Aromadendrin
 | |
| 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 | |
480-20-6  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:15401  |
| ChEMBL | ChEMBL9323 |
| ChemSpider | 109514 |
| ECHA InfoCard | 100.213.374 |
| PubChem | 122850 |
| |
| |
| 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). | |
| verify (what is ?) | |
| 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
- ↑ 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.
- ↑ Binutu, OA; Cordell, GA (2001). "Constituents of Afzelia bella stem bark". Phytochemistry. 56 (8): 827–30. doi:10.1016/S0031-9422(01)00006-1. PMID 11324912.
- ↑ 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. doi:10.1007/BF00393505.
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