Separation and characterization of individual mycolic acids in representative mycobacteria

Watanabe, Motoko; Aoyagi, Yutaka; Ridell, Malin; Minnikin, David E.

doi:10.1099/00221287-147-7-1825

Cited by 154 publications

(207 citation statements)

References 23 publications

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“…Moreover, different strains of M.tuberculosis contained significantly different components. Some selected examples are presented in Table 1 [24]. It is clear from this that there are considerable differences in each of the characteristics reported.…”

Section: Structural Properties Of Mycolic Acids Of Mycobacterium Specmentioning

confidence: 99%

“…The detailed patterns of the mycolic acid components of a number of strains of M. tuberculosis and some other mycobacteria have been elegantly collected through the work of Watanabe et al [24,25]. The total mixture of methyl esters was analysed first by 1 H NMR spectroscopy, then separated into α-, methoxy and ketomycolates.…”

Section: Structural Properties Of Mycolic Acids Of Mycobacterium Specmentioning

confidence: 99%

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Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis

Verschoor

Baird

Grooten

2012

Progress in Lipid Research

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Mycolic acids constitute the waxy layer of the outer cell wall of Mycobacterium spp and a few other genera. They are diverse in structure, providing a unique chromatographic foot-print for almost each of the more than seventy Mycobacterium species. Although mainly esterified to cell wall arabinogalactan, trehalose or glucose, some free mycolic acid is secreted during in vitro growth of M. tuberculosis. In M. tuberculosis, alpha-, keto-and methoxy-mycolic acids are the main classes, each differing in their ability to attract neutrophils, induce foamy macrophages or adopt an antigenic structure for antibody recognition. Of interest is their particular relationship to cholesterol, discovered by their ability to attract cholesterol, to bind Amphotericin B or to be recognised by monoclonal antibodies that cross-react with cholesterol. The structural elements that determine this diverse functionality include the carboxylic acid in the mycolic motif, as well as the nature and stereochemistry of the two functional groups in the merochain. The functional diversity of mycolic acid classes implies that much information may be contained in the selective expression and secretion of mycolic acids to establish tuberculosis after infection of the host. Their cholesteroid nature may relate to how they utilize host cholesterol for their persistent survival.

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Section: Structural Properties Of Mycolic Acids Of Mycobacterium Specmentioning

confidence: 99%

Section: Structural Properties Of Mycolic Acids Of Mycobacterium Specmentioning

confidence: 99%

Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis

Verschoor

Baird

Grooten

2012

Progress in Lipid Research

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“…The occurrence of three unsaturations on the mero-chain is not an unprecedented feature in mycobacteria. Small amounts of unusually long tri-unsaturated mycolates have been described in M. tuberculosis H37Ra, M. bovis BCG, M. microti (Minnikin, 1982;Watanabe et al, 2001Watanabe et al, , 2002 and M. fallax (Rafidinarivo et al, 1985). To address the question of the precise location of the double bonds, the mycolic acids were submitted to oxidative degradation to yield the formula for the main members of the three mycolic acids (Fig.…”

Section: Discussionmentioning

confidence: 99%

Structural elucidation and genomic scrutiny of the C60–C100 mycolic acids of Segniliparus rotundus

et al. 2013

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Mycolic acids, very long-chain a-alkyl, b-hydroxylated fatty acids, occur in the members of the order Corynebacteriales where their chain lengths (C 26 -C 88 ) and structural features (oxygen functions, cis or trans double bonds, cyclopropane rings and methyl branches) are genus-and species-specific. The molecular composition and structures of the mycolic acids of two species belonging to the genus Segniliparus were determined by a combination of modern analytical chemical techniques, which include MS and NMR. They consist of mono-ethylenic C 62-C 64 (a9), di-ethylenic C 77 -C 79 (a) and extremely long-chain mycolic acids (a + ) ranging from 92 to 98 carbon atoms and containing three unsaturations, cis and/or trans double bonds and/or cyclopropanes. The double bonds in each class of mycolic acids were positioned by oxidative cleavage and exhibit locations similar to those of a-and a9-mycolic acids of mycobacteria. For the ultralong chain a-mycolic acids, the three double bonds were located at equally spaced carbon intervals (C 13 -C 16 ), with the methyl branches adjacent to the proximal and distal trans double bonds. Examination of the Segniliparus rotundus genome compared with those of other members of the Corynebacteriales indicated two obvious differences in genes encoding the elongation fatty acid (FAS-II) enzymes involved in the biosynthesis of mycolic acids: the organization of 3-ketoacyl-ACP synthases (KasA and KasB) and (3R)-hydroxyacyl-ACP dehydratases (HadAB/ BC), on one hand, and the presence of two copies of the hadB gene encoding the catalytic domain of the latter enzyme type, on the other. This observation is discussed in light of the most recent data accumulated on the biosynthesis of this hallmark of Corynebacteriales.

