Chemical structure of strepsilin | |
A crystal cluster of strepsilin; B single crystal | |
Names | |
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IUPAC name 4,8-Dihydroxy-10-methyl-1H-[2]benzofuro[5,4-b][1]benzofuran-3-one | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
PubChem CID | |
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Properties | |
C15H10O5 | |
Molar mass | 270.24 g/mol |
Melting point | 324 °C (615 °F; 597 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Strepsilin is a chemical found in lichens. It produces an emerald green colour in the C test. It is a dibenzofuran dimer, with hydroxy, oxy and methyl side groups. It is named after Cladonia strepsilis . [1] Strepsilin was discovered by Wilhelm Zopf in 1903. [2] [3] The structure of strepsilin was determined by Shoji Shibata. [4]
Strepsilin is degraded in alkali to 1-methyl-3,7-dihydroxydibenzofuran. [1]
Strepsilin melts at 324 °C. [1]
Strepsilin is found in some Cladonia species. [5] It is also found in Siphula [6] and Stereocaulon azoreum . [7]
Cladonia rangiferina, also known as reindeer cup lichen, reindeer lichen or grey reindeer lichen, is a light-colored fruticose, cup lichen species in the family Cladoniaceae. It grows in both hot and cold climates in well-drained, open environments. Found primarily in areas of alpine tundra, it is extremely cold-hardy.
Usnic acid is a naturally occurring dibenzofuran derivative found in several lichen species with the formula C18H16O7. It was first isolated by German scientist W. Knop in 1844 and first synthesized between 1933 and 1937 by Curd and Robertson. Usnic acid was identified in many genera of lichens including Usnea, Cladonia, Hypotrachyna, Lecanora, Ramalina, Evernia, Parmelia and Alectoria. Although it is generally believed that usnic acid is exclusively restricted to lichens, in a few unconfirmed isolated cases the compound was found in kombucha tea and non-lichenized ascomycetes.
The Chichibabin pyridine synthesis is a method for synthesizing pyridine rings. The reaction involves the condensation reaction of aldehydes, ketones, α,β-Unsaturated carbonyl compounds, or any combination of the above, with ammonia. It was reported by Aleksei Chichibabin in 1924. Methyl-substituted pyridines, which show widespread uses among multiple fields of applied chemistry, are prepared by this methodology.
Pseudevernia is a genus of foliose lichens in the family Parmeliaceae. The type species of the genus, Pseudevernia furfuracea, has substantial commercial value in the perfume industry.
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.
FriedrichWilhelm Zopf was a well-known German botanist and mycologist. He dedicated to his whole life with fungal biology, particularly in classification of fungi and dye production in fungi and lichens. Besides, his textbook on fungi called “Die pilze in morphologischer, physiologischer, biologischer und systematischer beziehung ” in 1890 was also an outstanding work on the subject for many decades. The unicellular achlorophic microalgae Prototheca zopfii is named after him because of his profound suggestions and contributions to Krüger's pioneering work in Prototheca. Thus, his numerous contributions gave him a special status in mycological history.
Secalonic acids are a group of xanthone derivatives closely related to ergoflavin and ergochrysin A that are collectively called ergochromes and belong to a class of mycotoxins initially isolated as major ergot pigments from the fungi Claviceps purpurea that grows parasitically on rye grasses. From early times and particularly in medieval Europe the consumption of grains containing ergot has repeatedly lead to mass poisonings known as ergotism which was caused by toxic ergot alkaloids and mycotoxins such as the ergochromes, due to contamination of flour by C. purpurea. A cluster of genes responsible for the synthesis of secalonic acids in C. purpurea has been identified. Secalonic acid D the enantiomer of secalonic acid A is a major environmental toxin, isolated from the fungus Penicillium oxalicum, and is a major microbial contaminant of freshly-harvested corn which causes toxicity through contamination of foodstuffs.
A spot test in lichenology is a spot analysis used to help identify lichens. It is performed by placing a drop of a chemical on different parts of the lichen and noting the colour change associated with application of the chemical. The tests are routinely encountered in dichotomous keys for lichen species, and they take advantage of the wide array of lichen products produced by lichens and their uniqueness among taxa. As such, spot tests reveal the presence or absence of chemicals in various parts of a lichen. They were first proposed by the botanist William Nylander in 1866.
Organotantalum chemistry is the chemistry of chemical compounds containing a carbon-to-tantalum chemical bond. A wide variety of compound have been reported, initially with cyclopentadienyl and CO ligands. Oxidation states vary from Ta(V) to Ta(-I).
Jack Rodney Laundon was a British lichenologist and became President of the British Lichen Society.
Isolichenan, also known as isolichenin, is a cold-water-soluble α-glucan occurring in certain species of lichens. This lichen product was first isolated as a component of an extract of Iceland moss in 1813, along with lichenin. After further analysis and characterization of the individual components of the extract, isolichenan was named in 1881. It is the first α-glucan to be described from lichens. The presence of isolichenan in the cell walls is a defining characteristic in several genera of the lichen family Parmeliaceae. Although most prevalent in that family, it has also been isolated from members of the families Ramalinaceae, Stereocaulaceae, Roccellaceae, and Cladoniaceae. Experimental studies have shown that isolichenan is produced only when the two lichen components – fungus and alga – are growing together, not when grown separately. The biological function of isolichenan in the lichen thallus is unknown.
In chemistry, a transition metal chloride complex is a coordination complex that consists of a transition metal coordinated to one or more chloride ligand. The class of complexes is extensive.
Merochlorophaeic acid is a depside with the molecular formula C24H30O8 which has been isolated from the lichen Cladonia merochlorophaea.
Anziaic acid is a depside found in lichens. It gives a red reaction in the C test. The two phenolic rings have a pentyl side chain. It is an ester dimer of olivetolic acid.
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.
Lichexanthone is an organic compound in the structural class of chemicals known as xanthones. Lichexanthone was first isolated and identified by Japanese chemists from a species of leafy lichen in the 1940s. The compound is known to occur in many lichens, and it is important in the taxonomy of species in several genera, such as Pertusaria and Pyxine. More than a dozen lichen species have a variation of the word lichexanthone incorporated as part of their binomial name. The presence of lichexanthone in lichens causes them to fluoresce a greenish-yellow colour under long-wavelength UV light; this feature is used to help identify some species. Lichexanthone is also found in several plants, and some species of fungi that do not form lichens.
Thamnolic acid is a β-orcinol depside with the molecular formula C19H16O11. Thamnolic acid was first isolated from the lichen Thamnolia vermicularis, but it also occur in Cladonia species.
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 compound 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.
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.