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Volumn 54, Issue 18, 2006, Pages 6909-6915

Identification of 4-methylspinaceamine, a Pictet-Spengler condensation reaction product of histamine with acetaldehyde, in fermented foods and its metabolite in human urine

Author keywords

1,4 dimethyl 4,5,6,7 tetrahydro 1H imidazo 4,5 c pyridine; 1,4 dimethylspinaceamine; 4 methyl 4,5,6,7 tetrahydro 1H imidazo 4,5 c pyridine; 4 methylspinaceamine; Acetaldehyde; Fermented foods; Histamine; Metabolite; Pictet Spengler reaction

Indexed keywords

4 METHYLSPINACEAMINE; 4-METHYLSPINACEAMINE; ACETALDEHYDE; HISTAMINE; IMIDAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

EID: 33748905111     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf061364z     Document Type: Article
Times cited : (3)

References (42)
  • 1
    • 0001625508 scopus 로고
    • The Pictet-Spengler synthesis of tetrahydroisoquiolines and related compounds
    • Whaley, W. M.; Govindachari, T. R. The Pictet-Spengler synthesis of tetrahydroisoquiolines and related compounds. Org. React. 1951, 6, 151-190.
    • (1951) Org. React. , vol.6 , pp. 151-190
    • Whaley, W.M.1    Govindachari, T.R.2
  • 2
    • 4243241249 scopus 로고
    • The Pictet-Spengler condensation: A new direction for an old reaction
    • Cox, E. D.; Cook, J. M. The Pictet-Spengler condensation: A new direction for an old reaction. Chem. Rev. 1995, 95, 1797-1842.
    • (1995) Chem. Rev. , vol.95 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2
  • 3
    • 0018852663 scopus 로고
    • Biogenic amine-aldehyde condensation products: Tetrahydroisoquinolines and tryptolines (β-carbolines)
    • Deitrich, R.; Erwin, V. Biogenic amine-aldehyde condensation products: tetrahydroisoquinolines and tryptolines (β-carbolines). Ann. Rev. Pharmacol. Toxicol. 1980, 20, 55-80.
    • (1980) Ann. Rev. Pharmacol. Toxicol. , vol.20 , pp. 55-80
    • Deitrich, R.1    Erwin, V.2
  • 4
    • 0019406904 scopus 로고
    • β-Carboline, psychoactive compounds in the mammalian body part I: Occurrence, origin and metabolism
    • Airaksinen, M. M.; Kari, I. β-Carboline, psychoactive compounds in the mammalian body part I: occurrence, origin and metabolism. Med. Biol. 1981, 59, 21-34.
    • (1981) Med. Biol. , vol.59 , pp. 21-34
    • Airaksinen, M.M.1    Kari, I.2
  • 5
    • 0020216581 scopus 로고
    • The route and significance of endogenous synthesis of alkaloids in animals
    • Melchior, C.; Collins, M. A. The route and significance of endogenous synthesis of alkaloids in animals. CRC Crit. Rev. Toxicol. 1982, 9, 313-356.
    • (1982) CRC Crit. Rev. Toxicol. , vol.9 , pp. 313-356
    • Melchior, C.1    Collins, M.A.2
  • 6
    • 0020730819 scopus 로고
    • Analysis of 6-hydroxy-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline in alcoholic beverages and food
    • Beck, O.; Bosin, T. R.; Lundman, A. Analysis of 6-hydroxy-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline in alcoholic beverages and food. J. Agric. Food Chem. 1983, 31, 288-292.
    • (1983) J. Agric. Food Chem. , vol.31 , pp. 288-292
    • Beck, O.1    Bosin, T.R.2    Lundman, A.3
  • 7
    • 0029967653 scopus 로고    scopus 로고
    • Urinary excretion of tetrahydro-β-carbolines relating to ingestion of alcoholic beverages
    • Tsuchiya, H.; Yamada, K.; Tajima, K.; Hayashi, T. Urinary excretion of tetrahydro-β-carbolines relating to ingestion of alcoholic beverages. Alcohol Alcohol. 1996, 31, 197-203.
    • (1996) Alcohol Alcohol. , vol.31 , pp. 197-203
    • Tsuchiya, H.1    Yamada, K.2    Tajima, K.3    Hayashi, T.4
  • 8
    • 0029954844 scopus 로고    scopus 로고
    • Urinary excretion of tetrahydro-β-carbolines influenced by food and beverage ingestion implies their exogeneous supply via dietary sources
    • Tsuchiya, H.; Yamada, K.; Todoriki, H.; Hayashi, T. Urinary excretion of tetrahydro-β-carbolines influenced by food and beverage ingestion implies their exogeneous supply via dietary sources. J. Nutr. Biochem. 1996, 7, 237-242.
