Endogenous morphine synthetic pathway preceded and gave rise to catecholamine synthesis in evolution (Review)

International Journal of Molecular Medicine

Volumn 20, Issue 6, 2007, Pages 837-841

  Stefano, George B ^a   Kream, Richard M ^b  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b SUNY DOWNSTATE MEDICAL CENTER   (United States)

Author keywords

Catecholamine; Dopamine; Guanosine triphosphate cyclohydrolase; Morphine; mu3 opiate receptor subtype; Tetrahydrobiopterin

Indexed keywords

CATECHOL METHYLTRANSFERASE; CATECHOLAMINE; ISOPROTEIN; MORPHINE; MU OPIATE RECEPTOR; NITRIC OXIDE; PHENYLETHANOLAMINE N METHYLTRANSFERASE;

ANIMAL; BIOSYNTHESIS; CHEMISTRY; EVOLUTION; METABOLISM; PHYSIOLOGY; PLANT; REVIEW; SIGNAL TRANSDUCTION;

ANIMALS; CATECHOL O-METHYLTRANSFERASE; CATECHOLAMINES; EVOLUTION; MORPHINE; NITRIC OXIDE; PHENYLETHANOLAMINE N-METHYLTRANSFERASE; PLANTS; PROTEIN ISOFORMS; RECEPTORS, OPIOID, MU; SIGNAL TRANSDUCTION;

EID: 37249091465     PISSN: 11073756     EISSN: 1791244X     Source Type: Journal    
DOI: 10.3892/ijmm.20.6.837     Document Type: Review

References (65)

