Boletocrocin

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General structure. If R = OH (aspartic acid), boletocrocin A; R = NH2 (asparagine), boletocrocin B. Boletocrocin.svg
General structure. If R = OH (aspartic acid), boletocrocin A; R = NH2 (asparagine), boletocrocin B.

Boletocrocin is any one of a group of seven closely related organic compounds, individually named boletocrocin A through boletrocrocin G. [1] These compounds are polyene dicarboxylic acids that include both lipophilic and polar amino acids. [2] They were extracted from the brightly colored mushrooms Boletus laetissimus and B. rufoaureus . [2] The boletocrocins' conjugated systems account for the intense color.

Related biological pigments are present in other fungi, such as calostomal (from Calostoma cinnabarinum ), [3] melanocrocin (from Melanogaster broomeianus ), [4] and mycenaaruin A (from Mycena aurantiomarginata ). [1]

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<i>Melanogaster</i> (fungus) Genus of fungi

Melanogaster is a genus of fungus that resemble truffles, and are often mistaken for them. However, they do not have the characteristic aroma and value of truffles, although some have been used culinarily. None are known to be poisonous. The genus contains 25 species that collectively have a widespread distribution.

<i>Caloboletus calopus</i> Species of fungus in the family Boletaceae found in Asia, Northern Europe and North America

Caloboletus calopus, commonly known as the bitter beech bolete or scarlet-stemmed bolete, is a fungus of the bolete family, found in Asia, Northern Europe and North America. Appearing in coniferous and deciduous woodland in summer and autumn, the stout fruit bodies are attractively coloured, with a beige to olive cap up to 15 cm (6 in) across, yellow pores, and a reddish stipe up to 15 cm (6 in) long and 5 cm (2 in) wide. The pale yellow flesh stains blue when broken or bruised.

<i>Chalciporus piperatus</i> Species of fungus in the family Boletaceae found in mixed woodland in Europe and North America

Chalciporus piperatus, commonly known as the peppery bolete, is a small pored mushroom of the family Boletaceae found in mixed woodland in Europe and North America. It has been recorded under introduced trees in Brazil, and has become naturalised in Tasmania and spread under native Nothofagus cunninghamii trees. A small bolete, the fruit body has a 1.6–9 cm orange-fawn cap with cinnamon to brown pores underneath, and a 4–9.5 cm high by 0.6–1.2 cm thick stipe. The flesh has a very peppery taste. The rare variety hypochryseus, found only in Europe, has yellow pores and tubes.

<i>Gyrodon lividus</i> Species of fungus

Gyrodon lividus, commonly known as the alder bolete, is a pored mushroom bearing close affinity to the genus Paxillus. Although found predominantly in Europe, where it grows in a mycorrhizal association with alder, it has also recorded from China, Japan and California. Fruit bodies are distinguished from other boletes by decurrent bright yellow pores that turn blue-grey on bruising. G. lividus mushrooms are edible.

<i>Calostoma</i> Genus of fungi

Calostoma is a genus of 29 species of gasteroid fungi in the suborder Sclerodermatineae. Like other gasteroid fungi, Calostoma do not have the spore discharge mechanism associated with typical gilled fungi (ballistospory), and instead have enclosed spore-bearing structures. Resembling round puffballs with raised, brightly colored spore openings (ostioles), elevated on a thick, gelatinous stalks, species have been collected in regions of deciduous, temperate, tropical or subtropical forests. Their distribution includes eastern North America, Central America, Asia, and Australasia. The common name given to some species, "prettymouth", alludes to the brightly colored raised openings (ostioles) that may somewhat resemble lips. Other common names include "hotlips" and "puffball in aspic".

<span class="mw-page-title-main">Echinodontiaceae</span> Family of fungi

The Echinodontiaceae are a family of crust fungi in the order Russulales. Species of this family, divided amongst two genera—Echinodontium and Laurilia—have a widespread distribution, although they are especially predominant in north temperate zones. They are parasitic or saprobic on wood, and may cause white rot of angiosperms and gymnosperms.

<i>Xanthoria elegans</i> Species of lichenised fungi in the family Teleoschistaceae

Xanthoria elegans, commonly known as the elegant sunburst lichen, is a lichenized species of fungus in the genus Xanthoria, family Teloschistaceae. Recognized by its bright orange or red pigmentation, this species grows on rocks, often near bird or rodent perches. It has a circumpolar and alpine distribution. It was one of the first lichens to be used for the rock-face dating method known as lichenometry.

