Lipidomic analysis of endocannabinoid metabolism in biological samples

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 877, Issue 26, 2009, Pages 2755-2767

  Astarita, Giuseppe ^a   Piomelli, Daniele ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

2 Arachidonoylglycerol (2 AG); Anandamide; Arachidonic acid; Diacylglycerol (DAG); Fatty acid amide hydrolase (FAAH); Lipidomics; Monoacylglycerol; N acyl phosphatidylethanolamine (NAPE); Prostaglandin; Triacylglycerol (TAG)

Indexed keywords

2-ARACHIDONOYLGLYCEROL (2-AG); ANANDAMIDE; ARACHIDONIC ACID; DIACYLGLYCEROL (DAG); FATTY-ACID AMIDE HYDROLASE (FAAH); LIPIDOMICS; MONOACYLGLYCEROL; N-ACYL PHOSPHATIDYLETHANOLAMINE (NAPE); PROSTAGLANDIN; TRIACYLGLYCEROL (TAG);

ACIDS; AMIDES; CHROMATOGRAPHIC ANALYSIS; INFORMATION MANAGEMENT; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; SIGNALING;

GLYCEROL;

2 ARACHIDONOYLGLYCEROL; ANANDAMIDE; DIACYLGLYCEROL; ENDOCANNABINOID; ETHANOLAMINE; FATTY ACID AMIDASE; LYSOPHOSPHOLIPID; MONOACYLGLYCEROL; N ACYLPHOSPHATIDYLETHANOLAMINE; TRIACYLGLYCEROL; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ELECTROSPRAY MASS SPECTROMETRY; LIPID ANALYSIS; LIPID HYDROLYSIS; LIPID METABOLISM; LIPIDOMICS; LIPOGENESIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; REVIEW; SIGNAL TRANSDUCTION;

ANIMALS; COMPUTATIONAL BIOLOGY; ENDOCANNABINOIDS; HUMANS; LIPID METABOLISM; LIPIDS;

EID: 67650027307     PISSN: 15700232     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jchromb.2009.01.008     Document Type: Review

References (91)

