Mycena haematopus
Encyclopedia
Mycena haematopus, commonly known as the bleeding fairy helmet, the burgundydrop bonnet, or the bleeding Mycena, is a species of fungus
Fungus
A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds , as well as the more familiar mushrooms. These organisms are classified as a kingdom, Fungi, which is separate from plants, animals, and bacteria...

 in the Mycenaceae
Mycenaceae
The Mycenaceae are a family of fungi in the order Agaricales. According to the Dictionary of the Fungi , the family contains 10 genera and 705 species. This is one of several families that were separated from the Tricholomataceae as a result of phylogenetic analyses...

 family, of the order Agaricales
Agaricales
The fungal order Agaricales, also known as gilled mushrooms , or euagarics, contains some of the most familiar types of mushrooms. The order has 33 extant families, 413 genera, and over 13000 described species, along with five extinct genera known only from the fossil record...

. It is widespread and common in Europe and North America, and has also been collected in Japan and Venezuela. It is myco-heterotrophic
Myco-heterotrophy
Myco-heterotrophy is a symbiotic relationship between certain kinds of plants and fungi, in which the plant gets all or part of its food from parasitism upon fungi rather than from photosynthesis. A myco-heterotroph is the parasitic plant partner in this relationship...

—meaning that it obtains nutrients by consuming decomposing organic matter—and the fruit bodies
Basidiocarp
In fungi, a basidiocarp, basidiome or basidioma , is the sporocarp of a basidiomycete, the multicellular structure on which the spore-producing hymenium is borne. Basidiocarps are characteristic of the hymenomycetes; rusts and smuts do not produce such structures...

 appear in small groups or clusters on the decaying logs, trunks, and stumps of deciduous
Deciduous
Deciduous means "falling off at maturity" or "tending to fall off", and is typically used in reference to trees or shrubs that lose their leaves seasonally, and to the shedding of other plant structures such as petals after flowering or fruit when ripe...

 trees, particularly beech
Beech
Beech is a genus of ten species of deciduous trees in the family Fagaceae, native to temperate Europe, Asia and North America.-Habit:...

. The fungus, first described scientifically in 1799, is classified
Biological classification
Biological classification, or scientific classification in biology, is a method to group and categorize organisms by biological type, such as genus or species. Biological classification is part of scientific taxonomy....

 in the Lactipedes section
Section (botany)
In botany, a section is a taxonomic rank below the genus, but above the species. The subgenus, if present, is higher than the section, and the rank of series, if present, is below the section. Sections are typically used to help organise very large genera, which may have hundreds of species...

 of the genus Mycena
Mycena
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...

, along with other species that produce a milky or colored latex
Latex
Latex is the stable dispersion of polymer microparticles in an aqueous medium. Latexes may be natural or synthetic.Latex as found in nature is a milky fluid found in 10% of all flowering plants . It is a complex emulsion consisting of proteins, alkaloids, starches, sugars, oils, tannins, resins,...

.

The fruit bodies
Basidiocarp
In fungi, a basidiocarp, basidiome or basidioma , is the sporocarp of a basidiomycete, the multicellular structure on which the spore-producing hymenium is borne. Basidiocarps are characteristic of the hymenomycetes; rusts and smuts do not produce such structures...

 of M. haematopus have caps
Pileus (mycology)
The pileus is the technical name for the cap, or cap-like part, of a basidiocarp or ascocarp that supports a spore-bearing surface, the hymenium. The hymenium may consist of lamellae, tubes, or teeth, on the underside of the pileus...

 that are up to 4 cm (1.6 in) wide, whitish gills, and a thin, fragile reddish-brown stem
Stipe (mycology)
thumb|150px|right|Diagram of a [[basidiomycete]] stipe with an [[annulus |annulus]] and [[volva |volva]]In mycology a stipe refers to the stem or stalk-like feature supporting the cap of a mushroom. Like all tissues of the mushroom other than the hymenium, the stipe is composed of sterile hyphal...

