LBF20406LT02: Difference between revisions

Latest revision as of 00:00, 17 January 2014

Upper classes: LB LBF

Leukotriene B₄

Structural Information
	(5S,12R) -Dihydroxy- (cis-6,trans-8,trans-10,cis-14) -eicosatetraenoic acid
	Leukotriene B₄ (5S,12R) -Dihydroxy- (6Z,8E,10E,14Z) -eicosatraenoic acid 5 (S) ,12 (R) -Dihydroxyeicosa-6 (Z) ,8 (E) ,10 (E) ,14 (Z) -tetraenoic acid
	LTB4
Formula	C20H32O4
Exact Mass	336.23005951199997
Average Mass	336.46567999999996
SMILES	`C(CC=CC[C@H](C=CC=CC=C[C@H](CCCC(O)=O)O)O)CCC`
Physicochemical Information





	METHANOL Corey_EJ et al.
	Leukotriene B4 is produced by polymorphonuclear leukocytes and macrophages of various animal species upon various stimulations on the cells Samuelsson_B et al. Hammarstrom_S .
	Corey_EJ et al.
	Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee B4 by leukotriene A hydrolase Ford-Hutchinson_AW et al.. Leukotriene B4 is metabolized to lose its bioactivities either by omega -oxidation Hammarstrom_S or by leukotriene B4 12-hydroxydehydrogenase Yokomizo_T et al..
	Leukotriene B4 causes adhesion of leukocytes to endothelial cells, stimulates chemotaxis and chemokinesis of leukocytes Hammarstrom_S , and enhances superoxide anion production by human polymorphonuclear leukocytes Sumimoto_H et al.. Leukotriene B4 binds to a specific receptor with 7 transmembrane domains coupled to Gi/Go or Gq protein Yokomizo_T et al..
	cDNA and genomic DNA of 5-lipoxygenase Funk_CD and cDNA for Leukotriene A hydrolase Funk_CD were cloned. cDNA for leukotriene B 12-hydroxydehydrogenase was cloned Yokomizo_T et al..

Spectral Information
Mass Spectra	m/e 336, 319, 301 Yergey_JA et al.
UV Spectra	METHANOL : 260( ε 38,000), 270.5( ε 50,000), 281( ε 39,000)nm Corey_EJ et al.
IR Spectra
NMR Spectra	¹H-NMR(250MHz, D₂O) : δ 6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) Merrer_YL et al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies	ID	Compound Name	Reference
n.a.	LBF20406LT02	See above.	Corey_EJ et al. 1980
n.a.	LBF20406LT02	See above.	Ford-Hutchinson_AW et al. 1994
n.a.	LBF20406LT02	See above.	Funk_CD 1993
n.a.	LBF20406LT02	See above.	Hammarstrom_S 1983
n.a.	LBF20406LT02	See above.	Merrer_YL et al. 1989
n.a.	LBF20406LT02	See above.	Samuelsson_B et al. 1982
n.a.	LBF20406LT02	See above.	Sumimoto_H et al. 1984
n.a.	LBF20406LT02	See above.	Yergey_JA et al. 1986
n.a.	LBF20406LT02	See above.	Yokomizo_T et al. 1997
n.a.	LBF20406LT02	See above.	Yokomizo_T et al. 1993
n.a.	LBF20406LT02	See above.	Yokomizo_T et al. 1996

