2-acetyl-1-pyrroline Pathway (Arabidopsis thaliana)

From WikiPathways

Jump to: navigation, search
Mitochondria23HeatNot in plantsChloroplastMitochondriaPIIAcetyl group1-deoxyosone fructoseNOglucoseglucoseglutamate N-acetyltransferase carbamoyl-P-synthaseMaillardGlutamineCatalystGlc/ProNicotinatearg decarboxylasenitric oxide synthase nicotinate N-methyltransferase Apoptosis, stress-related metabolism, cell growth inhibitionCysteine/cystinecitrulline trigonelline PyrolysisagmatineL-arginino-succinateStreckerdelta-1-Pyrroline-5-carboxylate2-acetyl-1-pyrrolinePyrroleornithine carbamoyltransferase 1-deoxy-2,3-glucosoneProlino+fructoseargininosuccinatelyase dihiydro-diacetyl-formoincarbamoyl-phosphate argininosuccinate synthase adenosylmethionine decarboxylase24L-ornithine ammonia-lyase arginaseδ1-pyrroline-5-carboxylate synthetase dehydrogenase4-amino-butyraldehyde4-amino-butyraldehydeN-acetyl-L-glutamate-5-phosphateStrecker 2-oxopropanalN-acetyl-L-ornithinePutrescinebetaine aldehyde dehydrogenase BADH2, 9ornithine decarboxylase proline dehydrogenase 13, 23REDUCTASE 1-pyrrolineGlutamic-semialdehydePROC1polyamine oxidase 1-pyrroline-5-carboxylate dehydrogenase Spermidine11N-acetyl-L-glutamate synthaseL-ornithine acetylglutamate kinaseNicotine2-acetyl-1-pyrrolineChlorophyllMaillardGamma Aminobutyric AcidBADHArginineacetylornithine transaminase 2-oxopropanalS-adenosylmethionine spermidine synthase acetylornithine deacetylaseN-acetyl-L-glutamate 5-semialdehyde N-acetyl-glutamateOrn-δ-aminotransferase L-Glutamic acidL-Proline


Description

2-Acetyl-1-pyrroline, abbreviated 2AP, with the IUPAC name 1-(3,4-dihydro-2H-pyrrol-5-yl)ethanone, is an aroma compound and flavor that gives white bread, jasmine rice and basmati rice, the spice pandan (Pandanus amaryllifolius), and bread flowers (Vallaris glabra) their customary smell. Source: Wikipedia

Quality Tags

Ontology Terms

 

