa - Micarea lignaria. Sótt 4. mars 2017.
  3. Huneck, Siegfried; Lamb, I.Mackenzee (1975). "1′-Chloropannarin, a new depsidone from Argopsis friesiana: Notes on the structure of pannarin and on the chemistry of the lichen genus Argopsis". Phytochemistry. 14 (7): 1625–1628. doi:10.1016/0031-9422(75)85363-5.
  4. Hidalgo, M. E.; Fernández, E.; Quilhot, W.; Lissi, E. A. (1993). "Photohemolytic activity of lichen metabolites". Journal of Photochemistry and Photobiology. B, Biology. 21 (1): 37–40. doi:10.1016/1011-1344(93)80161-2. PMID 8289110.
  5. Fournet, Alain; Ferreira, Maria-Elena; De Arias, Antonieta Rojas; De Ortiz, Susana Torres; Inchausti, Alba; Yalaff, Gloria; Quilhot, Wanda; Fernandez, Ernesto; Hidalgo, Maria Elena (1997). "Activity of Compounds Isolated from Chilean Lichens Against Experimental Cutaneous Leishmaniasis". Comparative Biochemistry and Physiology Part C: Pharmacology, Toxicology and Endocrinology. 116 (1): 51–54. doi:10.1016/S0742-8413(96)00127-2. PMID 9080673.


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