# Depside

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Depside
> Markdown URL: https://mediated.wiki/source/Depside.md
> Source: https://en.wikipedia.org/wiki/Depside
> Source revision: 1347422933
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

Class of chemical compounds

- [Evernic acid](/source/Evernic_acid), a depside

A **depside** is a type of [polyphenolic](/source/Polyphenol) compound composed of two or more monocyclic [aromatic](/source/Aromaticity) units linked by an [ester](/source/Ester) group. Depsides are most often found in [lichens](/source/Lichen), but have also been isolated from [higher plants](/source/Vascular_plant), including species of the [Ericaceae](/source/Ericaceae), [Lamiaceae](/source/Lamiaceae), [Papaveraceae](/source/Papaveraceae) and [Myrtaceae](/source/Myrtaceae).[1][2][3][4] In lichens, depsides are [polyketide](/source/Polyketide)-derived [secondary metabolites](/source/Secondary_metabolite) biosynthesized via the polymalonate pathway. Most lichen depsides occur in the [medulla](/source/Medulla_(lichenology)), and their chemistry was historically used as a species-level [character](/source/Glossary_of_lichen_terms#character) in [lichen taxonomy](/source/Lichen_taxonomy), although [molecular](/source/Molecular_phylogenetics) methods have since changed how such variation is interpreted.[5]

Certain depsides have [antibiotic](/source/Antibiotic), anti-[HIV](/source/HIV), [antioxidant](/source/Antioxidant), and [anti-proliferative](/source/Antineoplastic) activity *[in vitro](/source/In_vitro)*.[4][6][7][8] As inhibitors of [prostaglandin](/source/Prostaglandin) synthesis and [leukotriene B4](/source/Leukotriene_B4) biosynthesis, some depsides have *in vitro* anti-inflammatory activity.[9][10][11][12] However, this research is still dominated by *[in vitro](/source/In_vitro)* work, with fewer *[in vivo](/source/In_vivo)* studies, and no [clinical trials](/source/Clinical_trial) had been reported in a 2023 review.[5]

A depsidase is a type of enzyme that cuts depside bonds. One such enzyme is [tannase](/source/Tannase).[13]

## Examples

[Gyrophoric acid](/source/Gyrophoric_acid), found in the lichen *[Cryptothecia rubrocincta](/source/Cryptothecia_rubrocincta)*, is a depside. [Merochlorophaeic acid](/source/Merochlorophaeic_acid), isolated from lichens of the genus *[Cladonia](/source/Cladonia)*,[14] is an inhibitor of [prostaglandin](/source/Prostaglandin) synthesis.

Some depsides are described as anti-HIV.[7]

## References

1. **[^](#cite_ref-Ono_et_al._2002_1-0)** Ono, Masateru; Masuoka, Chikako; Koto, Mihoko; Tateishi, Michiko; Komatsu, Haruki; Kobayashi, Hiromasa; Igoshi, Keiji; Ito, Yasuyuki; Okawa, Masafumi; Nohara, Toshihiro (2002). "Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein a, from the fruit of rabbiteye blueberry (vaccinium ashei)". *Chemical and Pharmaceutical Bulletin*. **50** (10): 1416–1417. [doi](/source/Doi_(identifier)):[10.1248/cpb.50.1416](https://doi.org/10.1248%2Fcpb.50.1416). [PMID](/source/PMID_(identifier)) [12372879](https://pubmed.ncbi.nlm.nih.gov/12372879).

1. **[^](#cite_ref-Zgórka_&_Głowniak_2001_2-0)** Zgórka, Grażyna; Głowniak, Kazimierz (2001). "Variation of free phenolic acids in medicinal plants belonging to the Lamiaceae family". *Journal of Pharmaceutical and Biomedical Analysis*. **26** (1): 79–87. [doi](/source/Doi_(identifier)):[10.1016/s0731-7085(01)00354-5](https://doi.org/10.1016%2Fs0731-7085%2801%2900354-5). [PMID](/source/PMID_(identifier)) [11451645](https://pubmed.ncbi.nlm.nih.gov/11451645).

1. **[^](#cite_ref-Hillenbrand_et_al._2004_3-0)** Hillenbrand, Marita; Zapp, Josef; Becker, Hans (2004). "Depsides from the Petals of *Papaver rhoeas*". *Planta Medica*. **70** (4): 380–382. [doi](/source/Doi_(identifier)):[10.1055/s-2004-818956](https://doi.org/10.1055%2Fs-2004-818956). [PMID](/source/PMID_(identifier)) [15095160](https://pubmed.ncbi.nlm.nih.gov/15095160).

1. ^ [***a***](#cite_ref-Reynertson_et_al._2006_4-0) [***b***](#cite_ref-Reynertson_et_al._2006_4-1) Reynertson, Kurt A.; Wallace, Alison M.; Adachi, Seiji; Gil, Roberto R.; Yang, Hui; Basile, Margaret J.; D'Armiento, Jeanine; Weinstein, I. Bernard; Kennelly, Edward J. (2006). "Bioactive depsides and anthocyanins from jaboticaba (*Myrciaria cauliflora*)". *Journal of Natural Products*. **69** (8): 1228–1230. [doi](/source/Doi_(identifier)):[10.1021/np0600999](https://doi.org/10.1021%2Fnp0600999). [PMID](/source/PMID_(identifier)) [16933884](https://pubmed.ncbi.nlm.nih.gov/16933884).

