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Names | |
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IUPAC name 10-Formyl-3,9-dihydroxy-4-(hydroxymethyl)-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
EC Number |
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PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C18H14O9 | |
Molar mass | 374.301 g·mol−1 |
Hazards | |
GHS labelling: | |
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Warning | |
H317 | |
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Protocetraric acid is a chemical compound with the molecular formula C18H14O9. It is a secondary metabolite produced by a variety of lichens and is classified as a depsidone.
In 1845 Knop and Schnedermann isolated crystalline cetraric acid from the lichen Cetraria islandica . O. Hesse proposed that cetraric acid does not exist in the lichen, but is rather the decomposition product of another acid that he called protocetraric acid, which is split up into fumaric and cetraric acids. In reviewing Hesse's work. O. Simon confirmed the statements of Knop and Schnedermann, finding cetraric acid in the plant in a free state. O. Simon did not find the protocetraric acid proposed by Hesse, but instead used that name for another acid he isolated. [1]
Protocetraric acid was first described in the 1930s. [2] [3]
Rao and colleagues published the ultraviolet and infrared spectra of some lichen depsidones, including protocetraric acid, in 1967. [4]
The molecular formula of protocetraric acid is C18H14O9; it has a molecular mass of 374.29 grams per mole. In its purified crystalline form, it exists as short needles with a melting point range of 245–250 °C (473–482 °F). Its ultraviolet spectrum has three peaks of maximum absorption (λmax) at 210, 238, and 312 nm. Its infrared spectrum has several peaks: 680, 745, 785, 814, 840, 990, 1020, 1080, 1115, 1150, 1190, 1270, 1380, 1440, 1562, 1642, 1738, 3000, and 3500 cm−1. [5] A number of ester derivatives of protocetraric acid, such as succinprotocetraric acid and fumarprotocetraric acid, have also been identified in lichens.
Preliminary research has been conducted into the potential pharmacology of protocetraric acid and related compounds. Protocetraric acid has broad spectrum antimicrobial properties against some pathogenic microbes such as Salmonella typhi . [6] It also has weak activity against SARS-CoV-2 3C-like protease (Ki of 3.95 μM), as does the related depsidone salazinic acid, and therefore it is being studied as a scaffold for the potential discovery of more potent drugs for the treatment of COVID-19. [7]
Laboratory experiments indicate that protocetraric acid has broad spectrum antimicrobial activity against some pathogenic microbes, including antibacterial activity against Salmonella typhi , and antifungal activity against Trichophyton rubrum . [8] It also has moderate antimycobacterial activity on the growth of Mycobacterium tuberculosis . [9]
Some authors have explicitly named protocetraric acid in the specific epithets of their published lichen species, thereby acknowledging the presence of this compound as an important taxonomic characteristic. These eponyms are listed here, followed by their author citation and year of publication.
Several derivatives of protocetraric acid were designed and synthesised using Diels-Alder reaction, esterification, and Friedel-Crafts alkylation of protocetraric acid with different reagents under Lewis acid. The products were tested for their α-Glucosidase inhibitory using molecular docking analysis. [15]
The related chemical 9'-(O-methyl)protocetraric acid was isolated from the lichen Cladonia convoluta . [16] Conhypoprotocetraric acid, identified from lichens Relicina cf. incongrua and Lecanora myriocarpoides , was synthesized and characterized in 1995. [17]
The Parmeliaceae is a large and diverse family of Lecanoromycetes. With over 2700 species in 71 genera, it is the largest family of lichen-forming fungi. The most speciose genera in the family are the well-known groups: Xanthoparmelia, Usnea, Parmotrema, and Hypotrachyna.
Vermilacinia, a genus of lichenized fungi in the family Ramalinaceae, is a yellow-green fruticose type of lichen with about 30 species that grow on rocks, trees, and soil within the fog zone along the Pacific Coast of North America and South America. The genus name refers to the thallus being divided into narrow worm-like (vermis) branches (lacinia);the latter part of the name (lacinia) generally applied in descriptions and taxonomic keys such as exemplified in a key to Sonoran Desert species of Ramalina.
Melanohalea is a genus of foliose lichens in the family Parmeliaceae. It contains 30 mostly Northern Hemisphere species that grow on bark or on wood. The genus is characterised by the presence of pseudocyphellae, usually on warts or on the tips of isidia, a non-pored epicortex and a medulla containing depsidones or lacking secondary metabolites. Melanohalea was circumscribed in 2004 as a segregate of the morphologically similar genus Melanelia, which was created in 1978 for certain brown Parmelia species. The methods used to estimate the evolutionary history of Melanohalea suggest that its diversification primarily occurred during the Miocene and Pliocene epochs.
Xanthoparmelia is a genus of foliose lichens in the family Parmeliaceae. This genus of lichen is commonly found in the United States, South America, southern Africa, Europe, Australia, and New Zealand.
