Lipoamino acid

(total 5)

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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
Id	Image	COMMON NAME	NAME	DATA No	Lipid class	INFORMANT	SYMBOL	FORMULA	MOL.WT(average)	Download cdx file / Mol format file	BIOOGICAL ACTIVITY	MELTING POINT	BOILING POINT	DENSITY	REFRACTIVE INDEX	OPTICAL ROTATION	SOLUBILITY	UV SPECTRA	IR SPECTRA	NMR SPECTRA	MASS SPECTRA	OTHER SPECTRA	CHROMATOGRAM DATA	SOURCE	CHEMICAL SYNTHESIS	METABOLISM	GENETIC INFORMATION	NOTE	REFERENCES
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 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>>	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.