Bibliography

View all...
  1. Bradbury; ''''; , PubMed Europe PMC
  2. Bradbury; ''Inactivation of an aminoaldehyde dehydrogenase is responsible for fragrance in rice''; , 2008 PubMed Europe PMC
  3. Chen; ''''; , PubMed Europe PMC
  4. Schieberle; ''THE ROLE OF FREE AMINO ACIDS PRESENT IN YEAST AS PRECURSORS OF THE ODORANTS 2-ACETYL-1-PYRROLINE AND 2-ACETYLTETRAHYDROPYRIDINE IN WHEAT BREAD CRUST''; , PubMed Europe PMC
  5. ''Process for the preparation of 2-acetyl-1-pyrroline, the basmati rice flavorant''; , PubMed Europe PMC
  6. Zhang; ''''; , PubMed Europe PMC
  7. YOSHIHASHI; ''PRECURSORS OF 2-ACETYL-1-PYRROLINE, A POTENT FLAVOR COMPOUND OF AN AROMATIC RICE VARIETY''; , PubMed Europe PMC
  8. Kalamaki; ''''; , PubMed Europe PMC
  9. ''M2P_SPE_REP_Quarterly Scientific Reports 2010.doc''; PMI report, 2010 PubMed Europe PMC
  10. Funck; ''''; , PubMed Europe PMC
  11. Szekely; ''''; , PubMed Europe PMC
  12. ''Expression pattern of a nuclear encoded mitochondrial arginineornithine translocator gene from Arabidopsis''; , PubMed Europe PMC
  13. Slocum; ''Genes, enzymes and regulation of arginine biosynthesis in plants''; , 2005 PubMed Europe PMC
  14. Turchetto-Zolet; ''''; , PubMed Europe PMC
  15. Sakthivel; ''''; , PubMed Europe PMC
  16. Thimmaraju,; ''In vitro culture of pandanus amaryllifolius and enhancement of 2-acetyl-1-pyrroline the major flavoring compound of aromatic rice, by precursor feeding of L-proline''; , PubMed Europe PMC
  17. Małgorzata; ''Effect of Cysteine and Cystine Addition on Sensory Profile and Potent Odorants of Extruded Potato Snacks''; , PubMed Europe PMC
  18. ''''; , PubMed Europe PMC
  19. Verbruggen; ''''; , PubMed Europe PMC
  20. Incharoensakdi A; ''''; , PubMed Europe PMC
  21. Buffo; ''Coffee flavour: an overview''; , PubMed Europe PMC
  22. Deuschle; ''THE ROLE OF [DELTA]1-PYRROLINE-5-CARBOXYLATE DEHYDROGENASE IN PROLINE DEGRADATION.''; , PubMed Europe PMC
  23. Chen YM, Ferrar TS, Lohmeier-Vogel EM, Morrice N, Mizuno Y, Berenger B, Ng KK, Muench DG, Moorhead GB; ''''; , PubMed Europe PMC
  24. Slocum RD; ''Genes, enzymes and regulation of arginine biosynthesis in plants.''; Plant Physiol Biochem, 2005 PubMed Europe PMC
  25. Blank; ''''; , PubMed Europe PMC
  26. Kiyosue T, Yoshiba Y, Yamaguchi-Shinozaki K, Shinozaki K; ''''; , PubMed Europe PMC
  27. YOSHIHASH; ''Formation of flavor compound in aromatic rice and its fluctuations with drought stress''; , PubMed Europe PMC
  28. Schieberle; ''formation of 2-acetyl-pyrroline and other important flavor compounds in wheat bread crust''; ,
  29. Adams; ''''; , PubMed Europe PMC
  30. Beker; ''''; , PubMed Europe PMC
  31. Heckman; ''THE ROLE OF TOBACCO LEAF PRECURSORS IN CIGARETTE FLAVOR''; , PubMed Europe PMC
  32. Pullabhatia; ''Process for the preparation of 2-acetyl-1-pyrroline, the basmati rice flavorant''; , PubMed Europe PMC
  33. Cona A, Manetti F, Leone R, Corelli F, Tavladoraki P, Polticelli F, Botta M; ''Molecular basis for the binding of competitive inhibitors of maize polyamine oxidase.''; Biochemistry, 2004 PubMed Europe PMC
  34. Huang; ''ä1-Pyrroline-5-carboxylic acid formed by proline dehydrogenase from the Bacillus subtilis ssp. natto expressed in Escherichia coli as a precursor for 2-acetyl-1-pyrroline''; , PubMed Europe PMC
  35. ''Ornithine biosynthesis enzymes''; US Patent 6184036, PubMed Europe PMC