<i>Mycena haematopus</i> Fungus species in the family Mycenaceae widespread and common in Europe and North America

Mycena haematopus, commonly known as the bleeding fairy helmet, the burgundydrop bonnet, or the bleeding Mycena, is a species of fungus in the family Mycenaceae, of the order Agaricales. It is widespread and common in Europe and North America, and has also been collected in Japan and Venezuela. It is saprotrophic—meaning that it obtains nutrients by consuming decomposing organic matter—and the fruit bodies appear in small groups or clusters on the decaying logs, trunks, and stumps of deciduous trees, particularly beech. The fungus, first described scientifically in 1799, is classified in the section Lactipedes of the genus Mycena, along with other species that produce a milky or colored latex.

<i>Mycena sanguinolenta</i> Species of fungus

Mycena sanguinolenta, commonly known as the bleeding bonnet, the smaller bleeding Mycena, or the terrestrial bleeding Mycena, is a species of mushroom in the family Mycenaceae. It is a common and widely distributed species, and has been found in North America, Europe, Australia, and Asia. The fungus produces reddish-brown to reddish-purple fruit bodies with conic to bell-shaped caps up to 1.5 cm (0.6 in) wide held by slender stipes up to 6 cm (2.4 in) high. When fresh, the fruit bodies will "bleed" a dark reddish-purple sap. The similar Mycena haematopus is larger, and grows on decaying wood, usually in clumps. M. sanguinolenta contains alkaloid pigments that are unique to the species, may produce an antifungal compound, and is bioluminescent. The edibility of the mushroom has not been determined.

<span class="mw-page-title-main">Haematopodin</span> Chemical compound

Haematopodin is the more stable breakdown product of Haematopodin B. Both compounds are found in the mushroom Mycena haematopus, although haematopodin only occurs in trace amounts in fresh fruit bodies. Similar pigments, known as batzellins and damirones, have been found in sea sponges. A chemical synthesis for haematopodin was reported in 1996. Key steps in the synthesis involved the addition of 3-[(2,4-dimethoxybenzyl)amino]-1-propanol to the indolo-6,7-quinone and cyclization of the resulting adduct with trifluoroacetic acid.

<i>Hygrophorus eburneus</i> Species of fungus

Hygrophorus eburneus, commonly known as the ivory waxy cap or the cowboy's handkerchief, is a species of edible mushroom in the waxgill family of fungi. It is widespread in Europe and North America, and has also been collected in northern Africa. The fruit bodies are medium-sized, pure white, and when wet are covered in a layer of slime thick enough to make the mushroom difficult to pick up. The gills are broadly attached to the stem or running down it; as the family name suggests, they feel waxy when rubbed between the fingers. Like all Hygrophorus species, the fungus is mycorrhizal—a symbiotic association whereby the underground fungal mycelia penetrate and exchange nutrients with tree roots. They are common in a variety of forest types, where they grow on the ground in thickets or grassy areas. Hygrophorus eburneus is the type species of the genus Hygrophorus. A number of biologically active chemicals have been purified from the fruit bodies of the fungus, including fatty acids with bactericidal and fungicidal activity.

<i>Mycena aurantiomarginata</i> Species of fungus in the family Mycenaceae common in Europe and North America

Mycena aurantiomarginata, commonly known as the golden-edge bonnet, is a species of agaric fungus in the family Mycenaceae. First formally described in 1803, it was given its current name in 1872. Widely distributed, it is common in Europe and North America, and has also been collected in North Africa, Central America, and Japan. The fungus is saprobic, and produces fruit bodies (mushrooms) that grow on the floor of coniferous forests. The mushrooms have a bell-shaped to conical cap up to 2 cm in diameter, set atop a slender stipe up to 6 cm long with yellow to orange hairs at the base. The fungus is named after its characteristic bright orange gill edges. A microscopic characteristic is the club-shaped cystidia that are covered with numerous spiky projections, resembling a mace. The edibility of the mushroom has not been determined. M. aurantiomarginata can be distinguished from similar Mycena species by differences in size, color, and substrate. A 2010 publication reported the discovery and characterization of a novel pigment named mycenaaurin A, isolated from the mushroom. The pigment is responsible for its color, and it has antibiotic activity that may function to prevent certain bacteria from growing on the mushroom.

