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Information on EC 2.4.1.236 - flavanone 7-O-glucoside 2''-O-beta-L-rhamnosyltransferase
for references in articles please use BRENDA:EC2.4.1.236Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
2.4.1.236 flavanone 7-O-glucoside 2''-O-beta-L-rhamnosyltransferaseIUBMB Comments
Acts on the 7-O-glucoside of naringenin and hesperetin, also the flavone 7-O-glucosides of luteolin and apigenin.
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Word Map
- 2.4.1.236
- flavonoid
-
bitter
- pummelo
-
orang
- glycosides
- flavones
- rhamnosyltransferases
-
taste
- grapefruit
-
mandarin
- naringin
-
flavor
-
rhamnosylation
- maxima
- glycosyltransferase
- lycopene
-
tasteless
- sinensis
-
non-bitter
- agriculture
- nutrition
- synthesis
- food industry
The expected taxonomic range for this enzyme is: Citrus
Reaction Schemes
Synonyms
cm1,2rhat, 1,2rhat, 1,2-rhamnosyltransferase, cit1,2rhat, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1,2-rhamnosyltransferase
1,2RhaT
Cm1,2RhaT
flavanone-7-O-glucose-1,2-rhamnosyltransferase
rhamnosyltransferase, uridine diphosphorhamnose-flavanone 7-O-glucoside 2''-O-
-
-
UDP-rhamnose flavanone-glucoside rhamnosyl-transferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-beta-L-rhamnose + a flavanone 7-O-beta-D-glucoside = UDP + a flavanone 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
UDP-beta-L-rhamnose + a flavanone 7-O-beta-D-glucoside = UDP + a flavanone 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
acts on the 7-O-glucoside of naringenin and hesperetin, also the flavone 7-O-glucosides of luteolin and apigenin
-
UDP-beta-L-rhamnose + a flavanone 7-O-beta-D-glucoside = UDP + a flavanone 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
UDP-L-rhamnose:flavanone-7-O-glucoside 2''-O-beta-L-rhamnosyltransferase
Acts on the 7-O-glucoside of naringenin and hesperetin, also the flavone 7-O-glucosides of luteolin and apigenin.
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CAS REGISTRY NUMBER
COMMENTARY
125752-89-8
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-beta-L-rhamnose + a flavanone 7-O-beta-D-glucoside
UDP + a flavanone 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
-
-
-
?
UDP-beta-L-rhamnose + naringenin-7-O-glucoside
UDP + naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
-
-
-
?
UDP-L-rhamnose + a flavanone 7-O-glucoside
UDP + a flavanone 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
UDP-L-rhamnose + apigenin 7-O-glucoside
UDP + apigenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
98% of the activity with hesperetin 7-O-glucoside as substrate, highly specific for UDP-rhamnose
-
-
?
UDP-L-rhamnose + diosmetin 7-O-glucoside
UDP + diosmetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
a flavone 7-O-glucoside
i.e. neodiosmin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
UDP-L-rhamnose + luteolin 7-O-glucoside
UDP + luteolin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
99% of the activity with hesperetin 7-O-glucoside as substrate, highly specific for UDP-rhamnose
-
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
UDP-L-rhamnose + a flavanone 7-O-glucoside
UDP + a flavanone 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
glucosylated flavanone is further rhamnosylated by a rhamnosyltransferase using UDP-rhamnose
-
-
?
UDP-L-rhamnose + a flavanone 7-O-glucoside
UDP + a flavanone 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
glucosylated flavanone is further rhamnosylated by a rhamnosyltransferase using UDP-rhamnose
-
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. neohesperidin
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. neohesperidin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
enzyme catalyzes the transfer of rhamnose from UDP-rhamnose to the C-2 hydroxyl group of glucose attached via C-7-O- of naringenin or hesperetin, lower activity than with naringenin 7-O-glucoside as substrate, highly specific for UDP-rhamnose
i.e. neohesperidin
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
a flavanone 7-O-glucoside
i.e. neohesperidin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. neohesperidin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. naringin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, endogenous substrate, flavonoid biosynthetic pathway
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, natural substrate
-
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, natural substrate, enzyme catalyzes the transfer of rhamnose from UDP-rhamnose to the C-2 hydroxyl group of glucose attached via C-7-O- of naringenin or hesperetin, best substrate, 141% of the activity with hesperetin 7-O-glucoside as substrate, highly specific for UDP-rhamnose
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
a flavanone 7-O-glucoside
i.e. naringin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
-
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, endogenous substrate, flavonoid biosynthetic pathway
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
the enzyme is involved in the flavonoid biosynthesis pathway in grapefruit
-
-
?
additional information
?
-
-
enzyme catalyzes the production of bitter flavanone-glucosides
-
-
?
additional information
?
