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Mycolic acid

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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
1Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C51:0 acid MMA0001Mycolic acidNagatoshi FujiwaraC49-diD(b-unit)+C22:0(a-unit) C71H138O3 1039.854Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001] Mycobacterium diernhoferi 41002,41004<< Ref. 0004/0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
2Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C52:0 acid MMA0002Mycolic acidNagatoshi FujiwaraC50-diD(b-unit)+C22:0(a-unit) C72H140O3 1053.880Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0002] Mycobacterium vaccae(VA-1) << Ref. 0004/0005>>
Mycobacterium parafortuitum(19686) << Ref. 0001/0004/0005>>
Mycobacterium diernhoferi(MD-1) << Ref. 0001/0004/0005>>
Mycobacterium phlei<< Ref. 0005/0010>>
Mycobacterium rhodesiae(RHO-1) << Ref. 0001/0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
3Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C53:0 acid MMA0003Mycolic acidNagatoshi FujiwaraC51-diD(b-unit+C22:0(a-unit) C73H142O3 1067.907Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0003] Mycobacterium vaccae(VA-1) << Ref. 0004/0005>>
Mycobacterium parafortuitum(19686) << Ref. 0001/0004/0005>>
Mycobacterium diernhoferi(MD-1) << Ref. 0004/0005>>
Mycobacterium phlei<< Ref. 0004/0010>>
Mycobacterium rhodesiae(RHO-1) << Ref. 0001/0004/0005)>>
Mycobacterium aurum << Ref. 0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
4Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C54:0 acid MMA0004Mycolic acidNagatoshi FujiwaraC52-diD(b-unit)+C22:0(a-unit) C74H144O3 1081.933Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0002] Mycobacterium vaccae(VA-1) << Ref. 0001/0004/0005>>
Mycobacterium parafortuitum(19686) << Ref. 0001/0004/0005>>
Mycobacterium diernhoferi(MD-1) << Ref. 0001/0004/0005>>
Mycobacterium phlei << Ref. 0005>>
Mycobacterium rhodesiae(RHO-1) << Ref. 0001/0004/0005>>
Mycobacterium aurum<< Ref. 0004/0005>>
Mycobacterium kansasii << Ref. 0001>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
5Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C55:0 acid MMA0005Mycolic acidNagatoshi FujiwaraC53-diD(b-unit)+C22:0(a-unit) C75H146O3 1095.960Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0003] Mycobacterium vaccae(VA-1) << Ref. 0004/0005>>
Mycobacterium parafortuitum(19686) << Ref. 0001/0004/0005>>
Mycobacterium diernhoferi(MD-1) << Ref. 0004/0005>>
Mycobacterium phlei<< Ref. 0001/0004/0005>>
Mycobacterium rhodesiae(RHO-1) << Ref. 0001/0004/0005>>
Mycobacterium aurum<< Ref. 0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
6Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C56:0 acid MMA0006Mycolic acidNagatoshi FujiwaraC54-diD(b-unit)+C22:0(a-unit) C76H148O3 1109.987Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+)[Spectrum 0001]<< Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0002] Mycobacterium vaccae(VA-1) << Ref. 0001/0004/0005>>
Mycobacterium parafortuitum(19686) << Ref. 0001/0004/0005>>
Mycobacterium diernhoferi(MD-1) << Ref. 0001/0004/0005>>
Mycobacterium phlei<< Ref. 0001/0004/0005>>
Mycobacterium rhodesiae(RHO-1) << Ref. 0001/0004/0005>>
Mycobacterium duvalii<< Ref. 0004>>
