Chalconoids

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: χαλκός ''khalkós'', "

copper Copper is a chemical element with the symbol Cu (from la, cuprum) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pink ...

", due to its color), also known as ''chalcones'', are natural

phenols In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (— O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds are ...

related to

chalcone Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. Chemical properties Chalcones have two absorption maxima at ...

. They form the central core for a variety of important biological compounds. They show

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention ...

antifungal An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as ...

antitumor Cancer can be treated by surgery, chemotherapy, radiation therapy, hormonal therapy, targeted therapy (including immunotherapy such as monoclonal antibody therapy) and synthetic lethality, most commonly as a series of separate treatments ...

and

anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as o ...

properties. Some chalconoids demonstrated the ability to block voltage-dependent potassium channels. Chalcones are also natural

aromatase inhibitor Aromatase inhibitors (AIs) are a class of drugs used in the treatment of breast cancer in postmenopausal women and in men, and gynecomastia in men. They may also be used off-label to reduce estrogen conversion when supplementing testosterone ex ...

s. Chalcones are aromatic ketones with two phenyl rings that are also intermediates in the synthesis of many biological compounds. The closure of hydroxychalcones causes the formation of the flavonoid structure. Flavonoids are substances in the

plant secondary metabolism Secondary metabolism produces a large number of specialized compounds (estimated 200,000) that do not aid in the growth and development of plants but are required for the plant to survive in its environment. Secondary metabolism is connected to ...

with an array of biological activities. Chalconoids are also intermediates in the

Auwers synthesis The Auwers synthesis is a series of organic reactions forming a flavonol from a coumarone. This reaction was first reported by Karl von Auwers in 1908.K. v. Auwers, E. Auffenberg, "Über Cumaranone und Hydrindone", '' Ber. Dtsch. Chem. Ges.'', 52, ...

of flavones.

Chemical properties

Biosynthesis and metabolism

Chalcone synthase Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, a ...

is an enzyme responsible for the production of chalconoids in plants.

Chalcone isomerase In enzymology, a chalcone isomerase () is an enzyme that catalyzes the chemical reaction :a chalcone \rightleftharpoons a flavanone Hence, this enzyme has one substrate, a chalcone, and one product, a flavanone. This enzyme belongs to the fa ...

is responsible for their conversion into flavanones and other flavonoids.

Naringenin-chalcone synthase Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, ...

uses

malonyl-CoA Malonyl-CoA is a coenzyme A derivative of malonic acid. Functions It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis. Fatty acid biosynthesis Malonyl-CoA provides 2-carbon units to fatty acids and com ...

and

4-coumaroyl-CoA Coumaroyl-coenzyme A is the thioester of coenzyme-A and coumaric acid. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include lignols (precursors to lignin and ligno ...

to produce

CoA Coa may refer to: Places * Coa, County Fermanagh, a rural community in County Fermanagh, Northern Ireland * Côa River, a tributary of the Douro, Portugal ** Battle of Coa, part of the Peninsular War period of the Napoleonic Wars ** Côa Valley ...

naringenin chalcone Naringenin chalcone 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 ...

, and CO₂.
In

aurones An aurone is a heterocyclic chemical compound which is a type of flavonoid. There are two isomers of the molecule, with (''E'')- and (''Z'')-configurations. The molecule contains a benzofuran element associated with a benzylidene linked in pos ...

, the chalcone-like structure closes into a 5-atom ring instead of the more typical 6-atom ring (C ring).

Related compounds

Dihydrochalcone Dihydrochalcone (DHC) is the organic compound with the formula C6H5C(O)(CH2)2C6H5. It is the reduced derivative of chalcone (C6H5C(O)(CH)2C6H5). It is white solid that is soluble in many organic solvents. Dihydrochalcone per se is often minor sig ...

References

External links

* {{chalconoid