related compounds in mycobacteria. J Gen
Microbiol 134:2043–2055
45. Asselineau J (1982) Branched fatty acids of
mycobacteria. Ind J Chest Dis 24:143–157
46. Geerdink D, ter Horst B, Lepore M et al
(2013) Total synthesis, stereochemical elucidation and biological evaluation of Ac 2 SGL; a
1,3-methyl branched sulfoglycolipid from
Mycobacterium
tuberculosis.
Chem
Sci
4:709–716
47. Daffe ´ M, Lacave C, Lane ´elle MA et al (1988)
Polyphthienoyl trehalose, glycoplipids specific
for virulent strains of the tubercle bacillus. Eur
J Biochem 172:579–584
48. Dittmer JC, Lester RL (1964) A simple, specific method for the detection of phospholipids
on thin-layer chromatograms. J Lipid Res
5:126–127
49. Sauton B (1912) Sur la nutrition mine ´rale du
bacille tuberculeux. C R Acad Sci
155:860–863
50. Nigou J, Gilleron M, Cahuzac B et al (1997)
The phosphatidyl-myo-inositol anchor of the
lipoarabinomannans from Mycobacterium bovis
Bacillus Calmette Gue ´rin. Heterogeneity,
structure, and role in the regulation of cytokine
secretion. J Biol Chem 272:23094–23103
51. Brennan PJ, Goren M (1979) Structural studies on the type specific antigens and lipids of the
Mycobacterium avium-Mycobacterium intracellulare-Mycobacterium scrofulaceum serocomplex. J Biol Chem 254:4205–4211
52. Daffe ´ M, Lane ´elle MA, Asselineau C et al
(1983) Taxonomic value of mycobacterial
fatty acids: proposal for a method of analysis.
Ann Microbiol (Inst Pasteur) 134:241–256
53. Kates M (1986) Techniques of lipidology. Isolation, analysis and identification of lipids. In:
Burdon RH, van Knippenberg PH (eds) Laboratory techniques in biochemistry and molecular biology, vol 3. Elsevier, Amsterdam
54. Watanabe M, Ohta A, Sasaki SI, Minnikin DE
(1999) Structure of a new glycolipid from the
Mycobacterium avium-Mycobacterium intracellulare complex. J Bacteriol 181:2293–2297
55. Luquin M, Roussel J, Lopez-Calahorra F,
Lane ´elle G, Ausina V, Lane ´elle MA (1990) A
novel mycolic acid in a Mycobacterium sp from
the environment. Eur J Biochem 192:753–759
56. Watanabe M, Aoyagi Y, Ridell M et al (2001)
Separation and characterization of individual
mycolic acids in representative mycobacteria.
Microbiology 147:1825–1837
57. Nigou J, Gilleron M, Brando T et al (2004)
Structural analysis of mycobacterial lipoglycans. Appl Biochem Biotechnol 118:253–268
58. Nigou J, Zelle-Rieser C, Gilleron M et al
(2001) Mannosylated lipoarabinomannans
inhibit IL-12 production by human dendritic
cells: evidence for a negative signal delivered
through the mannose receptor. J Immunol
166:7477–7485
59. Gilleron M, Bala L, Brando T et al (2000)
Mycobacterium tuberculosis H37Rv parietal
and cellular lipoarabinomannans. Characterization of the acyl- and glyco-forms. J Biol Chem
275:677–684
60. Nigou J, Gilleron M, Puzo G (2003) Lipoarabinomannans: from structure to biosynthesis.
Biochimie 85:153–166
61. Chatterjee D, Khoo KH (1998) Mycobacterial
lipoarabinomannan: an extraordinary lipoheteroglycan with profound physiological effects.
Glycobiology 8:113–120
62. Nigou J, Vercellone A, Puzo G (2000) New
structural insights into the molecular deciphering of mycobacterial lipoglycan binding to
C-type lectins: lipoarabinomannan glycoform
characterization and quantification by capillary
electrophoresis at the subnanomole level. J Mol
Biol 299:1353–1362
63. Guilhot C, Daffe ´ M (2008) Polyketides and
polyketides-containing
glycolipids
of
M. tuberculosis: structure, biosynthesis and
biological activities. In: Kaufman SGH, Rubin
EJ (eds) Handbook of tuberculosis: molecular
biology and biochemistry, vol 1. Wiley-VCH
Verlag GmBH & Co. GaA, Weinheim, pp
21–51
64. Layre E, Collman A, Bastian M et al (2009)
Mycolic acids constitute a scaffold for mycobacterial
lipid
antigens
stimulating
CD1-restricted T cells. Chem Biol 16:82–92
65. Soto CY, Cama M, Gibert I et al (2000) Application of an easy and reliable method for
sulfolipid-I in the study of its distribution in
Mycobacterium tuberculosis strains. FEMS
Microbiol Lett 187:103–107
66. Lane ´elle MA, Prome ´ D, Lane ´elle G et al (1990)
Ornithine lipid of Mycobacterium tuberculosis:
its distribution in some slow- and fast-growing
mycobacteria. J Gen Microbiol 136:773–778
67. Minnikin DE, Minnikin SM, Parlett JH et al
(1984) Mycolic acid patterns of some species of
Mycobacterium. Arch Microbiol 189:225–231
68. Minnikin DE, Parlett JH, Magnusson M et al
(1984) Mycolic acid patterns of representatives
of Mycobacterium bovis BCG. J Gen Microbiol
130:2733–2736
150
Marie-Antoinette Lane ´ elle et al.
