Aromadendrin
Chemical compound
From Wikipedia, the free encyclopedia
Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.[1]
| |
 | |
| Names | |
|---|---|
| IUPAC name
(2R,3R)-3,4′,5,7-Tetrahydroxyflavan-4-one | |
| Systematic IUPAC name
(2R,3R)-3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | |
| Other names
Aromadendrin Dihydrokaempferol Aromadendrol (+)-Aromadendrin (+)-Dihydrokaempferol | |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.213.374 |
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C15H12O6 | |
| Molar mass | 288.255 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Biosynthesis
Flavonoid biosynthesis in plants uses a phenylpropanoid metabolic pathway in which the amino acid phenylalanine is converted to 4-coumaroyl-CoA. This is combined with three units of malonyl-CoA to yield a group of compounds called chalcones, which contain two phenyl rings.[2] In the main pathway, the enzymes chalcone synthase and chalcone isomerase produce (S)-naringenin which is the immediate precursor for aromadendrin.[3][4]
The enzyme flavanone 3-dioxygenase inserts a hydroxyl group into the dihydropyran ring:[5]
This alpha-ketoglutarate-dependent hydroxylase requires α-ketoglutaric acid, which is converted to succinic acid as a by-product.[6]
Metabolism
The enzyme dihydrokaempferol 4-reductase converts aromadendrin to leucopelargonidin, using nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.[7][8]
Aromadendrin is alternatively converted to taxifolin in other pathways leading to anthocyanidins and anthocyanins.[9]
Glycosides
(2R,3R)-trans-Aromadendrin-7-O-beta-D-glucopyranoside-6′′-(4′′′-hydroxy-2′′′-methylene butanoate) is an acylated glucoside of aromadendrin isolated from the stem bark of Afzelia bella[10] (Fabaceae).
Phellamurin is the 8-prenyl 7-glucoside derivative of aromadendrin.
Chemistry
(+)-Leucopelargonidin, can be synthesized from (+)-aromadendrin in the laboratory by sodium borohydride reduction.[11]