Mycobacterium gilvum<< Ref. 0001>>
Mycobacterium aurum<< Ref. 0004/0005>>
Mycobacterium kansasii<< Ref. 0001/0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
7Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C57:0 acid MMA0007Mycolic acidNagatoshi FujiwaraC55-diD(b-unit)+C22:0(a-unit) C77H150O3 1124.013Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0003] Mycobacterium vaccae(VA-1) << Ref. 0004/0005>>
Mycobacterium parafortuitum(19686) << Ref. 0001/0004/0005>>
Mycobacterium diernhoferi(MD-1) << Ref. 0004>>Mycobacterium phlei<< Ref. 0001/0004/0005>>
Mycobacterium rhodesiae(RHO-1) << Ref. 0001/0005>>
Mycobacterium aurum<< Ref. 0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
8Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C58:0 acid MMA0008Mycolic acidNagatoshi FujiwaraC56-diD(b-unit)+C22:0(a-unit) C78H152O3 1138.040Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0002] Mycobacterium parafortuitum(19686) << Ref. 0001/0004/0005>>
Mycobacterium diernhoferi(MD-1) << Ref. 0004>>
Mycobacterium phlei<< Ref. 0001/0004/0005>>
Mycobacterium rhodesiae(RHO-1) << Ref. 0001/0004/0005>>
Mycobacterium vaccae(VA-1) << Ref. 0001/0004/0005>>
Mycobacterium agri<< Ref. 0001>>
Mycobacterium gilvum<< Ref. 0001/0004>>
Mycobacterium aurum<< Ref. 0004/0005>>
Mycobacterium thermoresistibile<< Ref. 0001>>
Mycobacterium pulveris<< Ref. 0004>>
Mycobacterium kansasii<< Ref. 0001/0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
9Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C59:0 acid MMA0009Mycolic acidNagatoshi FujiwaraC57-diD(b-unit)+C22:0(a-unit) C79H154O3 1152.066Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0003] Mycobacterium phlei<< Ref. 0001/0004/0005>>
Mycobacterium agri(90012) << Ref. 0001>>
Mycobacterium aurum<< Ref. 0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
10Dicyclopropanoyl-a-mycolic acid 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C60:0 acid MMA0010Mycolic acidNagatoshi FujiwaraC58-diD(b-unit)+C22:0(a-unit) C80H156O3 1166.093Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0002] Mycobacterium vaccae(VA-1) << Ref. 0005>>
Mycobacterium aurum(AU-1) << Ref. 0005>>
Mycobacterium thermoresistibile<< Ref. 0001/0004/0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
11Dicyclopropanoyl-a-mycolic acid 2-Docosanoyl,3-hydroxy-dicyclopropanoyl-C50:0 acid MMA0011Mycolic acidNagatoshi FujiwaraC48-diD(b-unit)+C24:0(a-unit) C72H140O3 1053.880Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+)[Spectrum 0002]<< Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001/CH0004] Mycobacterium vaccae(VA-1) << Ref. 0004/0005>>
Mycobacterium rhodesiae<< Ref. 0001/0005>>
Mycobacterium marinum<< Ref. 0005>>
Mycobacterium gordonae<< Ref. 0005>>
Mycobacterium phlei<< Ref. 0005>>
[Table 0001] [Table 0002]
DiD mycolic acids were existed in Mycobacterium tuberculosis.<< Ref. 0011>>
a-unit, C24:0,C26:0; carbon chain length, L=17,18,19, M=10, N=15,17,19,21<< Ref. 0016>>
a-unit, C26:0; carbon chain length C84<< Ref. 0005>>
DiD mycolic acids were existed in Mycobacterium microti.
a-unit, C26:0; carbon chain length, L+M+N=42,44,46,48,50,52<< Ref. 0008>>
DiD mycolic acids (C80H156O3) were existed in Mycobacterium kansaii.<< Ref. 0017>>
DiD mycolic acids were existed in Mycobacterium diernhoferi.