    • (1996) J. Nutr. Biochem. , vol.7 , pp. 237-242
    • Tsuchiya, H.1    Yamada, K.2    Todoriki, H.3    Hayashi, T.4
  • 9
    • 0033213519 scopus 로고    scopus 로고
    • Antiplatelet activity of soy sauce as functional seasoning
    • Tsuchiya, H.; Sato, M.; Watanabe, I. Antiplatelet activity of soy sauce as functional seasoning. J. Agric. Food Chem. 1999, 47, 4167-4174.
    • (1999) J. Agric. Food Chem. , vol.47 , pp. 4167-4174
    • Tsuchiya, H.1    Sato, M.2    Watanabe, I.3
  • 10
    • 0034625496 scopus 로고    scopus 로고
    • Analysis of the bioactive alkaloids tetrahydro-β-carboline and β-carboline in food
    • Herraiz, T. Analysis of the bioactive alkaloids tetrahydro-β- carboline and β-carboline in food. J. Chromatogr., A 2000, 881, 483-499.
    • (2000) J. Chromatogr., A , vol.881 , pp. 483-499
    • Herraiz, T.1
  • 11
    • 0033782286 scopus 로고    scopus 로고
    • Tetrahydro-β-carbolines, potential neuroactive alkaloids, in chocolate and cocoa
    • Herraiz, T. Tetrahydro-β-carbolines, potential neuroactive alkaloids, in chocolate and cocoa. J. Agric. Food Chem. 2000, 48, 4900-4904.
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 4900-4904
    • Herraiz, T.1
  • 12
    • 0242691743 scopus 로고    scopus 로고
    • Tetrahydro-β-carbolines alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers
    • Herraiz, T.; Galisteo, J. Tetrahydro-β-carbolines alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers. J. Agric. Food Chem. 2003, 51, 7156-7161.
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 7156-7161
    • Herraiz, T.1    Galisteo, J.2
  • 13
    • 2342527245 scopus 로고    scopus 로고
    • Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-β-carbolines in commercial sausages
    • Herraiz, T.; Papavergou, E. Identification and occurrence of tryptamine- and tryptophan-derived tetrahydro-β-carbolines in commercial sausages. J. Agric. Food Chem. 2004, 52, 2652-2658.
    • (2004) J. Agric. Food Chem. , vol.52 , pp. 2652-2658
    • Herraiz, T.1    Papavergou, E.2
  • 14
    • 0020080285 scopus 로고
    • Salsolinol and dopamine in alcoholic beverages
    • Duncan, M. W.; Smythe, G. A. Salsolinol and dopamine in alcoholic beverages. Lancet 1982, 1, 904-905.
    • (1982) Lancet , vol.1 , pp. 904-905
    • Duncan, M.W.1    Smythe, G.A.2
  • 15
    • 0031581896 scopus 로고    scopus 로고
    • Assay for the (R)- and (S)-enantiomers of salsolinols in biological samples and foods with ion-pair high-performance liquid chromatography using β-cyclodextrin as a chiral mobile phase additive
    • Deng, Y; Maruyama, W.; Kawai, M.; Dostert, P.; Yamamura, H.; Takahashi, T.; Naoi, M. Assay for the (R)- and (S)-enantiomers of salsolinols in biological samples and foods with ion-pair high-performance liquid chromatography using β-cyclodextrin as a chiral mobile phase additive. J. Chromatogr., B 1997, 689, 313-320.
    • (1997) J. Chromatogr., B , vol.689 , pp. 313-320
    • Deng, Y.1    Maruyama, W.2    Kawai, M.3    Dostert, P.4    Yamamura, H.5    Takahashi, T.6    Naoi, M.7
  • 16
    • 0034618789 scopus 로고    scopus 로고
    • Determination of salsolinol enantiomers by gas chromatography-mass spectrometry with cyclodextrin chiral columns
    • Liu, Y.; Gordon, P.; Green, S.; Sweedler, J. V. Determination of salsolinol enantiomers by gas chromatography-mass spectrometry with cyclodextrin chiral columns. Anal. Chim. Acta 2000, 420, 81-88.
