Sarah Brown
Mushrooms turning blue is a phenomenon that has puzzled researchers for decades. While the exact reason behind this colour change remains unknown, recent studies have shed some light on the biochemical processes involved. This intriguing transformation occurs in certain species, such as Psilocybe cubensis, when they are cut, bruised, or injured, and it is believed to be linked to the oxidation of specific compounds within the mushroom. The blue colour is thought to result from a complex mixture of linked psilocybin oxidation products, primarily composed of quinoid psilocyl oligomers, which share similarities with indigo, the dye used for blue jeans.
| Characteristics | Values |
|---|---|
| Type of Mushrooms | Psilocybe cyanescens, commonly known as "magic mushrooms" or "wavy caps" |
| Color | Dark blue, blue-green |
| Cause of Blueness | Oxidation of psilocybin and psilocin; oxidation of gyrocyanin or pulvinic acid in Boletales mushrooms |
| Bluing Occasions | When cut, bruised, or injured |
| Bluing Mechanism | A phosphatase enzyme removes phosphate group from psilocybin, converting it into psilocin; an oxidizing laccase then creates psilocyl radicals, which combine to form C-5 coupled subunits and polymerize via C-7 |
| Bluing Function | May serve a protective function as a repellent against predators |
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What You'll Learn
The blue colour is caused by the oxidation of psilocin
Some mushrooms, such as the Psilocybe cubensis, instantly develop a blue colour when they are injured, cut, or bruised. This phenomenon is known as an injury-triggered or wound-triggered blueing reaction. The blue colour is caused by the oxidation of psilocin, which is produced from the precursor compound psilocybin.
Psilocybin is a psychotropic compound produced by certain species of fungi, including Psilocybe cubensis. When these mushrooms are damaged, an enzyme called phosphatase removes a phosphate group from psilocybin, converting it into psilocin. This process is known as dephosphorylation and is a crucial step in the blueing reaction.
The psilocin then undergoes further chemical transformations that lead to the formation of blue pigments. An enzyme called laccase, specifically the PsiL enzyme in the case of Psilocybe mushrooms, oxidizes psilocin and facilitates the formation of psilocyl radicals. These radicals combine to form C-5 coupled subunits, which further polymerize via C-7 to create larger molecules.
The blue colour in Psilocybe mushrooms is not due to a single compound but is instead a complex mixture of linked psilocybin oxidation products. These products are mostly quinoid psilocyl oligomers, which share structural similarities with indigo, the deep blue pigment used to dye jeans. The presence of quinoid subunits and the oxidation of psilocin are key factors in the development of the blue colour.
The blueing reaction in Psilocybe mushrooms has long been a mystery, attracting the attention of natural product chemists for decades. While the chemical basis for the blue colour has been elucidated, the specific function of these blue pigments remains unknown. One hypothesis suggests that the blue compounds may serve a protective role, potentially acting as a repellent against predators.
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The blue pigment is a complex mixture of linked psilocybin oxidation products
Some mushrooms, such as the Psilocybe cyanescens, commonly known as the wavy cap or potent psilocybe, are known to turn blue when they are cut or bruised. This phenomenon is called an injury-triggered or wound-triggered blueing reaction.
The blue pigment is the result of a cascade reaction starting with psilocybin. A phosphatase enzyme removes its phosphate group, converting it into psilocin. An oxidizing laccase then creates psilocyl radicals, which combine to form C-5 coupled subunits and then further polymerise via C-7. The oxidation of psilocin is the primary cause of the blue staining observed in Psilocybe cyanescens.
The function of the blue pigments is still unknown, but it has been hypothesized that they may serve a protective role, acting as a repellent against predators. The presence of similar structure elements in anti-oxidative compounds that produce reactive oxygen species and create intestinal lesions supports this theory.
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The blue compounds are similar to indigo, a blue dye
Some mushrooms, including the Psilocybe cyanescens, commonly known as the wavy cap or potent psilocybe, turn blue when they are cut or bruised. This phenomenon is called an injury-triggered or wound-triggered blueing reaction.
The blue compounds in these mushrooms are similar to indigo, a blue dye used to produce blue jeans. The lead author of the study that revealed this similarity is Claudius Lenz. Lenz and their team identified six mushroom pigments that are products of a cascade reaction starting with psilocybin. A phosphatase enzyme takes off its phosphate group, converting it into psilocin. An oxidizing laccase then creates psilocyl radicals, which combine to form C-5 coupled subunits and then further polymerise via C-7.
