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 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

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. ^ a b 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 (2): 263–265. doi:10.1016/s0031-9422(98)00517-2.
  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 KCS, 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. ^ Haslam E, Stangroom JE (April 1966). "The esterase and depsidase activities of tannase". Biochem. J. 99 (1): 28–31. doi:10.1042/bj0990028. PMC 1264952. PMID 5965343.
  13. ^ Shibata, Shoji; Chiang, Hsüch-Ching (1965). "The structures of cryptochlorophaeic acid and merochlorophaeic acid". Phytochemistry. 4: 133–139. doi:10.1016/S0031-9422(00)86155-5.
  14. ^ Neamati, Nouri; Hong, Huixiao; Mazumder, Abhijit; Wang, Shaomeng; Sunder, Sanjay; Nicklaus, Marc C.; Milne, George W. A.; Proksa, Bohumil; Pommier, Yves (1997). "Depsides and Depsidones as Inhibitors of HIV-1 Integrase: Discovery of Novel Inhibitors through 3D Database Searching†". Journal of Medicinal Chemistry. 40 (6): 942–951. doi:10.1021/jm960759e. ISSN 0022-2623. PMID 9083483.

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