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Bergamottin
Bergamottin (5-geranoxypsoralen) is a natural furanocoumarin found in the pulp of pomelos and grapefruits. It is also found in the peel and pulp of the bergamot orange, from which it was first isolated and from which its name is derived. Chemistry Bergamottin and dihydroxybergamottin are linear furanocoumarins functionalized with side chains derived from geraniol. They are inhibitors of some isoforms of the cytochrome P450 enzyme, in particular CYP3A4. This prevents oxidative metabolism of certain drugs by the enzyme, resulting in an elevated concentration of drug in the bloodstream. Under normal circumstances, the grapefruit juice effect is considered to be a negative interaction, and patients are often warned not to consume grapefruit or its juice when taking medication. However, some current research is focused on the potential benefits of cytochrome P450 inhibition. Bergamottin, dihydroxybergamottin, or synthetic analogs may be developed as drugs that are targeted to i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bergamottin Biosynthesis
Bergamottin (5-geranoxypsoralen) is a natural furanocoumarin found in the pulp of pomelos and grapefruits. It is also found in the peel and pulp of the bergamot orange, from which it was first isolated and from which its name is derived. Chemistry Bergamottin and dihydroxybergamottin are linear furanocoumarins functionalized with side chains derived from geraniol. They are inhibitors of some isoforms of the cytochrome P450 enzyme, in particular CYP3A4. This prevents oxidative metabolism of certain drugs by the enzyme, resulting in an elevated concentration of drug in the bloodstream. Under normal circumstances, the grapefruit juice effect is considered to be a negative interaction, and patients are often warned not to consume grapefruit or its juice when taking medication. However, some current research is focused on the potential benefits of cytochrome P450 inhibition. Bergamottin, dihydroxybergamottin, or synthetic analogs may be developed as drugs that are targeted to i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Furanocoumarin
The furanocoumarins, or furocoumarins, are a class of organic chemical compounds produced by a variety of plants. Most of the plant species found to contain furanocoumarins belong to a handful of plant families. The families Apiaceae and Rutaceae include the largest numbers of plant species that contain furanocoumarins. The families Moraceae and Fabaceae include a few widely distributed plant species that contain furanocoumarins. Generally furanocoumarins are most abundant in plants that have flowered and in ripe seeds and fruits. (An exception is the common fig where furanocoumarins are found chiefly in the milky sap of the leaves and shoots but not the fruits. Cited in McGovern and Barkley 2000, section&nbsPhytophotodermatitis) During the early stages of plant growth, their presence is not easily detected. Structure The chemical structure of furanocoumarins consists of a furan ring fused with a coumarin. The furan ring may be fused in various ways producing several differen ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Furanocoumarins
The furanocoumarins, or furocoumarins, are a class of organic chemical compounds produced by a variety of plants. Most of the plant species found to contain furanocoumarins belong to a handful of plant families. The families Apiaceae and Rutaceae include the largest numbers of plant species that contain furanocoumarins. The families Moraceae and Fabaceae include a few widely distributed plant species that contain furanocoumarins. Generally furanocoumarins are most abundant in plants that have flowered and in ripe seeds and fruits. (An exception is the common fig where furanocoumarins are found chiefly in the milky sap of the leaves and shoots but not the fruits. Cited in McGovern and Barkley 2000, section&nbsPhytophotodermatitis) During the early stages of plant growth, their presence is not easily detected. Structure The chemical structure of furanocoumarins consists of a furan ring fused with a coumarin. The furan ring may be fused in various ways producing several different ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bergamot Orange
''Citrus bergamia'', the bergamot orange (pronounced ), is a fragrant citrus fruit the size of an orange, with a yellow or green color similar to a lime, depending on ripeness. Genetic research into the ancestral origins of extant citrus cultivars found bergamot orange to be a probable hybrid of lemon and bitter orange. Extracts have been used as an aromatic ingredient in food, tea, snus, perfumes, and cosmetics. Use on the skin can increase photosensitivity, resulting in greater damage from sun exposure. Etymology The word bergamot is derived from the Italian word , derived either from the Italian town of Bergamo or Ottoman Turkish ("prince's pear"). Description ''Citrus bergamia'' is a small tree that blossoms during the winter. The juice tastes less sour than lemon, but more bitter than grapefruit. Phytochemicals Bergamot fruit or oil contains flavonoids, such as neoeriocitrin, naringin, neohesperidin, ponceritin, melitidin, mitrocin, miriflin, brutieridin, and berg ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
CYP3A4 Inhibitors
Cytochrome P450 3A4 (abbreviated CYP3A4) () is an important enzyme in the body, mainly found in the liver and in the intestine. It oxidizes small foreign organic molecules (xenobiotics), such as toxins or drugs, so that they can be removed from the body. It is highly homologous to CYP3A5, another important CYP3A enzyme. While many drugs are deactivated by CYP3A4, there are also some drugs which are ''activated'' by the enzyme. Some substances, such as some drugs and furanocoumarins present in grapefruit juice, interfere with the action of CYP3A4. These substances will therefore either amplify or weaken the action of those drugs that are modified by CYP3A4. CYP3A4 is a member of the cytochrome P450 family of oxidizing enzymes. Several other members of this family are also involved in drug metabolism, but CYP3A4 is the most common and the most versatile one. Like all members of this family, it is a hemoprotein, i.e. a protein containing a heme group with an iron atom. In humans, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grapefruit
