Depside

{{Short description|Class of chemical compounds}} :[[File:Evernic acid.svg|class=skin-invert-image|thumb|right|upright|Evernic 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.<ref name="Ono et al. 2002"/><ref name="Zgórka & Głowniak 2001"/><ref name="Hillenbrand et al. 2004"/><ref name="Reynertson et al. 2006"/> In lichens, depsides are polyketide-derived secondary metabolites biosynthesized via the polymalonate pathway. Most lichen depsides occur in the medulla, and their chemistry was historically used as a species-level {{lichengloss|character}} in lichen taxonomy, although molecular methods have since changed how such variation is interpreted.<ref name="Ureña-Vacas et al. 2023"/>

Certain depsides have antibiotic, anti-HIV, antioxidant, and anti-proliferative activity ''in vitro''.<ref name="Reynertson et al. 2006"/><ref name="Kumar & Müller 1999b"/><ref name="Neamati et al. 1997"/><ref name="Nielsen et al. 1999"/> As inhibitors of prostaglandin synthesis and leukotriene B₄ biosynthesis, some depsides have ''in vitro'' anti-inflammatory activity.<ref name="Gerrard & Peterson 1984"/><ref name="Sankawa et al. 1982"/><ref name="Kumar & Müller 1999"/><ref name="Kumar 2000"/> However, this research is still dominated by ''in vitro'' work, with fewer ''in vivo'' studies, and no clinical trials had been reported in a 2023 review.<ref name="Ureña-Vacas et al. 2023"/>

A depsidase is a type of enzyme that cuts depside bonds. One such enzyme is tannase.<ref name="Haslam & Stangroom 1966"/>

==Examples== Gyrophoric acid, found in the lichen ''Cryptothecia rubrocincta'', is a depside. Merochlorophaeic acid, isolated from lichens of the genus ''Cladonia'',<ref name="Shibata & Chiang 1965"/> is an inhibitor of prostaglandin synthesis.

Some depsides are described as anti-HIV.<ref name="Neamati et al. 1997"/>

==References== <references>

<ref name="Gerrard & Peterson 1984">{{cite journal |last1=Gerrard |first1=J.M. |last2=Peterson |first2=D.A. |title=Structure of the active site of prostaglandin synthase from studies of depsides: An alternate view |journal=Prostaglandins, Leukotrienes and Medicine |year=1984 |volume=13 |issue=2 |pages=139–142 |doi=10.1016/0262-1746(84)90003-9 |pmid=6425861}}</ref>

<ref name="Haslam & Stangroom 1966">{{cite journal |last1=Haslam |first1=E. |last2=Stangroom |first2=J. |title=The esterase and depsidase activities of tannase |journal=Biochemical Journal |year=1966 |volume=99 |issue=1 |pages=28–31 |doi=10.1042/bj0990028 |pmid=5965343 |pmc=1264952}}</ref>

<ref name="Hillenbrand et al. 2004">{{cite journal |last1=Hillenbrand |first1=Marita |last2=Zapp |first2=Josef |last3=Becker |first3=Hans |title=Depsides from the Petals of ''Papaver rhoeas'' |journal=Planta Medica |year=2004 |volume=70 |issue=4 |pages=380–382 |doi=10.1055/s-2004-818956 |pmid=15095160}}</ref>

<ref name="Kumar & Müller 1999">{{cite journal |last1=Kumar |first1=Sunil |last2=Müller |first2=Klaus |title=Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth |journal=Journal of Natural Products |year=1999 |volume=62 |issue=6 |pages=821–823 |doi=10.1021/np980378z |pmid=10395495}}</ref>

<ref name="Kumar & Müller 1999b">{{cite journal |last1=Kumar |first1=Sunil |last2=Müller |first2=Klaus |title=Lichen Metabolites. 1. Inhibitory action against leukotriene B₄biosynthesis by a non-redox mechanism |journal=Journal of Natural Products |year=1999 |volume=62 |issue=6 |pages=817–820 |doi=10.1021/np9803777 |pmid=10395494}}</ref>

<ref name="Kumar 2000">{{cite journal |last=Kumar |first=S. |title=Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid |journal=European Journal of Medicinal Chemistry |year=2000 |volume=35 |issue=4 |pages=405–411 |doi=10.1016/s0223-5234(00)00132-x |pmid=10858601}}</ref>

