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Chalconoid
Chalconoids Greek: χαλκός ''khalkós'', "copper", due to its color), also known as ''chalcones'', are natural phenols related to 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. Chalcones are also natural aromatase inhibitors. 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 with an array of biological activities. Chalconoids are also intermediates in the Auwers synthesis of flavones. Chemical properties Biosynthesis and metabolism Chalcone synthase is an enzyme responsible for the production of chalconoids in plants. Chalcone isomerase is resp ...
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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 primary metabolism by using building blocks and biosynthetic enzymes derived from primary metabolism. Primary metabolism governs all basic physiological processes that allow a plant to grow and set seeds, by translating the genetic code into proteins, carbohydrates, and amino acids. Specialized compounds from secondary metabolism are essential for communicating with other organisms in mutualistic (e.g. attraction of beneficial organisms such as pollinators) or antagonistic interactions (e.g. deterrent against herbivores and pathogens). They further assist in coping with abiotic stress such as increased UV-radiation. The broad functional spectrum of specialized metabolism is still not fully understood. In any case, a good balance between ...
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Flavonoid Biosynthesis
Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics. Flavanoids can possess chiral carbons. Methods of analysis should take this element into account especially regarding bioactivity or enzyme stereospecificity. Enzymes The biosynthesis of flavonoids involves several enzymes. * Anthocyanidin reductase * Chalcone isomera ...
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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 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 commi ... by chalcone synthase (CHS), a key enzyme in the phenylpropanoid pathway. Naringenin chalcone can spontaneously cyclize to naringenin (a flavanone). In plant cells, this process is catalyzed by chalcone isomerase. References Chalconoids {{organic-compound-stub ...
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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, a class of organic compounds found mainly in plants as natural defense mechanisms and as synthetic intermediates. CHS was the first type III PKS to be discovered. It is the first committed enzyme in flavonoid biosynthesis. The enzyme catalyzes the conversion of 4-coumaroyl-CoA and malonyl-CoA to naringenin chalcone. Function CHS catalysis serves as the initial step for flavonoid biosynthesis. Flavonoids are important plant secondary metabolites that serve various functions in higher plants. These include pigmentation, UV protection, fertility, antifungal defense and the recruitment of nitrogen-fixing bacteria. CHS is believed to act as a central hub for the enzymes involved in the flavonoid pathway. Studies have shown that these enzym ...
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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 family of isomerases, specifically the class of intramolecular lyases. The systematic name of this enzyme class is flavanone lyase (decyclizing). This enzyme is also called chalcone-flavanone isomerase. This enzyme participates in flavonoid biosynthesis. The ''Petunia hybrida'' (Petunia) genome contains two genes In biology, the word gene (from , ; "... Wilhelm Johannsen coined the word gene to describe the Mendelian units of heredity..." meaning ''generation'' or ''birth'' or ''gender'') can have several different meanings. The Mendelian gene is a b ... coding for very similar enzymes, ChiA and ChiB, but only the first seems to encode a functional chalcone isomerase. Structural studies As of late 2007, 7 structures have been sol ...
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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 class of organic compounds found mainly in plants as natural defense mechanisms and as synthetic intermediates. CHS was the first type III PKS to be discovered. It is the first committed enzyme in flavonoid biosynthesis. The enzyme catalyzes the conversion of 4-coumaroyl-CoA and malonyl-CoA to naringenin chalcone. Function CHS catalysis serves as the initial step for flavonoid biosynthesis. Flavonoids are important plant secondary metabolites that serve various functions in higher plants. These include pigmentation, UV protection, fertility, antifungal defense and the recruitment of nitrogen-fixing bacteria. CHS is believed to act as a central hub for the enzymes involved in the flavonoid pathway. Studies have shown that these enzymes in ...
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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 280 nm and 340 nm. Synthesis Chalcone is usually prepared by an aldol condensation between benzaldehyde and acetophenone. : This reaction, which can be carried out without any solvent, is so reliable that it is used in as an example of green chemistry in undergraduate education. Biosynthesis Chalcones and chalconoids are synthesized in plants as secondary metabolites. The enzyme chalcone synthase, a type III polyketide synthase Polyketides are a class of natural products derived from a precursor molecule consisting of a chain of alternating ketone (or reduced forms of a ketone) and methylene groups: (-CO-CH2-). First studied in the early 20th century, discovery, biosynth ..., is responsible for the biosynthesis of thes ...
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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 (e.g. chemotherapy before surgery). The choice of therapy depends upon the location and grade of the tumor and the stage of the disease, as well as the general state of the patient (performance status). Cancer genome sequencing helps in determining which cancer the patient exactly has for determining the best therapy for the cancer. A number of experimental cancer treatments are also under development. Under current estimates, two in five people will have cancer at some point in their lifetime. Complete removal of the cancer without damage to the rest of the body (that is, achieving cure with near-zero adverse effects) is the ideal, if rarely achieved, goal of treatment and is often the goal in practice. Sometimes this can be accomplished by ...
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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 opposed to opioids, which affect the central nervous system to block pain signaling to the brain. Nonsteroidal anti-inflammatory drugs Nonsteroidal anti-inflammatory drugs (NSAIDs) alleviate pain by counteracting the cyclooxygenase (COX) enzyme. On its own, COX enzyme synthesizes prostaglandins, creating inflammation. In whole, the NSAIDs prevent the prostaglandins from ever being synthesized, reducing or eliminating the inflammation and resulting pain. Some common examples of NSAIDs are aspirin, ibuprofen, and naproxen. The newer specific COX-inhibitors are not classified together with the traditional NSAIDs, even though they presumably share the same mode of action. On the other hand, there are analgesics that are commonly associa ...
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Aromatase Inhibitor
Aromatase inhibitors (AIs) are a class of medication, drugs used in the treatment of breast cancer in menopause, postmenopausal women and in men, and gynecomastia in men. They may also be used off-label to reduce estrogen conversion when supplementing testosterone exogenously. They may also be used for chemoprevention in women at high risk for breast cancer. Aromatase is the enzyme that catalyzes a key aromatization step in the synthesis of estrogen. It converts the Alpha-beta Unsaturated carbonyl compounds, enone ring of androgen precursors such as testosterone, to a phenol, completing the synthesis of estrogen. As such, AIs are estrogen synthesis inhibitors. Because hormone-positive breast and ovarian cancers are dependent on estrogen for growth, AIs are taken to either block the production of estrogen or block the action of estrogen on receptors. Medical uses Cancer In contrast to premenopausal women, in whom most of the estrogen is produced in the ovary, ovaries, in postmeno ...
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Antifungal Drug
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 cryptococcal meningitis, and others. Such drugs are usually yes obtained by a doctor's prescription, but a few are available over the counter (OTC). Types of antifungal There are two types of antifungals: local and systemic. Local antifungals are usually administered topically or vaginally, depending on the condition being treated. Systemic antifungals are administered orally or intravenously. Of the clinically employed azole antifungals, only a handful are used systemically. These include ketoconazole, itraconazole, fluconazole, fosfluconazole, voriconazole, posaconazole, and isavuconazole. Examples of non-azole systemic antifungals include griseofulvin and terbinafine. Classes Polyenes A polyene is a molecule with multipl ...
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