a-unit, C22:0; carbon chain length C70<< Ref. 0001>>,C71<< Ref. 0004>>
It is reported that Mycobacterium phlei has mycolic acids with carbon chain length with C72,74,76,77,78,79,80 as diene<< Ref. 0014>>, with C70,72,74,76,77,78,80 as diene<< Ref. 0010>>
Increasing growth temperature resulted in an increase in longer chain species of mycolic acids with a concomitant decrease in shorter chain homologoues.<< Ref. 0010/0014>>
<< Ref.0001 >> AUTHOR: Kaneda, K., Imaizumi, S., and Yano, I. TITLE: Distribution of C22-, C24- and C26-alpha-unit-containing mycolic acid homologues in mycobacteria PubMed ID:7494494 JOURNAL: Microbiol Immunol. VOLUME: 39 PAGE: 563-570(1995)
<< Ref.0004 >> AUTHOR: Kaneda, K., Imaizumi, S., Mizuno, S., Baba, T., Tsukamura, M., and Yano, I. TITLE: Structure and molecular species composition of three homologous series of alpha-mycolic acids from Mycobacterium spp PubMed ID:3150979 JOURNAL: J Gen Microbiol. VOLUME: 134 PAGE: 2213-2229(1988)
<< Ref.0005 >> AUTHOR: Kaneda, K., Naito, S., Imaizumi, S., Yano, I., Mizuno, S., Tomiyasu, I., Baba, T., Kusunose, E., and Kusunose, M. TITLE: Determination of molecular species composition of C80 or longer-chain alpha-mycolic acids in Mycobacterium spp. by gas chromatography-mass spectrometry and mass chromatography PubMed ID:3782454 JOURNAL: J Clin Microbiol. VOLUME: 24 PAGE: 1060-1070(1986)
<< Ref.0008 >> AUTHOR: Davidson, L. A., Draper, P., and Minnikin, D. E. TITLE: Studies on the mycolic acids from the walls of Mycobacterium microti PubMed ID:7119747 JOURNAL: J Gen Microbiol. VOLUME: 128 PAGE: 823-828(1982)
<< Ref.0010 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, E., Kusunose, M., and Akimori, N. TITLE: Regulation of cell wall mycolic acid biosynthesis in acid-fast bacteria. I. Temperature-induced changes in mycolic acid molecular species and related compounds in Mycobacterium phlei PubMed ID:7410334 JOURNAL: J Biochem (Tokyo). VOLUME: 88 PAGE: 211-221(1980)
<< Ref.0011 >> AUTHOR: Minnikin,D.E.,Hutchinson,I.G., and Caldicott,A.B. TITLE: Thin-Layer Chromatography of Methanolysates of Mycolic Acid-Containing Bacteria. JOURNAL: J. Chromatogr. VOLUME: 188 PAGE: 221 -233 (1980)
<< Ref.0014 >> AUTHOR: Toriyama, S., Yano, I., Masui, M., Kusunose, M., and Kusunose, E. TITLE: Separation of C50--60 and C70--80 mycolic acid molecular species and their changes by growth temperatures in Mycobacterium phlei PubMed ID:720589 JOURNAL: FEBS Lett. VOLUME: 95 PAGE: 111-115(1978)
<< Ref.0016 >> AUTHOR: Qureshi, N., Takayama, K., Jordi, H. C., and Schnoes, H. K. TITLE: Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra PubMed ID:97292 JOURNAL: J Biol Chem. VOLUME: 253 PAGE: 5411-5417(1978)
<< Ref.0017 >> AUTHOR: Lederer, E., Adam, A., Ciorbaru, R., Petit, J. F., and Wietzerbin, J. TITLE: Cell walls of Mycobacteria and related organisms; chemistry and immunostimulant properties PubMed ID:1095912 JOURNAL: Mol Cell Biochem. VOLUME: 7 PAGE: 87-104(1975)
<< Ref.0029 >> AUTHOR: Beckman, E. M., Porcelli, S. A., Morita, C. T., Behar, S. M., Furlong, S. T., and Brenner, M. B. TITLE: Recognition of a lipid antigen by CD1-restricted alpha beta+ T cells PubMed ID:7527500 JOURNAL: Nature. VOLUME: 372 PAGE: 691-694(1994)