1. Katona I., and Freund T.F. Nat. Med. 14 (2008) 923
2. Di Marzo V. Nat. Rev. Drug Discov. 7 (2008) 438
3. Piomelli D., Astarita G., and Rapaka R. Nat. Rev. Neurosci. 8 (2007) 743
4. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., and Mechoulam R. Science 258 (1992) 1946
5. Okamoto Y., Morishita J., Wang J., Schmid P.C., Krebsbach R.J., Schmid H.H., and Ueda N. Biochem. J. 389 (2005) 241
6. Giuffrida A., and Piomelli D. FEBS Lett. 422 (1998) 373
7. Giuffrida A., and Piomelli D. In: Laychock S.G., and Rubin R.P. (Eds). Lipid Second Messengers (1998), CRC Press LLC, Boca Raton, FL 113
8. Hansen H.H., Hansen S.H., Bjornsdottir I., and Hansen H.S. J. Mass Spectrom. 34 (1999) 761
9. Schreiber D., Harlfinger S., Nolden B.M., Gerth C.W., Jaehde U., Schomig E., Klosterkotter J., Giuffrida A., Astarita G., Piomelli D., and Markus Leweke F. Anal. Biochem. 361 (2007) 162
10. Williams J., Wood J., Pandarinathan L., Karanian D.A., Bahr B.A., Vouros P., and Makriyannis A. Anal. Chem. 79 (2007) 5582
11. Lam P.M.W., Marczylo T.H., El-Talatini M., Finney M., Nallendran V., Taylor A.H., and Konje J.C. Anal. Biochem. (2008)
12. Astarita G., Ahmed F., and Piomelli D. J. Lipid. Res. 49 (2008) 48
13. Weber A., Ni J., Ling K.H.J., Acheampong A., Tang-Liu D.D.S., Burk R., Cravatt B.F., and Woodward D. J. Lipid Res. 45 (2004) 757
14. Fu J., Astarita G., Gaetani S., Kim J., Cravatt B.F., Mackie K., and Piomelli D. J. Biol. Chem. 282 (2007) 1518
15. Jung K.M., Astarita G., Zhu C., Wallace M., Mackie K., and Piomelli D. Mol. Pharmacol. 72 (2007) 612
16. Marczylo T.H., Lam P.M., Nallendran V., Taylor A.H., and Konje J.C. Anal. Biochem. 384 (2009) 106
17. P.J. Kingsley, L.J. Marnett, Lipidomics and Bioactive Lipids: Specialized Analytical Methods and Lipids in Disease (2007).
18. Wakelam M.J., Pettitt T.R., and Postle A.D. Methods Enzymol. 432 (2007) 233
19. Christie W.W. Advances in Lipid Methodology-Two (1993), Oily Press, Dundee p. 195
20. Schmid P., Calvert J., and Steiner R. Physiol. Chem. Phys. 5 (1973) 157
21. Bjerve K.S., Daae L.N.W., and Bremer J. Anal. Biochem. 58 (1974) 238
22. Radin N.S. Methods Enzymol. 72 (1981) 5
23. Hara A., and Radin N.S. Anal. Biochem. 90 (1978) 420
24. Carlson L.A. Clin. Chim. Acta 149 (1985) 89
25. Matyash V., Liebisch G., Kurzchalia T.V., Shevchenko A., and Schwudke D. J. Lipid Res. 49 (2008) 1137
26. Folch J., Lees M., and Stanley G.H.S. J. Biol. Chem. 226 (1957) 497
27. Wenk M.R., Lucast L., Di Paolo G., Romanelli A.J., Suchy S.F., Nussbaum R.L., Cline G.W., Shulman G.I., McMurray W., and De Camilli P. Nat. Biotechnol. 21 (2003) 813
28. Cadas H., di Tomaso E., and Piomelli D. J. Neurosci. 17 (1997) 1226
29. Cadas H., Gaillet S., Beltramo M., Venance L., and Piomelli D. J. Neurosci. 16 (1996) 3934
30. Cadas H., Schinelli S., and Piomelli D. J. Lipid Mediat. Cell Signal. 14 (1996) 63
31. Wang J., Okamoto Y., Morishita J., Tsuboi K., Miyatake A., and Ueda N. J. Biol. Chem. 281 (2006) 12325
32. Simon G.M., and Cravatt B.F. J. Biol. Chem. 281 (2006) 26465
33. Leung D., Saghatelian A., Simon G.M., and Cravatt B.F. Biochemistry 45 (2006) 4720
34. Sun Y.X., Tsuboi K., Okamoto Y., Tonai T., Murakami M., Kudo I., and Ueda N. Biochem. J. Pt. (2004)
35. Liu J., Wang L., Harvey-White J., Huang B.X., Kim H.Y., Luquet S., Palmiter R.D., Krystal G., Rai R., Mahadevan A., Razdan R.K., and Kunos G. Neuropharmacology (2007)