 with thick coarse hairs at the base. They are characterized by their reddish color, the scalloped cap edges, and the dark red latex they "bleed" when cut or broken. Both the fruit bodies and the mycelia
Mycelium
thumb|right|Fungal myceliaMycelium is the vegetative part of a fungus, consisting of a mass of branching, thread-like hyphae. The mass of hyphae is sometimes called shiro, especially within the fairy ring fungi. Fungal colonies composed of mycelia are found in soil and on or within many other...

 are weakly bioluminescent. M. haematopus produces various alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

 pigment
Pigment
A pigment is a material that changes the color of reflected or transmitted light as the result of wavelength-selective absorption. This physical process differs from fluorescence, phosphorescence, and other forms of luminescence, in which a material emits light.Many materials selectively absorb...

s unique to this species. The edibility
Edible mushroom
Edible mushrooms are the fleshy and edible fruiting bodies of several species of fungi. Mushrooms belong to the macrofungi, because their fruiting structures are large enough to be seen with the naked eye. They can appear either below ground or above ground where they may be picked by hand...

 of the fruit bodies is not known definitively.

Taxonomy and naming

The species was initially named Agaricus haematopus by Christian Hendrik Persoon
Christian Hendrik Persoon
Christiaan Hendrik Persoon was a mycologist who made additions to Linnaeus' mushroom taxonomy.-Early life:...

 in 1799, and later sanctioned
Sanctioned name
In mycology, a sanctioned name is a name that was adopted in certain works of Christiaan Hendrik Persoon or Elias Magnus Fries, which are considered major points in fungal taxonomy.-Definition and effects:...

 under this name by Elias Magnus Fries
Elias Magnus Fries
-External links:*, Authors of fungal names, Mushroom, the Journal of Wild Mushrooming.*...

 in his 1821 Systema Mycologicum. In the classification of Fries, only a few genera were named, and most agaric
Agaric
An agaric is a type of fungal fruiting body characterized by the presence of a pileus that is clearly differentiated from the stipe , with lamellae on the underside of the pileus. "Agaric" can also refer to a basidiomycete species characterized by an agaric-type fruiting body...

 mushrooms were grouped in Agaricus, which was organized into a large number of tribes
Tribe (biology)
In biology, a tribe is a taxonomic rank between family and genus. It is sometimes subdivided into subtribes.Some examples include the tribes: Canini, Acalypheae, Hominini, Bombini, and Antidesmeae.-See also:* Biological classification* Rank...

. Mycena haematopus gained its current name in 1871 when the German fungal taxonomist Paul Kummer
Paul Kummer
Paul Kummer was a priest, teacher, and scientist in Zerbst, Germany, known chiefly for his contribution to mycological nomenclature. Earlier classification of agarics by pioneering fungal taxonomist Elias Magnus Fries designated only a very small number of genera, with most species falling into...

 raised many of Fries' Agaricus tribes to the level of genus, including Mycena
Mycena
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...

. In 1909 Franklin Sumner Earle
Franklin Sumner Earle
Franklin Sumner Earle was an American mycologist. He was the first mycologist to work at the New York Botanical Garden, and was the author of The Genera of North American Gill Fungi .-References:...

 placed the species in Galactopus, a genus that is no longer considered separate from Mycena. Mycena haematopus is placed in the section
Section (botany)
In botany, a section is a taxonomic rank below the genus, but above the species. The subgenus, if present, is higher than the section, and the rank of series, if present, is below the section. Sections are typically used to help organise very large genera, which may have hundreds of species...

 Lactipedes, a grouping of Mycenas characterized by the presence of a milky or colored latex in the stem and flesh of the cap. The specific epithet is derived from Ancient Greek roots meaning "blood" (αἱματο-, haimato-) and "foot" (πους, pous). It is commonly
Common name
A common name of a taxon or organism is a name in general use within a community; it is often contrasted with the scientific name for the same organism...

 known as the blood-foot mushroom, the bleeding fairy helmet, the burgundydrop bonnet, or the bleeding Mycena.

