Chalcone

Definition

noun, plural: chalcones

An organic compound that is naturally produced and used as an intermediate in the flavonoid biosynthesis


Supplement

Chalcones are aromatic ketones an enones that form the core of various biological compounds, e.g. chalconoids. Chalcones are produced by natural means but can also be produced synthetically. In its natural form, the chalcone is the structural backbone of chalconoids. Chalconoids (which sometimes are also called chalcones) have antimicrobial and antitumor properties. They were found to possess the ability to block voltage-dependent potassium channels.1

Chalcones are intermediates to the formation of the flavonoid (flavonoid biosynthesis) as well as in the Auwers synthesis of flavones. In fact, it is the first flavonoid-specific intermediate in flavonoid biosynthesis.2 It is isomerized to flavanone compound through the enzyme chalcone isomerase.3 Most of the chalcones are yellow compounds. Although they occur in different parts of the plant, chalcones are mostly found in flowers. They are often found in ferns, Acanthaceae, Asteraceae, Fabaceae, Gesneriaceae, Liliaceae, Oxalidaceae, and Scrophulariaceae.3


Also called:

  • Benzalacetophenone
  • Chalkone
  • Phenyl styryl ketone
  • β-phenylacrylophenone
  • ɣ-oxo-α
  • ɣ-diphenyl-α-propylene
  • α-phenyl-β-benzoylethylene

IUPAC name: 1,3-Diphenyl-2-propen-1-one

See also:

Reference(s):
1 Yarishkin, O. V., Ryu, H. W., Park, J. Y., Yang, M. S., Hong, S. G., and Park, K. H. (2008). "Sulfonate chalcone as new class voltage-dependent K+ channel blocker". Bioorganic & Medicinal Chemistry Letters 18 (1): 137–140.
2 Keung, W. (2002). Pueraria the genus Pueraria. London New York: Taylor and Francis.
3 Seigler, D. (1999). Plant Secondary Metabolism. Boston, MA: Springer US.


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