Anziaic acid explained

Anziaic acid is a depside found in lichens. It gives a red reaction in the C test. The two phenolic rings have a pentyl side chain. It is an ester dimer of olivetolic acid.^[1]

Anziaic acid works as an antibacterial compound by inhibiting topoisomerase.^{[2] [3]}

Production

Anziaic acid has been artificially produced from olivetolic acid by benzylation of the O-phenol positions, and then condensing with trifluoroacetic anhydride.^[1]

Properties

Anziaic acid is colourless. It can be dissolved in ethanol, ethanol-water mixture, or cyclohexane-benzene mixture.^[1]

Related

Perlatolic acid, dihydropicrolichenic acid, 2'-O-methylanziaic acid, 2-O-methylperlatolic acid, 2'-O-methylperlatolic and planaic acid are derivatives of anziaic acid, where a methyl group replaces a hydrogen in some of the hydroxy positions on the rings.^[1]

Occurrence

Anziaic acid is found in Parmeliaceae including Hypotrachyna,^[2] Stereocaulon,^[4] and Cetrelia,^[5]

Notes and References

1. Elix . J. A. . Synthesis of para-olivetol depsides . Australian Journal of Chemistry . 1974 . 27 . 8 . 1767 . 10.1071/CH9741767.
2. Cheng . Bokun . Cao . Shugeng . Vasquez . Victor . Annamalai . Thirunavukkarasu . Tamayo-Castillo . Giselle . Clardy . Jon . Tse-Dinh . Yuk-Ching . Identification of Anziaic Acid, a Lichen Depside from Hypotrachyna sp., as a New Topoisomerase Poison Inhibitor . PLOS ONE . 8 April 2013 . 8 . 4 . e60770 . 10.1371/journal.pone.0060770. 23593306 . 3620467 . 2013PLoSO...860770C . free .
3. Kekuda . T.R Prashith . Lavanya . D . . Pooja . Rao . Lichens as promising resources of enzyme inhibitors: A review . Journal of Drug Delivery and Therapeutics . March 2019 . 9 . 2S . 10.22270/jddt.v9i2-s.2546. 31 January 2024 .
4. Ramaut . J. L. . Serusiaux . E. . Brouers . M. . Corvisier . M. . Lichen Acids of the Stereocaulon ramulosum Group in Central East Africa . The Bryologist . 1978 . 81 . 3 . 415 . 10.2307/3242244. 3242244 .
5. Mark . Kristiina . Randlane . Tiina . Thor . Göran . Hur . Jae-Seoun . Obermayer . Walter . Saag . Andres . Lichen chemistry is concordant with multilocus gene genealogy in the genus Cetrelia (Parmeliaceae, Ascomycota) . Fungal Biology . 2019 . 123 . 2 . 125–139 . 10.1016/j.funbio.2018.11.013 . 30709518. 73439650 .