Grevilline

Grevilline
Grevilline A
Grevilline B
Grevilline C
Grevilline D
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • A: InChI=1S/C18H12O6/c19-12-5-1-10(2-6-12)9-14-16(21)15(17(22)18(23)24-14)11-3-7-13(20)8-4-11/h1-9,19-21H/b14-9+
    Key: HIUMAIHELPNSFG-NTEUORMPSA-N
  • B: InChI=1S/C18H12O7/c19-11-4-2-10(3-5-11)15-16(22)14(25-18(24)17(15)23)8-9-1-6-12(20)13(21)7-9/h1-8,19-22H/b14-8+
    Key: OLZRNPOBVWGCKN-RIYZIHGNSA-N
  • C: InChI=1S/C18H12O8/c19-10-3-1-8(5-12(10)21)6-14-16(23)15(17(24)18(25)26-14)9-2-4-11(20)13(22)7-9/h1-7,19-23H/b14-6+
    Key: SFYPADSXJOTYIW-MKMNVTDBSA-N
  • D: InChI=1S/C18H12O8/c19-9-2-4-11(20)10(7-9)15-16(23)14(26-18(25)17(15)24)6-8-1-3-12(21)13(22)5-8/h1-7,19-23H/b14-6+
    Key: QKEFFIMFIWJNDJ-MKMNVTDBSA-N
  • A: C1=CC(=CC=C1/C=C/2\C(=C(C(=O)C(=O)O2)C3=CC=C(C=C3)O)O)O
  • B: C1=CC(=CC=C1C2=C(/C(=C\C3=CC(=C(C=C3)O)O)/OC(=O)C2=O)O)O
  • C: C1=CC(=C(C=C1/C=C/2\C(=C(C(=O)C(=O)O2)C3=CC(=C(C=C3)O)O)O)O)O
  • D: C1=CC(=C(C=C1/C=C/2\C(=C(C(=O)C(=O)O2)C3=C(C=CC(=C3)O)O)O)O)O
Properties
A: C18H12O6
B: C18H12O7
C: C18H12O8
D: C18H12O8
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Grevillines (also spelled grevillins) are a group of natural chemical pigments found in certain fungi, notably the tamarack jack mushroom (Suillus grevillei). There are four members of the class, named grevilline A through D. Grevillines were first isolated from Suillus grevillei, from which they derive their name, and were characterized by Wolfgang Steglich in 1972.

Grevillines are polyphenolic compounds and contain a keto-pyranone group that is similar to hydroquinone. As pigments, they contribute to yellow, orange, and red coloration of the mushrooms they occur in.

Laboratory syntheses of grevillines have been reported.

References

  1. ↑ Steglich, Wolfgang; Besl, Helmut; Prox, Axel (1972). "Zur struktur der grevilline, neuartiger pigmente aus dem goldröhrling, suillus grevillei (Boletaceae)". Tetrahedron Letters. 13 (48): 4895–4898. doi:10.1016/S0040-4039(01)94459-4.
  2. ↑ Gill, M.; Kiefel, MJ; Lally, DA; Ten, A. (1990). "Pigments of Fungi. XV. An Efficient, Unambiguous Route to Unsymmetrically Substituted Dibenzyl Acyloins and Their Use in the Synthesis of Fungus Pigments of the Pulvinone and Grevillin Types". Australian Journal of Chemistry. 43 (9): 1497–1518. doi:10.1071/CH9901497.
  3. ↑ Gill, Melvyn; Kiefel, Milton J. (1988). "Synthesis of fungus pigments of the grevillin and pulvinone types from benzylacyloins". Tetrahedron Letters. 29 (17): 2085–2087. doi:10.1016/S0040-4039(00)87841-7.
  4. ↑ Pattenden, Gerald; Pegg, Neil A.; Kenyon, Ronald W. (1987). "Synthesis of grevillins and their biogenetic interrelationship with terphenylquinones, xylerythrins and pulvinic acid". Tetrahedron Letters. 28 (40): 4749–4752. doi:10.1016/S0040-4039(00)96616-4.
  5. ↑ Lohrisch, Hans-Joachim; Steglich, Wolfgang (1975). "Synthese von grevillin C und verwandten 2H-pyran-2,5(6H)-dionen". Tetrahedron Letters. 16 (33): 2905–2908. doi:10.1016/S0040-4039(00)75026-X.