Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.
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. In the main pathway, the enzymes chalcone synthase and chalcone isomerase produce (S)-naringenin which is the immediate precursor for aromadendrin.
The enzyme flavanone 3-dioxygenase inserts a hydroxyl group into the dihydropyran ring:
This alpha-ketoglutarate-dependent hydroxylase requires ñ-ketoglutaric acid, which is converted to succinic acid as a by-product.
The enzyme dihydrokaempferol 4-reductase converts aromadendrin to leucopelargonidin, using nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.
Aromadendrin is alternatively converted to taxifolin in other pathways leading to anthocyanidins and anthocyanins.
(2R,3R)-trans-Aromadendrin-7-O-beta-<small>D</small>-glucopyranoside-6-(4-hydroxy-2-methylene butanoate) is an acylated glucoside of aromadendrin isolated from the stem bark of Afzelia bella (Fabaceae).
Phellamurin is the 8-prenyl 7-glucoside derivative of aromadendrin.
(+)-Leucopelargonidin, can be synthesized from (+)-aromadendrin in the laboratory by sodium borohydride reduction.