    • (2000) Anal. Chim. Acta , vol.420 , pp. 81-88
    • Liu, Y.1    Gordon, P.2    Green, S.3    Sweedler, J.V.4
  • 17
    • 0001165186 scopus 로고
    • Formation of 1-methyl-6-methoxy-1, 2, 3, 4-tetrahydro-2-carboline under physiological conditions
    • MacIsaac, W. M. Formation of 1-methyl-6-methoxy-1, 2, 3, 4-tetrahydro-2-carboline under physiological conditions. Biochim. Biophys. Acta 1961, 52, 607-609.
    • (1961) Biochim. Biophys. Acta , vol.52 , pp. 607-609
    • MacIsaac, W.M.1
  • 18
    • 0028227812 scopus 로고
    • The Pictet-Spengler reaction and biogenic tryptamines: Formation of tetrahydro-β-carbolines at physiological pH
    • Callaway, J. C.; Gynther, J.; Poso, A.; Vepsäläinen, J.; Airaksinen, M. M. The Pictet-Spengler reaction and biogenic tryptamines: formation of tetrahydro-β-carbolines at physiological pH. J. Heterocycl. Chem. 1994, 31, 431-435.
    • (1994) J. Heterocycl. Chem. , vol.31 , pp. 431-435
    • Callaway, J.C.1    Gynther, J.2    Poso, A.3    Vepsäläinen, J.4    Airaksinen, M.M.5
  • 20
    • 0029994831 scopus 로고    scopus 로고
    • Formation of tetrahydroharman (1-methyl-1,2,3,4-tetrahydro-beta- carboline) by Helicobacter pylori in the presence of ethanol and tryptamine
    • Callaway, J. C.; Airaksinen, M. M.; Salmela, K. S.; Salaspuro, M. Formation of tetrahydroharman (1-methyl-1,2,3,4-tetrahydro-beta-carboline) by Helicobacter pylori in the presence of ethanol and tryptamine. Life Sci. 1996, 58, 1817-1821.
    • (1996) Life Sci. , vol.58 , pp. 1817-1821
    • Callaway, J.C.1    Airaksinen, M.M.2    Salmela, K.S.3    Salaspuro, M.4
  • 21
    • 0014942629 scopus 로고
    • Salsolinol, an alkaloid derivative of dopamine formed in vitro during alcohol metabolism
    • Yamanaka, Y.; Walsh, M. J.; Davis, V. E. Salsolinol, an alkaloid derivative of dopamine formed in vitro during alcohol metabolism. Nature 1970, 227, 1143-1144.
    • (1970) Nature , vol.227 , pp. 1143-1144
    • Yamanaka, Y.1    Walsh, M.J.2    Davis, V.E.3
  • 22
    • 0014964412 scopus 로고
    • Alkaloids from catecholamines in adrenal tissue: Possible role in alcoholism
    • Cohen, G.; Collins, M. Alkaloids from catecholamines in adrenal tissue: possible role in alcoholism. Science 1970, 167, 1749-1751.
    • (1970) Science , vol.167 , pp. 1749-1751
    • Cohen, G.1    Collins, M.2
  • 23
    • 0018567695 scopus 로고
    • Dopamine-related tetrahydroisoquinolines: Significant urinary excretion by alcoholics after alcohol consumption
    • Collins, M. A.; Nijm, W. P.; Borge, G. F.; Teas, G.; Goldfarb, C. Dopamine-related tetrahydroisoquinolines: significant urinary excretion by alcoholics after alcohol consumption. Science 1979, 206, 1184-1186.
    • (1979) Science , vol.206 , pp. 1184-1186
    • Collins, M.A.1    Nijm, W.P.2    Borge, G.F.3    Teas, G.4    Goldfarb, C.5
  • 24
    • 0343006752 scopus 로고    scopus 로고
    • Determination of dopamine and dopamine-derived (R)-/(S)-salsolinol and norsalsolinol in various human brain areas using solid-phase extraction and gas chromatography/mass spectrometry
    • Musshoff, F.; Schmidt, P.; Dettmeyer, R.; Priemer, F.; Jachau, K.; Madea, B. Determination of dopamine and dopamine-derived (R)-/(S)-salsolinol and norsalsolinol in various human brain areas using solid-phase extraction and gas chromatography/mass spectrometry. Forensic Sci. Int. 2000, 113, 359-366.
