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. 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 character in lichen taxonomy, although molecular methods have since changed how such variation is interpreted. Certain depsides have antibiotic, anti-HIV, antioxidant, and anti-proliferative activity in vitro. As inhibitors of prostaglandin synthesis and leukotriene B4 biosynthesis, some depsides have in vitro anti-inflammatory activity. 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. A depsidase is a type of enzyme that cuts depside bonds. One such enzyme is tannase.
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.[1][2][3][4] 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 character in lichen taxonomy, although molecular methods have since changed how such variation is interpreted.[5]
Certain depsides have antibiotic, anti-HIV, antioxidant, and anti-proliferative activity in vitro.[4][6][7][8] As inhibitors of prostaglandin synthesis and leukotriene B4 biosynthesis, some depsides have in vitro anti-inflammatory activity.[9][10][11][12] 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.[5]
A depsidase is a type of enzyme that cuts depside bonds. One such enzyme is tannase.[13]
Examples
[edit]Gyrophoric acid, found in the lichen Cryptothecia rubrocincta, is a depside. Merochlorophaeic acid, isolated from lichens of the genus Cladonia,[14] is an inhibitor of prostaglandin synthesis.
Some depsides are described as anti-HIV.[7]
References
[edit]- ^ 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:10.1248/cpb.50.1416. PMID 12372879.
- ^ 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:10.1016/s0731-7085(01)00354-5. PMID 11451645.
- ^ Hillenbrand, Marita; Zapp, Josef; Becker, Hans (2004). "Depsides from the Petals of Papaver rhoeas". Planta Medica. 70 (4): 380–382. doi:10.1055/s-2004-818956. PMID 15095160.
- ^ a b 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:10.1021/np0600999. PMID 16933884.
- ^ a b Ureña-Vacas, Isabel; González-Burgos, Elena; Divakar, Pradeep Kumar; Gómez-Serranillos, María Pilar (2023). "Lichen depsides and tridepsides: progress in pharmacological approaches". Journal of Fungi. 9 (1): 116. doi:10.3390/jof9010116. PMC 9866793. PMID 36675938.
- ^ 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:10.1021/np9803777. PMID 10395494.
- ^ a b 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. PMID 9083483.
- ^ 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:10.1016/s0031-9422(98)00517-2.
- ^ 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:10.1016/0262-1746(84)90003-9. PMID 6425861.
- ^ 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:10.1016/0090-6980(82)90174-5. PMID 6812170.
- ^ 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:10.1021/np980378z. PMID 10395495.
- ^ 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:10.1016/s0223-5234(00)00132-x. PMID 10858601.
- ^ Haslam, E.; Stangroom, J. (1966). "The esterase and depsidase activities of tannase". Biochemical Journal. 99 (1): 28–31. doi:10.1042/bj0990028. PMC 1264952. PMID 5965343.
- ^ Shibata, Shoji; Chiang, Hsüch-Ching (1965). "The structures of cryptochlorophaeic acid and merochlorophaeic acid". Phytochemistry. 4 (1): 133–139. doi:10.1016/s0031-9422(00)86155-5.