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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 |
ALA0001 | Youko Kawai |
OL , Orn-lipid |
C37H72O5N2 | 624.978 | |
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  C |
[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) |
Synthesis of the ornithine containing lipid are described in the litarature (Ref. 0011) |
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| 2 |  |
Ornithine-containing lipid of Flavobacterium |
a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-L-ornithine |
ALA0002 | Youko Kawai |
C37H72O5N2 | 624.978 | |
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. |
[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. |
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| 3 |  |
OH-type ornithine-containing lipid of Flavovacterium |
a-N-[3-(2-hydroxyisopentadecanoyloxy)isoheptadecanoyl]-ornithine |
ALA0003 | Youko Kawai |
C37H72O6N2 | 640.977 | |
Macrophage activation was very weak (Ref. 0011) |
Ester and secondary amide linkages [Spectrum 0007] |
Flavobacterium meningosepticum (Ref. 0004) |
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| 4 |  |
Flavolipin, Ser-Gly-lipid, Ser-Gly-containing lipid |
a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-glycyl-serine |
ALA0004 | Youko Kawai |
C37H69O7N2 | 653.953 | |
Macrophage activation was observed (Ref. 0006). PGE2- and IL-1-inducing activities were strong. The structure is similar to the OL [Table 0011]. |
[Spectrum 0010] Negative FAB mass. Flavolipin and [Spectrum 0011]Synthetic Flavolipin. These spectra was identical. Positive FAB mass ( Molecular ion 654) (Ref. 0010) |
Ser-Gly-lipid is vary rare. It is found only in Flavobacterium. (Ref. 0004) |
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| 5 |  |
a-N-[3-(2-hydroxynonadecacyclopropanoyloxy)hexadecanoyl]-ornithine |
ALA0005 | Youko Kawai |
C40H76O6N2 | 681.041 | |
[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 |
This OL was found in Pseudomonas cepacia. |
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| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |