Aromadendrin

Aromadedrin
Names
IUPAC name
(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Other names
Aromadedrin
Dihydrokaempferol
Aromadendrol
(+)-Aromadendrin
(+)-Dihydrokaempferol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.213.374
Properties
C15H12O6
Molar mass 288.26 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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Infobox references

Aromadendrin (aromodedrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.[1]

Metabolism

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

Glycosides

(2R,3R)-trans-Aromadendrin-7-O-beta-D-glucopyranoside-6′′-(4′′&prime-hydroxy-2′′′-methylene butanoate) is an acylated glucoside of aromadendrin isolated from the stem bark of Afzelia bella[2] (Fabaceae).

Phellamurin is the 8-prenyl 7-glucoside derivative of aromadendrin.

Chemistry

(+)-Leucopelargonidin, (2R,3S,4R)-3,4,5,7,4-pentahydroxyflavan, can be synthesized from (+)-aromadendrin by sodium borohydride reduction.[3]

References

  1. ↑ V. I. Lutskii, A. S. Gromova and N. A. Tyukavkina (1971). "Aromadendrin, apigenin, and kaempferol from the wood of Pinus sibirica". Chemistry of Natural Compounds. 7 (2): 197. doi:10.1007/BF00568701.
  2. ↑ Binutu, OA; Cordell, GA (2001). "Constituents of Afzelia bella stem bark". Phytochemistry. 56 (8): 827–30. PMID 11324912. doi:10.1016/S0031-9422(01)00006-1.
  3. ↑ 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. PMID 24249337. doi:10.1007/BF00393505.
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