Naringenin chalcone
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| Preferred IUPAC name
2′,4,4′,6′-Tetrahydroxychalcone | |
| Other names
Chalconaringenin; Chalcononaringenin; Isosalipurpol
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| Properties | |
| C15H12O5 | |
| Molar mass | 272.256 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Naringenin chalcone[1] is a common chalconoid (or chalcone, not to be confused with the compound chalcone). It is synthesized from 4-coumaroyl-CoA and malonyl-CoA by chalcone synthase (CHS), a key enzyme in the phenylpropanoid pathway. Naringenin chalcone can spontaneously cyclize to naringenin (a flavanone). In plant cells, this process is catalyzed by chalcone isomerase.
Biosynthesis and metabolism
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 chalconoids, which contain two phenyl rings.[2] Naringenin chalcone is produced directly in this pathway by the enzyme chalcone synthase.[3]
It can cyclise spontaneously to naringenin but would provide racemic material. The enzyme chalcone isomerase constrains the reaction to give only the (S) isomer of the flavanone.[2][4]
Naringenin is then further transformed into naringin and other plant metabolites including anthocyanins.[5]
References
- ^ PubChem. "Naringenin chalcone". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-08-27.
- ^ a b 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.
- ^ 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.
- ^ 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.
- ^ Archetti, Marco; Döring, Thomas F.; Hagen, Snorre B.; et al. (2011). "Unravelling the evolution of autumn colours: an interdisciplinary approach". Trends in Ecology & Evolution. 24 (3): 166–73. doi:10.1016/j.tree.2008.10.006. PMID 19178979.