-
-
not: flavonoid 5-O-glucosides or aglycones, naringenin, hesperetin, quercetin, UDP-glucose, UDP-galactose, UDP-glucoronic acid
-
-
?
additional information
?
-
-
the enzyyme specifically catalyzes rhamnosylation of flavanone-7-O-glucose and flavone-7-O-glucose substrates at position 2 of the glucose moiety
-
-
?
additional information
?
-
-
the enzyme also catalyzes the rhamnosylation of diosmetin 7-O-glucoside at position 2 of the glucose moiety to give neodiosmin, but Cm1,2RhaT is specific for flavonoid-7-O-glucosides and utilizes no flavonoid-3-O-glucosides
-
-
?
additional information
?
-
Cm1,2RhaT has glycosyl transfer activity toward UDP-xylose as well as UDP-rhamnose, it is a branch-forming rhamnosyltransferase, substrate specificity of the recombinant enzyme, overview. No activity with quercetin-3-O-glucoside
-
-
?
additional information
?
-
-
Cm1,2RhaT has glycosyl transfer activity toward UDP-xylose as well as UDP-rhamnose, it is a branch-forming rhamnosyltransferase, substrate specificity of the recombinant enzyme, overview. No activity with quercetin-3-O-glucoside
-
-
?
additional information
?
-
-
flavonoid-7-O-glucosides are the preferred substrate. The enzyme Cit1,2RhaT converts flavonoid-7-O-glucosides into bitter-tasting flavonoid-7-O-neohesperidoside
-
-
-
additional information
?
-
-
flavanone-7-O-glucosides are catalysed by 1,2-rhamnosyltransferase to form bitter flavanone-7-O-neohesperidosides, such as naringin, neohsperidin, neoeriocitrin and poncirin
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-L-rhamnose + diosmetin 7-O-glucoside
UDP + diosmetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
a flavone 7-O-glucoside
i.e. neodiosmin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + hesperetin 7-O-glucoside
UDP + hesperetin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. neohesperidin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
-
i.e. naringin, a bitter 7-O-neohesperidoside
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, endogenous substrate, flavonoid biosynthetic pathway
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, natural substrate
-
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
i.e. prunin, endogenous substrate, flavonoid biosynthetic pathway
i.e. naringin
-
?
UDP-L-rhamnose + naringenin 7-O-glucoside
UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
-
the enzyme is involved in the flavonoid biosynthesis pathway in grapefruit
-
-
?
additional information
?
-
-
enzyme catalyzes the production of bitter flavanone-glucosides
-
-
?
additional information
?
-
-
the enzyyme specifically catalyzes rhamnosylation of flavanone-7-O-glucose and flavone-7-O-glucose substrates at position 2 of the glucose moiety
-
-
?
additional information
?
-
-
flavanone-7-O-glucosides are catalysed by 1,2-rhamnosyltransferase to form bitter flavanone-7-O-neohesperidosides, such as naringin, neohsperidin, neoeriocitrin and poncirin
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
not inhibited by neohesperidin, hesperidin, EDTA, arbutin, nitrophenyl-beta-glucopyranoside, nitrophenyl-L-rhamnopyranoside
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
F1 population derived from Citrus reticulata x Poncirus trifoliata
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
expression is higher in mature fruits compared to immature fruits
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
additional information
-
flavonois spectrum and levels of Citrus sinensis varieties and tissue distribution, overview
metabolism
-
the enzyme is involved in the biosynthesis of flavonoid branched-chain glycosides in citrus, overview. 1,2RhaT is the key branch-forming enzyme directing biosynthesis of the bitter flavanone neohesperidoside compounds in bitter Citrus species
metabolism
-
the activity of the enzyme is directly linked to the accumulation of the bitter-tasting flavonoid-7-O-neohesperidoside
metabolism
-
the enzyme is involved in the flavonoid biosynthesis pathway in grapefruit
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). FLRT_CITMA
452
0
51236
Swiss-Prot
other Location (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
52000
52000
x * 52000, recombinant C-terminally His6-Myc-tagged enzyme, SDS-PAGE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 52000, recombinant C-terminally His6-Myc-tagged enzyme, SDS-PAGE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
production of naringin and narirutin from naringenin-7-O-glucoside using the engineered Schizosaccharomyces expressing Arabidopsis thaliana rhamnose synthase 2, AtRHM2, and glycosyltransferases Cm1,2RhaT from Citrus maxima or Cs1,6RhaT from Citrus sinensis as a whole-cell-biocatalyst, overview