In 1914, Jakob Emanuel Lange
Jakob Emanuel Lange
Jakob Emanuel Lange , was a Danish mycologist who studied the systematics of gilled mushrooms.His most well-known work is Flora Agaricina Danica, a five-volume plate work on the Agaricales of Denmark....

 described the variety M. haematopus var. marginata, characterized by the reddish color on the edge of the gills; Mycena specialist Rudolph Arnold Maas Geesteranus
Rudolph Arnold Maas Geesteranus
Rudolph Arnold Maas Geesteranus, born 20 January 1911 in The Hague, died May 18 2003 in Oegstgeest, was a Dutch mycologist.-References:...

 considered the coloration of the gill edge too variable to have taxonomical significance. Mycena haematopus var. cuspidata was initially found in Colorado
Colorado
Colorado is a U.S. state that encompasses much of the Rocky Mountains as well as the northeastern portion of the Colorado Plateau and the western edge of the Great Plains...

 in 1976, and described as a new variety by American mycologists Duane Mitchel and Alexander H. Smith
Alexander H. Smith
Alexander Hanchett Smith was an American mycologist known for his extensive contributions to the taxonomy and phylogeny of the higher fungi, especially the agarics.-Early life:...

 two years later. The fruit bodies are characterized by a "beak" on the cap that often splits or collapses as the cap matures. It was treated as Mycena sanguinolenta
Mycena sanguinolenta
Mycena sanguinolenta, commonly known as the bleeding bonnet, the smaller bleeding Mycena, or the terrestrial bleeding Mycena, is a species of mushroom in the Mycenaceae family. It is a common and widely distributed species, and has been found in North America, Europe, Australia, and Asia...

var. cuspidata by Maas Geesteranus in 1988.

Description

The fruit bodies
Basidiocarp
In fungi, a basidiocarp, basidiome or basidioma , is the sporocarp of a basidiomycete, the multicellular structure on which the spore-producing hymenium is borne. Basidiocarps are characteristic of the hymenomycetes; rusts and smuts do not produce such structures...

 of Mycena haematopus are the reproductive structures produced by cellular threads or hypha
Hypha
A hypha is a long, branching filamentous structure of a fungus, and also of unrelated Actinobacteria. In most fungi, hyphae are the main mode of vegetative growth, and are collectively called a mycelium; yeasts are unicellular fungi that do not grow as hyphae.-Structure:A hypha consists of one or...

e which grow in rotting wood. The shape of the cap
Pileus (mycology)
The pileus is the technical name for the cap, or cap-like part, of a basidiocarp or ascocarp that supports a spore-bearing surface, the hymenium. The hymenium may consist of lamellae, tubes, or teeth, on the underside of the pileus...

 of the fruit body will vary depending on its maturity. Young caps, or "buttons", are ovoid (egg-shaped) to conical; later they are campanulate (bell-shaped), and as the fruit body matures, the margins (cap edge) lift upward so that the cap becomes somewhat flat with an umbo
Umbo (mycology)
thumb|right|[[Cantharellula umbonata]] has an umbo.thumb|right|The cap of [[Psilocybe makarorae]] is acutely papillate.An umbo is a raised area in the center of a mushroom cap. Caps that possess this feature are called umbonate. Umbos that are sharply pointed are called acute, while those that are...

 (a central nipple-shaped bump). The fully grown cap can reach up to 4 cm (1.6 in) in diameter. The surface of the cap initially appears dry and covered with what appears to be a very fine whitish powder, but it soon becomes polished and moist. Mature caps appear somewhat translucent, and develop radial grooves mirroring the position of the gills underneath. The color of the cap is reddish- or pinkish-brown, often tinged with violet, and paler towards the edge. The margin is wavy like the edge of a scallop, and may appear ragged because of lingering remnants of the partial veil
Partial veil
thumb|150px|right|Developmental stages of [[Agaricus campestris]] showing the role and evolution of a partial veilPartial veil is a mycological term used to describe a temporary structure of tissue found on the fruiting bodies of some basidiomycete fungi, typically agarics...

.

