Variegatorubin

Last updated
Variegatorubin
Variegatorubin.svg
Names
IUPAC name
(3E)-3-[4-(3,4-Dihydroxyphenyl)-3-hydroxy-5-oxo-2(5H)-furanylidene]-5,6-dihydroxy-1-benzofuran-2(3H)-one
Identifiers
  • 27286-59-5 X mark.svgN
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C18H10O9/c19-8-2-1-6(3-9(8)20)13-15(23)16(27-17(13)24)14-7-4-10(21)11(22)5-12(7)26-18(14)25/h1-5,19-23H/b16-14+
    Key: UMIYSJROYJXHSW-JQIJEIRASA-N
  • InChI=1/C18H10O9/c19-8-2-1-6(3-9(8)20)13-15(23)16(27-17(13)24)14-7-4-10(21)11(22)5-12(7)26-18(14)25/h1-5,19-23H/b16-14+
    Key: UMIYSJROYJXHSW-JQIJEIRABG
  • c1cc(c(cc1C2=C(/C(=C\3/c4cc(c(cc4OC3=O)O)O)/OC2=O)O)O)O
Properties
C18H10O9
Molar mass 370.267
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Variegatorubin is a pulvinic acid derivative. It is a red pigment that is present in many members of the Boletales, an order of the division Basidiomycota. It is generated from the oxidation of variegatic acid. Bolete species that contain variegatorubin include Neoboletus luridiformis , Chalciporus piperatus , Rhizopogon roseolus , Exsudoporus frostii , Suillellus luridus , Rubroboletus rhodoxanthus , and R. satanas . [1] Variegatorubin was discovered by Wolfgang Steglich and colleagues, and described as a new compound in 1970. [2]

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Haematopodin Chemical compound

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Variegatic acid Chemical compound

Variegatic 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 quinone methide anions, specifically chinonmethid anions. It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, and its genetic basis is unknown. In its oxidized form is variegatorubin, similar to xerocomorubin.

Pulvinic acid Chemical compound

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Norbadione A Chemical compound

Norbadione A is a pigment found in the bay bolete mushroom. A polyphenol, norbadione A is related to a family of mushroom pigments known as pulvinic acids. The molecule has also been reported as a potassium salt from the mushrooms Pisolithus tinctorius and Chalciporus piperatus.

Xerocomic acid Chemical compound

Xerocomic acid is a red-orange pigment found in fungi of the order Boletales. It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin. As an example, it is isolated from Serpula lacrymans. It is soluble in methanol. An oxidase acting on xerocomic acid is responsible for the "bluing" reaction seen in mushrooms.

Atromentic acid Chemical compound

Atromentic acid is a red-organge pigment found in fungi within the Boletales group. It is the precursor to variegatic acid and xerocomic acid, and is preceded by atromentin. As an example, it is isolated from Serpula lacrymans. It is soluble in methanol. Variants include homoatromentic acid. This pigment has been studied and elucidated by Wolfgang Steglich and colleagues over decades. When atromentin is oxidised with hydrogen peroxide a yellow product is produced. A sodium hydroxide solution is also yellow, but when this is neutralized with acid the red atromentic acid crystallises. Concentrated potassium hydroxide breaks up the compound to p-hydroxyphenylacetic acid and oxalic acid.

Xerocomorubin

Xerocomorubin is a pigment from the fungus group, the Boletales. It is the oxidized form of isoxerocomic acid. Air oxidation is responsible its formation, and oxidizes faster to a similar pulvinic acid type pigment oxidized variant, variegatorubin. The long wavelength has an absorption at 497 nm, 106 nm higher than its precursor isoxerocomic acid. Synthesis experiments have shown tetra-acetylation by acetic anhydride and sulphuric acid. Although xerocomorubin and variegatorubin give off the same deep red color and could simultaneously occur in a mushroom, extracts from the deep red colored mushroom Boletus rubellus Krombh. identified only variegatorubin by t.l.c, leading to the question the natural abundance of xerocomorubin.

Isoxerocomic acid Chemical compound

Isoxerocomic acid is a red-orange pigment found in Boletales. It is the precursor to variegatic acid, and is preceded by atromentic acid and atromentin. As an example, it is isolated from Serpula lacrymans. It is soluble in methanol. It is the isomer of xerocomic acid and precursor to xerocomorubin.

Cyclovariegatin Chemical compound

Cyclovariegatin is a pigment. Its chemical name is 1,4-Dihydro-2,7,8-trihydroxy-3-(3,4-dihydroxyphenyl)-l,4-dioxodibenzofuran. It is distinguishable by its UV-Vis spectra with maxima at 257, 296, and 430 nm. The variants cyclovariegatin-pentaacetate, cyclovariegatin-2,3',8-triacetate, and cyclovariegatin-2-acetate have also been described. It is derived from atromentin. It has been isolated from the browned skin of Suillus grevillei var. badius, and becomes the pigment thelephoric acid.

References

  1. Gill, M.; Steglich, W. (2012). Pigments of Fungi (Macromycetes). Progress in the Chemistry of Organic Natural Products. 51. Springer Science & Business Media. pp. 1–297 (see p. 35). ISBN   978-3-7091-6971-1.
  2. Steglich, W.; Furtner, W.; Prox, A. (1970). "Variegatorubin, an oxidation product of variegatic acid from Suillus piperatus (Bull. ex Fr.) O. Kuntze and other Boletaceae". Zeitschrift für Naturforschung B. 5: 557. doi:10.1515/znb-1970-0529. S2CID   95770276.