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Mycolic acid


DATA No : MMA0013 INFORMANT : Nagatoshi Fujiwara

NAME : 2-Docosanoyl,3-hydroxy-dicyclopropanoyl-C52:0 acid

COMMON NAME: Dicyclopropanoyl-a-mycolic acid
SYMBOL: C50-diD(b-unit)+C24:0(a-unit)
FORMULA: C74H144O3 MOL.WT (average) : 1081.933


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
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)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:Chloroform,n-Hexane
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:[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 0003](Ref. 0001/0004/0005)

OTHER SPECTRA:
CHROMATOGRAM DATA
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
[Chromatograms 0001/0004]
SOURCE
Mycobacterium vaccae(VA-1) (Ref. 0004/0005)
Mycobacterium rhodesiae(RHO-1) (Ref. 0001/0004/0005)
Mycobacterium phlei(Ref. 0005)Mycobacterium marinum(Ref. 0005)
Mycobacterium gordonae(Ref. 0005)
Mycobacterium aurum(Ref. 0004/0005)
Mycobacterium kansasii (Lab.) (Ref. 0001/0005)

[Table 0001]
[Table 0002]
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE
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)
REFERENCES
[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.
VOL:39 PAGE : 563-570 (1995)
[TOP]

[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.
VOL:134 PAGE : 2213-2229 (1988)
[TOP]

[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.
VOL:24 PAGE : 1060-1070 (1986)
[TOP]

[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.
VOL:128 PAGE : 823-828 (1982)
[TOP]

[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.
VOL:188 PAGE : 221 -233 (1980)
[TOP]

[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.
VOL:253 PAGE : 5411-5417 (1978)
[TOP]

[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.
VOL:7 PAGE : 87-104 (1975)
[TOP]

[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.
VOL:372 PAGE : 691-694 (1994)
[TOP]

[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:
VOL: PAGE : - ()
[TOP]

[0031]
AUTHOR:Goren,M.B. (1972) Mycobacterial Lipids: Selected Topics Bacteriological Reviews, pp33-64, American Society for Microbiology
TITLE:
JOURNAL:
VOL: PAGE : - ()
[TOP]

[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.
VOL:100 PAGE : 95-102 (1969)
[TOP]

[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.
VOL:27 PAGE : 375 -383 (1997)
[TOP]

[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.
VOL:129 PAGE : 860-866 (1982)
[TOP]

[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.
VOL:71 PAGE : 67-73 (1983)
[TOP]

[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.
VOL:65 PAGE : 1793-1799 (1997)
[TOP]

[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:
VOL: PAGE : - ()
[TOP]

[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.
VOL:15 PAGE : 193-197 (1971)
[TOP]

[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.
VOL:86 PAGE : 749-755 (1995)
[TOP]

[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.
VOL:24 PAGE : 141-149 (1999)
[TOP]

[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.
VOL:3 PAGE : 201 -204 (1991)
[TOP]

[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.
VOL:148 PAGE : 997-1001 (1993)
[TOP]

[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.
VOL:42 PAGE : 689 -696 (1998)
[TOP]

[0052]
AUTHOR:Kato, M.
TITLE:Antibody formation to trehalose-6,6'-dimycolate (cord factor) of Mycobacterium tuberculosis PubMed ID:4117880
JOURNAL:Infect Immun.
VOL:5 PAGE : 203-212 (1972)
[TOP]

[0053]
AUTHOR:Kato, M.
TITLE:Immunochemical properties of anti-cord factor antibody PubMed ID:4120358
JOURNAL:Infect Immun.
VOL:7 PAGE : 9-13 (1973)
[TOP]

[0054]
AUTHOR:Kato, M.
TITLE:Effect of anti-cord factor antibody on experimental tuberculosis in mice PubMed ID:4632133
JOURNAL:Infect Immun.
VOL:7 PAGE : 14-21 (1973)
[TOP]

[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.
VOL:11 PAGE : 140-145 (1997)
[TOP]

[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.
VOL:16 PAGE : 308-317 (1975)
[TOP]

[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.
VOL:63 PAGE : 41-48 (1970)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.