Lenz states that the blue compounds and indigo share structural similarities in the indole core, and in both cases, the basis for the colour is a quinoid. The pigments are not a single compound but a complex mixture of linked psilocybin oxidation products. Most of them are quinoid psilocyl oligomers. The study's hypothesis is that the blue pigments might serve a protective function, acting as an on-demand repellent against predators.
The blueing reaction in Psilocybe mushrooms has been catalysed by PsiP and PsiL. The PsiL gene encodes a 528 aa protein with a calculated mass of 57.5 kDa, which shows 63% amino acid identity to a yellow laccase of the mushroom Stropharia aeruginosa. PsiL is likely an extracellular enzyme, and PsiL-like laccases are encoded in all 1-producing fungi whose genomes have been sequenced.
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The blue colour develops when the mushrooms are cut or bruised
The blue colour that develops when mushrooms are cut or bruised is not caused by a single compound but a complex mixture of linked psilocybin oxidation products. These compounds are called quinoid psilocyl oligomers, which are similar to indigo, the dye used to produce blue jeans. This indigo-like feature is the basis for the blue colour.
The blue colour is a result of an injury-triggered reaction. When the mushrooms are wounded, a phosphatase enzyme removes the phosphate group from psilocybin, converting it into psilocin. An oxidizing laccase then creates psilocyl radicals, which combine to form C-5 coupled subunits and then further polymerise via C-7. This cascade reaction results in the production of the blue pigments.
The blue pigments are not limited to a specific species of mushrooms. For example, Psilocybe cubensis, also known as "magic mushrooms," exhibits this injury-triggered blueing reaction. Boletales mushrooms, on the other hand, attribute their blue colour to oxidised gyrocyanin or pulvinic acid rather than psilocybin oxidation. Additionally, the staining caused by bruising or cutting is most noticeable on the stem of Psilocybe cyanescens, a psychedelic mushroom species, but it can also appear on other parts, such as the gills, cap, and mycelium.
The purpose of the blue pigments in mushrooms is still a mystery. However, it is hypothesized that the blue colour may serve a protective function, acting as a defence mechanism or a repellent against predators. This hypothesis aligns with the observation that the blue compounds share structural similarities with anti-oxidative compounds, suggesting a potential role in protecting the mushrooms from oxidative damage.
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The blue compounds may serve a protective function
The blue colour of some mushrooms, such as the Psilocybe "magic" mushrooms, has been a mystery for decades. Chemists have unravelled the mystery, revealing that the dark blue pigments are similar to indigo, the dye used to produce blue jeans. However, the function of these blue pigments is still unknown. One hypothesis is that they may serve a protective function, acting as an on-demand repellent against predators.
The blue colour is the result of a complex mixture of linked psilocybin oxidation products, specifically quinoid psilocyl oligomers. These compounds are structurally similar to indigo, with both containing an indole core and a quinoid base. The blue colour is not caused by a single compound, but by various oxidative pathways that produce different chemical species. The oxidation of psilocybin leads to the formation of psilocin, which can then be oxidized, resulting in the blue staining observed in mushrooms like Psilocybe cyanescens.
Furthermore, the structure of the blue compounds resembles that of anti-oxidative compounds, such as flavonoids and polyphenolic tannins. These anti-oxidative compounds can create intestinal lesions in insects, acting as a toxic defence mechanism. The similar structure of the blue compounds suggests that they may have a defensive role, protecting the mushrooms from predators or infections. While there is no direct evidence for this hypothesis yet, it provides a plausible explanation for the presence of the blue pigments in mushrooms.
The protective function of the blue compounds may also extend beyond defence against external threats. The blue pigments could play a role in maintaining the health and integrity of the mushrooms themselves. For example, the blue compounds may possess antioxidant properties that help protect the mushrooms from the damaging effects of oxidation, similar to how antioxidants work in other organisms. Additionally, the blue pigments could be involved in the mushrooms' repair mechanisms, aiding in the healing process after injury.
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Frequently asked questions
The blue colour is caused by the oxidation of psilocybin and psilocin, the psychotropic compounds in the mushrooms.
Chemists have unravelled this mystery by using liquid chromatography, mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectroscopy.
The pigment is a complex mixture of linked psilocybin oxidation products, mainly quinoid psilocyl oligomers, which are similar to indigo, the dye used for blue jeans.
The function of the blue pigment is not yet known. However, it is hypothesised that it may serve a protective role, acting as a repellent against predators.
Psilocybe cyanescens, commonly known as the wavy cap or potent psilocybe, is a species of psychedelic mushroom that turns blue when bruised. Other types of psilocybe mushrooms, such as Psilocybe cubensis, also exhibit this property.
