Variegatic acid
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| Preferred IUPAC name
(E)-(3,4-Dihydroxyphenyl)[4-(3,4-dihydroxyphenyl)-3-hydroxy-5-oxofuran-2(5H)-ylidene]acetic acid | |
| Other names
3,3′,4,4′-Tetrahydroxy pulvinic acid
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| Identifiers | |
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3D model (JSmol)
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C18H12O9 | |
| Molar mass | 372.285 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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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[1] 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.[2] It has strong antioxidant properties,[3][4] and a nonspecific inhibitory effect on cytochrome P450 enzymes.[5] A total synthesis was reported in 2001 that uses a Suzuki cross coupling reaction.[6] It was found antibiotically inactive against an array of bacteria and fungi using the disk diffusion assay at 50 μg.[7] However, at similar concentrations it was found to inhibit swarming and (probably consequently) biofilm formation of Bacillus subtilis. In vitro data supports that this pigment is an Fe3+-reducant in Fenton chemistry during the initial attack of dead plant matter as part of the brown-rot saprobic lifestyle.[8]
Derivatives
[edit | edit source]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.[9][10]
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Variegatic acid methyl ester
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3-O-Methylvariegatic acid methyl ester
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3,3',4,4'-Tetra-O-methyl variegatic acid methyl ester
See also
[edit | edit source]References
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- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Open access icon
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- ^ Tauber, J. P., Schroeckh, V., Shelest, E., Brakhage, A. A. and Hoffmeister, D. (2016), Bacteria induce pigment formation in the basidiomycete Serpula lacrymans. Environ Microbiol, 18: 5218–5227. doi:10.1111/1462-2920.13558
- ^ Eastwood et al. (2011) The Plant Cell Wall- Decomposing Machinery Underlies the Functional Diversity of Forest Fungi. Science.
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Gill, M., and Steglich, W. (1987) Pigments of fungi (Macromycetes). Prog Chem Org Nat Prod 51: 1–317.