additional information
-
production of naringin and narirutin from naringenin-7-O-glucoside using the engineered Schizosaccharomyces expressing Arabidopsis thaliana rhamnose synthase 2, AtRHM2, and glycosyltransferases Cm1,2RhaT from Citrus maxima or Cs1,6RhaT from Citrus sinensis as a whole-cell-biocatalyst, overview
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
1,2RhaT cloning and DNA and amino acid sequence determination and analysis, phylogenetic analysis, two native frameshift mutations render the enzyme from orange catalytically inactive
-
cloned into the binary vector PH7WG2D under the control of the CAMV-35S promoter and translationally fused to the green fluorescent protein reporter gene. The recombinant vector is then transferred into Agrobacterium tumefaciens
-
DNA and amino acid sequence determiation and analysis, phylogenetic analysis, recombinant expression of C-terminally His6-Myc-tagged enzyme in Nicotiana tabacum BY-2 cells
gene 1,2-Rhat, DN and amino acid sequence determination and analysis of in varieties Anliu and Honganliu sweet orange, sequence comparisons
-
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
-
the study provides the basis for potentially improving the taste in citrus fruit through manipulation of the network by knocking-out 1,2-rhamnosyltransferase or by enhancing the expression of flavonoid-7-O-di-glucosyltransferases using genetic transformation
food industry
-
the study provides the basis for potentially improving the taste in citrus fruit through manipulation of the network by knocking-out 1,2-rhamnosyltransferase or by enhancing the expression of flavonoid-7-O-di-glucosyltransferases using genetic transformation
nutrition
-
the isolation of the rhamnosyltransferase gene may enable its use in genetic engineering directed to modifying grapefruit bitterness
synthesis
metabolically engineered plant cell suspension cultures expressing recombinant Cm1,2RhaT can biotransform hesperetin, the hesperidin aglycone, into neohesperidin
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lewinsohn, E.; Britsch, L.; Mazur, Y.; Gressel, J.
Flavanone glycoside biosynthesis in Citrus. Chalcone synthase, UDP-glucose: flavanone-7-O-glucosyltransferase and -rhamnosyltransferase activities in cell-free extracts
Plant Physiol.
91
1323-1328
1989
Citrus maxima, Citrus x paradisi
brenda
Bar-Peled, M.; Lewinsohn, E.; Fluhr, R.; Gressel, J.
UDP-rhamnose:flavanone-7-O-glucoside-2''-O-rhamnosyltransferase. Purification and characterization of an enzyme catalyzing the production of bitter compounds in citrus
J. Biol. Chem.
266
20953-20959
1991
Citrus maxima
brenda
Frydman, A.; Weisshaus, O.; Huhman, D.V.; Sumner, L.W.; Bar-Peled, M.; Lewinsohn, E.; Fluhr, R.; Gressel, J.; Eyal, Y.
Metabolic engineering of plant cells for biotransformation of hesperedin into neohesperidin, a substrate for production of the low-calorie sweetener and flavor enhancer NHDC
J. Agric. Food Chem.
53
9708-9712
2005
Citrus maxima (Q8GVE3)
brenda
Frydman, A.; Liberman, R.; Huhman, D.V.; Carmeli-Weissberg, M.; Sapir-Mir, M.; Ophir, R.; W Sumner, L.; Eyal, Y.
The molecular and enzymatic basis of bitter/non-bitter flavor of citrus fruit: evolution of branch-forming rhamnosyltransferases under domestication
Plant J.
73
166-178
2013
Citrus maxima, Citrus sinensis, Citrus sinensis valencia, no activity in Citrus reticulata
brenda
Ohashi, T.; Hasegawa, Y.; Misaki, R.; Fujiyama, K.
Substrate preference of citrus naringenin rhamnosyltransferases and their application to flavonoid glycoside production in fission yeast
Appl. Microbiol. Biotechnol.
100
687-696
2016
Citrus maxima (A0A0P0YNP7), Citrus maxima
brenda
Chen, J.; Zhang, H.; Pang, Y.; Cheng, Y.; Deng, X.; Xu, J.
Comparative study of flavonoid production in lycopene-accumulated and blonde-flesh sweet oranges (Citrus sinensis) during fruit development
Food Chem.
184
238-246
2015
Citrus sinensis
brenda
Chaudhary, P.R.; Bang, H.; Jayaprakasha, G.K.; Patil, B.S.
Variation in key flavonoid biosynthetic enzymes and phytochemicals in Rio Red Grapefruit (Citrus paradisi Macf.) during fruit development
J. Agric. Food Chem.
64
9022-9032
2016
Citrus x paradisi
brenda
Chen, J.; Yuan, Z.; Zhang, H.; Li, W.; Shi, M.; Peng, Z.; Li, M.; Tian, J.; Deng, X.; Cheng, Y.; Deng, C.H.; Xie, Z.; Zeng, J.; Yao, J.L.; Xu, J.
Cit1,2RhaT and two novel CitdGlcTs participate in flavor-related flavonoid metabolism during citrus fruit development
J. Exp. Bot.
70
2759-2771
2019
Citrus reticulata x Citrus trifoliata
brenda
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