Biomaterial Database

The nature, intergeneric distribution and biosynthesis of isoprenoid quinones and phenols in gram-negative bacteria. 1969

G R Whistance, and J F Dillon, and D R Threlfall

1. Twenty-two aerobically grown Gram-negative bacteria were analysed for demethylmenaquinones, menaquinones, 2-polyprenylphenols, 6-methoxy-2-polyprenylphenols and ubiquinones. 2. All the eight enterobacteria and both the two facultative organisms (Aeromonas punctata and Aeromonas hydrophila) examined contain all the compounds listed above. The principal homologues are octaprenyl; in addition lower (down to tri- or tetra-prenyl for the 2-polyprenylphenols) and sometimes higher homologues are also present. 3. Strict aerobes are of two types, those that contain 2-polyprenylphenols, 6-methoxy-2-polyprenylphenols and ubiquinones, and those that contain ubiquinones only. The principal homologues are generally octa- or nona-prenyl, although one organism (Agrobacterium tumefaciens) has ubiquinone-10 as its principal homologue. As in the enterobacteria, lower homologues of these compounds are also present. 4. In Escherichia coli W, Pseudomonas ovalis Chester and Pseudomonas fluorescens, radioactivity from p-hydroxy[U-(14)C]benzoic acid is incorporated into 2-polyprenylphenols, 6-methoxy-2-polyprenylphenols, 6-methoxy-3-methyl-2-polyprenyl-1,4-benzoquinones, ubiquinones and a compound tentatively identified as 2-polyprenyl-1,4-benzoquinone. The fact that radioactivity is incorporated into the first three compounds suggests that in these organisms, and indeed in all those Gram-negative bacteria that contain 2-polyprenylphenols and 6-methoxy-2-polyprenylphenols, ubiquinones are formed by a biosynthetic sequence similar to that in Rhodospirillum rubrum. 5. The finding in ;Vibrio O1' (Moraxella sp.) and organism PC4 that 2-polyprenylphenols and 6-methoxy-2-polyprenylphenols are chemically and radiochemically undetectable leads to the conclusion that they are not intermediates in the biosynthesis of ubiquinone by these and by other Gram-negative bacteria that do not contain detectable amounts of 2-polyprenylphenols and 6-methoxy-2-polyprenylphenols. However, ;Vibrio O1' (organism PC4 was not examined) does contain 6-methoxy-3-methyl-2-polyprenyl-1,4-benzoquinone. 6. In Ps. ovalis Chester, radioactivity from l-[Me-(14)C]methionine is incorporated into the nuclear C-methyl and O-methyl groups of 6-methoxy-3-methyl-2-polyprenyl-1,4-benzoquinones and ubiquinone-9, and into the O-methyl group of 6-methoxy-2-polyprenylphenols.

UI	MeSH Term	Description	Entries
D010636	Phenols	Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D011549	Pseudomonas	A genus of gram-negative, aerobic, rod-shaped bacteria widely distributed in nature. Some species are pathogenic for humans, animals, and plants.	Chryseomonas,Pseudomona,Flavimonas
D011809	Quinones	Hydrocarbon rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.
D002861	Chromobacterium	A genus of gram-negative, facultatively anaerobic, rod-shaped bacteria occurring in soil and water. Its organisms are generally nonpathogenic, but some species do cause infections of mammals, including humans.
D004755	Enterobacteriaceae	A family of gram-negative, facultatively anaerobic, rod-shaped bacteria that do not form endospores. Its organisms are distributed worldwide with some being saprophytes and others being plant and animal parasites. Many species are of considerable economic importance due to their pathogenic effects on agriculture and livestock.	Coliform Bacilli,Enterobacteria,Ewingella,Leclercia,Paracolobactrum,Sodalis
D004926	Escherichia coli	A species of gram-negative, facultatively anaerobic, rod-shaped bacteria (GRAM-NEGATIVE FACULTATIVELY ANAEROBIC RODS) commonly found in the lower part of the intestine of warm-blooded animals. It is usually nonpathogenic, but some strains are known to produce DIARRHEA and pyogenic infections. Pathogenic strains (virotypes) are classified by their specific pathogenic mechanisms such as toxins (ENTEROTOXIGENIC ESCHERICHIA COLI), etc.	Alkalescens-Dispar Group,Bacillus coli,Bacterium coli,Bacterium coli commune,Diffusely Adherent Escherichia coli,E coli,EAggEC,Enteroaggregative Escherichia coli,Enterococcus coli,Diffusely Adherent E. coli,Enteroaggregative E. coli,Enteroinvasive E. coli,Enteroinvasive Escherichia coli
D000333	Aeromonas	A genus of gram-negative, facultatively anaerobic, rod-shaped bacteria that occurs singly, in pairs, or in short chains. Its organisms are found in fresh water and sewage and are pathogenic to humans, frogs, and fish.
D001419	Bacteria	One of the three domains of life (the others being Eukarya and ARCHAEA), also called Eubacteria. They are unicellular prokaryotic microorganisms which generally possess rigid cell walls, multiply by cell division, and exhibit three principal forms: round or coccal, rodlike or bacillary, and spiral or spirochetal. Bacteria can be classified by their response to OXYGEN: aerobic, anaerobic, or facultatively anaerobic; by the mode by which they obtain their energy: chemotrophy (via chemical reaction) or PHOTOTROPHY (via light reaction); for chemotrophs by their source of chemical energy: CHEMOLITHOTROPHY (from inorganic compounds) or chemoorganotrophy (from organic compounds); and by their source for CARBON; NITROGEN; etc.; HETEROTROPHY (from organic sources) or AUTOTROPHY (from CARBON DIOXIDE). They can also be classified by whether or not they stain (based on the structure of their CELL WALLS) with CRYSTAL VIOLET dye: gram-negative or gram-positive.	Eubacteria
D001565	Benzoates	Derivatives of BENZOIC ACID. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain the carboxybenzene structure.	Benzoate,Benzoic Acids,Acids, Benzoic
D012231	Rhizobium	A genus of gram-negative, aerobic, rod-shaped bacteria that activate PLANT ROOT NODULATION in leguminous plants. Members of this genus are nitrogen-fixing and common soil inhabitants.