Aromadendrin

Aromadendrin
Names
	IUPAC name (2R,3R)-3,4′,5,7-Tetrahydroxyflavan-4-one
	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
Identifiers
CAS Number	480-20-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15401 ;
ChEMBL	ChEMBL9323 ;
ChemSpider	109514 ;
ECHA InfoCard	100.213.374
KEGG	C00974 ;
PubChem CID	122850;
UNII	7YA4640575 ;
CompTox Dashboard (EPA)	DTXSID8075411 ;
	InChI InChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,14-18,20H/t14-,15+/m0/s1 Key: PADQINQHPQKXNL-LSDHHAIUSA-N ; InChI=1/C15H12O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,14-18,20H/t14-,15+/m0/s1 Key: PADQINQHPQKXNL-LSDHHAIUBO;
	SMILES C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O;
Properties
Chemical formula	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 ?) Infobox references

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.

External links

Media related to Aromadedrin at Wikimedia Commons

[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): 197–198. doi:10.1007/BF00568701.

[2] 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.

[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): 191–196. doi:10.1007/BF00393505. PMID 24249337.

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v t e Flavanonols and their glycosides
3-Hydroxyflavanones:	Ampelopsin (Dihydromyricetin) Aromadedrin (Dihydrokaempferol) Dihydrogossypetin Dihydromorin Fustin (Dihydrofisetin) Garbanzol Pinobanksin Taxifolin (Dihydroquercetin)
O-methylated flavanonols	Dihydrokaempferide
dihydroflavonol 3-O-glycosides	Lecontin (+)-fustin glucoside
Glycosides	Astilbin Chrysandroside A Chrysandroside B Engeletin Eucryphin Smitilbin (Isoastilbin B) Xeractinol
Acetylated glycosides	Phellamurin