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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.213.374 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: PADQINQHPQKXNL-LSDHHAIUSA-N checkY
  • C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O
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).

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

Biosynthesis

Flavonoid biosynthesis in plants uses a phenylpropanoid metabolic pathway in which the amino acid phenylalanine is converted to 4-coumaroyl-CoA. This is combined with three units of malonyl-CoA to yield a group of compounds called chalcones, which contain two phenyl rings. In the main pathway, the enzymes chalcone synthase and chalcone isomerase produce (S)-naringenin which is the immediate precursor for aromadendrin.

The enzyme flavanone 3-dioxygenase inserts a hydroxyl group into the dihydropyran ring:

2D representation of the chemical structure of naringenin.
naringenin
+ α-ketoglutaric acid
 
 
O2
CO2
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of aromadendrin.
aromadendrin
+ succinic acid
 

This alpha-ketoglutarate-dependent hydroxylase requires α-ketoglutaric acid, which is converted to succinic acid as a by-product.

Metabolism

The enzyme dihydrokaempferol 4-reductase converts aromadendrin to leucopelargonidin, using nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.

2D representation of the chemical structure of aromadendrin .
aromadendrin
+ NADPH
 
 
H+
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
2D representation of the chemical structure of leucopelargonidin .
leucopelargonidin
+ NADP+
 

Aromadendrin is alternatively converted to taxifolin in other pathways leading to anthocyanidins and anthocyanins.

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 (Fabaceae).

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

Chemistry

(+)-Leucopelargonidin, can be synthesized from (+)-aromadendrin in the laboratory by sodium borohydride reduction.

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): 197–198. doi:10.1007/BF00568701.
  2. ↑ Ververidis Filippos, F; Trantas Emmanouil; Douglas Carl; Vollmer Guenter; Kretzschmar Georg; Panopoulos Nickolas (October 2007). "Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health". Biotechnology Journal. 2 (10): 1214–34. doi:10.1002/biot.200700084. PMID 17935117.
  3. ↑ Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, et al. (March 2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli". Journal of Agricultural and Food Chemistry. 65 (8): 1659–1668. Bibcode:2017JAFC...65.1659W. doi:10.1021/acs.jafc.6b05212. PMID 28168876.
  4. ↑ Moustafa E, Wong E (1967). "Purification and properties of chalcone-flavanone isomerase from soya bean seed". Phytochemistry. 6 (5): 625–632. Bibcode:1967PChem...6..625M. doi:10.1016/S0031-9422(00)86001-X.
  5. ↑ Forkmann, G.; Heller, W.; Grisebach, H. (1980). "Anthocyanin Biosynthesis in Flowers of Matthiola incana Flavanone 3-and Flavonoid 3′-Hydroxylases". Zeitschrift für Naturforschung C. 35 (9–10): 691–695. doi:10.1515/znc-1980-9-1004.
  6. ↑ Enzyme 1.14.11.9 at KEGG Pathway Database.
  7. ↑ Enzyme 1.1.1.219 at KEGG Pathway Database.
  8. ↑ Heller W, Forkmann G, Britsch L, Grisebach H (1985). "Enzymatic reduction of (+)-dihydroflavonols to flavan-3,4-cis- diols with flower extracts from Matthiola incana and its role in anthocyanin biosynthesis". Planta. 165 (2): 284–287. Bibcode:1985Plant.165..284H. doi:10.1007/BF00395052. PMID 24241054. S2CID 29590896.
  9. ↑ "Flavonoid Biosynthesis". ExplorEnz. Retrieved 2026-03-13.
  10. ↑ 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.
  11. ↑ 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.