Chemistry:Aromadendrin
Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.[1]
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.[2] In the main pathway, the enzymes chalcone synthase and chalcone isomerase produce (S)-naringenin which is the immediate precursor for aromadendrin.[3][4]
The enzyme flavanone 3-dioxygenase inserts a hydroxyl group into the dihydropyran ring:[5]
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This alpha-ketoglutarate-dependent hydroxylase requires α-ketoglutaric acid, which is converted to succinic acid as a by-product.[6]
Metabolism
The enzyme dihydrokaempferol 4-reductase converts aromadendrin to leucopelargonidin, using nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.[7][8]
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Aromadendrin is alternatively converted to taxifolin in other pathways leading to anthocyanidins and anthocyanins.[9]
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[10] (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.[11]
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.
- ↑ 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.
- ↑ "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. March 2017. doi:10.1021/acs.jafc.6b05212. PMID 28168876. Bibcode: 2017JAFC...65.1659W.
- ↑ "Purification and properties of chalcone-flavanone isomerase from soya bean seed". Phytochemistry 6 (5): 625–632. 1967. doi:10.1016/S0031-9422(00)86001-X. Bibcode: 1967PChem...6..625M.
- ↑ 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.
- ↑ Enzyme 1.14.11.9 at KEGG Pathway Database.
- ↑ Enzyme 1.1.1.219 at KEGG Pathway Database.
- ↑ "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. 1985. doi:10.1007/BF00395052. PMID 24241054. Bibcode: 1985Plant.165..284H.
- ↑ "Flavonoid Biosynthesis". https://www.enzyme-database.org/reaction/phenol/flavonoid.html.
- ↑ 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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