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Chalconoid

From Wikipedia, the free encyclopedia
Natural phenols related to chalcone
Chalcone, the structural backbone of chalconoids

Chalconoids (Greek:χαλκόςkhalkós, "copper", due to its color), also known aschalcones, are naturalphenols derived fromchalcone. They form the central core for a variety of important biological compounds.

They showantibacterial,antifungal,antitumor andanti-inflammatory properties. Some chalconoids demonstrated the ability to block voltage-dependent potassium channels.[1] Chalcones are also naturalaromatase inhibitors.[2]

Chalcones are aromatic ketones with two phenyl rings that are also intermediates in the synthesis of many biological compounds. The closure of hydroxy chalcones causes theformation of the flavonoid structure.[3] Flavonoids are substances in theplant's secondary metabolism with an array of biological activities.

Chalconoids are also intermediating in theAuwers synthesis of flavones.

The formation ofdihydrochalcones removes theconjugation between the two ring systems (via theketone) when the double bond is abolished. This causes the visible color of the chalcones to disappear in their dihydrochalcone derivatives.[4]

Biosynthesis and metabolism

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Chalcone synthase is an enzyme responsible for the production of chalconoids in plants.Chalcone isomerase is responsible for their conversion into flavanones and other flavonoids.Naringenin-chalcone synthase usesmalonyl-CoA and4-coumaroyl-CoA to produceCoA,naringenin chalcone, and CO2. Inaurones, the chalcone-like structure closes into a 5-atom ring instead of the more typical 6-atom ring (C ring).

Related compounds

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References

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  1. ^Yarishkin, O. V.; Ryu, H. W.; Park, J. Y.; Yang, M. S.; Hong, S. G.; Park, K. H. (2008). "Sulfonate chalcone as new class voltage-dependent K+ channel blocker".Bioorganic & Medicinal Chemistry Letters.18 (1):137–140.doi:10.1016/j.bmcl.2007.10.114.PMID 18032041.
  2. ^Le Bail, Jean-Christophe; Pouget, Christelle; Fagnere, Catherine; Basly, Jean-Philippe; Chulia, Albert-Jose; Habrioux, Gerard (2001). "Chalcones are potent inhibitors of aromatase and 17β-hydroxysteroid dehydrogenase activities".Life Sciences.68 (7):751–61.doi:10.1016/S0024-3205(00)00974-7.PMID 11205867.
  3. ^Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04)."Chalcones: Versatile intermediates in heterocyclic synthesis".Journal of Heterocyclic Chemistry jhet.4617.doi:10.1002/jhet.4617.ISSN 0022-152X.S2CID 255212828.
  4. ^Pratter, Paul J. (1981)."Neohesperidin dihydrochalcone: an updated review on a naturally derived sweetener and flavor potentiator"(PDF).Perfumer & Flavorist.5:12–18.

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Types of phenolic compounds
Natural monophenols
Polyphenols
Types ofpolyphenols
Flavonoids
(C6-C3-C6)
Types offlavonoids
Flavonoids
Anthoxanthins
Flavones
Flavonols
Isoflavones
Neoflavonoids
Flavans
Flavan
Flavan-3-ols
(flavanols)
Flavan-4-ols
(flavanols)
Flavan-3,4-diols
Flavanones
Flavanonols
Anthocyanidins
3-deoxyanthocyanidins
3-hydroxyanthocyanidin
Aurones
Chalcones
Chalcones
Dihydrochalcone
Miscellaneous
Flavonolignans
Lignans
((C6-C3)2)
Stilbenoids
(C6-C2-C6)
Curcuminoids
Tannins
Types of naturaltannins
Hydrolysable tannins
Ellagitannins
Gallotannins
Condensed tannins
Phlorotannins
Flavono-ellagitannins
(complex tannins)
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Misc:
Aromatic acids
Phenolic acids
Monohydroxybenzoic acids
Aglycones
Glycosides
Dihydroxybenzoic acids
Trihydroxybenzoic acids
Other phenolic acids
Hydroxycinnamic acids
Aromatic amino acids
Phenylethanoids
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Misc:
Chalconoids and theirglycosides
Chalconoids
Chalconoidglycosides
Acylated chalconoids
O-methylated chalconoids
Flavokavains
Synthetic
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