Chemistry:Aromadendrin
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| Names | |
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| IUPAC name
(2R,3R)-3,4′,5,7-Tetrahydroxyflavan-4-one
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| 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 | |
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3D model (JSmol)
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| 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). | |
 verify (what is   ?)
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| Infobox references | |
Tracking categories (test):
Aromadendrin (aromodendrin 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′′′-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): 197–198. 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): 191–196. doi:10.1007/BF00393505. PMID 24249337.
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