Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

. It can be found in the wood of ''

Pinus sibirica ''Pinus sibirica'', or Siberian pine, in the family Pinaceae is a species of pine tree that occurs in Siberia from 58°E in the Ural Mountains east to 126°E in the Stanovoy Range in southern Sakha Republic, and from Igarka at 68°N in the l ...

''.

Metabolism

The enzyme dihydrokaempferol 4-reductase uses ''cis''-3,4-leucopelargonidin and NADP⁺ to produce (+)-aromadendrin, NADPH, and H⁺.

Glycosides

(2''R'',3''R'')-''trans''-Aromadendrin-7-''O''-''beta''-D-glucopyranoside-6-(4-hydroxy-2-methylene butanoate) is an acylated

glucoside A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. Th ...

of aromadendrin isolated from the stem bark of ''

Afzelia bella ''Afzelia'' is a genus of plants in family (biology), family Fabaceae. The thirteen species all are trees, native to tropical Africa or Asia. The genus name of ''Afzelia'' is in honour of Adam Afzelius (1750–1837), a Swedish botanist and an ap ...

'' (Fabaceae). Phellamurin is the 8- prenyl 7-

derivative of aromadendrin.

Chemistry

(+)-

Leucopelargonidin 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 th ...

, (2''R'',3''S'',4''R'')-3,4,5,7,4'-pentahydroxyflavan, can be synthesized from (+)-aromadendrin by

sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula (sometimes written as ). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodi ...

reduction.

References

External links

* {{Flavanonol Flavanonols Resorcinols