Literature DB >> 10234605

4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone)--the odour of maple syrup urine disease.

F Podebrad1, M Heil, S Reichert, A Mosandl, A C Sewell, H Böhles.   

Abstract

Maple syrup urine disease is an autosomal recessive inherited disorder of branched-chain amino acid metabolism due to deficiency of the branched-chain alpha-keto acid dehydrogenase complex. The disease was originally named after the characteristic sweet aroma, reminiscent of maple syrup, present in the body fluids of affected patients. Until now, the substance responsible for the odour has not been positively identified. Using enantioselective multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS), we could demonstrate that 4,5-dimethyl-3-hydroxy-2[5H]-furanone (sotolone), a well-known flavour impact compound present in fenugreek and lovage, was present in urine from seven patients with maple syrup urine disease. Urine samples from healthy control persons lacked sotolone. We have shown that sotolone is responsible for the characteristic odour of maple syrup urine disease and, since maple syrup also contains sotolone, the naming of this disease appears to be correct.

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Year:  1999        PMID: 10234605     DOI: 10.1023/a:1005433516026

Source DB:  PubMed          Journal:  J Inherit Metab Dis        ISSN: 0141-8955            Impact factor:   4.982


  9 in total

1.  MAPLE SYRUP URINE DISEASE, WITH PARTICULAR REFERENCE TO DIETOTHERAPY.

Authors:  S E SNYDERMAN; P M NORTON; E ROITMAN; L E HOLT
Journal:  Pediatrics       Date:  1964-10       Impact factor: 7.124

2.  A new syndrome: progressive familial infantile cerebral dysfunction associated with an unusual urinary substance.

Authors:  J H MENKES; P L HURST; J M CRAIG
Journal:  Pediatrics       Date:  1954-11       Impact factor: 7.124

3.  Fenugreek odour in maple syrup urine disease.

Authors:  K Monastiri; K Limame; N Kaabachi; H Kharrat; S Bousnina; H Pousse; M Radhouane; M N Gueddiche; N Snoussi
Journal:  J Inherit Metab Dis       Date:  1997-08       Impact factor: 4.982

4.  Diagnosis and treatment: some diseases, syndromes, and conditions associated with an unusual odor.

Authors:  T E Cone
Journal:  Pediatrics       Date:  1968-05       Impact factor: 7.124

5.  Inborn errors of metabolism associated with unusual odors.

Authors:  D G Carpenter; C H Carter
Journal:  J Fla Med Assoc       Date:  1970-05

6.  Profiles of urinary volatiles from metabolic disorders characterized by unusual odors.

Authors:  D G Burke; B Halpern; D Malegan; E McCairns; D Danks; P Schlesinger; B Wilken
Journal:  Clin Chem       Date:  1983-10       Impact factor: 8.327

7.  "Maple-syrup" urine odor due to fenugreek ingestion.

Authors:  G B Bartley; M D Hilty; B D Andreson; A C Clairmont; S P Maschke
Journal:  N Engl J Med       Date:  1981-08-20       Impact factor: 91.245

8.  Maple syrup urine disease: report of two cases.

Authors:  C Y Yeung; S P Lin; H A Kao; E Y Shen; H C Lee; C H Lin; K J Hsiao
Journal:  J Formos Med Assoc       Date:  1993-08       Impact factor: 3.282

9.  Peculiar odours in newborns and maternal prenatal ingestion of spicy food.

Authors:  G J Hauser; D Chitayat; L Berns; D Braver; B Muhlbauer
Journal:  Eur J Pediatr       Date:  1985-11       Impact factor: 3.183

  9 in total
  8 in total

1.  Branched Chain Amino Acids.

Authors:  Michael Neinast; Danielle Murashige; Zoltan Arany
Journal:  Annu Rev Physiol       Date:  2018-11-28       Impact factor: 19.318

2.  The Thiamine diphosphate dependent Enzyme Engineering Database: a tool for the systematic analysis of sequence and structure relations.

Authors:  Michael Widmann; Robert Radloff; Jürgen Pleiss
Journal:  BMC Biochem       Date:  2010-02-01       Impact factor: 4.059

3.  Quantitative determination of common urinary odorants and their glucuronide conjugates in human urine.

Authors:  Maria Wagenstaller; Andrea Buettner
Journal:  Metabolites       Date:  2013-08-07

4.  Weight loss moderately affects the mixed meal challenge response of the plasma metabolome and transcriptome of peripheral blood mononuclear cells in abdominally obese subjects.

Authors:  Parastoo Fazelzadeh; Roland W J Hangelbroek; Peter J Joris; Casper G Schalkwijk; Diederik Esser; Lydia Afman; Thomas Hankemeier; Doris M Jacobs; Velitchka V Mihaleva; Sander Kersten; John van Duynhoven; Mark V Boekschoten
Journal:  Metabolomics       Date:  2018-03-05       Impact factor: 4.290

Review 5.  Impact of pregnancy on inborn errors of metabolism.

Authors:  Gisela Wilcox
Journal:  Rev Endocr Metab Disord       Date:  2018-03       Impact factor: 6.514

6.  Two-Dimensional Gas Chromatographic and Mass Spectrometric Characterization of Lipid-Rich Biological Matrices-Application to Human Cerumen (Earwax).

Authors:  Allix M Coon; A John Dane; Gavin Setzen; Robert B Cody; Rabi A Musah
Journal:  ACS Omega       Date:  2021-12-27

Review 7.  The Critical Role of the Branched Chain Amino Acids (BCAAs) Catabolism-Regulating Enzymes, Branched-Chain Aminotransferase (BCAT) and Branched-Chain α-Keto Acid Dehydrogenase (BCKD), in Human Pathophysiology.

Authors:  Aikaterini Dimou; Vasilis Tsimihodimos; Eleni Bairaktari
Journal:  Int J Mol Sci       Date:  2022-04-05       Impact factor: 5.923

8.  Whole-body metabolic fate of branched-chain amino acids.

Authors:  Megan C Blair; Michael D Neinast; Zoltan Arany
Journal:  Biochem J       Date:  2021-02-26       Impact factor: 3.766

  8 in total

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