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Literature summary for 2.4.1.17 extracted from

  • Niemeyer, E.D.; Brodbelt, J.S.
    Regiospecificity of human UDP-glucuronosyltransferase isoforms in chalcone and flavanone glucuronidation determined by metal complexation and tandem mass spectrometry (2013), J. Nat. Prod., 76, 1121-1132.
    View publication on PubMedView publication on EuropePMC

Organism

Organism UniProt Comment Textmining
Homo sapiens
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Source Tissue

Source Tissue Comment Organism Textmining
commercial preparation nonhepatic UGT supersomes of 1A1, 1A3, 1A4, 1A6, 1A7, 1A8, 1A9, and 1A10 Homo sapiens
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information human UGT1A enzymes display unique regioselectivity for the site of glucuronidation and this selectivity is affected strongly by structural differences among the dihydroxychalcones. Several of the UGT1A isoforms show poor reactivity toward the chalcones including UGT1A4, 1A6, and 1A10. UGT1A9 promotes glucuronidation at the 2'-OH-position, and formation of the 2'-O-glucuronide. Several UGT isoforms promote the formation of the 4'-O-glucuronide, particularly UGT1A8, which produces the monoglucuronide in high yield is enhanced for dihydroxychalcones with hydroxy substituents on the A-ring. Although UGT1A8 reacts with 3,2'-dihydroxychalcone and 4,2'-dihydroxychalcone to form 2'-O-glucuronides, the presence of the B-ring hydroxy group at the 4'-position in both cardamonin and 2',4'-dihydroxychalcone renders the OH-2'-position inactive to glucuronidation with the 1A8 isoform. For UGT1A7, hydroxy substituents on the chalcone A-ring enhance the overall yield of glucuronide product and especially promote formation of the corresponding flavanone glucuronide. UGT1A3 strongly promotes glucuronidation at the OH-7 position of the flavanone A-ring in 7-hydroxyflavanone and alpinetin, but leads to much lower glucuronide product yields for flavanones with B-ring hydroxy groups such as 3'-hydroxyflavanone and 4'-hydroxyflavanone. While UGT1A1 catalyzes the formation of glucuronide products in relatively high yields for all of the flavanones studied, in general, glucuronide product formation is less for the flavanones with a B-ring hydroxy group compared to those with an A-ring hydroxy moiety. Isozyme substrate specificity with analysis of multiple product reactions with dihydroxychalcones, product anaysis, detailed overview Homo sapiens ?
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UDP-glucuronate + 2',4'-dihydroxychalcone glucuronidation at the OH-4' position by UGT1A1 and UGT1A10 isoforms, both UGT1A6 and 1A9 produced two chalcone monoglucuronides, the 4'-Oglucuronide and the 2'-O-glucuronide Homo sapiens UDP + 2'-hydroxychalcone 4'-O-beta-D-glucuronoside
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UDP-glucuronate + 2',4'-dihydroxychalcone glucuronidation at the OH-2' position with low activity by UGT1A7, UGT1A6, and UGT1A10 isoforms, and with high activity by isozyme UGT1A9. Both UGT1A6 and 1A9 produced two chalcone monoglucuronides, the 4'-Oglucuronide and the 2'-O-glucuronide Homo sapiens UDP + 4'-hydroxychalcone 2'-O-beta-D-glucuronoside
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UDP-glucuronate + 2'-hydroxychalcone glucuronidation at the OH-2' position by UGT1A9 isoform Homo sapiens UDP + chalcone 2'-O-beta-D-glucuronoside
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UDP-glucuronate + 3,2'-dihydroxychalcone glucuronidation at the OH-2' position by UGT1A8 isoform Homo sapiens UDP + 3-hydroxychalcone 2'-O-beta-D-glucuronoside
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UDP-glucuronate + 3,2'-dihydroxychalcone very low activity with isozyme UGT1A6 Homo sapiens UDP + 3-hydroxychalcone 2'-O-beta-D-glucuronoside
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UDP-glucuronate + 4,2'-dihydroxychalcone glucuronidation at the OH-2' position by UGT1A8, UGT1A1, and UGT1A3 isoforms. The A-ring OH-4 group promotes glucuronidation at the 2' position for the reaction of the exclusive substrate 4,2'-dihydroxychalcone of UGT1A1 and 1A3 Homo sapiens UDP + 4-hydroxychalcone 2'-O-beta-D-glucuronoside
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UDP-glucuronate + 7-hydroxyflavanone
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Homo sapiens UDP + flavanone 7-O-beta-D-glucuronoside
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UDP-glucuronate + alpinetin
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Homo sapiens UDP + alpinetin beta-D-glucuronoside
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UDP-glucuronate + cardamonin UGT1A9 is the only isoform to glucuronidate cardamonin at the OH-2' position, lower activity with isozyme UGT1A7 Homo sapiens UDP + cardamonin beta-D-glucuronoside
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Synonyms

Synonyms Comment Organism
UDP-glucuronosyltransferase
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Homo sapiens
UGT
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Homo sapiens