Depside Explained

A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester group. 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]}

Certain depsides have antibiotic, anti-HIV, antioxidant, and anti-proliferative activity in vitro.^{[4] [5] [6] [7]} As inhibitors of prostaglandin synthesis and leukotriene B₄ biosynthesis, some depsides have in vitro anti-inflammatory activity.^{[8] [9] [10] [11]}

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

Examples

Gyrophoric acid, found in the lichen Cryptothecia rubrocincta, is a depside. Merochlorophaeic acid, isolated from lichens of the genus Cladonia,^[13] is an inhibitor of prostaglandin synthesis.

Some depsides are described as anti-HIV.^[14]

See also

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

Notes and References

1. Ono M, Masuoka C, Koto M, Tateishi M, Komatsu H, Kobayashi H, Igoshi K, Ito Y, Okawa M, Nohara T . Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (Vaccinium ashei) . Chem. Pharm. Bull. . 50 . 10 . 1416–7 . October 2002 . 12372879 . 10.1248/cpb.50.1416 . free .
2. Zgórka G, Głowniak K . Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family . J Pharm Biomed Anal . 26 . 1 . 79–87 . August 2001 . 11451645 . 10.1016/S0731-7085(01)00354-5.
3. Hillenbrand M, Zapp J, Becker H . Depsides from the petals of Papaver rhoeas . Planta Med. . 70 . 4 . 380–2 . April 2004 . 15095160 . 10.1055/s-2004-818956 .
4. Reynertson KA, Wallace AM, Adachi S, Gil RR, Yang H, Basile MJ, D'Armiento J, Weinstein IB, Kennelly EJ . Bioactive depsides and anthocyanins from jaboticaba (Myrciaria cauliflora) . J. Nat. Prod. . 69 . 8 . 1228–30 . August 2006 . 16933884 . 10.1021/np0600999 .
5. Kumar KC, Müller K . Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth . J. Nat. Prod. . 62 . 6 . 821–3 . June 1999 . 10395495 . 10.1021/np980378z.
6. Neamati N, Hong H, Mazumder A, Wang S, Sunder S, Nicklaus MC, Milne GW, Proksa B, Pommier Y . Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching . J. Med. Chem. . 40 . 6 . 942–51 . March 1997 . 9083483 . 10.1021/jm960759e.
7. Nielsen J, Nielsen PH, Frisvad JC . 1998 . Fungl depside, guisinol, from a marine derived strain of Emericella unguis . Phytochemistry . 50 . 2. 263–265 . 10.1016/s0031-9422(98)00517-2.
8. Gerrard JM, Peterson DA . Structure of the active site of prostaglandin synthase from studies of depsides: an alternate view . Prostaglandins Leukot Med . 13 . 2 . 139–42 . February 1984 . 6425861 . 10.1016/0262-1746(84)90003-9.
9. Sankawa U, Shibuya M, Ebizuka Y, Noguchi H, Kinoshita T, Iitaka Y, Endo A, Kitahara N . Depside as potent inhibitor of prostaglandin biosynthesis: a new active site model for fatty acid cyclooxygenase . Prostaglandins . 24 . 1 . 21–34 . July 1982 . 6812170 . 10.1016/0090-6980(82)90174-5.
10. Kumar KC, Müller K . Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism . J. Nat. Prod. . 62 . 6 . 817–20 . June 1999 . 10395494 . 10.1021/np9803777.
11. ((Kumar KCS)), Müller K . 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 . April 2000 . 10858601 . 10.1016/S0223-5234(00)00132-X.
12. 1264952 . 5965343 . 99 . 1 . The esterase and depsidase activities of tannase . April 1966 . Biochem. J. . 28–31 . Haslam E, Stangroom JE. 10.1042/bj0990028 .
13. 10.1016/S0031-9422(00)86155-5. The structures of cryptochlorophaeic acid and merochlorophaeic acid. Phytochemistry. 4. 133–139. 1965. Shibata. Shoji. Chiang. Hsüch-Ching.
14. Neamati. Nouri. Hong. Huixiao. Mazumder. Abhijit. Wang. Shaomeng. Sunder. Sanjay. Nicklaus. Marc C.. Milne. George W. A.. Proksa. Bohumil. Pommier. Yves. Depsides and Depsidones as Inhibitors of HIV-1 Integrase: Discovery of Novel Inhibitors through 3D Database Searching†. Journal of Medicinal Chemistry. 40. 6. 1997. 942–951. 0022-2623. 10.1021/jm960759e. 9083483.