Variegatic acid
Chemical compound
Variegatic acid (3,3',4,4'-tetrahydroxypulvinic 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-colored quinone methide anions It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, but the full biosynthetic pathway is unknown. In its oxidized form (due to the production of a second lactone ring) is variegatorubin, similar to xerocomorubin.
It was first isolated from Suillus variegatus, and a total synthesis that uses a Suzuki cross coupling reaction was reported in 2001. It has strong antioxidant properties, and appears part of S. variegatus' Fenton chemistry-based saprobic attack on dead plant matter, catalyzing the reduction of Fe3+.
Variegatic acid has a nonspecific inhibitory effect on cytochrome P450 enzymes. It was found antibiotically inactive against an array of bacteria and fungi using the disk diffusion assay at 50 μg. However, at similar concentrations it was found to inhibit swarming and (probably consequently) biofilm formation of Bacillus subtilis.
01Derivatives
Variegatic acid methyl ester, 3-O-methylvariegatic acid methyl ester, and 3,3',4,4'-tetra-O-methylvariegatic acid methyl ester are red-orange pigments found in Boletales.
Sources and credits
This article is adapted from the Wikipedia article “Variegatic acid”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Variegatic acid.svg by Ed (Edgar181), Public domain
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