Biofiles Volume 5, Number 7 Lipid Metabolism Biofilesonline Biofilescontents Your gateway to Biochemicals and Reagents for Life Science Research Introduction 3 Biofi les Online allows you to: Natural Abundance 4 • Easily navigate the content of Lipid Metabolites the current Biofi les issue • Access any issue of Biofi les Isotopically Labeled Metabolites 21 • Subscribe for email notifi cations of future eBiofi les issues Characteristic Metabolites for 25 Register today for upcoming issues and Inborn Errors of Lipid Metabolism eBiofi les announcements at sigma.com/biofi les Lipid Metabolites as Biomarkers for 26 the Diff erentiation of Diseased and Coming Next Issue: Cell Based Assay Healthy Cells Life scientists have long realized the value in analyzing Altered Lipid Metabolites in Aging 28 biological processes based on its most fundamental unit the cell. This issue will touch on a wide variety of topics ranging from ADMEtox to stem cell analysis to the most basic Lipid Metabolites in Natural 29 methods of analyzing and staining cells. The issue will Product Biosynthesis announce the addition of 1400 more ECACC cell lines available in the US, Canada and Mexico. Cover: XXX Receive this upcoming issue by subscribing to Biofi les at. sigma.com/biofi les-subscribe New—to come XXX sigma.com/XXX Order sigma.com/order Technical service sigma.com/techinfo sigma.com/lifescience 3 Introduction Roland Wohlgemuth Senior Product Specialist [email protected] After sequencing the human genome, life metabolites has been linked to disorders scientists are now in the era “beyond the of aging like osteoporosis and vascular genome” and confronting the challenges calcification. Additionally, research is now of bringing this information to life. For lipid trying to explain how dysregulations in lipid researchers, unraveling the complexities metabolism may underlie diseases such of lipid metabolism will bring answers and as Alzheimer’s, cancer, and asthma. Lipid opportunities in fields as diverse as medicine synthesis pathways, such as the methyl-D- and biofuels. Today, lipid research addresses erythritol 4-phosphate (MEP) pathway of all aspects of cell biology including cell isoprenoid synthesis, are being investigated structure, energy storage and generation, as potential targets for antibacterial therapies and cell signaling. The synergies between and drug targets. As changes in lipid profiles classical lipid research, systems biology, can mark developmental stages or more and the advancement of lipid detection ominously, pathological states, there is great technologies have led to a revolution in lipid potential for the use of lipids as biomarkers. biology and the emergence of lipidomics as Experimental quantification of the levels a branch of metabolomics. of lipids and lipid metabolites is therefore Lipid-based diseases are a growing essential for enhancing the understanding and expensive challenge to health care of different influences such as genetic, systems. As a population ages, chronic nutritional, behavioral, and environmental conditions associated with aging such as factors. As part of our committment to cardiovascular disease, neurodegenerative metabolomics research, Sigma offers disorders, and metabolic disorders take an expanding range of lipids and lipid increasing tolls in terms of morbidity and metabolites for the mapping and study of mortality. Oxidation of lipids and lipid healthy and diseased cells. 4 Natural Abundance Lipid Metabolites Natural Abundance Lipid Metabolites Glycerolipid Metabolism Name Structure Cat. No. 1-Deoxy- D -xylulose-5- O OH O 13368-1MG O HO P O + phosphate sodium salt CH3 • xNa 13368-5MG OH OH O CH2(CH2)6CH3 OH O 1,3-Dihydroxyacetone O D107204-5G OH dimer HO D107204-100G O CH2(CH2)6CH3 HO O D107204-500G Dihydroxyacetone O O D7137-5MG HO O P OLi O CH2(CH2)6CH3 phosphate dilithium salt D7137-10MG OLi D7137-25MG O D7137-100MG D7137-250MG Glycerol esterified with one, two, or three fatty acids make up O O 1,2-Dimyristoyl- sn -glycero- O- Na+ P3650-25MG P 3-phosphate monosodium H C(H C) O O P3650-50MG monoacyl-, diacyl- and triacylglycerols, with a chiral center at 3 2 12 O- Na+ salt carbon-2 of the glycerol moiety. Fats and oils from plants and animals O O P3650-250MG are triacylglycerols, while diacylglycerols are intermediates and (CH2)12CH3 cellular messengers, and monoacylglycerols, formed by hydrolysis, are 1,2-Dioctanoyl-sn -glycerol - P3591-50MG 3-phosphate sodium salt surfactants and intermediates. Because triacylglycerols are insoluble 1,2-Dipalmitoyl- sn -glycerol O D9135-25MG in water, combination or emulsification with other lipids, cellular H3C(H2C)14 O OH D9135-100MG compounds, or proteins is required before transport and metabolism O O can occur. Complete or partial lipase-catalyzed hydrolysis yields (CH2)14CH3 monoacylglycerols, glycerol, and fatty acids that can be transported 1,2-Dipalmitoyl-sn -glycero- O P4013-25MG 3-phosphate sodium salt H3C(H2C)14 O P4013-100MG and utilized for energy production or biosynthetic pathways of H3C(H2C)14 O H metabolism. O O O PO- Na+ Biosynthesis of triacylglycerols is achieved in a three-step sequence OH from 2-monoacylglycerols and fatty acids. First, the fatty acid is D -(+)-Glyceraldehyde, O 49800-1G viscous 49800-5G activated by acyl-CoA synthetase catalyzed conversion to the HO H OH corresponding fatty acyl thioester with coenzyme A. The fatty acyl- D -Glyceric acid calcium salt O 367494-1G CoA is then coupled with a 2-monoacylglycerol by the catalytic 2+ • 2H O dihydrate HO O Ca 2 367494-5G OH action of a monoacylglycerol transferase to yield a diacylglycerol. The 2 final triacylglycerol is obtained by coupling of fatty acyl-CoA with Glycerol, anhydrous OH 49767-100ML diacylglycerol through the action of diacylglycerol transferase. HO OH 49767-250ML 49767-1L Name Structure Cat. No. rac -Glycerol 1-myristate O M1890-100MG M1890-1G Acetylcholine chloride O A6625-10MG CH3(CH2)11CH2 O OH CH3 OH H3C O N CH3 A6625-25G CH rac -Glycerol 1-phosphate O G2138-10MG Cl 3 A6625-100G HO O P ONa A6625-500G disodium salt hexahydrate G2138-5G OH ONa • 6H O G2138-25G Choline chloride CH3 C7017-10MG 2 Cl G2138-100G HO NCH3 C7017-5G CH3 G2138-500G C7017-25G C7017-100G sn -Glycerol 3-phosphate O G7886-250MG bis(cyclohexylammonium) HO O P OH NH2 CH G7886-1G Choline chloride 3 26978-25G OH OH Cl salt G7886-5G HO NCH3 26978-100G 2 CH3 5 O ATP AMP + PPi O Caption Text? R OH 1 R1 S-CoA Fatty Acid Fatty Acyl-CoA HS-CoA HO CH2 O HC O R2 HO CH2 HS-CoA O O O CH2 O O CH2 O R1 R1 HC O HC O R2 R3 R2 HO CH2 O CH2 O HS-CoA O Diacylglycerol Triacylglycerol R3 S-CoA Name Structure Cat. No. Name Structure Cat. No. Glyceryl 1,3-dipalmitate O O D1639-1G Glyceryl trimyristate O O T5141-1G H3C(H2C)14 O O (CH2)14CH3 CH3(CH2)11CH2 O O CH2(CH2)11CH3 T5141-5G OH CH3(CH2)11CH2 O Glyceryl 1,3-distearate - D8269-10MG O D8269-100MG Glyceryl triacetate O O T5376-500ML Glyceryl trinonadecanoate - T4632-100MG H3C O O CH3 T5376-1L T4632-1G O CH3 Glyceryl trioctanoate O O T9126-100ML O CH3(CH2)5CH2 O O CH2(CH2)5CH3 T9126-500ML Glyceryl tributyrate O O T8626-25ML CH3(CH2)5CH2 O T9126-1L H3C O O CH3 T8626-100ML O H C O 3 Glyceryl trioleate O T7140-500MG O O CH2(CH2)6CH3 T7140-1G O Glyceryl tridecanoate CH2(CH2)7CH3 T7517-1G T7140-5G O T7517-5G O CH2(CH2)6CH3 T7140-10G O CH2 CH O T7140-50G O CH2(CH2)6CH3 O CH2 CH2(CH2)7CH3 O O O CH2(CH2)7CH3 Glyceryl trioleate O 92860-5ML Glyceryl tridodecanoate O O T4891-100MG O CH2(CH2)6CH3 92860-10ML O CH3(CH2)9CH2 O O CH2(CH2)9CH3 T4891-5G CH3(CH2)9CH2 O O CH2(CH2)6CH3 O O CH2(CH2)6CH3 O Glyceryl trielaidate - T7379-1G O Glyceryl triheptadecanoate - T2151-100MG Glyceryl tripalmitate T5888-100MG CH (CH ) CH T5888-500MG T2151-1G O 2 2 13 3 CH3(CH2)13CH2 O O CH2(CH2)13CH3 T5888-1G Glyceryl trilinoleate O T9517-50MG O O T5888-5G O CH O 3 T9517-100MG O CH3 T9517-500MG T9517-1G Glyceryl tripalmitelaidate - T5909-5MG O CH3 O T9517-5G Glyceryl tripalmitoleate - T2630-100MG T2630-1G Glyceryl trilinolenate O T6513-100MG Glyceryl tristearate O O T5016-5G CH O 3 CH (CH ) CH O O CH (CH ) CH T5016-25G O 3 2 15 2 2 2 15 3 CH CH (CH ) CH O O 3 3 2 15 2 O O CH 3 O Glyceryl tritricosanoate - T1412-25MG 6 Name Structure Cat. No. Name Structure Cat. No. Glyceryl tritridecanoate - T3882-500MG O -Phosphorylethanol- O P0503-10MG NH2 T3882-1G amine HO P O P0503-1G OH Glyceryl triundecanoate O O T5534-1G P0503-5G P0503-25G CH3(CH2)8CH2 O O CH2(CH2)8CH3 CH3(CH2)8CH2 O P0503-100G P0503-500G O OH 1-Lauroyl- rac -glycerol O M1765-100MG 1,2-Propanediol 12279-1ML-F OH H3C 12279-5ML-F CH3(CH2)9CH2 O OH M1765-500MG OH M1765-1G 1,3-Propanediol HO OH 81780-500ML M1765-5G 1-Propanol H3C 96566-5ML-F OH 1-Linoleoyl- rac -glycerol O M7640-100MG 96566-10ML-F H3C CH2(CH2)5CH2 O OH M7640-1G OH Propionaldehyde O 538124-250ML H C 3 H 538124-1L Lipoteichoic acid from - L3265-5MG 1-Stearoyl-rac -glycerol O M2015-100MG Bacillus subtilis L3265-25MG CH3(CH2)15CH2 O OH M2015-1G Lipoteichoic acid from - L2515-5MG OH M2015-5G Staphylococcus aureus L2515-10MG Tripentadecanoin - T4257-100MG L2515-25MG T4257-500MG Lipoteichoic acid from - L4015-5MG T4257-1G Streptococcus faecalis L4015-25MG Tripetroselaidin - T5784-25MG Lipoteichoic acid from - L3140-5MG T5784-100MG Streptococcus pyogenes L3140-10MG L3140-25MG 1-Monopalmitoleoyl- rac - - M7890-100MG Glycerophospholipid Metabolism glycerol M7890-1G O O O 1-Oleoyl-rac -glycerol M7765-25MG O P NH2 CH (CH ) CH CH2(CH2)5CH2 O OH H C(H C) O O 3 2 6 2 M7765-50MG 3 2 14 OH OH M7765-100MG O O M7765-1G (CH2)14CH3 O Oleoyl- L -α- CH3 L7260-1MG CH OC lysophosphatidic acid 2 Glycerol is the backbone of the fundamental phospholipids used HO C H L7260-5MG sodium salt O as the self-assembling units of lipid membranes.