Haematopodin is the more stable breakdown product of 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....

. Both compounds are found in the mushroom Mycena haematopus

Mycena haematopus

Mycena haematopus, commonly known as the bleeding fairy helmet, the burgundydrop bonnet, or the bleeding Mycena, is a species of fungus in the Mycenaceae family, of the order Agaricales. It is widespread and common in Europe and North America, and has also been collected in Japan and Venezuela...

, although haematopodin only occurs in trace amounts in fresh 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...

. Similar 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 (with the 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline structure), known as batzellins and damirones, have been found in sea sponge

Sea sponge

Sponges are animals of the phylum Porifera . Their bodies consist of jelly-like mesohyl sandwiched between two thin layers of cells. While all animals have unspecialized cells that can transform into specialized cells, sponges are unique in having some specialized cells, but can also have...

s. 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. Key steps in the synthesis involved the addition

Addition reaction

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one....

 of 3-[(2,4-dimethoxybenzyl)amino]-1-propanol to the indolo-6,7-quinone and cyclization

Cyclic compound

In chemistry, a cyclic compound is a compound in which a series of atoms is connected to form a loop or ring.While the vast majority of cyclic compounds are organic, a few inorganic substances form cyclic compounds as well, including sulfur, silanes, phosphanes, phosphoric acid, and triboric acid. ...

 of the resulting adduct

Adduct

An adduct is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components. The resultant is considered a distinct molecular species...

 with trifluoroacetic acid

Trifluoroacetic acid

Trifluoroacetic acid is the simplest stable perfluorinated carboxylic acid chemical compound, with the formula CF3CO2H. It is a strong carboxylic acid due to the influence of the electronegative trifluoromethyl group. TFA is almost 100,000-fold more acidic than acetic acid...

.