<ref name="Neamati et al. 1997">{{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 |year=1997 |volume=40 |issue=6 |pages=942–951 |doi=10.1021/jm960759e |pmid=9083483}}</ref>

<ref name="Nielsen et al. 1999">{{cite journal |last1=Nielsen |first1=Joan |last2=Nielsen |first2=Per Halfdan |last3=Frisvad |first3=Jens C. |title=Fungal depside, guisinol, from a marine derived strain of ''Emericella unguis'' |journal=Phytochemistry |year=1999 |volume=50 |issue=2 |pages=263–265 |doi=10.1016/s0031-9422(98)00517-2}}</ref>

<ref name="Ono et al. 2002">{{cite journal |last1=Ono |first1=Masateru |last2=Masuoka |first2=Chikako |last3=Koto |first3=Mihoko |last4=Tateishi |first4=Michiko |last5=Komatsu |first5=Haruki |last6=Kobayashi |first6=Hiromasa |last7=Igoshi |first7=Keiji |last8=Ito |first8=Yasuyuki |last9=Okawa |first9=Masafumi |last10=Nohara |first10=Toshihiro |title=Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein a, from the fruit of rabbiteye blueberry (vaccinium ashei). |journal=Chemical and Pharmaceutical Bulletin |year=2002 |volume=50 |issue=10 |pages=1416–1417 |doi=10.1248/cpb.50.1416 |pmid=12372879}}</ref>

<ref name="Reynertson et al. 2006">{{cite journal |last1=Reynertson |first1=Kurt A. |last2=Wallace |first2=Alison M. |last3=Adachi |first3=Seiji |last4=Gil |first4=Roberto R. |last5=Yang |first5=Hui |last6=Basile |first6=Margaret J. |last7=D'Armiento |first7=Jeanine |last8=Weinstein |first8=I. Bernard |last9=Kennelly |first9=Edward J. |title=Bioactive depsides and anthocyanins from jaboticaba (''Myrciaria cauliflora'') |journal=Journal of Natural Products |year=2006 |volume=69 |issue=8 |pages=1228–1230 |doi=10.1021/np0600999 |pmid=16933884}}</ref>

<ref name="Sankawa et al. 1982">{{cite journal |last1=Sankawa |first1=Ushio |last2=Shibuya |first2=Masaaki |last3=Ebizuka |first3=Yutaka |last4=Noguchi |first4=Hiroshi |last5=Iitaka |first5=Yoichi |last6=Endo |first6=Akira |last7=Kitahara |first7=Nobuaki |title=Depside as potent inhibitor of prostaglandin biosynthesis: A new active site model for fatty acid cyclooxygenase |journal=Prostaglandins |year=1982 |volume=24 |issue=1 |pages=21–34 |doi=10.1016/0090-6980(82)90174-5 |pmid=6812170}}</ref>

<ref name="Shibata & Chiang 1965">{{cite journal |last1=Shibata |first1=Shoji |last2=Chiang |first2=Hsüch-Ching |title=The structures of cryptochlorophaeic acid and merochlorophaeic acid |journal=Phytochemistry |year=1965 |volume=4 |issue=1 |pages=133–139 |doi=10.1016/s0031-9422(00)86155-5}}</ref>

<ref name="Ureña-Vacas et al. 2023">{{cite journal |last1=Ureña-Vacas |first1=Isabel |last2=González-Burgos |first2=Elena |last3=Divakar |first3=Pradeep Kumar |last4=Gómez-Serranillos |first4=María Pilar |title=Lichen depsides and tridepsides: progress in pharmacological approaches |journal=Journal of Fungi |year=2023 |volume=9 |issue=1 |pages=116 |doi=10.3390/jof9010116 |doi-access=free |pmid=36675938 |pmc=9866793}}</ref>

<ref name="Zgórka & Głowniak 2001">{{cite journal |last1=Zgórka |first1=Grażyna |last2=Głowniak |first2=Kazimierz |title=Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family |journal=Journal of Pharmaceutical and Biomedical Analysis |year=2001 |volume=26 |issue=1 |pages=79–87 |doi=10.1016/s0731-7085(01)00354-5 |pmid=11451645}}</ref>

</references>

Category:Polyphenols Category:Carboxylate esters *