The grapefruit (''Citrus'' × ''paradisi'') is a subtropical citrus tree known for its relatively large, sour to semi-sweet, somewhat bitter fruit. The interior flesh is segmented and varies in color from pale yellow to dark pink. Grapefruit is a citrus hybrid originating in Barbados. It is an accidental cross between the sweet orange (''C. sinensis'') and the pomelo or shaddock (''C. maxima''), both of which were introduced from Asia in the 17th century. It has also been called the '' forbidden fruit''. In the past it was referred to as the ''pomelo'', but that term is now mostly used as the common name for ''Citrus maxima''. In 2019, world production of grapefruits (combined with pomelos) was 9.3 million tonnes, of which 53% was in China. Other significant producers include Vietnam, United States and Mexico. Description The evergreen grapefruit trees usually grow to around tall, although they may reach . The leaves are long (up to ), thin, glossy, and dark green. They ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cytochrome P450
Cytochromes P450 (CYPs) are a superfamily of enzymes containing heme as a cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are important for the clearance of various compounds, as well as for hormone synthesis and breakdown. In 1963, Estabrook, Cooper, and Rosenthal described the role of CYP as a catalyst in steroid hormone synthesis and drug metabolism. In plants, these proteins are important for the biosynthesis of defensive compounds, fatty acids, and hormones. CYP enzymes have been identified in all kingdoms of life: animals, plants, fungi, protists, bacteria, and archaea, as well as in viruses. However, they are not omnipresent; for example, they have not been found in ''Escherichia coli''. , more than 300,000 distinct CYP proteins are known. CYPs are, in general, the terminal oxidase enzymes in electron transfer chains, broadly categorized as P450-containing systems. The term "P450" is deriv ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
CYP3A4
Cytochrome P450 3A4 (abbreviated CYP3A4) () is an important enzyme in the body, mainly found in the liver and in the intestine. It oxidizes small foreign organic molecules ( xenobiotics), such as toxins or drugs, so that they can be removed from the body. It is highly homologous to CYP3A5, another important CYP3A enzyme. While many drugs are deactivated by CYP3A4, there are also some drugs which are ''activated'' by the enzyme. Some substances, such as some drugs and furanocoumarins present in grapefruit juice, interfere with the action of CYP3A4. These substances will therefore either amplify or weaken the action of those drugs that are modified by CYP3A4. CYP3A4 is a member of the cytochrome P450 family of oxidizing enzymes. Several other members of this family are also involved in drug metabolism, but CYP3A4 is the most common and the most versatile one. Like all members of this family, it is a hemoprotein, i.e. a protein containing a heme group with an iron atom. In huma ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dimethylallyl Pyrophosphate
Dimethylallyl pyrophosphate (DMAPP; or alternatively, dimethylallyl diphosphate (DMADP); also isoprenyl pyrophosphate) is an isoprenoid precursor. It is a product of both the mevalonate pathway and the MEP pathway of isoprenoid precursor biosynthesis. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. The enzyme isopentenyl pyrophosphate isomerase catalyzes isomerization between DMAPP and IPP. In the mevalonate pathway DMAPP is synthesised from mevalonic acid. In contrast, DMAPP is synthesised from HMBPP in the MEP pathway. At present, it is believed that there is crossover between the two pathways in organisms that use both pathways to create terpenes and terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes" ...s, such as in plants, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Geranyl Pyrophosphate
Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many natural products. Occurrence GPP is an intermediate in the isoprenoid biosynthesis pathway that produces longer prenyl chains such as farnesyl pyrophosphate and geranylgeranyl pyrophosphate as well as many terpenes. It can be prepared in the laboratory from geraniol. Related compounds * Geraniol * Farnesyl pyrophosphate * Geranylgeranyl pyrophosphate See also * Dimethylallyltranstransferase Dimethylallyltranstransferase (DMATT), also known as farnesylpyrophosphate synthase (FPPS) or as farnesyldiphosphate synthase (FDPS), is an enzyme that in humans is encoded by the FDPS gene and catalyzes the transformation of dimethylallylpyr ... References Further reading *Kulkarni RS, Pandit SS, Chidley HG, Nagel R, Schmidt A, Gershenzon J, Pujari KH, Giri AP and Gupta VS, 2013Characterization of thre ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
S-adenosyl Methionine
''S''-Adenosyl methionine (SAM), also known under the commercial names of SAMe, SAM-e, or AdoMet, is a common cosubstrate involved in methyl group transfers, transsulfuration, and aminopropylation. Although these anabolic reactions occur throughout the body, most SAM is produced and consumed in the liver. More than 40 methyl transfers from SAM are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase. SAM was first discovered by Giulio Cantoni in 1952. In bacteria, SAM is bound by the SAM riboswitch, which regulates genes involved in methionine or cysteine biosynthesis. In eukaryotic cells, SAM serves as a regulator of a variety of processes including DNA, tRNA, and rRNA methylation; immune response; amino acid metabolism; transsulfuration; and more. In plants, SAM is crucial to the biosynthesis of ethylene, an important plant hormone ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Marmesin
Marmesin (nodakenetin) is a chemical compound precursor in psoralen and linear furanocoumarins biosynthesis Biosynthesis is a multi-step, enzyme-catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecul .... Marmesin plays a central role in the biosynthesis of furocoumarins in the plant ruta graveolens, more commonly known as rue. It acts as the natural intermediate in the formation of the furan ring that leads to a 4’,5’-dihydro furocoumarin-derivative. This substance can then be transformed into psoralen and other furocoumarins present in rue. Upon feeding the herb a dose of marmesin, radioactivity became strongly incorporated into psoralen and thus the plant itself. Spectra IR Spectra IR (ATR): νmax 3480, 2971, 1699, 1631, 1488 cm-1. Proton-NMR 1H-NMR (300 MHz, CDCl3): δ 7.59 (d, J = 9.5 Hz, 1H, aromatic), 7.22 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
