2-arachidonoyl-glycerol as an "endocannabinoid": Limelight for a formerly neglected metabolite

Biochemistry (Moscow)

Volumn 63, Issue 1, 1998, Pages 13-21

  Di Marzo, V ^a  

^a CNR   (Italy)

Author keywords

Anandamide; Arachidonic acid; Cannabinoid receptors; Cannabinoids; Eicosanoids; Oxylipins

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 2-ARACHIDONYLGLYCEROL; ACYLGLYCEROL; ARACHIDONIC ACID DERIVATIVE; CANNABINOID; CANNABINOID RECEPTOR; DRUG RECEPTOR; ENDOCANNABINOID;

ANIMAL; BIOLOGICAL MODEL; BIOSYNTHESIS; DRUG ANTAGONISM; KINETICS; METABOLISM; REVIEW;

ANIMALS; ARACHIDONIC ACIDS; CANNABINOIDS; ENDOCANNABINOIDS; GLYCERIDES; KINETICS; MODELS, BIOLOGICAL; RECEPTORS, CANNABINOID; RECEPTORS, DRUG;

BIOCHEMISTRY; BIOSYNTHESIS; DRUG PRODUCTS; LIPIDS; METABOLISM; PHARMACOKINETICS;

2-ARACHIDONOYL-GLYCEROL;

GLYCEROL;

EID: 0031605955     PISSN: 00062979     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (66)