The mushroom flesh
Trama (mycology)
In mycology trama is a term for the inner, fleshy portion of a mushroom's basidiocarp, or fruit body. It is distinct from the outer layer of tissue, known as the pileipellis or cuticle, and from the spore-bearing tissue layer known as the hymenium....

 can range from pale to the color of red wine (vinaceous), and has no distinctive odor. It oozes a red latex when cut. The gills have an adnate
Adnation
Adnation in plants is the "union of unlike parts; organically united or fused with another dissimilar part, e.g. an ovary to a calyx tube, or stamens to petals". This is in contrast to connation, the fusion of similar organs....

 attachment to the stem, meaning they are more or less directly attached to it. They are initially whitish or "grayish vinaceous" in color, and can develop reddish-brown stains. Between 20 and 30 gills reach from the cap edge to the stem, resulting in a gill spacing that is described as "close to subdistant"—gaps are visible between adjacent gills. There are additional gills, called lamellulae, that do not extend directly from the margin to the stem; these are arranged in two or three series (tiers) of equal length. The stem
Stipe (mycology)
thumb|150px|right|Diagram of a [[basidiomycete]] stipe with an [[annulus |annulus]] and [[volva |volva]]In mycology a stipe refers to the stem or stalk-like feature supporting the cap of a mushroom. Like all tissues of the mushroom other than the hymenium, the stipe is composed of sterile hyphal...

 is up to 9 cm (3.5 in) tall and 0.1 to 0.2 cm (0.0393700787401575 to 0.078740157480315 in) thick, hollow and brittle, and a dark reddish-brown color. In young fruit bodies, the upper part of the stem is densely covered with a pale cinnamon-colored powder which wears off with age. The stem has a mass of coarse hairs at the base. Like the cap, the stem also bleeds a red latex when it is cut or broken.

Mycena haematopus can be parasitized
Parasitism
Parasitism is a type of symbiotic relationship between organisms of different species where one organism, the parasite, benefits at the expense of the other, the host. Traditionally parasite referred to organisms with lifestages that needed more than one host . These are now called macroparasites...

 by Spinellus fusiger
Spinellus fusiger
Spinellus fusiger, commonly known as the bonnet mould, 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...

, another fungal species which gives the mushroom a strikingly hairy appearance.

Microscopic characteristics

The spore print
Spore print
thumb|300px|right|Making a spore print of the mushroom Volvariella volvacea shown in composite: mushroom cap laid on white and dark paper; cap removed after 24 hours showing pinkish-tan spore print...

 is white. The spore
Spore
In biology, a spore is a reproductive structure that is adapted for dispersal and surviving for extended periods of time in unfavorable conditions. Spores form part of the life cycles of many bacteria, plants, algae, fungi and some protozoa. According to scientist Dr...

s are elliptical, smooth, with dimensions of 8–11 by 5–7 µm
Micrometre
A micrometer , is by definition 1×10-6 of a meter .In plain English, it means one-millionth of a meter . Its unit symbol in the International System of Units is μm...

. They are amyloid
Amyloid (mycology)
In mycology the term amyloid refers to a crude chemical test using iodine in either Melzer's reagent or Lugol's solution, to produce a black to blue-black positive reaction. It is called amyloid because starch gives a similar reaction, and that reaction for starch is also called an amyloid reaction...

, meaning they will absorb iodine
Iodine
Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....

 when stained with Melzer's reagent
Melzer's Reagent
Melzer's reagent is a chemical reagent used by mycologists to assist with the identification of fungi.-Composition:...

. The spore-bearing cells (basidia) are 4-spored. Sterile cells called cystidia are numerous on the edges on the gills; they measure 33–60 µm (sometimes up to 80) by 9–12 µm. Cystidia that are present on the stipe (caulocystidia) appear in clusters, and clublike to irregular in shape, measuring 20–55 by 3.5–12.5 µm. The gill tissue contains numerous lactifers, cells that produce the latex that is secreted when it is cut.

The surface mycelium of M. haematopus is whitish and fluffy. Swelling at the terminal tips of hyphae (diameter up to 12 µm) is present, but not very abundant, and moniliform hyphae are very rare. Bioluminescence
Bioluminescence
Bioluminescence is the production and emission of light by a living organism. Its name is a hybrid word, originating from the Greek bios for "living" and the Latin lumen "light". Bioluminescence is a naturally occurring form of chemiluminescence where energy is released by a chemical reaction in...

 is present, but weak. Extracellular oxidase
Oxidase
An oxidase is any enzyme that catalyzes an oxidation-reduction reaction involving molecular oxygen as the electron acceptor. In these reactions, oxygen is reduced to water or hydrogen peroxide ....

 enzymes are present, consistent with its ecological role as a saprobe.

