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Mycolic acid
(total 203)
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(total 203)
| Id | Image | COMMON NAME | NAME | DATA No | Lipid class | INFORMANT | SYMBOL | FORMULA | MOL.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 POINT | BOILING POINT | DENSITY | REFRACTIVE INDEX | OPTICAL ROTATION | SOLUBILITY | UV SPECTRA | IR SPECTRA | NMR SPECTRA | MASS SPECTRA | OTHER SPECTRA | |||||||||||||||||||
| 1 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C51:0 acid | MMA0001 | Mycolic acid | Nagatoshi Fujiwara | C49-diD(b-unit)+C22:0(a-unit) | C71H138O3 | 1039.854 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 2 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C52:0 acid | MMA0002 | Mycolic acid | Nagatoshi Fujiwara | C50-diD(b-unit)+C22:0(a-unit) | C72H140O3 | 1053.880 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 3 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C53:0 acid | MMA0003 | Mycolic acid | Nagatoshi Fujiwara | C51-diD(b-unit+C22:0(a-unit) | C73H142O3 | 1067.907 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 4 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C54:0 acid | MMA0004 | Mycolic acid | Nagatoshi Fujiwara | C52-diD(b-unit)+C22:0(a-unit) | C74H144O3 | 1081.933 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 5 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C55:0 acid | MMA0005 | Mycolic acid | Nagatoshi Fujiwara | C53-diD(b-unit)+C22:0(a-unit) | C75H146O3 | 1095.960 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 6 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C56:0 acid | MMA0006 | Mycolic acid | Nagatoshi Fujiwara | C54-diD(b-unit)+C22:0(a-unit) | C76H148O3 | 1109.987 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 7 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C57:0 acid | MMA0007 | Mycolic acid | Nagatoshi Fujiwara | C55-diD(b-unit)+C22:0(a-unit) | C77H150O3 | 1124.013 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 8 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C58:0 acid | MMA0008 | Mycolic acid | Nagatoshi Fujiwara | C56-diD(b-unit)+C22:0(a-unit) | C78H152O3 | 1138.040 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 9 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C59:0 acid | MMA0009 | Mycolic acid | Nagatoshi Fujiwara | C57-diD(b-unit)+C22:0(a-unit) | C79H154O3 | 1152.066 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 10 |  | Dicyclopropanoyl-a-mycolic acid | 2-Eicosanoyl,3-hydroxy-dicyclopropanoyl-C60:0 acid | MMA0010 | Mycolic acid | Nagatoshi Fujiwara | C58-diD(b-unit)+C22:0(a-unit) | C80H156O3 | 1166.093 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 11 |  | Dicyclopropanoyl-a-mycolic acid | 2-Docosanoyl,3-hydroxy-dicyclopropanoyl-C50:0 acid | MMA0011 | Mycolic acid | Nagatoshi Fujiwara | C48-diD(b-unit)+C24:0(a-unit) | C72H140O3 | 1053.880 | Download ChemDraw structure data | CD1b-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) | ||||||||||||
| 12 |  | Dicyclopropanoyl-a-mycolic acid | 2-Docosanoyl,3-hydroxy-dicyclopropanoyl-C51:0 acid | MMA0012 | Mycolic acid | Nagatoshi Fujiwara | C49-diD(b-unit)+C24:0(a-unit) | C73H142O3 | 1067.907 | Download ChemDraw structure data | CD1b-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] | ||||||||||||||
![[Chromatogram 0001]](image/MMA0001CH0001.gif){kind=link}
![[Table 0001]](image/MMA0001FT0001.gif){kind=link}
![[Table 0002]](image/MMA0001FT0002.gif){kind=link}
![[Chromatogram 0001/CH0002]](image/MMA0002CH0001/CH0002.gif){kind=link}
![[Table 0001]](image/MMA0002FT0001.gif){kind=link}
![[Table 0002]](image/MMA0002FT0002.gif){kind=link}
![[Chromatogram 0001/CH0003]](image/MMA0003CH0001/CH0003.gif){kind=link}
![[Table 0001]](image/MMA0003FT0001.gif){kind=link}
![[Table 0002]](image/MMA0003FT0002.gif){kind=link}
![[Chromatogram 0001/CH0002]](image/MMA0004CH0001/CH0002.gif){kind=link}
![[Table 0001]](image/MMA0004FT0001.gif){kind=link}
![[Table 0002]](image/MMA0004FT0002.gif){kind=link}
![[Chromatogram 0001/CH0003]](image/MMA0005CH0001/CH0003.gif){kind=link}
![[Table 0001]](image/MMA0005FT0001.gif){kind=link}
![[Table 0002]](image/MMA0005FT0002.gif){kind=link}
![[Spectrum 0001]](image/MMA0006SP0001.gif){kind=link}
![[Chromatogram 0001/CH0002]](image/MMA0006CH0001/CH0002.gif){kind=link}
![[Table 0001]](image/MMA0006FT0001.gif){kind=link}
![[Table 0002]](image/MMA0006FT0002.gif){kind=link}
![[Chromatogram 0001/CH0003]](image/MMA0007CH0001/CH0003.gif){kind=link}
![[Table 0001]](image/MMA0007FT0001.gif){kind=link}
![[Table 0002]](image/MMA0007FT0002.gif){kind=link}
![[Chromatogram 0001/CH0002]](image/MMA0008CH0001/CH0002.gif){kind=link}
![[Table 0001]](image/MMA0008FT0001.gif){kind=link}
![[Table 0002]](image/MMA0008FT0002.gif){kind=link}
![[Chromatogram 0001/CH0003]](image/MMA0009CH0001/CH0003.gif){kind=link}
![[Table 0001]](image/MMA0009FT0001.gif){kind=link}
![[Table 0002]](image/MMA0009FT0002.gif){kind=link}
![[Chromatogram 0001/CH0002]](image/MMA0010CH0001/CH0002.gif){kind=link}
![[Table 0001]](image/MMA0010FT0001.gif){kind=link}
![[Table 0002]](image/MMA0010FT0002.gif){kind=link}
![[Spectrum 0002]](image/MMA0011SP0002.gif){kind=link}
![[Chromatogram 0001/CH0004]](image/MMA0011CH0001/CH0004.gif){kind=link}
![[Table 0001]](image/MMA0011FT0001.gif){kind=link}
![[Table 0002]](image/MMA0011FT0002.gif){kind=link}
![[Chromatogram 0001]](image/MMA0012CH0001.gif){kind=link}
![[Table 0001]](image/MMA0012FT0001.gif){kind=link}
![[Table 0002]](image/MMA0012FT0002.gif){kind=link}