1. Vance, D. E., and Vance, J. (1991) Biochemistry of Lipids, Lipoproteins and Membranes, Elsevier, Amsterdam.
2. Gerwich, W. H., Moghaddam, M. F., and Hamberg, M. (1991) Arch. Biochem. Biophys., 290, 436-444.
3. Hasegawa-Sasaki, H. (1985) Biochem. J., 232, 99-109.
4. Prescott, S. M., and Majerus, P. W. (1983) J. Biol. Chem., 258, 764-769.
5. Allen, A. C., Gammon, C. M., Ousley, A. H., McCarthy, K. D., and Morell, P. (1992) J. Neurochem., 58, 1130-1139.
6. Gobbetti, A., and Zerani, M. (1993) Cell Signalling, 5, 63-67.
7. Rapuano, B., and Bookman, R. S. (1991) Biochim. Biophys. Acta, 1091, 374-384.
8. Bell, R. L., Kennedy, D. A., Stanford, N., and Majerus, P. W. (1979) Proc. Natl. Acad. Sci. USA, 76, 3238-3241.
9. Di Marzo, V. (1995) Prostaglandins Leukot. Essent. Fatty Acids, 53, 239-254.
10. Farooqui, A. A., Anderson, D. K., Flynn, C., Bradel, A., Means, E. D., and Horrocks, L. A. (1990) Biochem. Biophys. Res. Commun., 166, 1001-1009.
11. Dixon, J. F., and Hokin, L. E. (1984) J. Biol. Chem., 259, 14418-14425.
12. Gammon, C. M., Allen, A. C., and Morell, P. (1989) J. Neurochem., 53, 95-101.
13. Askari, A., Xie, Z., Wang, Y., Periyasamy, S., and Huang, W. (1991) Biochim. Biophys. Acta, 1069, 127-130.
14. Ueda, H., Kobayashi, T., Kishimoto, M., Tsutsumi, T., and Okuyama, H. (1993) J. Neurochem., 61, 1874-1881.
15. Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R. (1992) Science, 258, 1946-1949.
16. Fride, E., and Mechoulam, R. (1993) Eur. J. Pharmacol., 231, 313-314.
17. Crawley, J. N., Corwin, R. L., Robinson, J. K., Felder, C. C., Devane, W. A., and Axelrod, J. (1993) Pharmacol. Biochem. Behav., 46, 967-972.
18. Smith, P. B., Compton, D. R., Welch, S. P., Razdan, R. K., Mechoulam, R., and Martin, B. R. (1994) J. Pharmacol. Exp. Ther., 270, 219-227.
19. Felder, C. C., Briley, E. M., Axelrod, J., Simpson, J. T., Mackie, K., and Devane, W. A. (1993) Proc. Natl. Acad. Sci. USA, 90, 7656-7660.
20. Vogel, Z., Barg, J., Levy, R., Saya, D., Heldman, E., and Mechoulam, R. (1993) J. Neurochem., 61, 352-355.
21. Di Marzo, V., De Petrocellis, L., Bisogno, T., and Maurelli, S. (1995) J. Drug Dev. Clin. Pract., 7, 199-219.
22. Shohami, E., Weidenfeld, J., Ovadia, H., Vogel, Z., Hanus, L., Fride, E., Breuer, A., Ben-Shabat, S., Sheskin, T., and Mechoulam, R. (1997) CNS Drug Rev., 4, 429-451.
23. Dewey, W. L. (1986) Pharmacol. Rev., 38, 151-178.
24. Di Marzo, V., Fontana, A., Cadas, H., Schinelli, S., Cimino, G., Schwartz, J. C., and Piomelli, D. (1994) Nature, 372, 686-691.
25. Schmid, H. H. O., Schmid, P. C., and Natarajan, V. (1990) Prog. Lipid Res., 29, 1-43.
26. Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., Ishima, Y., and Waku, K. (1996) Eur. J. Biochem., 240, 53-62.
27. Cadas, H., Gaillet, S., Beltramo, M., Venance, L., and Piomelli, D. (1996) J. Neurosci., 16, 3934-3942.
28. Di Marzo, V., De Petrocellis, L., Sugiura, T., and Waku, K. (1996) Biochem. Biophys. Res. Commun., 227, 281-288.
29. Cadas, H., di Tomaso, E., and Piomelli, D. (1997) J. Neurosci., 17, 1226-1242.
30. Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., and Waku, K. (1996) Biochem. Biophys. Res. Commun., 218, 113-117.
31. Bisogno, T., Maurelli, S., Melck, D., De Petrocellis, L., and Di Marzo, V. (1997) J. Biol. Chem., 272, 3315-3323.
32. Di Marzo, V., De Petrocellis, L., Sepe, N., and Buono, A. (1996) Biochem. J., 316, 977-984.
33. Bisogno, T., Ventriglia, M., Mosca, M., Milone, A., Cimino, G., and Di Marzo, V. (1997) Biochim. Biophys. Acta, 1345, 338-348.
34. Kruszka, K. K., and Gross, R. W. (1994) J. Biol. Chem., 269, 14345-14348.
35. Devane, W. A., and Axelrod, J. (1994) Proc. Natl. Acad. Sci. USA, 91, 6698-6701.
36. Matsuda, L. A., Lolait, S. J., Brownstein, M. J., Young, A. C., and Bonner, T. I. (1990) Nature, 346, 561-564.
37. Munro, S., Thomas, K. L., and Abu-Shaar, M. (1993) Nature, 365, 61-65.