  36. Stránská; ''Ornithine delta-aminotransferase: An enzyme implicated in salt tolerance in higher plants.''; Plant Signal Behav (2008) 3: 929-35., PubMed Europe PMC
  37. Harrison TJ, Dake GR; ''''; , PubMed Europe PMC
  38. Bovet; ''PMI document;''; , PubMed Europe PMC
  39. Kishor; ''Overexpression of delta1-pyrroline-5-carboxylate synthetase increases proline production and confers osmotolerance in transgenic plants.''; , PubMed Europe PMC
  40. ''''; ,
  41. Less; ''Principal transcriptional programs regulating plant amino Acid metabolism in response to abiotic stresses.''; , PubMed Europe PMC
  42. Hofmann; ''''; , PubMed Europe PMC
  43. Hu CA, Delauney AJ, Verma DP; ''Hu CA, Delauney AJ, Verma DP (1992). "A bifunctional enzyme (delta 1-pyrroline-5-carboxylate synthetase) catalyzes the first two steps in proline biosynthesis in plants." Proc Natl Acad Sci U S A 89(19);9354-8. PMID: 1384052''; , PubMed Europe PMC
  44. ''Correlation between Ornithine Decarboxylase and Putrescine in Tomato Plants lnfected by Citrus Exocortis Viroid or Treated with Ethephon''; , PubMed Europe PMC
  45. Schmeltz; ''NITROGEN CONTAINING COMPOUNDS IN TOBACCO AND TOBACCO SMOKE''; , PubMed Europe PMC
  46. Roosens; ''Overexpression of ornithine--aminotransferase increases proline biosynthesis and confers osmotolerance in transgenic plants''; Molecular Breeding, Volume 9, Number 2, 2002 , pp. 73-80(8), PubMed Europe PMC
  47. Adams; ''Formation of pyrazines and 2-acetyl-1-pyrroline by Bacillus cereus''; , PubMed Europe PMC
  48. Leffingwell; ''CHEMICAL CONSTITUENTS OF TOBACCO LEAF AND DIFFERENCES AMONG TOBACCO TYPES''; , PubMed Europe PMC
  49. Singh; ''SNP haplotypes of the BADH1 gene and their association with aroma in rice (Oryza sativa L.)''; , 2010 PubMed Europe PMC
  50. Niu; ''''; , PubMed Europe PMC
  51. ''GENETIC ENGINEERING OF THE BIOSYNTHESIS OF GLYCINEBETAINE LEADS TO INCREASED TOLERANCE OF PHOTOSYNTHESIS TO SALT STRESS IN TRANSGENIC TOBACCO PLANTS.''; , PubMed Europe PMC
  52. Mohapatra S, Minocha R, Long S, Minocha SC; ''Transgenic manipulation of a single polyamine in poplar cells affects the accumulation of all amino acids.''; Amino Acids, 2010 PubMed Europe PMC
  53. ''Metabolic engineering in plants for food security''; , PubMed Europe PMC
  54. Blank; ''''; , 2003 PubMed Europe PMC
  55. ''Molecular regulation of nicotine biosynthesis''; , PubMed Europe PMC
  56. Tischner R, Galli M, Heimer YM, Bielefeld S, Okamoto M, Mack A, Crawford NM; ''Interference with the citrulline-based nitric oxide synthase assay by argininosuccinate lyase activity in Arabidopsis extracts.''; FEBS J, 2007 PubMed Europe PMC
  57. Mayer; ''Polyamine Homeostasis in Transgenic Plants Overexpressing Ornithine Decarboxylase Includes Ornithine Limitation''; J. Biochem, 2003, Vol. 134, No. 5 765-772 © 2003 Japanese Biochemical Society, PubMed Europe PMC
  58. huang; ''''; , PubMed Europe PMC
  59. Bovet; ''GM approaches to modify proline content''; , 2010 PubMed Europe PMC
  60. Adams; ''''; , PubMed Europe PMC
  61. Kenyon,; ''STIMULATION OF PHENOLICS FORMATION BY INHIBITION ORNITHINE DECARBOXYLASE AND GLUTAMIC ACID DECARBOXYLASE ACTIVITY''; , PubMed Europe PMC
  62. Hecht; ''Nitrogenous compounds in cigarette smoke and their possible precursors''; , PubMed Europe PMC
