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Mycolic acid


DATA No : MMA0002 INFORMANT : Nagatoshi Fujiwara

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

COMMON NAME: Dicyclopropanoyl-a-mycolic acid
SYMBOL: C50-diD(b-unit)+C22:0(a-unit)
FORMULA: C72H140O3 MOL.WT (average) : 1053.880


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]+) (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 0001/0002]
SOURCE
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]
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)
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)
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]

[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).
VOL:88 PAGE : 211-221 (1980)
[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]

[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.
VOL:95 PAGE : 111-115 (1978)
[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]

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