Isoprenoid phenol and quinone precursors of ubiguinones and dihydroubiguinones (ubiguinones (H 2 )) in fungi.
1. Ten moulds and two yeasts were analysed for the presence of 2-polyprenylphenols, 2-polyprenyl(H(2))phenols, 6-methoxy-2-polyprenylphenols, 6-methoxy-2-polyprenyl(H(2))phenols, 6-methoxy-2-polyprenyl-1,4-benzoquinones, 6-methoxy-2-polyprenyl(H(2))-1,4-benzoquinones, 5-demethoxyubiquinones, 5-demethoxyubiquinones(H(2)), ubiquinones and ubiquinones(H(2)). 2. The organisms were found to be of three types: (a) those that contained only ubiquinones (Aspergillus fumigatus and Penicillium brevi-compactum) or ubiquinones(H(2)) (Alternaria solani, Claviceps purpurae and Penicillium stipitatum); (b) those that contained 5-demethoxyubiquinones and ubiquinones (Agaricus campestris, Aspergillus niger, Phycomyces blakesleeanus, Rhodotorula glutinis and Saccharomyces cerevisiae) or 5-demethoxyubiquinones(H(2)) and ubiquinones(H(2)) (Aspergillus quadrilineatus and Neurospora crassa); (c) one that contained 2-decaprenyl(H(2))phenol, 6-methoxy-2-decaprenyl(H(2))phenol, 6-methoxy-2-decaprenyl(X-H(2))-1,4-benzoquinone, 5-demethoxyubiquinone-10(X-H(2)) and ubiquinones(H(2)) (Aspergillus flavus). 3. Studies were made on the biosynthesis of ubiquinones and ubiquinones(H(2)) by Asp. flavus, Phyc. blakesleeanus and S. cerevisiae. These provided evidence that in Phyc. blakesleeanus 5-demethoxyubiquinone-9 is a precursor of ubiquinone-9 and that in S. cerevisiae 5-demethoxyubiquinone-6 is a precursor of ubiquinone-6. In addition they yielded results that may be interpreted as providing evidence that in Asp. flavus 6-methoxy-2-decaprenyl(X-H(2))-1,4-benzoquinone and 5-demethoxyubiquinone-10(X-H(2)) are precursors of ubiquinone-10(X-H(2)).
D001203:Ascomycota; D001230:Aspergillus / Q000378:metabolism; D001565:Benzoates / Q000378:metabolism; D002247:Carbon Isotopes / Q000378:metabolism; D005658:Fungi / Q000378:metabolism*; D003904:Mitosporic Fungi; D009491:Neurospora / Q000378:metabolism; D010407:Penicillium / Q000378:metabolism; D010636:Phenols / Q000378:metabolism*; D011809:Quinones / Q000378:metabolism*; D012440:Saccharomyces / Q000378:metabolism; D013729:Terpenes / Q000378:metabolism*; D014451:Ubiquinone / Q000096:biosynthesis / Q000378:metabolism*
D001565:Benzoates; D002247:Carbon Isotopes; D010636:Phenols; D011809:Quinones; D013729:Terpenes; D014451:Ubiquinone