Depside

Gyrophoric acid, a depside

A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond. Depsides are most often found in lichens, but have also been isolated from higher plants, including species of the Ericaceae, Lamiaceae, Papaveraceae and Myrtaceae.^[1][2][3][4] Depsides have antibiotic, anti-HIV, antioxidant, and anti-proliferative activity.^[4][5][6][7] As inhibitors of prostaglandin synthesis and leukotriene B₄ biosynthesis, depsides are potent non-steroidal anti-inflammatories.^{[8][9][10][11]}

A depsidase is a type of enzyme that cuts depside bonds. One such enzyme is tannase.^[12]

Gyrophoric acid, found in the lichen Cryptothecia rubrocincta, is a depside.

See also

• Salsalate homodimer formed from self-condensation of salicylic acid to form ester linkage.

References

1. Ono M, Masuoka C, Koto M, Tateishi M, Komatsu H, Kobayashi H, Igoshi K, Ito Y, Okawa M, Nohara T (October 2002). "Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (Vaccinium ashei)". Chem. Pharm. Bull. 50 (10): 1416–7. doi:10.1248/cpb.50.1416. PMID 12372879.
2. Zgórka G, Głowniak K (August 2001). "Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family". J Pharm Biomed Anal 26 (1): 79–87. doi:10.1016/S0731-7085(01)00354-5. PMID 11451645.
3. Hillenbrand M, Zapp J, Becker H (April 2004). "Depsides from the petals of Papaver rhoeas". Planta Med. 70 (4): 380–2. doi:10.1055/s-2004-818956. PMID 15095160.
4. Reynertson KA, Wallace AM, Adachi S, Gil RR, Yang H, Basile MJ, D'Armiento J, Weinstein IB, Kennelly EJ (August 2006). "Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora)". J. Nat. Prod. 69 (8): 1228–30. doi:10.1021/np0600999. PMID 16933884.
5. Kumar KC, Müller K (June 1999). "Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth". J. Nat. Prod. 62 (6): 821–3. doi:10.1021/np980378z. PMID 10395495.
6. Neamati N, Hong H, Mazumder A, Wang S, Sunder S, Nicklaus MC, Milne GW, Proksa B, Pommier Y (March 1997). "Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching". J. Med. Chem. 40 (6): 942–51. doi:10.1021/jm960759e. PMID 9083483.
7. Nielsen J, Nielsen PH, Frisvad JC.(1998). Fungl depside, guisinol, from a marine derived strain of Emericella unguis. Phytochemistry 50: 263-265.
8. Gerrard JM, Peterson DA (February 1984). "Structure of the active site of prostaglandin synthase from studies of depsides: an alternate view". Prostaglandins Leukot Med 13 (2): 139–42. doi:10.1016/0262-1746(84)90003-9. PMID 6425861.
9. Sankawa U, Shibuya M, Ebizuka Y, Noguchi H, Kinoshita T, Iitaka Y, Endo A, Kitahara N (July 1982). "Depside as potent inhibitor of prostaglandin biosynthesis: a new active site model for fatty acid cyclooxygenase". Prostaglandins 24 (1): 21–34. doi:10.1016/0090-6980(82)90174-5. PMID 6812170.
10. Kumar KC, Müller K (June 1999). "Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism". J. Nat. Prod. 62 (6): 817–20. doi:10.1021/np9803777. PMID 10395494.
11. Kumar KC S, Müller K (April 2000). "Depsides as non-redox inhibitors of leukotriene B₄ biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid". Eur J Med Chem 35 (4): 405–11. doi:10.1016/S0223-5234(00)00132-X. PMID 10858601.
12. The esterase and depsidase activities of tannase. E. Haslam and J. E. Stangroom, Biochem J. 1966 April; 99(1): 28–31.