  63. Khuo; ''The Betaine Aldehyde Dehydrogenase (BAD2) Gene Is not Responsible for the Aroma Trait of SA0420 Rice Mutant Derived by Sodium Azide Mutagenesis''; , PubMed Europe PMC
  64. Thimmaraju,; ''IN VITRO CULTURE OF PANDANUS AMARYLLIFOLIUS AND ENHANCEMENT OF 2-ACETYL-1-PYRROLINE, THE MAJOR FLAVOURING COMPOUND OF AROMATIC RICE, BY PRECURSOR FEEDING OF L-PROLINE''; ,
  65. Kochetov; ''''; , PubMed Europe PMC
  66. Fitzegerald; ''''; , PubMed Europe PMC
  67. Leffigwell; ''CHEMICAL CONSTITUENTS OF TOBACCO LEAF AND DIFFERENCES AMONG TOBACCO TYPES''; , PubMed Europe PMC
  68. PATENT; ''''; , PubMed Europe PMC
  69. Brownfield; ''''; , PubMed Europe PMC
  70. Munch; ''comparison of key odorants generated by thermal treatment of commercial and self-prepared yeast extracts''; , PubMed Europe PMC
  71. Schieberle; ''''; , PubMed Europe PMC
  72. Huang et al.; ''''; J agric Food Chem 56: 7399, 2008
  73. Christlbauer; ''''; , PubMed Europe PMC
  74. Zheng; ''''; , PubMed Europe PMC
  75. Kerler; ''ALPHA-ACETYL-N-HETEROCYCLES IN THE MAILLARD REACTION''; , PubMed Europe PMC
  76. Kerler; ''ALPHA-ACETYL-N-HETEROCYCLES IN THE MAILLARD REACTION''; , PubMed Europe PMC
  77. ''Hypersensitivity of an Arabidopsis Sugar Signaling Mutant toward Exogenous Proline Application''; , PubMed Europe PMC
  78. Hofmann; ''Flavor Contribution and Formation of the Intense Roast-Smelling Odorants 2-Propionyl-1-pyrroline and 2-Propionyltetrahydropyridine in Maillard-Type Reactions"''; , PubMed Europe PMC
  79. Rodgman and Perfetti; ''''; , PubMed Europe PMC
  80. Shoji; ''Clustered Transcription Factor Genes Regulate Nicotine Biosynthesis in Tobacco''; , 2010 PubMed Europe PMC
  81. ISHIHARA A., MATSUDA F., MIYAGAWA H., WAKASA K.; ''METABOLOMICS FOR METABOLICALLY MANIPULATED PLANTS: EFFECTS OF TRYPTOPHAN OVERPRODUCTION''; , PubMed Europe PMC
  82. PATENT; ''NUCLEIC ACIDS THAT ENHANCE THE SYNTHESIS OF 2-ACETYL-l-PYRROLINE IN PLANTS AND FUNGI''; , PubMed Europe PMC
  83. ''''; , PubMed Europe PMC
  84. ''''; , PubMed Europe PMC
  85. ''''; , PubMed Europe PMC
  86. ''''; , PubMed Europe PMC
  87. ''''; , PubMed Europe PMC
  88. ''''; , PubMed Europe PMC
  89. Fitzgerald TL, Waters DL, Henry RJ; ''Betaine aldehyde dehydrogenase in plants.''; Plant Biol (Stuttg), 2009 PubMed Europe PMC
  90. ''''; , PubMed Europe PMC
  91. Hanzawa Y, Imai A, Michael AJ, Komeda Y, Takahashi T; ''''; , PubMed Europe PMC
  92. ''''; , PubMed Europe PMC
  93. Deuschle K, Funck D, Forlani G, Stransky H, Biehl A, Leister D, van der Graaff E, Kunze R, Frommer WB; ''''; , PubMed Europe PMC
  94. ''''; , PubMed Europe PMC
  95. ''''; , PubMed Europe PMC
  96. ''''; , PubMed Europe PMC
  97. ''''; , PubMed Europe PMC
  98. ''''; , PubMed Europe PMC
  99. ''''; , PubMed Europe PMC
  100. ''''; , PubMed Europe PMC
  101. ''''; , PubMed Europe PMC
  102. ''''; , PubMed Europe PMC
  103. Huang TC, Huang YW, Hung HJ, Ho CT, Wu ML; ''Delta1-pyrroline-5-carboxylic acid formed by proline dehydrogenase from the Bacillus subtilis ssp. natto expressed in Escherichia coli as a precursor for 2-acetyl-1-pyrroline''; , PubMed Europe PMC
  104. Park SJ, Cho YD; ''''; , PubMed Europe PMC
  105. ''''; , PubMed Europe PMC
  106. ''''; , PubMed Europe PMC
  107. ''''; , PubMed Europe PMC
  108. ''''; , PubMed Europe PMC
  109. ''''; , PubMed Europe PMC
  110. ''''; , PubMed Europe PMC