38. Bayewitch, M., Avidor-Reiss, T., Levy, R., Barg,J., Mechoulam, R., and Vogel, Z. (199S) FEBS Lett., 375, 143-147.
39. Facci, L., Dal Toso, R., Romanello, S., Buriani, A., Skaper, S. D., and Leon, A. (1995) Proc. Natl. Acad. Sci. USA, 92, 3376-3380.
40. Sheskin, T., Hanuš, L., Slager, J., Vogel, Z., and Mechoulam, R. (1997) J. Med. Chem., 40, 659-667.
41. Mechoulam, R., Ben-Shabat, S., Hanus, L., Ligumsky, M., Kaminski, N. E., Schatz, A. R., Gopher, A., Almog, S., Martin, B. R., Compton, D. R., Pertwee, R. G., Griffin, G., Bayewitch, M., Barg, J., and Vogel, Z. (1995) Biochem. Pharmacol., 50, 83-90.
42. Martin, B. R., Thomas, B. F., and Razdan, R. K. (1995) in Cannabinoid Receptors (Pertwee, R. G., ed.) Academic Press, London, pp. 35-79.
43. De Petrocellis, L., Orlando, P., and Di Marzo, V. (1995) Biochem. Mol. Biol. Int., 36, 1127-1133.
44. Sugiura, T., Tokumura, A., Gregory, L., Nouchi, T., Weintraub, S. T., and Hanahan, D. J. (1994) Arch. Biochem. Biophys., 311, 358-368.
45. Sugiura, T., Itoh, K., Waku, K., and Hanahan, D. J. (1994) in Proc. Japan. Conf. on the Biochemistry of Lipids [in Japanese], 36, 71-74.
46. Sugiura, T., Kondo, S., Sukagawa, A., Nakane, S., Shinoda, A., Itoh, K., Yamashita, A., and Waku, K. (1995) Biochem. Biophys. Res. Commun., 215, 89-97.
47. Bisogno, T., Sepe, N., Melck, D., Maurelli, S., De Petrocellis, L., and Di Marzo, V. (1997) Biochem. J., 322, 671-677.
48. Sugiura, T., Kodaka, T., Kondo, S., Tonegawa, T., Nakane, S., Kishimoto, S., Yamashita, A., and Waku, K. (1996) Biochem. Biophys. Res. Commun., 229, 58-64.
49. Sugiura, T., Kodaka, T., Kondo, S., Tonegawa, T., Nakane, S., Kishimoto, S., Yamashita, A., and Waku, K. (1997) Biochem. Biophys. Res. Commun., 233, 207-210.
50. Stella, N., Schweitzer, P., and Piomelli, D. (1997) Nature, 388, 773-778.
51. Mallet, P. E., and Beninger, R. J. (1996) Behav. Pharmacol., 7, 276-284.
52. Lee, M., Yang, K. H., and Kaminski, N. E. (1995) J. Pharmacol. Exp. Ther., 275, 529-536.
53. Schatz,A. R.,Lee,M.,Condie,R. B.,Pulaski,J. T.,and Kaminski, N. E. (1997) Toxicol. Appl. Pharmacol., 142, 278-287.
54. 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., submitted.
55. Tsutsumi, T., Kobayashi, T., Ueda, H., Yamauchi, E., Watanabe, S., and Okuyama, H. (1994) Neurochem. Res., 19, 399-406.
56. Cravatt, B. F., Giang, D. K., Mayfield, S. P., Boger, D. L., Lerner, R. A., and Gilula, N. B. (1996) Nature, 384, 83-87.
57. Maurelli, S., Bisogno, T., De Petrocellis, L., Di Luccia, A., Marino, G., and Di Marzo, V. (1995) FEBS Lett., 377, 82-86.
58. Ueda, N., Kurahashi, Y., Yamamoto, K., and Yamamoto, S. (1997) Adv. Exp. Med. Biol., 407, 323-328.
59. Koutek, B., Prestwich, G. D., Hewlett, A. C., Chin, S. A., Salehani, D., Akhavan, N., and Deutsch, D. G. (1994) J. Biol. Chem., 269, 22937-22940.
60. Fride, E., Bisogno,T., Di Marzo, V., Bayewitch, M., Vogel, Z., and Mechoulam, R. (1997) in Abstract Book of the Society for Neuroscience Annual Meeting, New Orleans, 25-30 October.
61. Di Tomaso, E., Beltramo, M., and Piomelli, D. (1996) Nature, 382, 677-678.
62. Mackie, K., Devane, W. A., and Hille, B. (1993) Mol. Pharmacol., 44, 498-503.
63. Kearn, C. S., and Hillard, C. J. (1997) in Abstract Book of the 7th ICRS Conference, Stone Mountain, Atlanta, Georgia, 19-22 June, p. 61.
64. Jeon, Y. J., Yang, K. H., Pulaski, J. T., and Kaminski, N. E. (1996) Mol. Pharmacol., 50, 334-341.
65. Bouaboula, M., Poinot-Chazel, C., Marchand, J., Canat, X., Bourrie, B., Rinaldi-Carmona, M., Calandra, B., Le Fur, G., and Casellas, P. (1996) Eur. J. Biochem., 237, 704-711.
66. Barth, F., Rinaldi-Carmona, M., Millan, J., Derocq, J.-M., Bouaboula, M., Casellas, P., Congy, C., Oustric, D., Sarran, M., Calandra, B., Portier, M., Shire, D., Breliere, J.-C., and Le Fur, G. (1997) in Abstract Book of the 7th ICRS Conference, Stone Mountain, Atlanta, Georgia, 19-22 June, p. 11.