    • (2000) Forensic Sci. Int. , vol.113 , pp. 359-366
    • Musshoff, F.1    Schmidt, P.2    Dettmeyer, R.3    Priemer, F.4    Jachau, K.5    Madea, B.6
  • 25
    • 0037094393 scopus 로고    scopus 로고
    • Tetrahydroisoquinoline derivatives of enkephalins: Synthesis and properties
    • Foppoli, C.; Coccia, R.; Blarzino, C.; Cini, C.; Rosei, M. A. Tetrahydroisoquinoline derivatives of enkephalins: synthesis and properties. Biochem. Pharmacol. 2002, 63, 1885-1892.
    • (2002) Biochem. Pharmacol. , vol.63 , pp. 1885-1892
    • Foppoli, C.1    Coccia, R.2    Blarzino, C.3    Cini, C.4    Rosei, M.A.5
  • 26
    • 0038366850 scopus 로고    scopus 로고
    • In vivo formation of salsolinol induced by high acetaldehyde concentration in rat striatum employing microdialysis
    • Jamal, M.; Ameno, K.; Kubota, T.; Ameno, S.; Zhang, X.; Kumihashi, M.; Ijiri, I. In vivo formation of salsolinol induced by high acetaldehyde concentration in rat striatum employing microdialysis. Alcohol Alcohol. 2003, 38, 197-201.
    • (2003) Alcohol Alcohol. , vol.38 , pp. 197-201
    • Jamal, M.1    Ameno, K.2    Kubota, T.3    Ameno, S.4    Zhang, X.5    Kumihashi, M.6    Ijiri, I.7
  • 27
    • 10944273810 scopus 로고
    • The condensation of histamine with carbonyl compounds
    • Habermehl, G. G.; Ecsy, W. The condensation of histamine with carbonyl compounds. Heterocycles 1976, 5, 127-134.
    • (1976) Heterocycles , vol.5 , pp. 127-134
    • Habermehl, G.G.1    Ecsy, W.2
  • 28
    • 2142710033 scopus 로고    scopus 로고
    • Relative reactivities of histamine and indoleamines with acetaldehyde
    • Ohya, T.; Niitsu, M. Relative reactivities of histamine and indoleamines with acetaldehyde. Biol. Pharm. Bull. 2003, 26, 1215-1218.
    • (2003) Biol. Pharm. Bull. , vol.26 , pp. 1215-1218
    • Ohya, T.1    Niitsu, M.2
  • 29
    • 11844283259 scopus 로고    scopus 로고
    • Identification of 4-methylspinaceamine - A Pictet-Spengler condensation reaction product of histamine with acetaldehyde - in human urine
    • Ohya, T.; Niitsu, M. Identification of 4-methylspinaceamine - a Pictet-Spengler condensation reaction product of histamine with acetaldehyde - in human urine. Life Sci. 2005, 76, 1199-1209.
    • (2005) Life Sci. , vol.76 , pp. 1199-1209
    • Ohya, T.1    Niitsu, M.2
  • 30
    • 0000121029 scopus 로고
    • Chemical and technological factors determining tetrahydro-β- carboline-3-carboxylic acid content in fermented alcoholic beverages
    • Herraiz, T.; Ough, C. S. Chemical and technological factors determining tetrahydro-β-carboline-3-carboxylic acid content in fermented alcoholic beverages J. Agric. Food Chem. 1993, 41, 959-964.
    • (1993) J. Agric. Food Chem. , vol.41 , pp. 959-964
    • Herraiz, T.1    Ough, C.S.2
  • 31
    • 0015029133 scopus 로고
    • Measurement of histamine in California wines
    • Ough, C. S. Measurement of histamine in California wines. J. Agric. Food Chem. 1971, 19, 241-244.
    • (1971) J. Agric. Food Chem. , vol.19 , pp. 241-244
    • Ough, C.S.1
  • 33
    • 84964316661 scopus 로고
    • Biogenic amines in cheese and other fermented foods: A review
    • Stratton, J. E.; Hutkins, R. W.; Taylor, S. L. Biogenic amines in cheese and other fermented foods: a review. J. Food Prot. 1991, 54, 460-470.
    • (1991) J. Food Prot. , vol.54 , pp. 460-470
    • Stratton, J.E.1    Hutkins, R.W.2    Taylor, S.L.3
  • 35
    • 0034625531 scopus 로고    scopus 로고
    • Liquid chromatographic determination of biogenic amines in fermented foods after derivatization with 3, 5-dinitrobenzoyl chloride
    • Kirschbaum, J.; Rebscher, K.; Brückner, H. Liquid chromatographic determination of biogenic amines in fermented foods after derivatization with 3, 5-dinitrobenzoyl chloride. J. Chromatogr., A 2000, 881, 517-530.
