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.
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).
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
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Natural monophenols |
- Benzenediols
- Benzenetriols
- Apiole
- Carnosol
- Carvacrol
- Dillapiole
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Polyphenols | |
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Flavonoids (C6-C3-C6) | |
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Flavonoids | Anthoxanthins | |
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Flavans | Flavan | |
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Flavan-3-ols (flavanols) |
- Catechin, Gallocatechol, et.c.
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Flavan-4-ols (flavanols) |
- Apiforol, Luteoforol, et.c.
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Flavan-3,4-diols |
- Leucocyanidin, Leucodelphinidin, et.c.
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Flavanones |
- Hesperidin
- Naringenin
- Eriodictyol
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Flavanonols |
- Taxifolin
- Aromadendrin, et.c.
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Anthocyanidins | 3-deoxyanthocyanidins |
- Cyanidin, Delphinidin, et.c.
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3-hydroxyanthocyanidin |
- Apigeninidin, Guibourtinidin, et.c.
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Aurones | |
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Chalcones | Chalcones |
- Butein, Isoliquiritigenin, et.c.
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Dihydrochalcone | |
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Miscellaneous | |
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Flavonoid biosynthesis |
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Flavonolignans | Silymarin |
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Lignans ((C6-C3)2) |
- Matairesinol
- Secoisolariciresinol
- Pinoresinol
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Stilbenoids (C6-C2-C6) |
- Resveratrol
- Pterostilbene
- Piceatannol
- Pinosylvin
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Curcuminoids | Curcumin |
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Tannins | |
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Hydrolysable tannins | Ellagitannins |
- Punicalagins
- Castalagins
- Vescalagins
- Castalins
- Casuarictins
- Grandinins
- Punicalins
- Roburin A
- Tellimagrandin IIs
- Terflavin B
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Gallotannins |
- Digalloyl glucose
- 1,3,6-Trigalloyl glucose
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Condensed tannins |
- Proanthocyanidins
- Polyflavonoid tannins
- Catechol-type tannins
- Pyrocatecollic type tannins
- Flavolans
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Phlorotannins |
- Eckol
- 8,8′-Bieckol
- 6,6'-Bieckol
- Dieckol
- Eckstolonol
- Diphlorethol
- Difucol
- Phlorofucofuroeckol A
- Tetrafucol A
- Trifucol
- Bifuhalol
- 7-Phloroeckol
- Phlorofucofuroeckol B
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Flavono-ellagitannins (complex tannins) |
- Epicutissimin A
- Acutissimin A
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Other Miscellaneous |
- Tannin sources
- Pseudo tannins
- Synthetic tannins
- Tannin uses
- Enological
- Drilling
- Ink
- Tanning
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Others | |
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Misc: | |
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Aromatic acids | Aromatic acids |
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Phenolic acids | Monohydroxybenzoic acids | Aglycones |
- 3-Hydroxybenzoic acid
- 4-Hydroxybenzoic acid
- Salicylic acid
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Glycosides |
- p-Hydroxybenzoic acid glucoside
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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
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Trihydroxybenzoic acids |
- Bergenin
- Chebulic acid
- Ethyl gallate
- Eudesmic acid
- Gallic acid
- Tannic acid
- Norbergenin
- Phloroglucinol carboxylic acid
- Syringic acid
- Theogallin
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Other phenolic acids | |
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Hydroxycinnamic acids |
- α-Cyano-4-hydroxycinnamic acid
- Caffeic acid
- Chicoric acid
- Cinnamic acid
- Chlorogenic acid
- Diferulic acids
- Coumaric acid
- Coumarin
- Ferulic acid
- Sinapinic acid
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Aromatic amino acids |
- phenylalanine
- tryptophan
- histidine
- tyrosine
- thyroxine
- 5-hydroxytryptophan
- L-DOPA
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Phenylethanoids |
- Tyrosol
- Hydroxytyrosol
- Oleocanthal
- Oleuropein
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Others |
- Capsaicin
- Gingerol
- Alkylresorcinols
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Misc: |
- Phenolic compounds
- Phlorotannins)
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Chalconoids and their glycosides |
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Chalconoids |
- Butein
- Isoliquiritigenin
- Methyl hydroxychalcone
- Okanin
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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
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Acylated chalconoids |
- Licochalcone A
- Sophoradin (prenylated)
- Tephrospinosin (3′,5′-diisopentenyl-2′,4′-dihydroxychalcone) (prenylated)
- Xanthohumol (prenylated)
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O-methylated chalconoids |
- Cardamomin
- Flavokawin B
- Okanin 3,4,3′,4′-tetramethyl ether
- Pashanone (2',6'-Dihydroxy-3',4'-dimethoxychalcone)
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Flavokavains |
- Flavokavain A
- Flavokavain B
- Flavokavain C
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Synthetic | |
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