Lecanoric acid is a chemical produced by several species of lichen. Lecanoric acid is classified as a polyphenol and a didepside, and it functions as an antioxidant. It is an ester of orsellinic acid with itself.
Parmotrema zollingeri is a species of lichen in the family Parmeliaceae. It was originally described in 1860 as a species of Parmelia by German lichenologist Johann Adam Philipp Hepp, and named after Swiss botanist Heinrich Zollinger. Mason Hale transferred it to the genus Parmotrema in 1974.
Remototrachyna is a genus of foliose lichens in the large family Parmeliaceae. It was separated from the genus Hypotrachyna based on the structure of the excipulum and genetic differences.
John Alan (Jack) Elix emeritus professor in chemistry at the Australian National University, is an organic chemist who has contributed in many fields: lichenology, lichen chemotaxonomy, plant physiology and biodiversity and natural product chemistry. He has authored 2282 species names, and 67 genera in the field of mycology. Elix edited the exsiccata series Lichenes Australasici exsiccati.
Salazinic acid is a depsidone with a lactone ring. It is found in some lichens, and is especially prevalent in Parmotrema and Bulbothrix, where its presence or absence is often used to help classify species in those genera.
Xanthoparmelia salazinica is a species of lichen in the family Parmeliaceae. Found in South Africa, it was described as a new species in 1989 by American lichenologist Mason Hale. He classified it in Karoowia, a genus that has since been placed in synonymy with Xanthoparmelia following molecular phylogenetic analysis published in 2010.
Lichen products, also known as lichen substances, are organic compounds produced by a lichen. Specifically, they are secondary metabolites. Lichen products are represented in several different chemical classes, including terpenoids, orcinol derivatives, chromones, xanthones, depsides, and depsidones. Over 800 lichen products of known chemical structure have been reported in the scientific literature, and most of these compounds are exclusively found in lichens. Examples of lichen products include usnic acid, atranorin, lichexanthone, salazinic acid, and isolichenan, an α-glucan. Many lichen products have biological activity, and research into these effects is ongoing.
Sekikaic acid is an organic compound in the structural class of chemicals known as depsides. It is found in some lichens. First isolated from Ramalina sekika, it is a fairly common lichen product in Ramalina and Cladonia, both genera of lichen-forming fungi. The species epithet of the powdery lichen Lepraria sekikaica refers to the presence of this substance—a rarity in genus Lepraria.
Barbatic acid is an organic compound that is made by some lichens. It is in the structural class known as depsides. It is particularly common in the genera Usnea and Cladonia.
Siegfried Huneck was a German chemist and lichenologist. Much of his scientific career was hampered by the political situation in the former German Democratic Republic. He rejected pursuing a career in academia, and instead ended up working at the Leibniz Institute of Plant Biochemistry, a public research institute, from 1969 until his retirement in 1993. Despite his relative isolation and restricted freedoms in East Germany, Huneck had numerous professional contacts both in Germany and abroad, and was a highly published scholar. Many of his more than 400 scientific publications dealt with the chemistry of lichen products. He was awarded the Acharius Medal for lifetime achievements in lichenology in 1996.
Constictic acid is a chemical compound of the depsidone class. It was first isolated in 1968 from lichen of the genus Usnea. It has since been found in many other lichen genera including Menegazzia, Crespoa, and Xanthoparmelia.
Solorinic acid is an anthraquinone pigment found in the leafy lichen Solorina crocea. It is responsible for the strong orange colour of the medulla and the underside of the thallus in that species. In its purified crystalline form, it exists as orange-red crystals with a melting point of 201 °C (394 °F).
Succinprotocetraric acid is an organic chemical compound with the formula C22H18O12. It is the ester of succinic acid and protocetraric acid and it is classified as a depsidone.
Connorstictic acid is an organic compound in the structural class of chemicals known as depsidones. It occurs as a secondary metabolite in many lichen species in several genera.
Confluentic acid is an organic compound belonging to the chemical class known as depsides. It serves as a secondary metabolite in certain lichens and plays a role in distinguishing closely related species within the genus Porpidia. In 1899, Friedrich Wilhelm Zopf isolated a compound from Lecidea confluens, which he initially named confluentin and noted for its melting point of 147–148 °C. This substance demonstrated the ability to turn litmus paper red and, when interacting with alkali, decomposed into carbon dioxide and phenol-like compounds. Zopf subsequently revised the chemical formula and melting point of the compound. Siegfried Huneck renamed it confluentinic acid in 1962, characterising it as optically inactive, with distinct colour reactions and solubility properties, and determined its molecular formula as C28H36O8.
Consalazinic acid is a chemical compound with the molecular formula C18H14O10. It is classified as a depsidone and is a secondary metabolite produced by a variety of lichens.