36. Liu J., Wang L., Harvey-White J., Osei-Hyiaman D., Razdan R., Gong Q., Chan A.C., Zhou Z., Huang B.X., Kim H.Y., and Kunos G. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 13345
37. Piomelli D. Nat. Rev. Neurosci. 4 (2003) 873
38. Piomelli D., Beltramo M., Glasnapp S., Lin S.Y., Goutopoulos A., Xie X.Q., and Makriyannis A. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 5802
39. Beltramo M., Stella N., Calignano A., Lin S.Y., Makriyannis A., and Piomelli D. Science 277 (1997) 1094
40. Cravatt B.F., Giang D.K., Mayfield S.P., Boger D.L., Lerner R.A., and Gilula N.B. Nature 384 (1996) 83
41. Wei B.Q., Mikkelsen T.S., McKinney M.K., Lander E.S., and Cravatt B.F. J. Biol. Chem. 281 (2006) 36569
42. McKinney M.K., and Cravatt B.F. Annu. Rev. Biochem. 74 (2005) 411
43. Want E.J., Cravatt B.F., and Siuzdak G. Chembiochem 6 (2005) 1941
44. Saghatelian A., Trauger S.A., Want E.J., Hawkins E.G., Siuzdak G., and Cravatt B.F. Biochemistry 43 (2004) 14332
45. Kozak K.R., Crews B.C., Morrow J.D., Wang L.H., Ma Y.H., Weinander R., Jakobsson P.J., and Marnett L.J. J. Biol. Chem. 277 (2002) 44877
46. Kozak K.R., Crews B.C., Ray J.L., Tai H.H., Morrow J.D., and Marnett L.J. J. Biol. Chem. 276 (2001) 36993
47. Kozak K.R., Prusakiewicz J.J., and Marnett L.J. Curr. Pharm. Des. 10 (2004) 659
48. Snider N.T., Sikora M.J., Sridar C., Feuerstein T.J., Rae J.M., and Hollenberg P.F. J. Pharm. Exp. Ther. (2008)
49. Hampson A.J., Hill W.A., Zan-Phillips M., Makriyannis A., Leung E., Eglen R.M., and Bornheim L.M. Biochim. Biophys. Acta 1259 (1995) 173
50. Fowler C.J. Br. J. Pharmacol. 152 (2007) 594
51. Snider N.T., Kornilov A.M., Kent U.M., and Hollenberg P.F. J. Pharm. Exp. Ther. 321 (2007) 590
52. Ueda N., Yamamoto K., Yamamoto S., Tokunaga T., Shirakawa E., Shinkai H., Ogawa M., Sato T., Kudo I., Inoue K., et al. Biochim. Biophys. Acta 1254 (1995) 127
53. Hanus L., Gopher A., Almog S., and Mechoulam R. J. Med. Chem. 36 (1993) 3032
54. Felder C.C., Joyce K.E., Briley E.M., Mansouri J., Mackie K., Blond O., Lai Y., Ma A.L., and Mitchell R.L. Mol. Pharmacol. 48 (1995) 443
55. Farrell E.K., and Merkler D.J. Drug Discov. Today 13 (2008) 558
56. Schwartz G.J., Fu J., Astarita G., Li X., Gaetani S., Campolongo P., Cuomo V., and Piomelli D. Cell Metab. 8 (2008) 281
57. Astarita G., Di Giacomo B., Gaetani S., Oveisi F., Compton T.R., Rivara S., Tarzia G., Mor M., and Piomelli D. J. Pharmacol. Exp. Ther. 318 (2006) 563
58. LoVerme J., Russo R., La Rana G., Fu J., Farthing J., Mattace-Raso G., Meli R., Hohmann A., Calignano A., and Piomelli D. J. Pharmacol. Exp. Ther. 319 (2006) 1051
59. Lo Verme J., Fu J., Astarita G., La Rana G., Russo R., Calignano A., and Piomelli D. Mol. Pharmacol. 67 (2005) 15
60. Fu J., Gaetani S., Oveisi F., Lo Verme J., Serrano A., Rodriguez de Fonseca F., Rosengarth A., Luecke H., Di Giacomo B., Tarzia G., and Piomelli D. Nature 425 (2003) 90
61. Maccarrone M., Cartoni A., Parolaro D., Margonelli A., Massi P., Bari M., Battista N., and Finazzi-Agrò A. Mol. Cell. Neurosci. 21 (2002) 126
62. Terrazzino S., Berto F., Carbonare M.D., Fabris M., Guiotto A., Bernardini D., and Leon A. FASEB J. (2004) 1580
63. Dalle Carbonare M., Del Giudice E., Stecca A., Colavito D., Fabris M., D'Arrigo A., Bernardini D., Dam M., and Leon A. J. Neuroendocrinol. 20 (2008) 26