Microbiol 134:2043–2055
45. Asselineau J (1982) Branched fatty acids of
mycobacteria. Ind J Chest Dis 24:143–157
46. Geerdink D, ter Horst B, Lepore M et al
(2013) Total synthesis, stereochemical elucidation and biological evaluation of Ac 2 SGL; a
1,3-methyl branched sulfoglycolipid from
Mycobacterium
tuberculosis.
Chem
Sci
4:709–716
47. Daffe ´ M, Lacave C, Lane ´elle MA et al (1988)
Polyphthienoyl trehalose, glycoplipids specific
for virulent strains of the tubercle bacillus. Eur
J Biochem 172:579–584
48. Dittmer JC, Lester RL (1964) A simple, specific method for the detection of phospholipids
on thin-layer chromatograms. J Lipid Res
5:126–127
49. Sauton B (1912) Sur la nutrition mine ´rale du
bacille tuberculeux. C R Acad Sci
155:860–863
50. Nigou J, Gilleron M, Cahuzac B et al (1997)
The phosphatidyl-myo-inositol anchor of the
lipoarabinomannans from Mycobacterium bovis
Bacillus Calmette Gue ´rin. Heterogeneity,
structure, and role in the regulation of cytokine
secretion. J Biol Chem 272:23094–23103
51. Brennan PJ, Goren M (1979) Structural studies on the type specific antigens and lipids of the
Mycobacterium avium-Mycobacterium intracellulare-Mycobacterium scrofulaceum serocomplex. J Biol Chem 254:4205–4211
52. Daffe ´ M, Lane ´elle MA, Asselineau C et al
(1983) Taxonomic value of mycobacterial
fatty acids: proposal for a method of analysis.
Ann Microbiol (Inst Pasteur) 134:241–256
53. Kates M (1986) Techniques of lipidology. Isolation, analysis and identification of lipids. In:
Burdon RH, van Knippenberg PH (eds) Laboratory techniques in biochemistry and molecular biology, vol 3. Elsevier, Amsterdam
54. Watanabe M, Ohta A, Sasaki SI, Minnikin DE
(1999) Structure of a new glycolipid from the
Mycobacterium avium-Mycobacterium intracellulare complex. J Bacteriol 181:2293–2297
55. Luquin M, Roussel J, Lopez-Calahorra F,
Lane ´elle G, Ausina V, Lane ´elle MA (1990) A
novel mycolic acid in a Mycobacterium sp from
the environment. Eur J Biochem 192:753–759
56. Watanabe M, Aoyagi Y, Ridell M et al (2001)
Separation and characterization of individual
mycolic acids in representative mycobacteria.
Microbiology 147:1825–1837
57. Nigou J, Gilleron M, Brando T et al (2004)
Structural analysis of mycobacterial lipoglycans. Appl Biochem Biotechnol 118:253–268
58. Nigou J, Zelle-Rieser C, Gilleron M et al
(2001) Mannosylated lipoarabinomannans
inhibit IL-12 production by human dendritic
cells: evidence for a negative signal delivered
through the mannose receptor. J Immunol
166:7477–7485
59. Gilleron M, Bala L, Brando T et al (2000)
Mycobacterium tuberculosis H37Rv parietal
and cellular lipoarabinomannans. Characterization of the acyl- and glyco-forms. J Biol Chem
275:677–684
60. Nigou J, Gilleron M, Puzo G (2003) Lipoarabinomannans: from structure to biosynthesis.
Biochimie 85:153–166
61. Chatterjee D, Khoo KH (1998) Mycobacterial
lipoarabinomannan: an extraordinary lipoheteroglycan with profound physiological effects.
Glycobiology 8:113–120
62. Nigou J, Vercellone A, Puzo G (2000) New
structural insights into the molecular deciphering of mycobacterial lipoglycan binding to
C-type lectins: lipoarabinomannan glycoform
characterization and quantification by capillary
electrophoresis at the subnanomole level. J Mol
Biol 299:1353–1362
63. Guilhot C, Daffe ´ M (2008) Polyketides and
polyketides-containing
glycolipids
of
M. tuberculosis: structure, biosynthesis and
biological activities. In: Kaufman SGH, Rubin
EJ (eds) Handbook of tuberculosis: molecular
biology and biochemistry, vol 1. Wiley-VCH
Verlag GmBH & Co. GaA, Weinheim, pp
21–51
64. Layre E, Collman A, Bastian M et al (2009)
Mycolic acids constitute a scaffold for mycobacterial
lipid
antigens
stimulating
CD1-restricted T cells. Chem Biol 16:82–92
65. Soto CY, Cama M, Gibert I et al (2000) Application of an easy and reliable method for
sulfolipid-I in the study of its distribution in
Mycobacterium tuberculosis strains. FEMS
Microbiol Lett 187:103–107
66. Lane ´elle MA, Prome ´ D, Lane ´elle G et al (1990)
Ornithine lipid of Mycobacterium tuberculosis:
its distribution in some slow- and fast-growing
mycobacteria. J Gen Microbiol 136:773–778
67. Minnikin DE, Minnikin SM, Parlett JH et al
(1984) Mycolic acid patterns of some species of
Mycobacterium. Arch Microbiol 189:225–231
68. Minnikin DE, Parlett JH, Magnusson M et al
(1984) Mycolic acid patterns of representatives
of Mycobacterium bovis BCG. J Gen Microbiol
130:2733–2736
150
Marie-Antoinette Lane ´ elle et al.