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Leucopelargonidin

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
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 ☒N
    Key: FSVMLWOLZHGCQX-SOUVJXGZSA-N ☒N
  • 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 °C [77 °F], 100 kPa).
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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]

(+)-Leucopelargonidin can be synthesized from (+)-aromadendrin by sodium borohydride reduction.[2]

Metabolism

Dihydrokaempferol 4-reductase uses cis-3,4-leucopelargonidin and NADP+ to produce (+)-aromadendrin, NADPH, and H+.

Leucoanthocyanidin reductase transforms cis-3,4-leucopelargonidin into afzelechin.

References

  1. ^ Leucopelargonidin on liberherbarum.com
  2. ^ Heller, Werner; Britsch, Lothar; Forkmann, Gert; Grisebach, Hans (1985). "Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br". Planta. 163 (2): 191–196. doi:10.1007/BF00393505. PMID 24249337. S2CID 20854538.


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