Haematopodin B

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Haematopodin B
Haematopodin B.png
Names
Preferred IUPAC name
(6aR)-2-Imino-2,4,6,6a,9,10-hexahydro-3H,8H-[1,3]oxazino[3,2-a]pyrrolo[4,3,2-de]quinolin-3-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C13H13N3O2/c14-8-5-9-11-7(6-15-12(11)13(8)17)4-10-16(9)2-1-3-18-10/h5-6,10,14-15H,1-4H2/t10-/m1/s1
    Key: CLAPNKMEQIYQLC-SNVBAGLBSA-N
  • C1CN2[C@@H](CC3=CNC4=C3C2=CC(=N)C4=O)OC1
Properties
C13H13N3O2
Molar mass 243.266 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Haematopodin B is a chemical compound that is found in the mushroom Mycena haematopus . [1] It decomposes to haematopodin under the influence of air and light. [1]

Related Research Articles

Oystercatcher Genus of birds

The oystercatchers are a group of waders forming the family Haematopodidae, which has a single genus, Haematopus. They are found on coasts worldwide apart from the polar regions and some tropical regions of Africa and South East Asia. The exceptions to this are the Eurasian oystercatcher, the South Island oystercatcher, and the Magellanic oystercatcher, which also breed inland, far inland in some cases. In the past there has been a great deal of confusion as to the species limits, with discrete populations of all black oystercatchers being afforded specific status but pied oystercatchers being considered one single species.

Eurasian oystercatcher Species of bird

The Eurasian oystercatcher also known as the common pied oystercatcher, or palaearctic oystercatcher, or just oystercatcher, is a wader in the oystercatcher bird family Haematopodidae. It is the most widespread of the oystercatchers, with three races breeding in western Europe, central Eurosiberia, Kamchatka, China, and the western coast of Korea. No other oystercatcher occurs within this area. The extinct Canary Islands oystercatcher, formerly considered a distinct species, may have actually been an isolated subspecies or distinct population of the Eurasian oystercatcher.

Sooty oystercatcher Species of bird

The sooty oystercatcher is a species of oystercatcher. It is a wading bird endemic to Australia and commonly found on its coastline. It prefers rocky coastlines, but will occasionally live in estuaries. All of its feathers are black. It has a red eye, eye ring and bill, and pink legs.

<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 cyanorrhiza</i> Species of fungus

Mycena cyanorrhiza is a small white mushroom which has blue colors. Unlike hallucinogenic mushrooms, the blue color is not related to psilocin polymerization. It grows in forests on wood and has a white spore print.

<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.

<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 galericulata</i> Species of fungus

Mycena galericulata is a mushroom species commonly known as the common bonnet, the toque mycena, or the rosy-gill fairy helmet. The type species of the genus Mycena was first described scientifically in 1772, but was not considered a Mycena until 1821. It is quite variable in color, size, and shape, which makes it somewhat difficult to reliably identify in the field. The mushrooms have caps with distinct radial grooves, particularly at the margin. The cap's color varies from grayish brown to dark brown and the shape ranges from bell-like to bluntly conical to flattened with an umbo. The stem is hollow, white, tough and thin, without a ring and often roots deeply into the wood on which it grows. The gills are white to grayish or even pinkish when mature and are connected by distinct cross-veins. The caps can reach 4 cm (1.6 in) in diameter, and have a mealy odor and taste. The spore print is white and the gills are pink at maturity, which can lead to possible confusion with species of the genus Pluteus. M. galericulata mushrooms grow mostly in clusters on the well-decayed stumps of deciduous and coniferous trees from spring to autumn. The species can generally be considered inedible. It is common and widespread in the entire temperate zone of the Northern Hemisphere, but it has also been reported from Africa.

<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 vitilis</i> Species of fungus

Mycena vitilis, commonly known as the snapping bonnet, is a species of inedible mushroom in the family Mycenaceae. It is found in Europe and North America, where it grows on the ground among leaves in damp places, especially under alder. The small pale gray to whitish fruit bodies are usually attached to small sticks buried in the leaves and detritus. They are distinguished by their long, slender stems that root into the ground, and by the grooved cap that reaches diameters of up to 2.2 cm (0.9 in). The grayish-white gills on the underside of the cap are distantly spaced, and adnately attached to the stem. M. vitilis contains strobilurin B, a fungicidal compound with potential use in agriculture.

<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.

<i>Spinellus fusiger</i> Species of fungus

Spinellus fusiger, commonly known as the bonnet mold, is a species of fungus in the Zygomycota phylum. It is a pin mold that is characterized by erect sporangiophores that are simple in structure, brown or yellowish-brown in color, and with branched aerial filaments that bear the zygospores. It grows as a parasitic mold on mushrooms, including several species from the genera Mycena, including M. haematopus, M. pura, M. epipterygia, M. leptocephala, and various Collybia species, such as C. alkalivirens, C. luteifolia, C. dryophila, and C. butyracea. It has also been found growing on agaric species in Amanita, Gymnopus, and Hygrophorus.

Haematopodin 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>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 arcangeliana</i> Species of fungus

Mycena arcangeliana is a species of Mycenaceae fungus. It has been known by a number of scientific names, and its taxonomy is still somewhat disputed. It produces small mushrooms with caps varying in colour from whitish to a darker grey-brown, and stems of an olive-greyish that fade with age. The mushrooms can be mistaken for the similar Mycena flavescens. They have a mild taste, but a strong smell of iodoform; they are not edible. The species grows on dead wood in autumn months, and can be found throughout Europe.

<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.; Steffan, 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.