<i>Calostoma cinnabarinum</i> Species of fungus

Calostoma cinnabarinum is a species of gasteroid fungus in the family Sclerodermataceae, and is the type species of the genus Calostoma. It is known by several common names, including stalked puffball-in-aspic and gelatinous stalked-puffball. The fruit body has a distinctive color and overall appearance, featuring a layer of yellowish jelly surrounding a bright red, spherical head approximately 2 centimeters (0.8 in) in diameter atop a red or yellowish brown spongy stipe 1.5 to 4 cm tall. The innermost layer of the head is the gleba, containing clear or slightly yellowish elliptical spores, measuring 14–20 micrometers (µm) long by 6–9 µm across. The spore surface features a pattern of small pits, producing a net-like appearance. A widely distributed species, it grows naturally in eastern North America, Central America, northeastern South America, and East Asia. C. cinnabarinum grows on the ground in deciduous forests, where it forms mycorrhizal associations with oaks.

<span class="mw-page-title-main">Calostomal</span> Chemical compound

Calostomal is an organic compound that has a carboxylic acid and an aldehyde group. It is an orange solid that is extracted from the mushroom Calostoma cinnabarinum, hence its name. The structure of this compound was confirmed by NMR and mass spectrometry of the methyl ester derivative. This compound is a polyene; its conjugated system accounts for its intense color, similar to lycopene found in tomatoes.

<span class="mw-page-title-main">Variegatic acid</span> Chemical compound

Variegatic acid is an orange pigment found in some mushrooms. It is responsible for the bluing reaction seen in many bolete mushrooms when they are injured. When mushroom tissue containing variegatic acid is exposed to air, the chemical is enzymatically oxidized to blue quinone methide anions, specifically chinonmethid anions. It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, and its genetic basis is unknown. In its oxidized form is variegatorubin, similar to xerocomorubin.

<span class="mw-page-title-main">Oudemansin A</span> Chemical compound

Oudemansin A is a natural product first isolated from the basidiomycete fungus Oudemansiella mucida. Its chemical structure was determined by X-ray crystallography in 1979 and absolute stereochemistry by total synthesis. Two closely related derivatives, oudemansin B and X have also been isolated from other basidiomycetes. They are all biologically active against many filamentous fungi and yeasts but with insufficient potency and stability to become useful commercial products. However, their discovery, together with the strobilurins led to agricultural fungicides including azoxystrobin with the same mechanism of action.

<span class="mw-page-title-main">Variegatorubin</span> Chemical compound

Variegatorubin is a pulvinic acid derivative. It is a red pigment that is present in many members of the Boletales, an order of the division Basidiomycota. It is generated from the oxidation of variegatic acid. Bolete species that contain variegatorubin include Neoboletus luridiformis, Chalciporus piperatus, Rhizopogon roseolus, Exsudoporus frostii, Suillellus luridus, Rubroboletus rhodoxanthus, and R. satanas. Variegatorubin was discovered by Wolfgang Steglich and colleagues, and described as a new compound in 1970.

<i>Phlomoides tuberosa</i> Species of flowering plant

Phlomoides tuberosa, the sage-leaf mullein, is a perennial herbaceous flowering plant in the family Lamiaceae, native to China, Kazakhstan, Kyrgyzstan, Mongolia, Russia; SW Asia and Europe. Enlarged, tuberous roots give rise to erect stems to 150 cm bearing purple-red flowers.

<span class="mw-page-title-main">Xerocomic acid</span> Chemical compound

Xerocomic acid is a red-orange pigment found in fungi of the order Boletales. It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin. As an example, it is isolated from Serpula lacrymans. It is soluble in methanol. An oxidase acting on xerocomic acid is responsible for the "bluing" reaction seen in mushrooms.

References

  1. 1 2 Jaeger RJ, Spiteller P (2010). "Mycenaaurin A, an Antibacterial Polyene Pigment from the Fruiting Bodies of Mycena aurantiomarginata". Journal of Natural Products. 73 (8): 1350–1354. doi:10.1021/np100155z. PMID   20617819.
  2. 1 2 Kahner L, Dasenbrock J, Spiteller P, Steglich W, Marumoto R, Spiteller M (1998). "Polyene pigments from fruit-bodies of boletus laetissimus and B. rufo-aureus (basidiomycetes)". Phytochemistry. 49 (6): 1693–1697. doi:10.1016/S0031-9422(98)00319-7. PMID   11711083.
  3. Gruber G, Steglich W (2007). "Calostomal, a polyene pigment from the gasteromycete Calostoma cinnabarinum (Boletales)" (PDF). Zeitschrift für Naturforschung B. 62 (1): 129–131. doi:10.1515/znb-2007-0120. S2CID   28501033.
  4. Aulinger K, Besl H, Spiteller P, Spiteller M, Steglich W (2001). "Melanocrocin, a polyene pigment from Melanogaster broomeianus (Basidiomycetes)". Zeitschrift für Naturforschung C. 56 (7–8): 495–498. doi: 10.1515/znc-2001-7-803 . PMID   11531079. S2CID   41177931.