1. Bird DA and Facchini PJ: Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant. Planta 213: 888-897, 2001.
2. Facchini PJ and De Luca V: Differential and tissue-specific expression of a gene family for tyrosine/dopa decarboxylase in opium poppy. J Biol Chem 269: 26684-26690, 1994.
3. Facchini PJ and Park SU: Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy. Phytochemistry 64: 177-186, 2003.
4. Facchini PJ and De Luca V: Expression in Escherichia coli and partial characterization of two tyrosine/dopa decarboxylases from opium poppy. Phytochemistry 38: 1119-1126, 1995.
5. Park SU, Johnson AG, Penzes-Yost C and Facchini PJ: Analysis of promoters from tyrosine/dihydroxyphenylalanine decarboxylase and berberine bridge enzyme genes involved in benzylisoquinoline alkaloid biosynthesis in opium poppy. Plant Mol Biol 40: 121-131, 1999. (Pubitemid 29300733)
6. Samanani N and Facchini PJ: Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline biosynthesis, from poppy. Planta 213: 898-906, 2001.
7. Samanani N and Facchini PJ: Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants. J Biol Chem 277: 33878-33883, 2002.
8. De-Eknamkul W and Zenk MH: Enzymatic formation of (R)-reticuline from 1,2-dehydroreticuline in the opium poppy plant. Tetrahedron Lett 31: 4855-4858, 1990. (Pubitemid 20251227)
9. Frenzel T and Zenk MH: S-Adenosyl-L-methionine: 3′-hydroxy-N- methyl-(S)-coclaurine 4′-O-methyltransferase, a regio- and stereoselective enzyme of the (S)-reticuline pathway. Phytochemistry 29: 3505-3511, 1990.
10. Gerady R and Zenk MH: Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum. Phytochemistry 32: 79-86, 1992.
11. Herbert RB: The biosynthesis of isoquinoline alkaloids. In: The Chemistry and Biology of Isoquinoline Alkaloids. Phillipson JD, Roberts MF and Zenk MH (eds). Springer-Verlag, Berlin, Heidelberg pp213-228, 1985.
12. Lenz R and Zenk MH: Closure of the oxide bridge in morphine biosynthesis. Tetrahedron Lett 35: 3897-3900, 1994.
13. Lenz R and Zenk MH: Stereospecific reduction of codeinone, the penultimate enzymatic step during morphine biosynthesis in Papaver somniferum. Tetrahedron Lett 36: 2449-2452, 1995.
14. Lenz R and Zenk MH: Purification and properties of codeinone reductase (NADPH) from Papaver somniferum cell cultures. Eur J Biochem 233: 132-139, 1995.
15. Loeffler S and Zenk MH: The hydroxylation step in the biosynthesis pathway leading from norcoclaurine to reticuline. Phytochemistry 29: 3499-3503, 1990.
16. Zhu W, Ma Y, Bell A, et al: Presence of morphine in rat amygdala: Evidence for the mu3 opiate receptor subtype via nitric oxide release in limbic structures. Med Sci Monit 10: BR433-BR439, 2004.
17. Zhu W, Mantione KJ, Shen L and Stefano GB: In vivo and in vitro L-DOPA exposure increases ganglionic morphine levels. Med Sci Monit 11: MS1-MS5, 2005.
18. Zhu W, Mantione KJ, Shen L, et al: Tyrosine and tyramine increase endogenous ganglionic morphine and dopamine levels in vitro and in vivo: CYP2D6 and tyrosine hydroxylase modulation demonstrates a dopamine coupling. Med Sci Monit 11: BR397-BR404, 2005.
19. Stefano GB and Aiello E: Histoflourescent localization of serotonin and dopamine in the nervous system and gill of Mytilus edulis (Bivalvia). Biol Bull 148: 141-156, 1975.
20. Stefano GB, Catapane EJ and Aiello E: Dopaminergic agents: Influence on serotonin in the molluscan nervous system. Science 194: 539-541, 1976.
21. Stefano GB: Comparative aspects of opioid-dopamine interaction. Cell Mol Neurobiol 2: 167-178, 1982.
22. Stefano GB: Norepinephrine: Presence and interaction with endogenous biogenic amines. In: Neurobiology of Mytilus Edulis. Stefano GB (ed). Manchester University Press, Manchester pp93-103, 1990.
23. Iversen LL, Iversen SD and Snyder SH: Biochemistry of Biogenic Amines. Plenum Press, New York, 1975.
24. Zhu W, Cadet P, Baggerman G, Mantione KJ and Stefano GB: Human white blood cells synthesize morphine: CYP2D6 modulation. J Immunol 175: 7357-7362, 2005.
25. Kream RM and Stefano GB: De novo biosynthesis of morphine in animal cells: An evidence-based model. Med Sci Monit 12: RA207-RA219, 2006.
26. Stefano GB and Scharrer B: Endogenous morphine and related opiates, a new class of chemical messengers. Adv Neuroimmunol 4: 57-68, 1994.
27. Stefano GB: Autoimmunovascular regulation: Morphine and anandamide stimulated nitric oxide release. J Neuroimmunol 83: 70-76, 1998. (Pubitemid 28280953)
28. Stefano GB, Goumon Y, Bilfinger TV, Welters I and Cadet P: Basal nitric oxide limits immune, nervous and cardiovascular excitation: Human endothelia express a mu opiate receptor. Prog Neurobiol 60: 513-530, 2000.
29. Stefano GB, Goumon Y, Casares F, et al: Endogenous morphine. Trends Neurosci 9: 436-442, 2000.
30. Stefano GB and Fricchione GL: The biology of deception: The evolution of cognitive coping as a denial-like process. Med Hypotheses 44: 311-314, 1995.
31. Stefano GB and Fricchione GL: The biology of deception: Emotion and morphine. Med Hypotheses 49: 51-54, 1995.
32. Stefano GB, Scharrer B, Smith EM, et al: Opioid and opiate immunoregulatory processes. Crit Rev Immunol 16: 109-144, 1996.
33. Stefano GB and Liu Y: Opiate antagonism of opioid actions on immunocyte activation and nitric oxide release. Anim Biol 1: 11-16, 1996.