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“…The samples used in the present study were MeO-MAs from M. kansasii 304, Mtb Canetti MNC1485, and Mtb H37Ra, and keto-MAs from MAC KK41-24 and Mtb H37Ra, prepared as described previously (Watanabe et al, 2001(Watanabe et al, , 2002. These natural products all consist of a series of homologues.…”

Section: Methodsmentioning

confidence: 99%

“…MW of B-series is 12 higher than that given at the head of each column. Y, each is further grouped into three main types, with the major type-1 having Y as a cis-or trans-cyclopropane group (Watanabe et al, 2001(Watanabe et al, , 2002. In the present study, type-1 MeO-MA and type-1 keto-MA (hereafter referred to simply as MeO-MA and keto-MA, respectively) were used.…”

Section: Introductionmentioning

confidence: 99%

Conformational folding of mycobacterial methoxy- and ketomycolic acids facilitated by α-methyl trans-cyclopropane groups rather than cis-cyclopropane units

et al. 2013

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Conformational folding of mycobacterial methoxyand ketomycolic acids facilitated by a-methyl trans-cyclopropane groups rather than cis-cyclopropane units The oxygenated long-chain mycolic acids from many mycobacteria are characterized by the presence of mid-chain cyclopropane groups, which can have either cis-configuration or transconfiguration with an adjacent methyl branch. To determine the effect of these functional groups on mycolic acid conformation, surface pressure (p) versus mean molecular area isotherms of methoxy-(MeO-) mycolic acids (MAs) from Mycobacterium kansasii, Mycobacterium tuberculosis (Mtb) Canetti and Mtb H37Ra, and of keto-MAs from Mycobacterium avium-intracellulare complex (MAC) and Mtb H37Ra were recorded and analysed. The MeO-and keto-MAs from Mtb H37Ra, containing scarcely any trans-cyclopropyl groups, apparently took no fully folded 'Wform' conformations. Keto-MA from MAC, whose trans-cyclopropyl group content is nearly 90 %, showed a very solid W-form conformation. MeO-MAs from M. kansasii and Mtb Canetti gave stable W-form conformations at lower temperatures and surface pressures and extended conformations at higher temperatures and surface pressures; their W-form conformation was not as stable as expected from their cis-cyclopropyl group content, probably because they had a wide range of constituent homologues. Energy level calculations of cis-or a-methyl transcyclopropane-containing model molecules and computer simulation studies confirmed the superior folding properties of the latter functional unit. The present results were compared with those of MeO-and keto-MAs from Mtb and from M. bovis Bacillus Calmette-Gué rin (BCG) reported previously. Among the oxygenated MAs, those having higher trans-cyclopropane content tended to take W-form conformations more firmly, implying that the meromycolate proximal intrachain a-methyl trans-cyclopropane groups facilitated MA folding more than cis-cyclopropane groups. INTRODUCTIONMycobacterial mycolic acids (MAs) are characteristic components of the mycobacterial cell envelope, where major proportions of the acids are covalently bonded to the cell wall penta-arabinosyl units (Minnikin, 1982;Draper, 1998;Dmitriev et al., 2000). As shown in the general structure below, MAs are long chain 2-alkyl branched, 3-hydroxy fatty acids, with two intra-chain groups X and Y in the major chain, termed the meromycolate chain:According to the distal intra-chain functional group X, the MAs in this study are classified into three major groups: a nonoxygenated a-, and two oxygenated groups, methoxy-(MeO-) and keto-MAs. According to the proximal intra-chain group Abbreviations: BCG, Mycobacterium bovis Bacillus Calmette-Gué rin; MAC, Mycobacterium avium-intracellulare complex; MA, mycolic acid; Mtb, Mycobacterium tuberculosis.

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Separation and characterization of individual mycolic acids in representative mycobacteria

Cited by 154 publications

References 23 publications

Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis

Towards understanding the functional diversity of cell wall mycolic acids of Mycobacterium tuberculosis

Structural elucidation and genomic scrutiny of the C60–C100 mycolic acids of Segniliparus rotundus

Conformational folding of mycobacterial methoxy- and ketomycolic acids facilitated by α-methyl trans-cyclopropane groups rather than cis-cyclopropane units

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