Leucopelargonidin
| Names | |
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| IUPAC name
(2R,3S,4S)-Flavan-3,4,4′,5,7-pentol
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| 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)
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| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
Infobox references
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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]
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]
Leucopelargonidin can also be synthesized from aromadendrin in the laboratory by sodium borohydride reduction.[4]
Metabolism
Leucoanthocyanidin reductase transforms leucopelargonidin into afzelechin.[5][6]
References
- ^ Leucopelargonidin on liberherbarum.com
- ^ Enzyme 1.1.1.219 at KEGG Pathway Database.
- ^ Heller W, Forkmann G, Britsch L, Grisebach H (1985). "Enzymatic reduction of (+)-dihydroflavonols to flavan-3,4-cis- diols with flower extracts from Matthiola incana and its role in anthocyanin biosynthesis". Planta. 165 (2): 284–287. Bibcode:1985Plant.165..284H. doi:10.1007/BF00395052. PMID 24241054. S2CID 29590896.
- ^ 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.
- ^ Enzyme 1.17.1.3 at KEGG Pathway Database.
- ^ Tanner, Gregory J.; Francki, Kathy T.; Abrahams, Sharon; Watson, John M.; Larkin, Philip J.; Ashton, Anthony R. (2003). "Proanthocyanidin Biosynthesis in Plants". Journal of Biological Chemistry. 278 (34): 31647–31656. doi:10.1074/jbc.M302783200. PMID 12788945.
External links