History

View all...
CompareRevisionActionTimeUserComment
105904view11:36, 16 August 2019MkutmonHMDB identifier normalization
102413view08:46, 23 December 2018EgonwCompleted a few references.
96603view10:55, 23 March 2018EgonwReplaced a secondary ChEBI identifier with a primary identifier.
96262view19:36, 2 March 2018EgonwReplaced a Wikipedia URL with the corresponding Wikidata ID.
94916view00:39, 13 October 2017Khanspersupdate in progress
92695view18:57, 28 June 2017Khansperscleanup
92691view18:41, 28 June 2017Khansperscleanup
92690view18:25, 28 June 2017Khanspersupdates to style
91901view20:44, 3 April 2017KhanspersModified description
91899view20:29, 3 April 2017KhanspersRemoved comment
89052view22:48, 18 August 2016AriuttaOntology Term : 'classic metabolic pathway' added !
89050view22:44, 18 August 2016AriuttaConsistent TextLabel for 2-acetyl-1-pyrroline. Annotate as CHEBI:67125.
89049view22:31, 18 August 2016AriuttaModified title
85617view09:47, 3 June 2016EgonwNumeric NCBI gene ID for the gene.
80415view17:57, 18 June 2015KhanspersModified title
80406view09:17, 16 June 2015Mkutmonremoved whitespaces from identifiers
79837view07:49, 18 April 2015EgonwFixed the PubChem-compound data source names, and looked up the CID for PubChem-substance identifiers.
79824view08:25, 17 April 2015EgonwFixed the PubChem-compound data source name.
79800view16:19, 16 April 2015Mkutmonfixed unconnected lines
79683view19:27, 4 April 2015AlexanderPicoModified title
79663view08:33, 2 April 2015EgonwUpdated a few 'PubChem' identifiers to be 'PubChem-compound' identifiers.
79662view08:14, 2 April 2015EgonwUpdated the 'Enzyme Nomenclature' data source name.
79661view08:13, 2 April 2015EgonwUpdated the 'KEGG Compound' data source name.
79660view06:00, 2 April 2015EgonwFixed the type of two metabolites.
79614view21:36, 27 March 2015CarlopozziNew pathway

