Ensiklopedia Dunia

From Wikipedia, the free encyclopedia

(Redirected from Chalcones)

Chalcone, the structural backbone of chalconoids

Chalconoids (Greek: χαλκός khalkós, "copper", due to its color), also known as chalcones, are natural phenols derived from chalcone. They form the central core for a variety of important biological compounds.

They show antibacterial, antifungal, antitumor and anti-inflammatory properties. Some chalconoids demonstrated the ability to block voltage-dependent potassium channels.^[1] Chalcones are also natural aromatase 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 the formation of the flavonoid structure.^[3] Flavonoids are substances in the plant's secondary metabolism with an array of biological activities.

Chalconoids are also intermediating in the Auwers synthesis of flavones.

Biosynthesis and metabolism

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 uses malonyl-CoA and 4-coumaroyl-CoA to produce CoA, naringenin chalcone, and CO₂.
In aurones, the chalcone-like structure closes into a 5-atom ring instead of the more typical 6-atom ring (C ring).

Related compounds

Dihydrochalcones

References

^ 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.
^ 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.
^ 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.

External links

"Chalcones". Reference.MD. Archived from the original on 2020-09-25. Retrieved 2011-04-30.

Types of phenolic compounds

Natural monophenols

Polyphenols

Types of polyphenols

Flavonoids
(C6-C3-C6)

Types of flavonoids

Flavonoids

Anthoxanthins

Flavones	Apigenin, Chrysin, et.c.
Flavonols	Quercetin, Kaempferol, et.c.
Isoflavones	Daidzein, Genistein, Orobol et.c.
Neoflavonoids	Dalbergichromene

Flavans

Flavan	Luteoliflavan
Flavan-3-ols (flavanols)	Catechin, Gallocatechol, et.c.
Flavan-4-ols (flavanols)	Apiforol, Luteoforol, et.c.
Flavan-3,4-diols	Leucocyanidin, Leucodelphinidin, et.c.
Flavanones	Hesperidin Naringenin Eriodictyol
Flavanonols	Taxifolin Aromadendrin, et.c.

Anthocyanidins

3-deoxyanthocyanidins	Cyanidin, Delphinidin, et.c.
3-hydroxyanthocyanidin	Apigeninidin, Guibourtinidin, et.c.

Aurones

Chalcones

Chalcones	Butein, Isoliquiritigenin, et.c.
Dihydrochalcone	Phloretin

Miscellaneous

Flavonoid biosynthesis

Flavonolignans

Silymarin

Lignans
((C6-C3)₂)

Stilbenoids
(C6-C2-C6)

Curcuminoids

Curcumin

Tannins

Types of natural tannins

Hydrolysable tannins

Ellagitannins	Punicalagins Castalagins Vescalagins Castalins Casuarictins Grandinins Punicalins Roburin A Tellimagrandin IIs Terflavin B
Gallotannins	Digalloyl glucose 1,3,6-Trigalloyl glucose

Condensed tannins

Phlorotannins

Flavono-ellagitannins
(complex tannins)

Other Miscellaneous

Tannin sources
Pseudo tannins
Synthetic tannins
Tannin uses
- Enological
- Drilling
- Ink
- Tanning

Others

Misc:

Polyphenols

Aromatic acids

Phenolic acids

Monohydroxybenzoic acids

Aglycones	3-Hydroxybenzoic acid 4-Hydroxybenzoic acid Salicylic acid
Glycosides	p-Hydroxybenzoic acid glucoside

Dihydroxybenzoic acids

2,3-Dihydroxybenzoic acid (Hypogallic acid)
2,4-Dihydroxybenzoic acid
2,6-Dihydroxybenzoic acid
3,5-Dihydroxybenzoic acid
Ethyl protocatechuate
Gentisic acid
Homogentisic acid
Orsellinic acid
Protocatechuic acid

Trihydroxybenzoic acids

Other phenolic acids

Hydroxycinnamic acids

Aromatic amino acids

Phenylethanoids

Others

Misc:

v t e Chalconoids and their glycosides
Chalconoids	Butein Isoliquiritigenin Methyl hydroxychalcone Okanin
Chalconoid glycosides	Carthamin Marein okanin 3,4,3′-trimethyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside monoacetate Okanin 3,4-dimethyl ether 4′-glucoside
Acylated chalconoids	Licochalcone A Sophoradin (prenylated) Tephrospinosin (3′,5′-diisopentenyl-2′,4′-dihydroxychalcone) (prenylated) Xanthohumol (prenylated)
O-methylated chalconoids	Cardamomin Flavokawin B Okanin 3,4,3′,4′-tetramethyl ether Pashanone (2',6'-Dihydroxy-3',4'-dimethoxychalcone)
Flavokavains	Flavokavain A Flavokavain B Flavokavain C
Synthetic	Sofalcone

Category:

Chalconoids

Hidden categories: