Identification of endogenous acyl amino acids based on a targeted lipidomics approach

Using a partially purified bovine brain extract, our lab identified three novel endogenous acyl amino acids in mammalian tissues. The presence of numerous amino acids in the body and their ability to form amides with several saturated and unsaturated fatty acids indicated the potential existence of a large number of heretofore unidentified acyl amino acids. Reports of several additional acyl amino acids that activate G-protein coupled receptors (e.g., N-arachidonoyl glycine, N-arachidonoyl serine) and transient receptor potential channels (e.g., N-arachidonoyl dopamine, N-acyl taurines) suggested that some or many novel acyl amino acids could serve as signaling molecules. Here, we used a targeted lipidomics approach including specific enrichment steps, nano-LC/MS/MS, high-throughput screening of the datasets with a potent search algorithm based on fragment ion analysis, and quantification using the multiple reaction monitoring mode in Analyst software to measure the biological levels of acyl amino acids in rat brain. We successfully identified 50 novel endogenous acyl amino acids present at 0.2 to 69 pmol g−1 wet rat brain. Using a partially purified bovine brain extract, our lab identified three novel endogenous acyl amino acids in mammalian tissues. The presence of numerous amino acids in the body and their ability to form amides with several saturated and unsaturated fatty acids indicated the potential existence of a large number of heretofore unidentified acyl amino acids. Reports of several additional acyl amino acids that activate G-protein coupled receptors (e.g., N-arachidonoyl glycine, N-arachidonoyl serine) and transient receptor potential channels (e.g., N-arachidonoyl dopamine, N-acyl taurines) suggested that some or many novel acyl amino acids could serve as signaling molecules. Here, we used a targeted lipidomics approach including specific enrichment steps, nano-LC/MS/MS, high-throughput screening of the datasets with a potent search algorithm based on fragment ion analysis, and quantification using the multiple reaction monitoring mode in Analyst software to measure the biological levels of acyl amino acids in rat brain. We successfully identified 50 novel endogenous acyl amino acids present at 0.2 to 69 pmol g−1 wet rat brain. Conjugates of fatty acids and amino acids, lipoamino acids, have been identified in biological systems for at least 50 years (1Cartwright N.J. Serratamic acid, a derivative of L-serine produced by organisms of the serratia group.Biochem. J. 1955; 60: 238-242Crossref PubMed Scopus (7) Google Scholar), mostly from bacteria and marine organisms. Significant biological activities have been demonstrated by many lipoamino acids, such as N-(3-hydroxydecanoyl)-L-serine (2Cartwright N.J. The structure of serratamic acid.Biochem. J. 1957; 67: 663-669Crossref PubMed Scopus (23) Google Scholar), acyl homoserine lactone (3Pearson J.P. Gray K.M. Passador L. Tucker K.D. Eberhard A. Iglewski B.H. Greenberg E.P. Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes.Proc. Natl. Acad. Sci. USA. 1994; 91: 197-201Crossref PubMed Scopus (782) Google Scholar), mololipids (4Ross S.A. Weete J.D. Schinazi R.F. Wirtz S.S. Tharnish P. Scheuer P.J. Hamann M.T. Mololipids, a new series of anti-HIV bromotyramine-derived compounds from a sponge of the order Verongida.J. Nat. 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Mololipids, a new series of anti-HIV bromotyramine-derived compounds from a sponge of the order Verongida.J. Nat. Prod. 2000; 63: 501-503Crossref PubMed Scopus (41) Google Scholar), and the pro-nociceptive transient receptor potential vanilloid type 1 (TRPV1) channel activators N-arachidonoyl dopamine and N-oleoyl dopamine (8Huang S.M. Bisogno T. Trevisani M. Al-Hayani A. De Petrocellis L. Fezza F. Tognetto M. Petros T.J. Krey J.F. Chu C.J. et al.An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors.Proc. Natl. Acad. Sci. USA. 2002; 99: 8400-8405Crossref PubMed Scopus (810) Google Scholar, 9Chu C.J. Huang S.M. De Petrocellis L. Bisogno T. Ewing S.A. Miller J.D. Zipkin R.E. Daddario N. Appending G. Di Marzo V. et al.N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia.J. Biol. Chem. 2003; 278: 13633-13639Abstract Full Text Full Text PDF PubMed Scopus (303) Google Scholar, 10Huang S.M. Walker J.M. Enhancement of spontaneous and heat-evoked activity in spinal nociceptive neurons by the endovanilloid/endocannabinoid N-arachidonoyldopamine (NADA).J. Neurophysiol. 2006; 95: 1207-1212Crossref PubMed Scopus (28) Google Scholar). Earlier we reported the presence of N-arachidonoyl glycine (NAGly) and N-arachidonoyl gamma aminobutyric acid (GABA) in rats (11Huang S.M. Bisogno T. Petros T.J. Chang S.Y. Zavitsanos P.A. Zipkin R.E. Sivakumar R. Coop A. Maeda D.Y. De Petrocellis L. et al.Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.J. Biol. Chem. 2001; 276: 42639-42644Abstract Full Text Full Text PDF PubMed Scopus (270) Google Scholar), which produced anti-inflammatory and anti-nociceptive effects (11Huang S.M. Bisogno T. Petros T.J. Chang S.Y. Zavitsanos P.A. Zipkin R.E. Sivakumar R. Coop A. Maeda D.Y. De Petrocellis L. et al.Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.J. Biol. Chem. 2001; 276: 42639-42644Abstract Full Text Full Text PDF PubMed Scopus (270) Google Scholar, 12Vuong L.A.Q. Mitchell V.A. Vaughan C.W. Actions of N-arachidonyl-glycine in a rat neuropathic pain model.Neuropharmacology. 2008; 54: 189-193Crossref PubMed Scopus (69) Google Scholar, 13Burstein S.H. The cannabinoid acids: nonpsychoactive derivatives with therapeutic potential.Pharmacol. Ther. 1999; 82: 87-96Crossref PubMed Scopus (89) Google Scholar, 14Burstein S.H. Adams J.K. Bradshaw H.B. Fraioli C. Rossetti R.G. Salmonsen R.A. Shaw J.W. Walker J.M. Zipkin R.E. Zurier R.B. Potential anti-inflammatory actions of the elmiric (lipoamino) acids.Bioorg. Med. Chem. 2007; 15: 3345-3355Crossref PubMed Scopus (39) Google Scholar). 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Assignment of endogenous substrates to enzymes by global metabolite profiling.Biochemistry. 2004; 43: 14332-14339Crossref PubMed Scopus (271) Google Scholar) including N-arachidonoyl taurine, a TRPV1, and TRPV4 receptor activator (18Saghatelian A. McKinney M.K. Bandell M. Patapoutian A. Cravatt B.F. A FAAH-regulated class of N-acyl taurines that activates TRP ion channels.Biochemistry. 2006; 45: 9007-9015Crossref PubMed Scopus (171) Google Scholar); and N-palmitoyl glycine, which inhibits the heat-evoked response of nociceptive neurons in the rat dorsal horn (19Rimmerman N. Bradshaw H.B. Hughes H.V. Chen J. S-C. Hu S. S-J. McHugh D. Vefring E. Jahnsen J.A. Thompson E.L. Masuda K. et al.N-palmitoyl glycine, a novel endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons.Mol. Pharmacol. 2008; 74: 213-224Crossref PubMed Scopus (66) Google Scholar). NAGly, N-arachidonoyl GABA, N-arachidonoyl serine, and N-arachidonoyl taurine also bind to GPR72 at submicromolar concentrations (20Roy M-O. Hannedouche S. Ligand for G-protein coupled receptor GPR72 and uses thereof. Canadian Patent Scholar). A of effects have also been reported for several acyl amino acids A. N. and of the N-palmitoyl Google Scholar, N. G. A. and of some new 43: Google Scholar, A. of glycine on the of rats by 1987; Scholar, A. N. of and glycine in in of glycine Google Scholar, A. in rats and some new Google Scholar) their existence as endogenous the that the brain and tissues several acyl amino acids and the that some of also biological The that NAGly could by an of acid and glycine (11Huang S.M. Bisogno T. Petros T.J. Chang S.Y. Zavitsanos P.A. Zipkin R.E. Sivakumar R. Coop A. Maeda D.Y. De Petrocellis L. et al.Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.J. Biol. 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Pharmacol. 2008; 74: 213-224Crossref PubMed Scopus (66) Google Scholar). The of of GABA, acid, and L-serine, a structure in with the or of the amide and using the order to of N-acyl and with T. M. Y. S. of and a Res. PubMed Google Scholar). N-acyl also to the T. Hanus L. J. Mechoulam R. for of compounds to the brain cannabinoid Med. Chem. 40: PubMed Scopus Google Scholar). N-arachidonoyl by the of to the with a of the fatty acid, as for the of D. novel from of Chem. 2003; PubMed Scopus Google Scholar). to the and characterization of N-acyl amino acids using and the as reported (19Rimmerman N. Bradshaw H.B. Hughes H.V. Chen J. S-C. Hu S. S-J. McHugh D. Vefring E. Jahnsen J.A. Thompson E.L. Masuda K. et al.N-palmitoyl glycine, a novel endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons.Mol. Pharmacol. 2008; 74: 213-224Crossref PubMed Scopus (66) Google Scholar). to a rat brain at of the and to the and the lipids with The an coupled with a 50 a of and a a with 1 with 1 and a of 0.2 the as The multiple reaction monitoring containing the of acyl amino acids and the amino acid fragment the the Other of using of We the reported (11Huang S.M. Bisogno T. Petros T.J. Chang S.Y. Zavitsanos P.A. Zipkin R.E. Sivakumar R. Coop A. Maeda D.Y. De Petrocellis L. et al.Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.J. Biol. Chem. 2001; 276: 42639-42644Abstract Full Text Full Text PDF PubMed Scopus (270) Google Scholar, Hughes H.V. Walker J.M. lipidomics approach for endogenous N-acyl amino acids in rat brain PubMed Scopus Google Scholar). rat by and using a at The purified using and The and in to using a and an The ion for mode and for ion mode the for the using of N-oleoyl The coupled with a and a at a of and by using targeted or mode with the Hughes H.V. Walker J.M. lipidomics approach for endogenous N-acyl amino acids in rat brain PubMed Scopus Google Scholar). The with on a with a using a with acid and with the as a the three in the for the for targeted used to identification of by the in the to identification of successfully identified with additional to with of bovine spinal or three rat in at to the and the The in with and and with The purified by a including and a by a The used systems with a of The as the in and using with ion in 1 using the with the with the and a ion ion coupled with a for The the and the used in the the as the used in The in mode and to one with the and with the ion and the used in to for in the of novel acyl amino acids identified using targeted lipidomics approach in a new The and to the that using the of Analyst software and of the Hughes H.V. Walker J.M. lipidomics approach for endogenous N-acyl amino acids in rat brain PubMed Scopus Google Scholar). The used or in of acyl amino acids with with to identification in or and in pmol the rat brain as an from and using the as Hughes H.V. Walker J.M. lipidomics approach for endogenous N-acyl amino acids in rat brain PubMed Scopus Google Scholar) to that the of a acyl amino acid and one of the putative fragment or using the of and with the of acyl amino acids at a of using the or in the and ion at the and to the to form the The compounds that we identified using and the the for the ion for the of the amino acid fragment a and a number of the ion and one fragment ion that could to based the of the using the of the the in the ion with The compounds identified in the or ion the of the for the of the for the of the amino acid and a number of three that could to of the in the presence of acyl amino acids from the brain purified using and by using an We the and the amino acid fragment or as the for to their high ion and reported Hughes H.V. Walker J.M. lipidomics approach for endogenous N-acyl amino acids in rat brain PubMed Scopus Google Scholar), to numerous acyl amino acids in the of the rat for acyl amino acids of acid, acid, acid, acid, and acid and amino we for of We to our on the with high which acyl amino acids. Identification based on the and the of the in tissues with the for our targeted acyl amino acids, we the identification several the using to with high and with acyl amino acids using several on NAGly and acyl amino acids, our a specific based on the of acyl amino acids by and to acyl amino acids (11Huang S.M. Bisogno T. Petros T.J. Chang S.Y. Zavitsanos P.A. Zipkin R.E. Sivakumar R. Coop A. Maeda D.Y. De Petrocellis L. et al.Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.J. Biol. Chem. 2001; 276: 42639-42644Abstract Full Text Full Text PDF PubMed Scopus (270) Google Scholar, Hughes H.V. Walker J.M. lipidomics approach for endogenous N-acyl amino acids in rat brain PubMed Scopus Google Scholar). steps, to rat brain in such a with has demonstrated the ability to with of acyl amino acids on (11Huang S.M. Bisogno T. Petros T.J. Chang S.Y. Zavitsanos P.A. Zipkin R.E. Sivakumar R. Coop A. Maeda D.Y. De Petrocellis L. et al.Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain.J. Biol. Chem. 2001; 276: 42639-42644Abstract Full Text Full Text PDF PubMed Scopus (270) Google Scholar). and used in also used in our and to several compounds in one to the of for we with high and high we or with the we a as to one in with the one acyl amino acids. The algorithm of to search the and the and the amino acid fragment or The to the to with the we used to identified acyl amino acids with high and Hughes H.V. Walker J.M. lipidomics approach for endogenous N-acyl amino acids in rat brain PubMed Scopus Google Scholar). an to the number of identified novel we the and has for the a and for the fragment in the ion in compounds identified in the have of 1 with 1 and and with of and in our of the the using the the fragment such as the amino acid that a for the of for acyl We by the which has and the ability to to our and using the and to of 50 We used targeted on the for additional amino acids, identified in the tissues the and with the and N-palmitoyl acid, in for the endogenous lipids and the the presence of compounds in mammalian tissues reported to a of biological by at by and and A. in rats and some new Google Scholar, A. of three new on and in 1987; Google Scholar, A. of GABA, glycine or acid derivatives in the in Google Scholar, A. on the of or in the of Google Scholar, A. A. of some new on rat and Pharmacol. Google Scholar, A. of acid or on by Google Scholar). N-palmitoyl GABA, N-palmitoyl acid, and acid similar effects A. in rats and some new Google Scholar, A. of three new on and in 1987; Google Scholar, A. of GABA, glycine or acid derivatives in the in Google Scholar, A. on the of or in the of Google Scholar, A. A. of some new on rat and Pharmacol. Google Scholar, A. of acid or on by Google Scholar). also have or effects A. in rats and some new Google Scholar, A. of three new on and in 1987; Google Scholar, A. of GABA, glycine or acid derivatives in the in Google Scholar, A. on the of or in the of Google Scholar, A. A. of some new on rat and Pharmacol. Google Scholar, A. of acid or on by Google Scholar). the of acyl amino acids identified and activity bacteria and A. M. and and biological of amino Chem. 2001; Scopus Google Scholar). Using acyl amino acids in a of the of the of which the number of novel compounds in one using of the of in and for three and identified compounds of using in the that N-acyl acids present only in the of purified and by targeted using the We identified the N-acyl acids and acid the acid such as N-palmitoyl acid in to with high The of acyl amino acids only such as with as for The from acid series to the reaction of acid to the of and acid in which acid on the A. M. and and biological of amino Chem. 2001; Scopus Google Scholar). The in the Using 1 we to acyl amino acids, which of the number of acyl amino acids with high in our the identification of additional the to the rat and with only three acyl amino acids using to using the that indicated the presence of acyl amino acids to targeted in the and the novel acyl amino acids identified in to identified using 1 our of the existence of acyl amino acids in to bovine spinal which to the identification of acyl amino acids we also identified several fatty acid of or The N-acyl and N-acyl the of the and a the compounds identified in our could or series of and in marine H. G. T. N-acyl amino acid in marine Biophys. PubMed Scopus Google Scholar) and N-arachidonoyl reported to the of by fatty acid amide at concentrations M. A. A. G. S. Di Marzo V. A on acids as endogenous of fatty acid amide Biophys. Res. Commun. 2004; PubMed Scopus Google Scholar). The with a of 0.2 used to on the and the endogenous a by which the as the The from with the as in identified acyl amino acids, the have the as the the concentrations of our lipids in rat brain we used as an to for effects the only acyl amino acid The and used as the for acyl amino acids. we N-acyl amino acid their high of to the only of the rat and the of in with by to the levels of required to the of rat Res. PubMed Scopus Google Scholar) and by and to the of by J. fatty acid and concentrations in rat brain Res. PubMed Scopus Google Scholar) in rat to of the J. fatty acid and concentrations in rat brain Res. PubMed Scopus Google Scholar) and amino acids of J.M. amino acid concentrations in rats by and PubMed Scopus Google Scholar). on the of and by in of N-acyl amino acids in the on and in our of or that amino acids could Using quantification we rat brain concentrations for of 50 novel acyl amino acids. some lipids with in the rat such as the and bovine spinal used to identification the biological levels in the rat lipids identified from tissues such as of and on biological levels could The of the compounds some at levels (e.g., 0.2 pmol and at levels (e.g., N-palmitoyl 69 pmol the compounds with the fatty acid the and acid series the and the with the The high concentrations of N-acyl taurine Hughes H.V. Walker J.M. lipidomics approach for endogenous N-acyl amino acids in rat brain PubMed Scopus Google Scholar) and acid the of taurine and acid in of of acyl amino acids in tissues to The high concentrations of N-acyl to of N-acyl brain S. Shaw W.A. Identification of in 2007; PubMed Scopus Google Scholar), in the on and the compounds with the amino acid with and with and which the of fatty acids as acids or as of and Res. PubMed Scopus Google Scholar, M. C. K. G. acid of brain in and in PubMed Scopus Google Scholar), in These suggested that acyl amino acids by of fatty acids and amino acids in biological systems or of the required for the in and in the production of from and with an bond from and by in the of that an with similar to and the of N-acyl amino acids. by reports that an from rat the of and acids with T. of acids by rat and the of the Biol. Chem. Full Text PDF PubMed Google Scholar) and that has in to the of N-acyl and N-arachidonoyl dopamine, serine, and J.M. the in of Biophys. Res. Commun. 2008; PubMed Scopus Google Scholar, of by to a novel for the production of lipid signaling Biol. 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Using a targeted lipidomics approach from we identified and 50 novel endogenous acyl amino acids with high the of compounds in mammalian tissues and our that a large family of endogenous acyl amino acids that based of the presence of a endogenous acyl amino acids. These the and of an targeted lipidomics approach as several acyl amino acids identified the presence of The the of identification and biological characterization of and many novel signaling lipids in the

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