A new glycolipid from Mycobacterium avium—Mycobacterium intracellulare complex

Watanabe, Motoko; Kudoh, S; Yamada, Yasuji; Iguchi, Kazuo; Minnikin, David E.

doi:10.1016/0005-2760(92)90075-7

Cited by 25 publications

(29 citation statements)

References 22 publications

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“…All mycolates could be identified without ambiguity by comparison of the 1 H-NMR spectra obtained with those reported elsewhere (Watanabe et al, 1999(Watanabe et al, , 2001. Illustrating these results, the 1 H-NMR spectrum of a-mycolates from strains 'M.…”

Section: Resultssupporting

confidence: 64%

Analysis of the structure of mycolic acids of Mycobacterium simiae reveals a particular composition of α-mycolates in strain ‘habana’ TMC 5135, considered as immunogenic in tuberculosis and leprosy

2007

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Section: Resultssupporting

confidence: 64%

Analysis of the structure of mycolic acids of Mycobacterium simiae reveals a particular composition of α-mycolates in strain ‘habana’ TMC 5135, considered as immunogenic in tuberculosis and leprosy

2007

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“…Notably, peaks that we assigned as dicarboxy-MAs corresponding to wax-MAs lost their long carbon-chain secondary alcohols (C18-C22) in the process of methyl esteri cation. 30,31) e MALDI mass spectrum of the total FA ME fraction from M. smegmatis displayed a typical pattern of rapid growth that produced both even-and odd-numbered homologs; peaks corresponding to α′-MAs were observed in the range of m/z 900-1000, and peaks corresponding to α-and epoxy-MAs were observed in the range of m/z 1100-1300 (Fig. 4d).…”

Section: Analysis Of Ma Subclasses In Tlc Fractionsmentioning

confidence: 98%

Characterization of Mycolic Acids in Total Fatty Acid Methyl Ester Fractions from <i>Mycobacterium</i> Species by High Resolution MALDI-TOFMS

et al. 2015

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Mycolic acids (MAs) are characteristic components of bacteria in the suborder Corynebacterineae, such as Mycobacterium. MAs are categorized into subclasses based on their functional bases (cyclopropane ring, methoxy, keto, and epoxy group). Since MAs have heterogeneity among bacterial species, analyzing of MAs are required in the chemotaxonomic eld. However, their structural analysis is not easy because of their long carbon-chain lengths and several functional groups. In this study, total fatty acid (FA) methyl ester (ME) fraction of M. tuberculosis H37Rv was analyzed by matrix-assisted laser desorption/ionization (MALDI) time-of-ight mass spectrometry (TOFMS) with a spiral ion trajectory (MALDI spiral-TOFMS).e distributions of carbon-chain length and their relative peak intensities were con rmed with those obtained by analysis of each subclass fraction which was separated from total FA ME fraction using thin-layer chromatography (TLC). e observed major peaks were reliably assigned as MAs owing to the high mass accuracy (error<3 ppm). e types of MA subclasses, their distributions of carbon-chain lengths, their relative peak intensities, and the ratio of even-and odd-numbered carbon-chain MAs for the total FA ME fraction were consistent with those of MA subclass fractions. To visualize whole MAs, contour maps of relative peak intensities for whole MAs were created. e contour maps indicated the MA subclasses and their distributions of carbon-chains with relative peak intensities at a glance. Our proposed method allows simple characterization in a short time and thus enables the analysis of large numbers of samples, and it would contribute to the chemotaxonomy.Please cite this article as: Mass Spectrom (Tokyo) 2015; 4(1): A0035

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“…4) has been isolated from the Mycobacterium avium-Mycobacterium intracellulare complex [59]. Even a very simple monomycolylglycerol (MMG) has the ability to stimulate human dendritic cells, while a model based on just a C 32 chain has similar effects [60].…”

Section: -Mycolyl-α-arabinofuranyosyl(1→1')-glycerol (9) (Rcooh R'cmentioning

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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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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A new glycolipid from Mycobacterium avium—Mycobacterium intracellulare complex

Cited by 25 publications

References 22 publications

Analysis of the structure of mycolic acids of Mycobacterium simiae reveals a particular composition of α-mycolates in strain ‘habana’ TMC 5135, considered as immunogenic in tuberculosis and leprosy

Analysis of the structure of mycolic acids of Mycobacterium simiae reveals a particular composition of α-mycolates in strain ‘habana’ TMC 5135, considered as immunogenic in tuberculosis and leprosy

Characterization of Mycolic Acids in Total Fatty Acid Methyl Ester Fractions from <i>Mycobacterium</i> Species by High Resolution MALDI-TOFMS

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

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