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Lipoamino acid

(total 5)
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No Structure COMMON NAME NAME DATA No INFORMANT SYMBOL FORMULA MOL.WT(ave) Download 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
typical bacterial ornithine-containing lipid
a-N-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-L-ornithine (Ref. 0001/0003/0005/0011)
ALA0001
Youko Kawai
OL , Orn-lipid
C37H72O5N2 624.978 Download ChemDraw structure file
Hemagglutinating-activity , minimum hemagglutinating concentration on human erythrocyte is 1 mg/ml.
[Table 0001] (Ref. 0001/0003) , Hemolitic activity of O-deacylated OL,
[Table 0003] (Ref. 0001), Inhibition of hemagglutination
[Table 0002] (Ref. 0001), Macrophage activation , PGE2 and IL-1- inducing activities, nontoxic (nonlethality, and non TNF-inducing activity) (Ref. 0009/0011), the structure of the OL is similar to the structure of lipid A of bacterial LPS
[Table 0004].
155-156 degC
[a]D25 +1.8
Soluble in chloroform/methanol (2:1)

[Spectrum 0001] Ester linkage (1730 cm-1), Secondary amide linkage (1640 and 1540 cm-1)(Ref. 0001) (Ref. 0005)


[Spectrum 0002] OL of B. pertussis, Trimethylsilyl OL, Molecular ion 606 (M-90, loss of trimethylsilyl) ,
[Spectrum 0003] OL of B. pertussis, Trimethylsilyl O-deacylated OL, Molecular ion 425 ( M-105, loss of trimethylsilyl and methyl),
[Spectrum 0004] OL of P. fluorescens, two Molecular ions , 623 (typical OL) and 651 (Orn-3-OH 18:1-16:0 plus Orn-3-OH 16:0-18:1) (Ref. 0001/0003/0005)


[Chromatogram 0001] TLC pattern of neutral solvent extractable lipid of B. pertussis . the OL is located just below of phosphatidylethanolamine (Ref. 0002).
[Chromatogram 0002] TLC pattern of neutral solvent extractable lipid of Pseudomonas (Ref. 0005)
distributed in various bacteria such as Bordetella pertussis, B. parapertussis, B. bronchisepticum , Pseudomonas fluorescens, P. aeruginosa, P. stuteri, P. cepacia, Achromobacter xylosoxidans, Serratia marcescens and Rhodopseudomonas spheroides. (Ref. 0001/0005/0011/0012)
Synthesis of the ornithine containing lipid are described in the litarature (Ref. 0011)



2
Ornithine-containing lipid of Flavobacterium
a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-L-ornithine
ALA0002
Youko Kawai
C37H72O5N2 624.978 Download ChemDraw structure file
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.

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


[Spectrum 0006] Molecular ion 625.


[Chromatogram 0003] TLC of free lipids of Flavobacterium meningosepticum. Two OLs and Ser-containing lipid are detected.
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.




3
OH-type ornithine-containing lipid of Flavovacterium
a-N-[3-(2-hydroxyisopentadecanoyloxy)isoheptadecanoyl]-ornithine
ALA0003
Youko Kawai
C37H72O6N2 640.977 Download ChemDraw structure file
Macrophage activation was very weak (Ref. 0011)
Ester and secondary amide linkages
[Spectrum 0007]


[Spectrum 0008] Molecular ion 641


Flavobacterium meningosepticum (Ref. 0004)




[Chromatogram 0001](Data No. 0002)
4
Flavolipin, Ser-Gly-lipid, Ser-Gly-containing lipid
a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-glycyl-serine
ALA0004
Youko Kawai
C37H69O7N2 653.953 Download ChemDraw structure file
Macrophage activation was observed (Ref. 0006). PGE2- and IL-1-inducing activities were strong. The structure is similar to the OL
[Table 0011].

[Spectrum 0009]Ester-linkage 1730 and secondary amide linkage, (Ref. 0004)

[Spectrum 0012]The spectra of Flavolipin and the synthetic Flavolipin was identical. (Ref. 0010)

[Spectrum 0010] Negative FAB mass. Flavolipin and
[Spectrum 0011]Synthetic Flavolipin. These spectra was identical. Positive FAB mass ( Molecular ion 654) (Ref. 0010)


[Chromatogram 0003] TLC of the free lipid of Flavobacterium
Ser-Gly-lipid is vary rare. It is found only in Flavobacterium. (Ref. 0004)




5
a-N-[3-(2-hydroxynonadecacyclopropanoyloxy)hexadecanoyl]-ornithine
ALA0005
Youko Kawai
C40H76O6N2 681.041 Download ChemDraw structure file


[Spectrum 0013] Ester and secondary amide linkages were detected.


[Spectrum 0014]Molecular ion was detected. a-N-[3-(2-hydroxyoctadecenoyloxy)hexadecanoyl-ornithine was found with the OL.
[Spectrum 0015] 2-hydroxynonadecacyclopropanoic acid and 2-hydroxyoctadecenoic acid


[Chromatogram 0001] The OL was located lower position than that of the typical bacterial OLs.
This OL was found in Pseudomonas cepacia.





Reference
[0001]
AUTHOR:Kawai, Y., and Yano, I.
TITLE:Ornithine-containing lipid of Bordetella pertussis, a new type of hemagglutinin PubMed ID:6315433
JOURNAL:Eur J Biochem.
VOL:136 PAGE : 531-538 (1983)

[0002]
AUTHOR:Kawai, Y.
TITLE:Characteristic cellular fatty acid composition and an ornithine-containing lipid as a new type of hemagglutinin in Bordetella pertussis PubMed ID:2872110
JOURNAL:Dev Biol Stand.
VOL:61 PAGE : 249-254 (1985)

[0003]
AUTHOR:Kawai, Y., Moribayashi, A., and Yano, I.
TITLE:Ornithine-containing lipid of Bordetella pertussis that carries hemagglutinating activity PubMed ID:6290456
JOURNAL:J Bacteriol.
VOL:152 PAGE : 907-910 (1982)

[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)

[0005]
AUTHOR:Kawai, Y., Yano, I., Kaneda, K., and Yabuuchi, E.
TITLE:Ornithine-containing lipids of some Pseudomonas species PubMed ID:3409887
JOURNAL:Eur J Biochem.
VOL:175 PAGE : 633-641 (1988)

[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)

[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)

[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)

[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)

[0010]
AUTHOR:Shiozaki, M., Deguchi, N., Mochizuki, T., Wakabayashi, T., Ishikawa, T., Haruyama, H., Kawai, Y., and Nishijima, M.
TITLE:Revised structure and synthesis of Flavolipin.
JOURNAL:Tetra hedron
VOL:54 PAGE : 11861-11876 (1998)

[0011]
AUTHOR:Kawai, Y., Nakagawa, Y., Matuyama, T., Akagawa, K., Itagawa, K., Fukase, K., Kusumoto, S., Nishijima, M., and Yano, I.
TITLE:A typical bacterial ornithine-containing lipid Nalpha-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-ornithine is a strong stimulant for macrophages and a useful adjuvant PubMed ID:10030549
JOURNAL:FEMS Immunol Med Microbiol.
VOL:23 PAGE : 67-73 (1999)

[0012]
AUTHOR:Miyazaki, Y., Oka, S., Hara-Hotta, H., and Yano, I.
TITLE:Stimulation and inhibition of polymorphonuclear leukocytes phagocytosis by lipoamino acids isolated from Serratia marcescens PubMed ID:8388762
JOURNAL:FEMS Immunol Med Microbiol.
VOL:6 PAGE : 265-271 (1993)

[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)