Edibility

Although some sources claim that M. haematopus is edible
Edible mushroom
Edible mushrooms are the fleshy and edible fruiting bodies of several species of fungi. Mushrooms belong to the macrofungi, because their fruiting structures are large enough to be seen with the naked eye. They can appear either below ground or above ground where they may be picked by hand...

, it is "hardly worth collecting because of its small size." Other sources consider the species inedible, or recommend avoiding consumption, "since most of them have not yet been tested for toxins." The taste of the mushroom is mild to slightly bitter.

Similar species

Another Mycena that produces a reddish latex is Mycena sanguinolenta
Mycena sanguinolenta
Mycena sanguinolenta, commonly known as the bleeding bonnet, the smaller bleeding Mycena, or the terrestrial bleeding Mycena, is a species of mushroom in the Mycenaceae family. It is a common and widely distributed species, and has been found in North America, Europe, Australia, and Asia...

, the "terrestrial bleeding Mycena". It may be distinguished from M. haematopus in several ways: it is smaller, with cap diameters between 0.3 to 1 cm (0.118110236220472 to 0.393700787401575 in) wide; grows in groups rather than clusters; is found on leaves, dead branches, moss beds and pine needle beds rather than decaying wood; and the edges of its gills are consistently dark brownish-red. Furthermore, range of cap color in M. sanguinolenta is different than in M. haematopus, varying from reddish-to orange-brown, and it lacks a band of partial veil remnants hanging from the margin.

Ecology, distribution and habitat

Mycena haematopus obtains nutrients from decomposing organic matter (saprobic) and the fruit bodies can typically be found growing on stumps and well-decayed logs, usually in groups that are joined together by a common base. The decomposition of woody debris on the forest floor is the result of the combined activity of a community of fungal species. In the sequential succession
Ecological succession
Ecological succession, is the phenomenon or process by which a community progressively transforms itself until a stable community is formed. It is a fundamental concept in ecology, and refers to more or less predictable and orderly changes in the composition or structure of an ecological community...

 of mushrooms species, M. haematopus is a "late colonizer" fungus: its fruit bodies appear after the wood has first been decayed by white rot species. The initial stage of wood decay by white rot fungi involves the breakdown of "acid-unhydrolyzable residue" and holocellulose (a mixture of cellulose
Cellulose
Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to over ten thousand β linked D-glucose units....

 and hemicellulose
Hemicellulose
A hemicellulose is any of several heteropolymers , such as arabinoxylans, present along with cellulose in almost all plant cell walls. While cellulose is crystalline, strong, and resistant to hydrolysis, hemicellulose has a random, amorphous structure with little strength...

).

In North America, Mycena haematopus is known to be distributed from Alaska
Alaska
Alaska is the largest state in the United States by area. It is situated in the northwest extremity of the North American continent, with Canada to the east, the Arctic Ocean to the north, and the Pacific Ocean to the west and south, with Russia further west across the Bering Strait...

 southward. According to Mycena specialist Alexander H. Smith
Alexander H. Smith
Alexander Hanchett Smith was an American mycologist known for his extensive contributions to the taxonomy and phylogeny of the higher fungi, especially the agarics.-Early life:...

, it is "the commonest and the most easily recognized one in the genus." The species is common in Europe, and it has also been collected from Japan, and Mérida
Mérida (state)
Mérida State is one of the 23 states of Venezuela. The state capital is Mérida.Mérida State covers a total surface area of 11,300 km² and, in 2007, had an estimated population of 843,800.- Climate and Vegetation :...

, Venezuela, as the variety M. haematopus var. marginata. In the Netherlands, M. haematopus is one of many mushrooms that can regularly be found fruiting on ancient timber wharves
Wharf
A wharf or quay is a structure on the shore of a harbor where ships may dock to load and unload cargo or passengers.Such a structure includes one or more berths , and may also include piers, warehouses, or other facilities necessary for handling the ships.A wharf commonly comprises a fixed...

