Haematopodin

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Haematopodin
Haematopodin.png
Names
Preferred IUPAC name
(6aR)-6,6a,9,10-Tetrahydro-2H,8H-[1,3]oxazolo[3,2-a]pyrrolo[4,3,2-de]quinoline-2,3(4H)-dione
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H12N2O3/c16-9-5-8-11-7(6-14-12(11)13(9)17)4-10-15(8)2-1-3-18-10/h5-6,10,14H,1-4H2/t10-/m1/s1 Yes check.svgY
    Key: GTVMGUBGOSWMOJ-SNVBAGLBSA-N Yes check.svgY
  • O=C3/C=C2/N4CCCO[C@@H]4Cc1c[nH]c(c12)C3=O
Properties
C13H12N2O3
Molar mass 244.250 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Haematopodin is the more stable breakdown product of Haematopodin B. [1] Both compounds are found in the mushroom Mycena haematopus , although haematopodin only occurs in trace amounts in fresh fruit bodies. Similar pigments (with the 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline structure), known as batzellins and damirones, have been found in sea sponges. [1] 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. [2]

Related Research Articles

Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.

Muscarine Chemical compound

Muscarine, L-(+)-muscarine, or muscarin is a natural product found in certain mushrooms, particularly in Inocybe and Clitocybe species, such as the deadly C. dealbata. Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula. Trace concentrations of muscarine are also found in Amanita muscaria, though the pharmacologically more relevant compound from this mushroom is the Z-drug-like alkaloid muscimol. A. muscaria fruitbodies contain a variable dose of muscarine, usually around 0.0003% fresh weight. This is very low and toxicity symptoms occur very rarely. Inocybe and Clitocybe contain muscarine concentrations up to 1.6%.

<i>Mycena</i> Genus of fungi

Mycena is a large genus of small saprotrophic mushrooms that are rarely more than a few centimeters in width. They are characterized by a white spore print, a small conical or bell-shaped cap, and a thin fragile stem. Most are gray or brown, but a few species have brighter colors. Most have a translucent and striate cap, which rarely has an incurved margin. The gills are attached and usually have cystidia. Some species, like Mycena haematopus, exude a latex when the stem is broken, and many species have a chlorine or radish-like odor.

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

Mycena galopus, commonly known as the milking bonnet or the milk-drop mycena, is an inedible species of fungus in the family Mycenaceae of the order Agaricales. It produces small mushrooms that have grayish-brown, bell-shaped, radially-grooved caps up to 2.5 cm (1 in) wide. The gills are whitish to gray, widely spaced, and squarely attached to the stem. The slender stems are up to 8 cm (3 in) long, and pale gray at the top, becoming almost black at the hairy base. The stem will ooze a whitish latex if it is injured or broken. The variety nigra has a dark gray cap, while the variety candida is white. All varieties of the mushroom occur during summer and autumn on leaf litter in coniferous and deciduous woodland.

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

Mycena leaiana, commonly known as the orange mycena or Lea's mycena, is a species of saprobic fungi in the genus Mycena, family Mycenaceae. Characterized by their bright orange caps and stalks and reddish-orange gill edges, they usually grow in dense clusters on deciduous logs. The pigment responsible for the orange color in this species has antibiotic properties. A variety of the species, Mycena leaiana var. australis, can be found in Australia and New Zealand.

Pulvinone Chemical compound

Pulvinone, an organic compound belonging to the esters, lactones, alcohols and butenolides classes, is a yellow crystalline solid. Although the pulvinone is not a natural product, several naturally occurring hydroxylated derivatives are known. These hydroxylated pulvinones are produced by fungal species, such as the in Europe common Larch Bolete, or by moulds such as Aspergillus terreus.

<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 rosea</i> Species of fungus

Mycena rosea, commonly known as the rosy bonnet, is a species of mushroom in the family Mycenaceae. First named Agaricus roseus in 1803 by Danish botanist Heinrich Christian Friedrich Schumacher, it was given its present name in 1912 by Gramberg.

