Leucopelargonidin

Chemical compound From Wikipedia, the free encyclopedia

Leucopelargonidin is a colorless chemical compound related to leucoanthocyanins. It can be found in Albizia lebbeck (East Indian walnut), in the fruit of Anacardium occidentale (Cashew), in the fruit of Areca catechu (Areca nut), in the fruit of Hydnocarpus wightianus (Hindi Chaulmoogra), in the rhizome of Rumex hymenosepalus (Arizona dock), in Zea mays (Corn) and in Ziziphus jujuba (Chinese date).[1]

Quick facts Names, Identifiers ...
Leucopelargonidin
Names
IUPAC name
(2R,3S,4S)-Flavan-3,4,4′,5,7-pentol
Systematic IUPAC name
(2R,3S,4S)-2-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
Other names
(+)-Leucopelargonidin
cis-3,4-Leucopelargonidin
Leucopelargonidine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C15H14O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,13-20H/t13-,14-,15+/m0/s1 checkY
    Key: FSVMLWOLZHGCQX-SOUVJXGZSA-N checkY
  • c1cc(ccc1[C@@H]2[C@H]([C@H](c3c(cc(cc3O2)O)O)O)O)O
Properties
C15H14O6
Molar mass 290.271 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Biosynthesis

In flavonoid biosynthesis in plants, the enzyme dihydrokaempferol 4-reductase converts aromadendrin to leucopelargonidin, using nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.[2][3]

 
 
H+
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
 

Leucopelargonidin can also be synthesized from aromadendrin in the laboratory by sodium borohydride reduction.[4]

Metabolism

Leucoanthocyanidin reductase transforms leucopelargonidin into afzelechin.[5][6]

+ NADPH
 
 
H+
H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
+ NADP+
 

References

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