<< Ref.0030 >> AUTHOR: Asselineau,C., and Asselineau,J. (1978) Trehalose-containing Glycolipids (Prog. Chem. Fats other Lipids. Vol. 16, pp59-99, Pergamon Press, Great Britain TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0031 >> AUTHOR: Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0032 >> AUTHOR: Bekierkunst, A., Levij, I. S., Yarkoni, E., Vilkas, E., Adam, A., and Lederer, E. TITLE: Granuloma formation induced in mice by chemically defined mycobacterial fractions PubMed ID:4981067 JOURNAL: J Bacteriol. VOLUME: 100 PAGE: 95-102(1969)
<< Ref.0033 >> AUTHOR: S.S.Syed,B.S., and Hunter,L.L.,Jr. TITLE: Studies on the Toxic Effects of Quartz and a Mycobacterial Glycolipid, Trehalose 6,6'-Dimycolate. PubMed ID:9303177 JOURNAL: Ann. Clin. Lab. Sci. VOLUME: 27 PAGE: 375 -383 (1997)
<< Ref.0037 >> AUTHOR: Lepoivre, M., Tenu, J. P., Lemaire, G., and Petit, J. F. TITLE: Antitumor activity and hydrogen peroxide release by macrophages elicited by trehalose diesters PubMed ID:6806386 JOURNAL: J Immunol. VOLUME: 129 PAGE: 860-866(1982)
<< Ref.0039 >> AUTHOR: Orbach-Arbouys, S., Tenu, J. P., and Petit, J. F. TITLE: Enhancement of in vitro and in vivo antitumor activity by cord factor (6-6'-dimycolate of trehalose) administered suspended in saline PubMed ID:6403475 JOURNAL: Int Arch Allergy Appl Immunol. VOLUME: 71 PAGE: 67-73(1983)
<< Ref.0040 >> AUTHOR: Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., and Yano, I. TITLE: In vivo induction of apoptosis in the thymus by administration of mycobacterial cord factor (trehalose 6,6'-dimycolate) PubMed ID:9125563 JOURNAL: Infect Immun. VOLUME: 65 PAGE: 1793-1799(1997)
<< Ref.0041 >> AUTHOR: Bekierkunst,A. (1984) Adjuvanticity of Mycobacteria and their Glycolipid Components, Wax D and Cord Factors (Kubica,G.P. and Wayne,L.G., eds), pp761-786, The Mycobacteria: A Sourcebook Part B Marcel Dekker, New York TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0042 >> AUTHOR: Azuma, I., Kishimoto, S., Yamamura, Y., and Petit, J. F. TITLE: Adjuvanticity of mycobacterial cell walls PubMed ID:4930810 JOURNAL: Jpn J Microbiol. VOLUME: 15 PAGE: 193-197(1971)
<< Ref.0043 >> AUTHOR: Sueoka, E., Nishiwaki, S., Okabe, S., Iida, N., Suganuma, M., Yano, I., Aoki, K., and Fujiki, H. TITLE: Activation of protein kinase C by mycobacterial cord factor, trehalose 6-monomycolate, resulting in tumor necrosis factor-alpha release in mouse lung tissues PubMed ID:7559098 JOURNAL: Jpn J Cancer Res. VOLUME: 86 PAGE: 749-755(1995)
<< Ref.0045 >> AUTHOR: Fujiwara, N., Pan, J., Enomoto, K., Terano, Y., Honda, T., and Yano, I. TITLE: Production and partial characterization of anti-cord factor (trehalose-6,6'-dimycolate) IgG antibody in rabbits recognizing mycolic acid subclasses of Mycobacterium tuberculosis or Mycobacterium avium PubMed ID:10378413 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 24 PAGE: 141-149(1999)
<< Ref.0046 >> AUTHOR: He,H.,Oka,S.,Han,Y.,Yamamura,Y.,Kusunose,E.,Kusunose,M., and Yano,I. TITLE: Rapid Serodiagnosis of Human Mycobacteriosis by ELISA Using Cord Factor (Trehalose-6,6'-Dimycolate) Purified from Mycobacterium tuberculosis as Antigen.. PubMed ID:1931132 JOURNAL: FEMS Microbiol.Immunol. VOLUME: 3 PAGE: 201 -204 (1991)
<< Ref.0047 >> AUTHOR: Maekura, R., Nakagawa, M., Nakamura, Y., Hiraga, T., Yamamura, Y., Ito, M., Ueda, E., Yano, S., He, H., Oka, S., et al. TITLE: Clinical evaluation of rapid serodiagnosis of pulmonary tuberculosis by ELISA with cord factor (trehalose-6,6'-dimycolate) as antigen purified from Mycobacterium tuberculosis PubMed ID:8214957 JOURNAL: Am Rev Respir Dis. VOLUME: 148 PAGE: 997-1001(1993)