34. Pryor SC, Zhu W, Cadet P, Bianchi E, Guarna M and Stefano GB: Endogenous morphine: opening new doors for the treatment of pain and addiction. Expert Opin Biol Ther 5: 893-906, 2005.
35. Moncada S, Higgs A and Furchgott R: International Union of Pharmacology Nomenclature in Nitric Oxide Research. Pharmacol Rev 49: 137-142, 1997.
36. Ignarro LJ: Signal transduction mechanisms involving nitric oxide. Biochemical Pharmacology 41: 485-490, 1991.
37. Moncada S, Palmer RMJ and Higgs EA: Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol Rev 43: 109-142, 1991.
38. Moncada S and Higgs A: The L-arginine-nitric oxide pathway. New Eng J Med 329: 2002-2012, 1993.
39. Moncada S: Nitric oxide in the vasculature: physiology and pathophysiology. Ann NY Acad Sci 811: 60-67, 1997.
40. Fimiani C, Liberty T, Aquirre AJ, Amin I, Ali N and Stefano GB: Opiate, cannabinoid, and eicosanoid signaling converges on common intracellular pathways: Nitric oxide coupling. Prostaglandins Lipid Mediators 57: 23-34, 1999.
41. Welters ID, Fimiani C, Bilfinger TV and Stefano GB: NF-kB, nitric oxide and opiate signaling. Med Hypotheses 54: 263-268, 1999.
42. Benz D, Cadet P, Mantione K, Zhu W and Stefano GB: Tonal nitric oxide and health: A free radical and a scavenger of free radicals. Med Sci Monit 8: 1-4, 2002.
43. Esch T, Stefano GB, Fricchione GL and Benson H: Stress-related diseases: A potential role for nitric oxide. Med Sci Monit 8: RA103-RA118, 2002.
44. Stefano GB and Esch T: Integrative medical therapy: Examination of meditation's therapeutic and global medicinal outcomes via nitric oxide (Review). Int J Mol Med 16: 621-630, 2005.
45. Tegeder I, Costigan M, Griffin RS, et al: GTP cyclohydrolase and tetrahydrobiopterin regulate pain sensitivity and persistence. Nat Med 12: 1269-1277, 2006.
46. El-Yacoubi B, Bonnett S, Anderson JN, Swairjo MA, Iwata-Reuyl D and de Crecy-Lagard V: Discovery of a new prokaryotic type I GTP cyclohydrolase family. J Biol Chem 281: 37586-37593, 2006.
47. Breu-Gonzalez P, Gonzalez-Hernandez T, Fonso-Oramas D, Cruz-Muros I, Barroso-Chinea P and Gonzalez MC: Tetrahydrobiopterin stimulates L-DOPA release from striatal tissue. Eur J Pharmacol 541: 33-37, 2006.
48. Urano F, Hayashi N, Arisaka F, Kurita H, Murata S and Ichinose H: Molecular mechanism for pterin-mediated inactivation of tyrosine hydroxylase: formation of insoluble aggregates of tyrosine hydroxylase. J Biochem 139: 625-635, 2006.
49. Werner-Felmayer G, Golderer G and Werner ER: Tetrahydrobiopterin biosynthesis, utilization and pharmacological effects. Curr Drug Metab 3: 159-173, 2002.
50. Gorren AC and Mayer B: Nitric-oxide synthase: A cytochrome P450 family foster child. Biochim Biophys Acta 1770: 432-445, 2007.
51. Xu Q, Wink DA and Colton CA: Nitric oxide production and regulation of neuronal NOS in tyrosine hydroxylase containing neurons. Exp Neurol 188: 341-350, 2004.
52. Giulivi C, Kato K and Cooper CE: Nitric oxide regulation of mitochondrial oxygen consumption I: cellular physiology. Am J Physiol Cell Physiol 291: C1225-C1231, 2006.
53. Kato K and Giulivi C: Critical overview of mitochondrial nitric-oxide synthase. Front Biosci 11: 2725-2738, 2006.
54. Guo FQ, Okamoto M and Crawford NM: Identification of a plant nitric oxide synthase gene involved in hormonal signaling. Science 302: 100-103, 2003.
55. Riobo NA, Melani M, Sanjuan N, et al: The modulation of mitochondrial nitric-oxide synthase activity in rat brain development. J Biol Chem 277: 42447-42455, 2002.
56. Stefano GB, Digenis A, Spector S, et al: Opiate-like substances in an invertebrate, an opiate receptor on invertebrate and human immunocytes, and a role in immunosuppression. Proc Natl Acad Sci USA 90: 11099-11103, 1993.
57. Cadet P, Mantione KJ and Stefano GB: Molecular identification and functional expression of mu3, a novel alternatively spliced variant of the human mu opiate receptor gene. J Immunol 170: 5118-5123, 2003.
58. Kotturi MF, Hunt SV and Jefferies WA: Roles of CRAC and Cav-like channels in T cells: more than one gatekeeper? Trends Pharmacol Sci 27: 360-367, 2006.
59. Bianchi E, Alessandrini C, Guarna M and Tagliamonte A: Endogenous codeine and morphine are stored in specific brain neurons. Brain Res 627: 210-215, 1993.
60. Bianchi E, Guarna M and Tagliamonte A: Immunocytochemical localization of endogenous codeine and morphine. Adv Neuroimmunol 4: 83-92, 1994.
61. Esch T, Guarna M, Bianchi E, Zhu W and Stefano GB: Commonalities in the central nervous system's involvement with complementary medical therapies: Limbic morphinergic processes. Med Sci Monit 10: MS6-MS17, 2004.
62. Guarna M, Bianchi E, Bartolini A, et al: Endogenous morphine modulates acute thermonociception in mice. J Neurochem 80: 271-277, 2002.
63. Guarna M, Ghelardini C, Galeotti N, Stefano GB and Bianchi E: Neurotransmitter role of endogenous morphine in CNS. Med Sci Monit 11: RA190-RA193, 2005.
64. Neri C, Guarna M, Bianchi E, Sonetti D, Matteucci G and Stefano GB: Endogenous morphine and codeine in the brain of non-human primate. Med Sci Monit 10: MS1-MS5, 2004.
65. Zhu W, Ma Y, Cadet P, et al: Presence of reticuline in rat brain: A pathway for morphine biosynthesis. Mol Brain Res 117: 83-90, 2003.