. The fruit bodies can be found year-round in mild weather.

Bioluminescence

Both the mycelia and the fruit bodies of M. haematopus (both young and mature specimens) are reported to be bioluminescent. However, the luminescence is quite weak, and not visible to the dark-adapted eye; in one study, light emission was detectable only after 20 hours of exposure
Exposure (photography)
In photography, exposure is the total amount of light allowed to fall on the photographic medium during the process of taking a photograph. Exposure is measured in lux seconds, and can be computed from exposure value and scene luminance over a specified area.In photographic jargon, an exposure...

 to X-ray film
Photographic film
Photographic film is a sheet of plastic coated with an emulsion containing light-sensitive silver halide salts with variable crystal sizes that determine the sensitivity, contrast and resolution of the film...

. Although the biochemical basis of bioluminescence in M. haematopus has not been scientifically investigated, in general, bioluminescence is caused by the action of luciferase
Luciferase
Luciferase is a generic term for the class of oxidative enzymes used in bioluminescence and is distinct from a photoprotein. One famous example is the firefly luciferase from the firefly Photinus pyralis. "Firefly luciferase" as a laboratory reagent usually refers to P...

s, enzymes that produce light by the oxidation of a luciferin
Luciferin
Luciferins are a class of light-emitting biological pigments found in organisms that cause bioluminescence...

 (a pigment
Pigment
A pigment is a material that changes the color of reflected or transmitted light as the result of wavelength-selective absorption. This physical process differs from fluorescence, phosphorescence, and other forms of luminescence, in which a material emits light.Many materials selectively absorb...

). The biological purpose of bioluminescence in fungi is not definitively known, although several hypotheses have been suggested: it may help attract insects to help with spore dispersal, it may be a by-product of other biochemical functions, or it may help deter heterotroph
Heterotroph
A heterotroph is an organism that cannot fix carbon and uses organic carbon for growth. This contrasts with autotrophs, such as plants and algae, which can use energy from sunlight or inorganic compounds to produce organic compounds such as carbohydrates, fats, and proteins from inorganic carbon...

s that might consume the fungus.

Natural products

Several unique chemicals are produced by Mycena haematopus. The primary pigment
Pigment
A pigment is a material that changes the color of reflected or transmitted light as the result of wavelength-selective absorption. This physical process differs from fluorescence, phosphorescence, and other forms of luminescence, in which a material emits light.Many materials selectively absorb...

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

, which is so chemically sensitive (breaking down upon exposure to air and light) that its more stable breakdown product, haematopodin
Haematopodin
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...

, was known before its eventual discovery and characterization in 2008. A chemical synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

 for haematopodin was reported in 1996. Haematopodins are the first pyrroloquinoline alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

s discovered in fungi; pyrroloquinolines combine the structures of pyrrole
Pyrrole
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. It is a colourless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3...

 and quinoline
Quinoline
Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, if exposed to light, become yellow and later brown...

, both heterocyclic aromatic organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

s. Compounds of this type also occur in marine sponges and are attracting research interest due to various biological properties
Biological activity
In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or pharmacophore but can be modified by the other...

, such as cytotoxicity against tumor cell lines
Cell culture
Cell culture is the complex process by which cells are grown under controlled conditions. In practice, the term "cell culture" has come to refer to the culturing of cells derived from singlecellular eukaryotes, especially animal cells. However, there are also cultures of plants, fungi and microbes,...

, and both antifungal
Antifungal drug
An antifungal medication is a medication used to treat fungal infections such as athlete's foot, ringworm, candidiasis , serious systemic infections such as cryptococcal meningitis, and others...

 and antimicrobial
Antimicrobial
An anti-microbial is a substance that kills or inhibits the growth of microorganisms such as bacteria, fungi, or protozoans. Antimicrobial drugs either kill microbes or prevent the growth of microbes...

activities. Additional alkaloid compounds in M. haematopus include the red pigments mycenarubins D, E and F. Prior to the discovery of these compounds, pyrroloquinoline alkaloids were considered to be rare in terrestrial sources.

External links

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