The isoprenoid compounds in gram-negative methanol-, methane-, and methylamine-utilizing bacteria were investigated. All strains tested contained ubiquinone, but none contained menaquinone. The ubiquinone types were Q-8, Q-9, or Q-10. The so-called obligate methylotrophs and methanotrophs (genus Methylobacillus, Methylophaga, Methylomonas, Methylococcus, and Methylovibrio) contained ubiquinone Q-8. The Hyphomicrobium strains contained Q-9. The other facultative methylotrophs and methylamine-utilizing bacteria contained Q-10. A large amount of squalene occurred in the Methylobacillus, Methylophaga, Methylomonas, and Methylococcus strains which utilize one-carbon compounds via the ribulose monophosphate pathway. The Pro tomonas extorquens and Methylobacterium organophilum strains contained a large amount of sterols , carotenoid pigments, and a small amount of squalene. The Hyphomicrobium strains contained a small amount of squalene and Hop-22(29)-ene. The Xanthobacter strains contained a large amount of carotenoid pigments (zeaxanthin, zeaxanthin monorhamnoside, and zeaxanthin dirhamnoside). The Protomonas and Methylobacterium strains were unique in the existence of sterols and large amounts of total isoprenoid compounds, 4.68 to 7.97 mg/g of dry cell. The distribution of squalene, sterols, quinones, and carotenoid pigments conforms with the morphological, physiological, and other chemotaxonomic characteristics in gram-negative methanol-, methane-, and methylamine-utilizing bacteria. The ubiquinone, menaquinone, squalene, sterols, and carotenoid pigments contained in bacterial cells are known as isoprenoid compounds. The taxonomic significance of ubiquinone and menaquinone in the classification of bacteria has been pointed out (1-3). On the other hand, until 1967, squalene and sterols had been encountered only in eukaryotic organisms, and not in prokaryotic organisms, bacteria and blue-green algae (4). In recent years, sterols and the sterol precursor, squalene, have been detected in Azotobacter chrococcum (5), Staphylococcus aureus (6, 7), Halobacterium cutirubrum (8), Methylococcus capsulatus (9,10), Bacillus acidocaldarius (I1), and Acetobacter xylinum (12), and methanol-utilizing bacteria such as Methylobacterium organophilum (13), Pseudomonas sp. C (14), "Pseudomonas methylotropha" (14), "Methylomonas me thanolica" (14), Pseudomonas sp. C45 (15), Pseudomonas AM-1(15), Pseudomonas M27 (15), and "Protaminobacter ruber" (15).In this paper, we describe the distribution of ubiquinone, squalene, sterols, and carotenoid pigments in gram-negative bacteria that use methanol, methane, and methylamine. The significance of these isoprenoid compounds is discussed with regard to the classification of bacteria.
MATERIALS AND METHODSBacterial strains. The strains studied and other strain designations are listed in Table 1. In addition to the bacteria described previously (16-24), bacteria closely related to gram-negative methanol-, methane-, and methylamine-utilizing bacteria were included in this study. The methanol-utilizi...