Id | Image | COMMON NAME | NAME | DATA No | Lipid class | INFORMANT | SYMBOL | FORMULA | MOL.WT(average) | Download cdx file / Mol format file | BIOOGICAL ACTIVITY | PHYSICAL AND CHEMICAL PROPERTIES | SPECTRAL DATA | CHROMATOGRAM DATA | SOURCE | CHEMICAL SYNTHESIS | METABOLISM | GENETIC INFORMATION | NOTE | REFERENCES | |||||||||
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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 | Lipoamino acid | Youko Kawai | OL , Orn-lipid | C37H72O5N2 | 624.978 | Download ChemDraw structure data | 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 ![]() | [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>> | << Ref.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. VOLUME: 136 PAGE: 531-538(1983) << Ref.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. VOLUME: 61 PAGE: 249-254(1985) << Ref.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. VOLUME: 152 PAGE: 907-910(1982) << Ref.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. VOLUME: 175 PAGE: 633-641(1988) << Ref.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. VOLUME: 64 PAGE: 2101-2105(1996) << Ref.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. VOLUME: 23 PAGE: 67-73(1999) << Ref.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. VOLUME: 6 PAGE: 265-271(1993) | |||||||||
2 | ![]() | Ornithine-containing lipid of Flavobacterium | a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-L-ornithine | ALA0002 | Lipoamino acid | Youko Kawai | C37H72O5N2 | 624.978 | Download ChemDraw structure data | 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. [Table 0007/FT0008] << 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. | << Ref.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. VOLUME: 171 PAGE: 73-80(1988) << Ref.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. VOLUME: 57 PAGE: 2086-2091(1989) << Ref.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. VOLUME: 67 PAGE: 127-129(1991) << Ref.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. VOLUME: 59 PAGE: 2560-2566(1991) << Ref.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. VOLUME: 64 PAGE: 2101-2105(1996) << Ref.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. VOLUME: 171 PAGE: 952-957(1989) | ||||||||||||||
3 | ![]() | OH-type ornithine-containing lipid of Flavovacterium | a-N-[3-(2-hydroxyisopentadecanoyloxy)isoheptadecanoyl]-ornithine | ALA0003 | Lipoamino acid | Youko Kawai | C37H72O6N2 | 640.977 | Download ChemDraw structure data | 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) | << Ref.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. VOLUME: 171 PAGE: 73-80(1988) << Ref.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. VOLUME: 23 PAGE: 67-73(1999) | ||||||||||||||
4 | ![]() | Flavolipin, Ser-Gly-lipid, Ser-Gly-containing lipid | a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-glycyl-serine | ALA0004 | Lipoamino acid | Youko Kawai | C37H69O7N2 | 653.953 | Download ChemDraw structure data | 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>> | << Ref.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. VOLUME: 171 PAGE: 73-80(1988) << Ref.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. VOLUME: 57 PAGE: 2086-2091(1989) << Ref.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 VOLUME: 54 PAGE: 11861 -11876 (1998) | |||||||||||||
5 | ![]() | a-N-[3-(2-hydroxynonadecacyclopropanoyloxy)hexadecanoyl]-ornithine | ALA0005 | Lipoamino acid | Youko Kawai | C40H76O6N2 | 681.041 | Download ChemDraw structure data | [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. |