64. Astarita G., Rourke B.C., Andersen J.B., Fu J., Kim J.H., Bennett A.F., Hicks J.W., and Piomelli D. Am. J. Physiol. Regul. Integr. Comp. Physiol. 290 (2006) R1407
65. Cravatt B.F., Próspero-García O., Siuzdak G., Gilula N.B., Heriksen S.J., Boger D.L., and Lerner R.A. Science 268 (1995) 1506
66. Vuong L.A.Q., Mitchell V.A., and Vaughan C.W. Neuropharmacology 54 (2008) 189
67. Burstein S. Neuropharmacology 55 (2008) 1259
68. McDonald G.R., Hudson A.L., Dunn S.M., You H., Baker G.B., Whittal R.M., Martin J.W., Jha A., Edmondson D.E., and Holt A. Science 322 (2008) 917
69. Jung K.M., Mangieri R., Stapleton C., Kim J., Fegley D., Wallace M., Mackie K., and Piomelli D. Mol. Pharmacol. 68 (2005) 1196
70. Bisogno T., Melck D., De Petrocellis L., and Di Marzo V. J. Neurochem. 72 (1999) 2113
71. Nakane S., Oka S., Arai S., Waku K., Ishima Y., Tokumura A., and Sugiura T. Arch. Biochem. Biophys. 402 (2002) 51
72. Oka S., Yanagimoto S., Ikeda S., Gokoh M., Kishimoto S., Waku K., Ishima Y., and Sugiura T. J. Biol. Chem. 280 (2005) 18488
73. Nomura D.K., Hudak C.S.S., Ward A.M., Burston J.J., Issa R.S., Fisher K.J., Abood M.E., Wiley J.L., Lichtman A.H., and Casida J.E. Bioorg. Med. Chem. Lett. (2008)
74. Sugiura T., Kishimoto S., Oka S., and Gokoh M. Prog. Lipid Res. 45 (2006) 405
75. Bisogno T., Howell F., Williams G., Minassi A., Cascio M.G., Ligresti A., Matias I., Schiano-Moriello A., Paul P., Williams E.J., Gangadharan U., Hobbs C., Di Marzo V., and Doherty P. J. Cell. Biol. 163 (2003) 463
76. Blankman J.L., Simon G.M., and Cravatt B.F. Chem. Biol. 14 (2007) 1347
77. Dinh T.P., Kathuria S., and Piomelli D. Mol. Pharmacol. 66 (2004) 1260
78. Dinh T.P., Carpenter D., Leslie F.M., Freund T.F., Katona I., Sensi S.L., Kathuria S., and Piomelli D. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 10819
79. Kozak K.R., Gupta R.A., Moody J.S., Ji C., Boeglin W.E., DuBois R.N., Brash A.R., and Marnett L.J. J. Biol. Chem. 15 (2002) 15
80. Moody J.S., Kozak K.R., Ji C., and Marnett L.J. Biochemistry 40 (2001) 861
81. Kozak K.R., Rowlinson S.W., and Marnett L.J. J. Biol. Chem. 275 (2000) 33744
82. Kozak K.R., and Marnett L.J. Prostaglandins Leukot. Essent. Fatty Acids 66 (2002) 211
83. Woodward D.F., Carling R.W.C., Cornell C.L., Fliri H.G., Martos J.L., Pettit S.N., Liang Y., and Wang J.W. Pharmacol. Ther. (2008)
84. Chen J.K., Chen J., Imig J.D., Wei S., Hachey D.L., Guthi J.S., Falck J.R., Capdevila J.H., and Harris R.C. J. Biol. Chem. (2008)
85. Hanus L., Abu-Lafi S., Fride E., Breuer A., Vogel Z., Shalev D.E., Kustanovich I., and Mechoulam R. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 3662
86. Fezza F., Bisogno T., Minassi A., Appendino G., Mechoulam R., and Di Marzo V. FEBS Lett. 513 (2002) 294
87. Oka S., Tsuchie A., Tokumura A., Muramatsu M., Suhara Y., Takayama H., Waku K., and Sugiura T. J. Neurochem. 85 (2003) 1374
88. Ben-Shabat S., Fride E., Sheskin T., Tamiri T., Rhee M.H., Vogel Z., Bisogno T., De Petrocellis L., Di Marzo V., and Mechoulam R. Eur. J. Pharmacol. 353 (1998) 23
89. King A.R., Duranti A., Tontini A., Rivara S., Rosengarth A., Clapper J.R., Astarita G., Geaga J.A., Luecke H., Mor M., Tarzia G., and Piomelli D. Chem. Biol. 14 (2007) 1357
90. Larsen A., Uran S., Jacobsen P.B., and Skotland T. Rapid Commun. Mass Spectrom. 15 (2001) 2393
91. Stella N., Schweitzer P., and Piomelli D. Nature 388 (1997) 773