<< Ref.0051 >> AUTHOR: Enomoto,K.,Oka,S.,Fujiwara,N.,Okamoto,T.,Okuda,Y.,Maekura,R.,Kuroki,T., and Yano,I. TITLE: Rapid Serodiagnosis of Mycobacterium avium-intracellulare Complex Infection by ELISA with Cord Factor (Trehalose 6,6'-Dimycolate), and Serotyping Using the Glycopeptidolipid Antigen. PubMed ID:9858464 JOURNAL: Microbiol.Immunol. VOLUME: 42 PAGE: 689 -696 (1998)
<< Ref.0052 >> AUTHOR: Kato, M. TITLE: Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880 JOURNAL: Infect Immun. VOLUME: 5 PAGE: 203-212(1972)
<< Ref.0053 >> AUTHOR: Kato, M. TITLE: Immunochemical properties of anti-cord factor antibody PubMed ID:4120358 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 9-13(1973)
<< Ref.0054 >> AUTHOR: Kato, M. TITLE: Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133 JOURNAL: Infect Immun. VOLUME: 7 PAGE: 14-21(1973)
<< Ref.0055 >> AUTHOR: Kawamura, M., Sueshige, N., Imayoshi, K., Yano, I., Maekura, R., and Kohno, H. TITLE: Enzyme immunoassay to detect antituberculous glycolipid antigen (anti-TBGL antigen) antibodies in serum for diagnosis of tuberculosis PubMed ID:9138102 JOURNAL: J Clin Lab Anal. VOLUME: 11 PAGE: 140-145(1997)
<< Ref.0059 >> AUTHOR: Takayama, K., Schnoes, H. K., Armstrong, E. L., and Boyle, R. W. TITLE: Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:806645 JOURNAL: J Lipid Res. VOLUME: 16 PAGE: 308-317(1975)
<< Ref.0060 >> AUTHOR: Winder, F. G., and Collins, P. B. TITLE: Inhibition by isoniazid of synthesis of mycolic acids in Mycobacterium tuberculosis PubMed ID:5500025 JOURNAL: J Gen Microbiol. VOLUME: 63 PAGE: 41-48(1970)
12Dicyclopropanoyl-a-mycolic acid 2-Docosanoyl,3-hydroxy-dicyclopropanoyl-C51:0 acid MMA0012Mycolic acidNagatoshi FujiwaraC49-diD(b-unit)+C24:0(a-unit) C73H142O3 1067.907Download ChemDraw structure dataCD1b-restricted antigen<< Ref. 0029>>
Inhibition of the biosynthesis of mycolic acid by isoniazid<< Ref. 0059/0060>>
(As mycoloyl glycolipid)
Granuloma forming activity<< Ref. 0031/0032>>
Toxicity<< Ref. 0030/0033>>
Immunomodifying activities<< Ref. 0030>>
Antitumor activity<< Ref. 0037/0039>>
Adjuvanticity<< Ref. 0041/0042>>
Tumor-necrosis-factor-priming activity<< Ref. 0043>>
In vivo induction of apoptosis in the thymus<< Ref. 0040>>
Activation of protein kinase C<< Ref. 0043>>
Antigenic properties<< Ref. 0052/0053/0054>>
Production of anti-cord factor antibody<< Ref. 0045>>
Increase of anti-cord factor IgG antibody in tuberculous patient<< Ref. 0046/0047/0051/0055>>
Chloroform,n-Hexane [M]+(molecular Ion),[M-15]+(loss of -CH3),[M-90]+(loss of trimethylsilanol),[A]+(TMS-alkoxy ion resulting from C2-C3 cleavage),[A-90]+(loss of trimethylsilanol from [A]+),[B]+(TMS-oxymethylene carboxylic acid ester resulting from C3-C4 cleavage),[B-29]+(loss of CHO from [B]+) << Ref. 0001/0004/0005>> Thin-layer chromatogram of mycolic acid methyl esters,Chromatogram was developed with a solvent of n-hexane-diethyl ether(4:1, v/v) and visualized with charring after being sprayed with 50% H2SO4 [Chromatogram 0001] Mycobacterium vaccae(VA-1) << Ref. 0004/0005>>
Mycobacterium aurum(AU-1) << Ref. 0005>>
Mycobacterium rhodesiae(RHO-1) << Ref. 0001/0004/0005>>
Mycobacterium gordonae<< Ref. 0005>>
Mycobacterium marinum<< Ref. 0005>>
Mycobacterium phlei<< Ref. 0005>>
[Table 0001] [Table 0002]