Literature DB >> 1929872

Endogenous formation of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3- carboxylic acid in man as the possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan.

J Adachi1, K Yamamoto, Y Ogawa, Y Ueno, Y Mizoi, Y Tatsuno.   

Abstract

1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (MTCA) is now thought to be a possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. In the present study a factor affecting endogenous formation of MTCA in 32 healthy men is studied. Urinary excretions of MTCA and 1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (TCCA) were measured by high-performance liquid chromatography (HPLC) with fluorometric detection after administration of a high or low protein diet as well as peroral tryptophan (0.5 g) or ethanol (0.4 g/kg). Blood ethanol and acetaldehyde levels were determined by gas chromatography after ethanol consumption. Both, the high protein diet and tryptophan resulted in a significant rise of urinary TCCA. In contrast, ethanol intake caused increased excretion of MTCA, though a relationship between blood acetaldehyde level and urinary excretion of MTCA was not shown. We showed for the first time that an elevation of urinary excretion of MTCA following ethanol consumption in man without ingestion of L-tryptophan tablets implicated eosinophilia-myalgia syndrome.

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Year:  1991        PMID: 1929872     DOI: 10.1007/bf01977365

Source DB:  PubMed          Journal:  Arch Toxicol        ISSN: 0340-5761            Impact factor:   5.153


  10 in total

1.  The cause of the eosinophilia-myalgia syndrome associated with tryptophan use.

Authors:  K Sakimoto
Journal:  N Engl J Med       Date:  1990-10-04       Impact factor: 91.245

2.  Analysis of L-tryptophan for the etiology of eosinophilia-myalgia syndrome.

Authors: 
Journal:  MMWR Morb Mortal Wkly Rep       Date:  1990-08-31       Impact factor: 17.586

3.  The eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan.

Authors:  L E Shulman
Journal:  Arthritis Rheum       Date:  1990-07

4.  Alkaloids in mammalian tissues. 3. Condensations of L-tryptophan and L-5-hydroxytryptophan with formaldehyde and acetaldehyde.

Authors:  A Brossi; A Focella; S Teitel
Journal:  J Med Chem       Date:  1973-04       Impact factor: 7.446

5.  The nitrosation of alcohol-induced metabolites produces mutagenic substances.

Authors:  N Valin; D Haybron; L Groves; H F Mower
Journal:  Mutat Res       Date:  1985-12       Impact factor: 2.433

6.  Presence of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, a precursor of a mutagenic nitroso compound, in soy sauce.

Authors:  K Wakabayashi; M Ochiai; H Saitô; M Tsuda; Y Suwa; M Nagao; T Sugimura
Journal:  Proc Natl Acad Sci U S A       Date:  1983-05       Impact factor: 11.205

7.  Identification of tetrahydro-beta-carboline-3-carboxylic acid in foodstuffs, human urine and human milk.

Authors:  J Adachi; Y Mizoi; T Naito; Y Ogawa; Y Uetani; I Ninomiya
Journal:  J Nutr       Date:  1991-05       Impact factor: 4.798

8.  Reductive decyanization of alpha-amino nitriles with NaBH. A new synthetic approach to isoquinoline- and indole-alkaloids.

Authors:  S I Yamada; H Akimoto
Journal:  Tetrahedron Lett       Date:  1969-08       Impact factor: 2.415

9.  Alcohol sensitivity related to polymorphism of alcohol-metabolizing enzymes in Japanese.

Authors:  Y Mizoi; Y Tatsuno; J Adachi; M Kogame; T Fukunaga; S Fujiwara; S Hishida; I Ijiri
Journal:  Pharmacol Biochem Behav       Date:  1983       Impact factor: 3.533

10.  An investigation of the cause of the eosinophilia-myalgia syndrome associated with tryptophan use.

Authors:  E A Belongia; C W Hedberg; G J Gleich; K E White; A N Mayeno; D A Loegering; S L Dunnette; P L Pirie; K L MacDonald; M T Osterholm
Journal:  N Engl J Med       Date:  1990-08-09       Impact factor: 91.245

  10 in total
  3 in total

1.  Nitrogen-Containing Constituents of Black Cohosh: Chemistry, Structure Elucidation, and Biological Activities.

Authors:  Dejan Nikolić; David C Lankin; Tamara Cisowska; Shao-Nong Chen; Guido F Pauli; Richard B van Breemen
Journal:  Recent Adv Phytochem       Date:  2015

2.  Accumulation of 1-methyl-tetrahydro-beta-carboline-3-carboxylic acid in blood and organs of rat. A possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan.

Authors:  Y Ogawa; J Adachi; Y Tatsuno
Journal:  Arch Toxicol       Date:  1993       Impact factor: 5.153

3.  Metabolism and distribution in the rat of peak E substance, a constituent in L-tryptophan product implicated in eosinophilia-myalgia syndrome.

Authors:  J Adachi; T Naito; Y Ueno; Y Ogawa; I Ninomiya; Y Tatsuno
Journal:  Arch Toxicol       Date:  1993       Impact factor: 5.153

  3 in total

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