View source for Depside

{{Short description|Class of chemical compounds}}
[[File:Gyrophoric acid.svg|thumb|right|upright|[[Gyrophoric acid]], a depside]]
A '''depside''' is a type of [[polyphenol]]ic compound composed of two or more monocyclic [[Aromaticity|aromatic]] units linked by an [[ester]] group. Depsides are most often found in [[lichen]]s, but have also been isolated from [[Vascular plant|higher plants]], including species of the [[Ericaceae]], [[Lamiaceae]], [[Papaveraceae]] and [[Myrtaceae]].<ref name="pmid12372879">{{cite journal |vauthors=Ono M, Masuoka C, Koto M, Tateishi M, Komatsu H, Kobayashi H, Igoshi K, Ito Y, Okawa M, Nohara T |title=Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (''Vaccinium ashei'') |journal=Chem. Pharm. Bull. |volume=50 |issue=10 |pages=1416–7 |date=October 2002 |pmid=12372879 |doi=10.1248/cpb.50.1416 |doi-access=free }}</ref><ref name="pmid11451645">{{cite journal |vauthors=Zgórka G, Głowniak K |title=Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family |journal=J Pharm Biomed Anal |volume=26 |issue=1 |pages=79–87 |date=August 2001 |pmid=11451645 |doi= 10.1016/S0731-7085(01)00354-5}}</ref><ref name="pmid15095160">{{cite journal |vauthors=Hillenbrand M, Zapp J, Becker H |title=Depsides from the petals of ''Papaver rhoeas'' |journal=Planta Med. |volume=70 |issue=4 |pages=380–2 |date=April 2004 |pmid=15095160 |doi=10.1055/s-2004-818956 }}</ref><ref name="pmid16933884">{{cite journal |vauthors=Reynertson KA, Wallace AM, Adachi S, Gil RR, Yang H, Basile MJ, D'Armiento J, Weinstein IB, Kennelly EJ |title=Bioactive depsides and anthocyanins from jaboticaba (''Myrciaria cauliflora'') |journal=J. Nat. Prod. |volume=69 |issue=8 |pages=1228–30 |date=August 2006 |pmid=16933884 |doi=10.1021/np0600999 }}</ref>
Certain depsides have [[antibiotic]], anti-[[HIV]], [[antioxidant]], and [[Antineoplastic|anti-proliferative]] activity ''[[in vitro]]''.<ref name="pmid16933884"/><ref name="pmid10395495">{{cite journal |vauthors=Kumar KC, Müller K |title=Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth |journal=J. Nat. Prod. |volume=62 |issue=6 |pages=821–3 |date=June 1999 |pmid=10395495 |doi=10.1021/np980378z}}</ref><ref name="pmid9083483">{{cite journal |vauthors=Neamati N, Hong H, Mazumder A, Wang S, Sunder S, Nicklaus MC, Milne GW, Proksa B, Pommier Y |title=Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching |journal=J. Med. Chem. |volume=40 |issue=6 |pages=942–51 |date=March 1997 |pmid=9083483 |doi=10.1021/jm960759e}}</ref><ref>{{cite journal | vauthors = Nielsen J, Nielsen PH, Frisvad JC | year = 1998 | title = Fungl depside, guisinol, from a marine derived strain of ''Emericella unguis'' | journal = Phytochemistry | volume = 50 | issue = 2| pages = 263–265 | doi=10.1016/s0031-9422(98)00517-2}}</ref> As inhibitors of [[prostaglandin]] synthesis and [[leukotriene B4|leukotriene B<sub>4</sub>]] biosynthesis, some depsides have ''in vitro'' anti-inflammatory activity.<ref name="pmid6425861">{{cite journal |vauthors=Gerrard JM, Peterson DA |title=Structure of the active site of prostaglandin synthase from studies of depsides: an alternate view |journal=Prostaglandins Leukot Med |volume=13 |issue=2 |pages=139–42 |date=February 1984 |pmid=6425861 |doi= 10.1016/0262-1746(84)90003-9}}</ref><ref name="pmid6812170">{{cite journal |vauthors=Sankawa U, Shibuya M, Ebizuka Y, Noguchi H, Kinoshita T, Iitaka Y, Endo A, Kitahara N |title=Depside as potent inhibitor of prostaglandin biosynthesis: a new active site model for fatty acid cyclooxygenase |journal=Prostaglandins |volume=24 |issue=1 |pages=21–34 |date=July 1982 |pmid=6812170 |doi= 10.1016/0090-6980(82)90174-5}}</ref><ref name="pmid10395494">{{cite journal |vauthors=Kumar KC, Müller K |title=Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism |journal=J. Nat. Prod. |volume=62 |issue=6 |pages=817–20 |date=June 1999 |pmid=10395494 |doi=10.1021/np9803777}}</ref><ref name="pmid10858601">{{cite journal |vauthors=((Kumar KCS)), Müller K |title=Depsides as non-redox inhibitors of leukotriene B<sub>4</sub> biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid |journal=Eur J Med Chem |volume=35 |issue=4 |pages=405–11 |date=April 2000 |pmid=10858601 |doi= 10.1016/S0223-5234(00)00132-X}}</ref>
A depsidase is a type of enzyme that cuts depside bonds. One such enzyme is [[tannase]].<ref>{{cite journal | pmc = 1264952 | pmid=5965343 | volume=99 | issue=1 | title=The esterase and depsidase activities of tannase | date=April 1966 | journal=Biochem. J. | pages=28–31 | vauthors=Haslam E, Stangroom JE| doi=10.1042/bj0990028 }}</ref>
==Examples==
[[Gyrophoric acid]], found in the lichen ''[[Cryptothecia rubrocincta]]'', is a depside.  [[Merochlorophaeic acid]], isolated from lichens of the genus ''[[Cladonia]]'',<ref>{{Cite journal | doi = 10.1016/S0031-9422(00)86155-5| title = The structures of cryptochlorophaeic acid and merochlorophaeic acid| journal = Phytochemistry| volume = 4| pages = 133–139| year = 1965| last1 = Shibata| first1 = Shoji| last2 = Chiang| first2 = Hsüch-Ching}}</ref> is an inhibitor of [[prostaglandin]] synthesis.
Some depsides are described as anti-HIV.<ref name="NeamatiHong1997">{{cite journal|last1=Neamati|first1=Nouri|last2=Hong|first2=Huixiao|last3=Mazumder|first3=Abhijit|last4=Wang|first4=Shaomeng|last5=Sunder|first5=Sanjay|last6=Nicklaus|first6=Marc C.|last7=Milne|first7=George W. A.|last8=Proksa|first8=Bohumil|last9=Pommier|first9=Yves|title=Depsides and Depsidones as Inhibitors of HIV-1 Integrase: Discovery of Novel Inhibitors through 3D Database Searching†|journal=Journal of Medicinal Chemistry|volume=40|issue=6|year=1997|pages=942–951|issn=0022-2623|doi=10.1021/jm960759e|pmid=9083483}}</ref>
==See also==
*[[Salsalate]] homodimer formed from self-condensation of [[salicylic acid]] to form ester linkage.
==References==
{{reflist|2}}
[[Category:Polyphenols]]
[[Category:Carboxylate esters]]