@@ Line 1: / Line 1: @@
+{{Lipid/Header}}
 {{Hierarchy|{{PAGENAME}}}}
-{{Lipid/Header}}
 {{Metabolite
 |LipidBank=XPR3101
 |LipidMaps=LMFA03020001
-|SysName=5 (S) ,12 (R) -Dihydroxyeicosa-6 (Z) ,8 (E) ,10 (E) ,14 (Z) -tetraenoic acid
+|SysName=(5S,12R) -Dihydroxy- (cis-6,trans-8,trans-10,cis-14) -eicosatetraenoic acid
-|Common Name=&&LEUKOTRIENE B4&&5 (S) ,12 (R) -Dihydroxyeicosa-6 (Z) ,8 (E) ,10 (E) ,14 (Z) -tetraenoic acid&&
+|Common Name=&&Leukotriene B_4&&(5S,12R) -Dihydroxy- (6Z,8E,10E,14Z) -eicosatraenoic acid&&5 (S) ,12 (R) -Dihydroxyeicosa-6 (Z) ,8 (E) ,10 (E) ,14 (Z) -tetraenoic acid&&
 |Solubility=METHANOL [[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]]
 |Mass Spectra=m/e 336, 319, 301 [[Reference:Yergey_JA:Kim_HY:Salem_N_Jr:,Anal. Chem.,1986,58,1344|{{RelationTable/GetFirstAuthor|Reference:Yergey_JA:Kim_HY:Salem_N_Jr:,Anal. Chem.,1986,58,1344}}]]
-|UV Spectra=METHANOL : 260(<FONT FACE="Symbol">e</FONT> 38,000), 270.5(<FONT FACE="Symbol">e</FONT> 50,000), 281(<FONT FACE="Symbol">e</FONT> 39,000)nm [[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]]
+|UV Spectra=METHANOL : 260( epsilon  38,000), 270.5( epsilon  50,000), 281( epsilon  39,000)nm [[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]]
-|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(250MHz, D<SUB><FONT SIZE=-1>2</FONT></SUB>O) : <FONT FACE="Symbol">d</FONT> 6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) [[Reference:Merrer_YL:Gravier-Pelletier_C:Micas-Languin_D:Mestre_F:Durreault_A:Depezay_JC:,J. Org. Chem.,1989,54,2409|{{RelationTable/GetFirstAuthor|Reference:Merrer_YL:Gravier-Pelletier_C:Micas-Languin_D:Mestre_F:Durreault_A:Depezay_JC:,J. Org. Chem.,1989,54,2409}}]]
+|NMR Spectra=^1 H-NMR(250MHz, D_2 O) :  delta  6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) [[Reference:Merrer_YL:Gravier-Pelletier_C:Micas-Languin_D:Mestre_F:Durreault_A:Depezay_JC:,J. Org. Chem.,1989,54,2409|{{RelationTable/GetFirstAuthor|Reference:Merrer_YL:Gravier-Pelletier_C:Micas-Languin_D:Mestre_F:Durreault_A:Depezay_JC:,J. Org. Chem.,1989,54,2409}}]]
+|Source=Leukotriene B4 is produced by polymorphonuclear leukocytes and macrophages of various animal species upon various stimulations on the cells [[Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1}}]][[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]].
+|Chemical Synthesis=[[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]] {{Image200|LBF20406LT02FT0001.gif}}
+|Metabolism=Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee B4 by leukotriene A hydrolase [[Reference:Ford-Hutchinson_AW:Gresser_M:Young_RN:,Annu. Rev. Biochem.,1994,63,383|{{RelationTable/GetFirstAuthor|Reference:Ford-Hutchinson_AW:Gresser_M:Young_RN:,Annu. Rev. Biochem.,1994,63,383}}]]. Leukotriene B4 is metabolized to lose its bioactivities either by  omega -oxidation [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]] or by leukotriene B4 12-hydroxydehydrogenase [[Reference:Yokomizo_T:Izumi_T:Takahashi_T:Kasama_T:Kobayashi_Y:Sato_F:Taketani_Y:Shimizu_T:,J. Biol. Chem.,1993,268,18128|{{RelationTable/GetFirstAuthor|Reference:Yokomizo_T:Izumi_T:Takahashi_T:Kasama_T:Kobayashi_Y:Sato_F:Taketani_Y:Shimizu_T:,J. Biol. Chem.,1993,268,18128}}]].
+|Symbol=LTB4
+|Biological Activity=Leukotriene B4 causes adhesion of leukocytes to endothelial cells, stimulates chemotaxis and chemokinesis of leukocytes[[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]], and enhances superoxide anion production by human polymorphonuclear leukocytes [[Reference:Sumimoto_H:Takeshige_K:Minakami_S:,Biochim. Biophys. Acta,1984,803,271|{{RelationTable/GetFirstAuthor|Reference:Sumimoto_H:Takeshige_K:Minakami_S:,Biochim. Biophys. Acta,1984,803,271}}]]. Leukotriene B4 binds to a specific receptor with 7 transmembrane domains coupled to Gi/Go or Gq protein [[Reference:Yokomizo_T:Izumi_T:Chang_K:Takuwa_Y:Shimizu_T:,Nature,1997,387,620|{{RelationTable/GetFirstAuthor|Reference:Yokomizo_T:Izumi_T:Chang_K:Takuwa_Y:Shimizu_T:,Nature,1997,387,620}}]].
+|Genetic Information=cDNA and genomic DNA of 5-lipoxygenase [[Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67|{{RelationTable/GetFirstAuthor|Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67}}]] and cDNA for Leukotriene A hydrolase [[Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67|{{RelationTable/GetFirstAuthor|Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67}}]] were cloned. cDNA for leukotriene B 12-hydroxydehydrogenase was cloned [[Reference:Yokomizo_T:Ogawa_Y:Uozumi_N:Kume_K:Izumi_T:Shimizu_T:,J. Biol. Chem.,1996,271,2844|{{RelationTable/GetFirstAuthor|Reference:Yokomizo_T:Ogawa_Y:Uozumi_N:Kume_K:Izumi_T:Shimizu_T:,J. Biol. Chem.,1996,271,2844}}]].
+}}
+{{MassbankSpectra|
+UT000280
+UT000281
+UT000282
+UT000283
+UT000284
+UT000285
+UT000286
+UT000287
+UT000288
 }}
 {{Lipid/Footer}}

IDs and Links
LipidBank	XPR3101
LipidMaps	LMFA03020001
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}

mol	LBF20406LT02

LBF20406LT02: Difference between revisions

Latest revision as of 00:00, 17 January 2014

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