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Lipoamino acid


DATA No : ALA0002 INFORMANT : Youko Kawai

NAME : a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-L-ornithine

COMMON NAME: Ornithine-containing lipid of Flavobacterium
SYMBOL:
FORMULA: C37H72O5N2 MOL.WT (average) : 624.978


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Macrophage activation by the OL was studied. TNF-inducing activity was very low
[Table 0006]. Prostaglandin (PGE2)- and interleukin (IL)-1-inducing avtivities were strong.
[Tables 0007/0008] (Ref. 0006/0009). B-lymphocyte mitogenicity was strong
[Table 0009] (Ref. 0007). LPS antagonist activity
[Table 0010] (Ref. 0008). Preadministration of the OL protects mice from the endotoxin lethality.
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:
[Spectrum 0005] Esterlinkage 1730 cm -1, Secondary amide linkage 1640 and 1540 -1.

NMR SPECTRA:

MASS SPECTRA:
[Spectrum 0006] Molecular ion 625.

OTHER SPECTRA:
CHROMATOGRAM DATA

[Chromatogram 0003] TLC of free lipids of Flavobacterium meningosepticum. Two OLs and Ser-containing lipid are detected.
SOURCE
These OLs containing branched fatty acids are very rare. This type of the OLs are found Flavobacterium meningosepticum, F. indologenes (Ref. 0004), and Cytophaga johnsonae (Ref. 0013).
[Table 0005] Structures of the lipid A of LPS and the OLs are similar in amide and ester linkages of the fatty acids.
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0004]
AUTHOR:Kawai, Y., Yano, I., and Kaneda, K.
TITLE:Various kinds of lipoamino acids including a novel serine-containing lipid in an opportunistic pathogen Flavobacterium. Their structures and biological activities on erythrocytes PubMed ID:3123236
JOURNAL:Eur J Biochem.
VOL:171 PAGE : 73-80 (1988)
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[0006]
AUTHOR:Kawai, Y., and Akagawa, K.
TITLE:Macrophage activation by an ornithine-containing lipid or a serine-containing lipid PubMed ID:2499544
JOURNAL:Infect Immun.
VOL:57 PAGE : 2086-2091 (1989)
[TOP]

[0007]
AUTHOR:Kawai, Y., Kamoshita, K., and Akagawa, K.
TITLE:B-lymphocyte mitogenicity and adjuvanticity of an ornithine-containing lipid or a serine-containing lipid PubMed ID:1778427
JOURNAL:FEMS Microbiol Lett.
VOL:67 PAGE : 127-129 (1991)
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[0008]
AUTHOR:Kawai, Y., Kaneda, K., Morisawa, Y., and Akagawa, K.
TITLE:Protection of mice from lethal endotoxemia by use of an ornithine-containing lipid or a serine-containing lipid PubMed ID:1906840
JOURNAL:Infect Immun.
VOL:59 PAGE : 2560-2566 (1991)
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[0009]
AUTHOR:Kawai, Y., Takasuka, N., Akagawa, K., and Naito, S.
TITLE:Hypothermic response of mice to ornithine-containing lipids and to endotoxin PubMed ID:8675313
JOURNAL:Infect Immun.
VOL:64 PAGE : 2101-2105 (1996)
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[0013]
AUTHOR:Pitta, T. P., Leadbetter, E. R., and Godchaux, W., 3rd
TITLE:Increase of ornithine amino lipid content in a sulfonolipid-deficient mutant of Cytophaga johnsonae PubMed ID:2914878
JOURNAL:J Bacteriol.
VOL:171 PAGE : 952-957 (1989)
[TOP]

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