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

Mycena polygramma, commonly known as the grooved bonnet, is a species of mushroom in the family Mycenaceae. The inedible fruit bodies are small, pale gray-brown mushrooms with broadly conical caps, pinkish gills. They are found in small troops on stumps and branches of deciduous and occasionally coniferous trees. The mushroom is found in Asia, Europe, and North America, where it is typically found on twigs or buried wood, carrying out its role in the forest ecosystem by decomposing organic matter, recycling nutrients, and forming humus in the soil. M. polygramma contains two uncommon hydroxy fatty acids and is also a bioluminescent fungus whose intensity of light emission follows a diurnal pattern.

<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.

Haematopodin B Chemical compound

Haematopodin B is a chemical compound that is found in the mushroom Mycena haematopus. It decomposes to haematopodin under the influence of air and light.

<i>Mycena maculata</i> Species of fungus in the family Mycenaceae

Mycena maculata, commonly known as the reddish-spotted Mycena, is a species of fungus in the family Mycenaceae. The fruit bodies, or mushrooms, have conic to bell-shaped to convex caps that are initially dark brown but fade to brownish-gray when young, reaching diameters of up to 4 cm. They are typically wrinkled or somewhat grooved, and have reddish-brown spots in age, or after being cut or bruised. The whitish to pale gray gills also become spotted reddish-brown as they mature. The stem, up to 8 cm (3 in) long and covered with whitish hairs at its base, can also develop reddish stains. The mycelium of M. maculata has bioluminescent properties. The saprobic fungus is found in Europe and North America, where it grows in groups or clusters on the rotting wood of both hardwoods and conifers. The edibility of the fungus is unknown. Although the species is known for, and named after its propensity to stain reddish, occasionally these stains do not appear, making it virtually indistinguishable from M. galericulata.

<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>Mycena chlorophos</i> Species of agaric fungus in the family Mycenaceae

Mycena chlorophos is a species of agaric fungus in the family Mycenaceae. First described in 1860, the fungus is found in subtropical Asia, including India, Japan, Taiwan, Polynesia, Indonesia, and Sri Lanka, in Australia, and Brazil. Fruit bodies (mushrooms) have pale brownish-grey sticky caps up to 30 mm (1.2 in) in diameter atop stems 6–30 mm (0.2–1.2 in) long and up to a millimeter thick. The mushrooms are bioluminescent and emit a pale green light. Fruiting occurs in forests on fallen woody debris such as dead twigs, branches, and logs. The fungus can be made to grow and fruit in laboratory conditions, and the growth conditions affecting bioluminescence have been investigated.

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

<i>Tricholoma aurantium</i> Species of fungus

Tricholoma aurantium, commonly known as the golden orange tricholoma, is a mushroom of the agaric genus Tricholoma. Originally described by Jacob Christian Schäffer in 1774, it was transferred to the genus Tricholoma by Adalbert Ricken in 1915.

Variegatic acid 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.

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

Mycena purpureofusca, commonly known as the purple edge bonnet, is a species of agaric fungus in the family Mycenaceae. First described by Charles Horton Peck in 1885, the species is found in Europe and North America, where it grows on the decaying wood and debris of conifers, including cones. Fruit bodies have conical to bell-shaped purple caps up to 2.5 cm (1 in) set atop slender stipes up to 10 cm (4 in) long. The mushroom is named for the characteristic dark greyish-purple color of its gill edges. In the field, M. purpureofusca mushrooms can usually be distinguished from similar species by characteristics such as the dark purple gill edges, the deep purple cap center, and its cartilagineous consistency. The fungus contains a laccase enzyme that has been investigated scientifically for its potential to detoxify recalcitrant industrial dyes used in textile dyeing and printing processes.

References

  1. 1 2 Baumann, C.; Bröckelmann, M.; Fugmann, B.; Steglich, W.; Sheldrick, W. S. (1993). "Pigments of fungi. 62. Haematopodin, an unusual pyrrologuinone derivative isolated from the fungus Mycena haematopus, Agaricales". Angewandte Chemie International Edition in English. 32 (7): 1087–89. doi:10.1002/anie.199310871.
  2. Hopmann, C.; Steglish, W. (1996). "Synthesis of haematopodin – A pigment from the mushroom Mycena haematopus (Basidiomycetes)". Liebigs Annalen. 1996 (7): 1117–20. doi:10.1002/jlac.199619960709.