External references

DataNodes

View all...
NameTypeDatabase referenceComment
2-oxopropanalMetabolite880 (PubChem-compound) this is the active sugar fragment in the formation of 2AP
trigonelline Metabolite535-83-1 (CAS)
1-deoxy-2,3-glucosoneMetabolite
1-deoxyosone fructoseMetabolite470-23-5 (CAS)
1-pyrroline-5-carboxylate dehydrogenase GeneProduct836373 (Entrez Gene) R00707
1-pyrrolineMetabolite79803 (PubChem-compound)
2-acetyl-1-pyrrolineMetaboliteCHEBI:67125 (ChEBI) 99583-29-6 CAS
4-amino-butyraldehydeMetaboliteC00555 (KEGG Compound)
Acetyl group
Apoptosis, stress-related metabolism, cell growth inhibitionPathway
ArginineMetabolite5231987 (PubChem-compound)
  • Not found in smoke
  • N storage form in plants
BADHGeneProductEC 1.2.1.8 (KEGG Genes)
CatalystGeneProduct3.5.3.11 (Enzyme Nomenclature)
ChlorophyllMetaboliteC05307 (KEGG Compound)
Cysteine/cystineMetabolite
Gamma Aminobutyric AcidMetaboliteQ210021 (Wikidata)
Glc/ProMetabolite
Glutamic-semialdehydeMetabolite193305 (PubChem-compound)
GlutamineMetabolite56-85-9 (CAS)
L-Glutamic acidMetaboliteHMDB0000148 (HMDB)
  • one of the major sources of free aa in burley
  • Present even in smoke
L-ProlineMetaboliteHMDB0000162 (HMDB)
  • Proline in burley: Sweet, caramelized, slightly ash like, rather flat Nutty/Toasted, Sweet, earthy. Proline in FC: Slightly phenolic, smokey, nutty/ pyrazine, meaty, slightly green/ vegetable, acidic Smoky, ashes like, toasted, earthy
  • Present even in Smoke (Schmeltz and Hoffman, 1977)
  • increase (anomaly) during curing for both FC and AC
  • More proline in green does not translate into more proline in cured (Bovet et al., 2010, Q2 report)
L-arginino-succinateMetaboliteC03406 (KEGG Compound)
L-ornithine Metabolite6992088 (PubChem-compound)
  • Present even in smoke
  • when ornithine was used in a thermal desorber, traces amounts of 2AP were formed
L-ornithine ammonia-lyase GeneProduct4.3.1.12 (Enzyme Nomenclature) R00671
MaillardR0013PMI
N-acetyl-L-glutamate 5-semialdehyde Metabolite192878 (PubChem-compound)
N-acetyl-L-glutamate synthaseGeneProduct2.3.1.1 (Enzyme Nomenclature) R00259
N-acetyl-L-glutamate-5-phosphateMetabolite440236 (PubChem-compound)
N-acetyl-L-ornithineMetabolite439232 (PubChem-compound)
N-acetyl-glutamateMetaboliteC00624 (KEGG Compound)
NOMetabolite10102-43-9 (CAS)
NicotinateMetaboliteC00253 (KEGG Compound)
NicotineMetabolite
Orn-δ-aminotransferase GeneProduct2.6.1.13 (Enzyme Nomenclature)
PIIGeneProduct
PROC1GeneProductAT5G14800 (Ensembl) R01248
Prolino+fructoseMetabolite
  • The addition of proline + fructose in Burley tobacco reduced typical Burley harshness and provided some sweetness, thereby confirming the evaluation made by F. Aramendy and S. Battram (see above). On the other hand, addition of proline + fructose in FC tobacco showed no significant difference at 95% confidence level.
  • • The addition of proline plus fructose or prolinofructose enhances nutty/roasted notes in distillation in both cut-filler and tobacco extrudate most likely due, based on GC-O analyses, to the formation of 2-acetyl-1-pyrroline (pop-corn) in the aerosol
PutrescineMetaboliteC00134 (KEGG Compound)
PyrolysisPathway
PyrroleMetabolite109-97-7 (CAS) pyrrole is not the major decomposition product of proline under smoking conditions
REDUCTASE GeneProduct1.2.1.38 (Enzyme Nomenclature) R03443
S-adenosylmethionine Metabolite24762165 (PubChem-compound)
SpermidineMetabolite6992097 (PubChem-compound) used in tobacco, in thermal desorbtion, in comb. with 2-oxopropanol
StreckerR0012PMI
acetylglutamate kinaseGeneProduct2.7.2.8 (Enzyme Nomenclature) R02649
acetylornithine deacetylaseGeneProduct3.5.1.16 (Enzyme Nomenclature)
  • R00669
  • R00669
acetylornithine transaminase GeneProduct2.6.1.11 (Enzyme Nomenclature)
  • Available also in tomato
  • R02283
adenosylmethionine decarboxylase GeneProduct
agmatineMetaboliteC00179 (KEGG Compound)
arg decarboxylaseGeneProduct4.1.1.19 (Enzyme Nomenclature)
arginaseGeneProduct3.5.3.1 (Enzyme Nomenclature) R02458
argininosuccinate lyase GeneProduct4.3.2.1 (Enzyme Nomenclature)
argininosuccinate synthase GeneProduct6.3.4.5 (Enzyme Nomenclature)
betaine aldehyde dehydrogenase BADHGeneProductC00555 (KEGG Compound) R02549
carbamoyl-P-synthaseGeneProduct6.3.5.5 (Enzyme Nomenclature)
carbamoyl-phosphate MetaboliteC00169 (KEGG Compound)
citrulline MetaboliteC00327 (KEGG Compound)
dehydrogenaseGeneProduct1.5.1.12 (Enzyme Nomenclature)
delta-1-Pyrroline-5-carboxylateMetaboliteC03912 (KEGG Compound)
dihiydro-diacetyl-formoinMetabolite
glucoseMetaboliteCHEBI:17234 (ChEBI)
glutamate N-acetyltransferase GeneProduct2.3.1.35 (Enzyme Nomenclature)
nicotinate N-methyltransferase GeneProduct2.1.1.7 (Enzyme Nomenclature)
nitric oxide synthase GeneProduct1.14.13.39 (Enzyme Nomenclature)
ornithine carbamoyltransferase GeneProduct2.1.3.3 (Enzyme Nomenclature)
ornithine decarboxylase GeneProduct4.1.1.17 (Enzyme Nomenclature) R00670
polyamine oxidase GeneProduct1.5.99.6 (Enzyme Nomenclature) R01915
proline dehydrogenase GeneProduct1.5.99.8 (Enzyme Nomenclature)
  • R01248
  • R01253 corresponding to 1.5.99.8
spermidine synthase GeneProduct2.5.1.16 (Enzyme Nomenclature)
  • R01151
  • R01155
  • R08714
  • R01920 sperimidine synthase
δ1-pyrroline-5-carboxylate synthetase GeneProduct1.5.1.12 (Enzyme Nomenclature)
  • NtPMIestA83C_CL2057Contig2
  • R00245

Annotated Interactions

No annotated interactions

Personal tools