1. ^ [***a***](#cite_ref-Ureña-Vacas_et_al._2023_5-0) [***b***](#cite_ref-Ureña-Vacas_et_al._2023_5-1) Ureña-Vacas, Isabel; González-Burgos, Elena; Divakar, Pradeep Kumar; Gómez-Serranillos, María Pilar (2023). ["Lichen depsides and tridepsides: progress in pharmacological approaches"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9866793). *Journal of Fungi*. **9** (1): 116. [doi](/source/Doi_(identifier)):[10.3390/jof9010116](https://doi.org/10.3390%2Fjof9010116). [PMC](/source/PMC_(identifier)) [9866793](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9866793). [PMID](/source/PMID_(identifier)) [36675938](https://pubmed.ncbi.nlm.nih.gov/36675938).

1. **[^](#cite_ref-Kumar_&_Müller_1999b_6-0)** Kumar, Sunil; Müller, Klaus (1999). "Lichen Metabolites. 1. Inhibitory action against leukotriene B4biosynthesis by a non-redox mechanism". *Journal of Natural Products*. **62** (6): 817–820. [doi](/source/Doi_(identifier)):[10.1021/np9803777](https://doi.org/10.1021%2Fnp9803777). [PMID](/source/PMID_(identifier)) [10395494](https://pubmed.ncbi.nlm.nih.gov/10395494).

1. ^ [***a***](#cite_ref-Neamati_et_al._1997_7-0) [***b***](#cite_ref-Neamati_et_al._1997_7-1) 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](/source/Doi_(identifier)):[10.1021/jm960759e](https://doi.org/10.1021%2Fjm960759e). [PMID](/source/PMID_(identifier)) [9083483](https://pubmed.ncbi.nlm.nih.gov/9083483).

1. **[^](#cite_ref-Nielsen_et_al._1999_8-0)** Nielsen, Joan; Nielsen, Per Halfdan; Frisvad, Jens C. (1999). "Fungal depside, guisinol, from a marine derived strain of *Emericella unguis*". *Phytochemistry*. **50** (2): 263–265. [doi](/source/Doi_(identifier)):[10.1016/s0031-9422(98)00517-2](https://doi.org/10.1016%2Fs0031-9422%2898%2900517-2).

1. **[^](#cite_ref-Gerrard_&_Peterson_1984_9-0)** Gerrard, J.M.; Peterson, D.A. (1984). "Structure of the active site of prostaglandin synthase from studies of depsides: An alternate view". *Prostaglandins, Leukotrienes and Medicine*. **13** (2): 139–142. [doi](/source/Doi_(identifier)):[10.1016/0262-1746(84)90003-9](https://doi.org/10.1016%2F0262-1746%2884%2990003-9). [PMID](/source/PMID_(identifier)) [6425861](https://pubmed.ncbi.nlm.nih.gov/6425861).

1. **[^](#cite_ref-Sankawa_et_al._1982_10-0)** Sankawa, Ushio; Shibuya, Masaaki; Ebizuka, Yutaka; Noguchi, Hiroshi; Iitaka, Yoichi; Endo, Akira; Kitahara, Nobuaki (1982). "Depside as potent inhibitor of prostaglandin biosynthesis: A new active site model for fatty acid cyclooxygenase". *Prostaglandins*. **24** (1): 21–34. [doi](/source/Doi_(identifier)):[10.1016/0090-6980(82)90174-5](https://doi.org/10.1016%2F0090-6980%2882%2990174-5). [PMID](/source/PMID_(identifier)) [6812170](https://pubmed.ncbi.nlm.nih.gov/6812170).

1. **[^](#cite_ref-Kumar_&_Müller_1999_11-0)** Kumar, Sunil; Müller, Klaus (1999). "Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth". *Journal of Natural Products*. **62** (6): 821–823. [doi](/source/Doi_(identifier)):[10.1021/np980378z](https://doi.org/10.1021%2Fnp980378z). [PMID](/source/PMID_(identifier)) [10395495](https://pubmed.ncbi.nlm.nih.gov/10395495).

1. **[^](#cite_ref-Kumar_2000_12-0)** Kumar, S. (2000). "Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth, 2. Novel analogues of obtusatic acid". *European Journal of Medicinal Chemistry*. **35** (4): 405–411. [doi](/source/Doi_(identifier)):[10.1016/s0223-5234(00)00132-x](https://doi.org/10.1016%2Fs0223-5234%2800%2900132-x). [PMID](/source/PMID_(identifier)) [10858601](https://pubmed.ncbi.nlm.nih.gov/10858601).

1. **[^](#cite_ref-Haslam_&_Stangroom_1966_13-0)** Haslam, E.; Stangroom, J. (1966). ["The esterase and depsidase activities of tannase"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1264952). *Biochemical Journal*. **99** (1): 28–31. [doi](/source/Doi_(identifier)):[10.1042/bj0990028](https://doi.org/10.1042%2Fbj0990028). [PMC](/source/PMC_(identifier)) [1264952](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1264952). [PMID](/source/PMID_(identifier)) [5965343](https://pubmed.ncbi.nlm.nih.gov/5965343).

1. **[^](#cite_ref-Shibata_&_Chiang_1965_14-0)** Shibata, Shoji; Chiang, Hsüch-Ching (1965). "The structures of cryptochlorophaeic acid and merochlorophaeic acid". *Phytochemistry*. **4** (1): 133–139. [doi](/source/Doi_(identifier)):[10.1016/s0031-9422(00)86155-5](https://doi.org/10.1016%2Fs0031-9422%2800%2986155-5).

---
Adapted from the Wikipedia article [Depside](https://en.wikipedia.org/wiki/Depside) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Depside?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.