Pigments terphenyls

Very recently, ganbajunin A (28), a further orange pigment related to atromentin, the methoxy atromentin 22 and other fully aromatic p-terphenyls (reported here in the following) were isolated from fruiting bodies of the Chinese mushroom Thelephora ganbajun [57],... 

Tryptophan and its relative indolylpyruvic acid (3.42) have been shown to precursors of hinnuliquinone (3.41), which is a pigment of Nodulisporium hin-nuleum. Typical of many fungal indoles in which alkylation by a dimethylallyl or isopentenyl group has occurred, mevalonate was also a precursor. However, the stage at which prenylation of a monomer or a dimer took place was unclear. Asterriquinone (3.43) from Aspergillus terreus and cochliodinol (3.44) from Chaetomium cochliodes are similar metabolites. Fission of the hydroxyquinone in the latter followed by lactonization leads to cochliodinone (3.45) in a sequence that is similar to that which inter-relates the terphenyls and pulvinic acids described in Chapter 7. 

Terphenyl C-i8Hi4CaN206S D C Red No. 7 C18H14F3N5O3 Pigment yellow 154 Ci8Hi4N2Na20eS Cl 15850 D C Red No. 6 Cl8Hi4N2Na207S2 Acid red 26 C18H14N2O2 H2SO4 8-Hydroxyquinoline sulfate... 

The isolation of polyporic acid (11) [Stahlschmidt, 1877 (597, 592)], atromentin (13) [Thorner, 1878 (653)] and thelephoric acid (16) [ZOPF, 1889 (730)] marked the start of the chemical investigation of fungal pigments. The structure elucidation and chemistry of these compounds has been amply covered in Thomson s book (655) and does not need to be repeated here. In recent years several papers dealing with ultraviolet (311), infrared (208) and mass spectra (304, 465) and with the chromatography (267) and detection (274) of simple terphenyl-quinones have been published. Details of their known distribution in fungi are given in Table 3 and their physical properties are summarised in Table 4. 

The terphenyl quinones are closely related to the pulvinic acid pigments (e.g. 132,133) which are confined to lichens and when they... 

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