    • (2000) J. Chromatogr., A , vol.881 , pp. 517-530
    • Kirschbaum, J.1    Rebscher, K.2    Brückner, H.3
  • 36
    • 0141535353 scopus 로고    scopus 로고
    • Biogenic amines in dry fermented sausages: A review
    • Suzzi, G.; Gardini, F. Biogenic amines in dry fermented sausages: a review. Int. J. Food Microbiol. 2003, 88, 41-54.
    • (2003) Int. J. Food Microbiol. , vol.88 , pp. 41-54
    • Suzzi, G.1    Gardini, F.2
  • 37
    • 0041734111 scopus 로고
    • Acetaldehyde determination in fermented food products by direct 2, 4-dinitrophenylhydrazine derivatization, extraction and high performance liquid chromatography
    • Shmidt, R. H.; Davidson, S. M.; Bates, R. P. Acetaldehyde determination in fermented food products by direct 2, 4-dinitrophenylhydrazine derivatization, extraction and high performance liquid chromatography. J. Food Sci. 1983, 48, 1556-1557.
    • (1983) J. Food Sci. , vol.48 , pp. 1556-1557
    • Shmidt, R.H.1    Davidson, S.M.2    Bates, R.P.3
  • 38
    • 85008546371 scopus 로고
    • Determination of acetoin, diacetyl and acetaldehyde in foods by HPLC
    • Matsuura, H.; Fujiyama, K.; Minagawa, N.; Sawa, J. Determination of acetoin, diacetyl and acetaldehyde in foods by HPLC. Bunseki Kagaku 1990, 39, 405-409.
    • (1990) Bunseki Kagaku , vol.39 , pp. 405-409
    • Matsuura, H.1    Fujiyama, K.2    Minagawa, N.3    Sawa, J.4
  • 39
    • 0001632295 scopus 로고
    • Quantitative analysis of acetaldehyde in foods and beverages
    • Miyake, T.; Shibamoto, T. Quantitative analysis of acetaldehyde in foods and beverages. J. Agric. Food Chem. 1993, 41, 1968-1970.
    • (1993) J. Agric. Food Chem. , vol.41 , pp. 1968-1970
    • Miyake, T.1    Shibamoto, T.2
  • 40
    • 33748901530 scopus 로고    scopus 로고
    • New use of 4,5,6,7-tetrahydroimidazo-[4,5-c]pyridine derivatives as inhibitors of semicarbazide-sesitive amine oxidase (SSAO) for treatment of, e.g., diabetic complications. PICT Int. Appl. WO0238153, 2002
    • Caldirola, P.; Bensencon, O.; Olsson, R.; Oehman, J. New use of 4,5,6,7-tetrahydroimidazo-[4,5-c]pyridine derivatives as inhibitors of semicarbazide-sesitive amine oxidase (SSAO) for treatment of, e.g., diabetic complications. PICT Int. Appl. WO0238153, 2002.
    • Caldirola, P.1    Bensencon, O.2    Olsson, R.3    Oehman, J.4
  • 41
    • 0026540846 scopus 로고
    • Improvement of extraction procedure for biogenic amines in foods and their high-performance liquid chromatographic determination
    • Moret, S.; Bortolomeazzi, R.; Lercker, G. Improvement of extraction procedure for biogenic amines in foods and their high-performance liquid chromatographic determination. J. Chromatogr. 1992, 591, 175-180.
    • (1992) J. Chromatogr. , vol.591 , pp. 175-180
    • Moret, S.1    Bortolomeazzi, R.2    Lercker, G.3
  • 42
    • 0028171673 scopus 로고
    • Determination of tetrahydro-β-carobolines in urine by high-perfomance liquid chromatography with suppression of artefact formation
    • Tsuchiya, H.; Ohtani, S.; Yamada, K.; Takagi, N.; Hayashi, T. Determination of tetrahydro-β-carobolines in urine by high-perfomance liquid chromatography with suppression of artefact formation. J. Pharm. Biomed. Anal. 1994, 12, 1547-1553.
    • (1994) J. Pharm. Biomed. Anal. , vol.12 , pp. 1547-1553
    • Tsuchiya, H.1    Ohtani, S.2    Yamada, K.3    Takagi, N.4    Hayashi, T.5


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