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Dihydroxybergamottin
6',7'-Dihydroxybergamottin is a natural furanocoumarin found in pomelos, grapefruits, and sour oranges, in both the peel and the pulp. Along with the chemically related compound bergamottin, it is believed to be responsible for a number of grapefruit–drug interactions, in which the consumption of citrus containing one or both of these compounds (especially grapefruit) affects the metabolism of a variety of pharmaceutical drugs. References {{DEFAULTSORT:Dihydroxybergamottin, 6',7'- CYP3A4 inhibitors Furanocoumarins Terpeno-phenolic compounds Vicinal diols ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 inc ... [...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] |
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 produc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grapefruit–drug Interactions
Some fruit juices and fruits can interact with numerous drugs, in many cases causing adverse effects. The effect is most studied with grapefruit and grapefruit juice, but similar effects have been observed with certain other citrus fruits. The effect was first discovered accidentally in 1991, when a test of drug interactions with alcohol used grapefruit juice to hide the taste of the ethanol. A 2005 medical review advised patients to avoid all citrus juices until further research clarifies the risks. It was reported in 2008 that similar effects had been observed with apple juice. One whole grapefruit, or a small glass () of grapefruit juice, can cause drug overdose toxicity. Fruit consumed three days before the medicine can still have an effect. The relative risks of different types of citrus fruit have not been systematically studied. Affected drugs typically have an auxiliary label saying "''Do not take with grapefruit''" on the container, and the interaction is elaborated u ... [...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 differen ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pomelo
The pomelo ( ), ''Citrus maxima'', is the largest citrus fruit from the family Rutaceae and the principal ancestor of the grapefruit. It is a natural, non-hybrid, citrus fruit, native to Southeast Asia. Similar in taste to a sweet grapefruit, the pomelo is commonly consumed and used for festive occasions throughout Southeast Asia. As with the grapefruit, phytochemicals in the pomelo have the potential for drug interactions. Etymology and common names According to the Oxford English Dictionary, the etymology of the word "pomelo" is uncertain. It may be derived from Dutch ''pompelmoes''. Its botanical name, ''Citrus maxima'', means "the biggest citrus". In English, the word "pomelo" (also spelled pummelo, pumelo, pomello, pommelo) has become the more common name, although "pomelo" has historically been used for grapefruit. After introduction to Barbados by 'Captain Shaddock' of the East India Company (apparently Philip Chaddock, who visited the island in the late 1640s), ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sour Orange
Bitter orange, Seville orange, bigarade orange, or marmalade orange is the citrus tree ''Citrus'' × ''aurantium'' and its fruit. It is native to Southeast Asia and has been spread by humans to many parts of the world. It is probably a cross between the pomelo, ''Citrus maxima'', and the mandarin orange, ''Citrus reticulata''. History Wild trees are found near small streams in generally secluded and wooded parts of Florida and the Bahamas after it was introduced species, introduced to the area from Spain, where it had been introduced and cultivated heavily beginning in the 10th century by the Moors. Identification Citrus × aurantium can be identified through its orange fruit with a distinctly bitter or sour taste. The tree has alternate simple leaves and thorns on its petiole. Usage Many varieties of bitter orange are used for their essential oil, and are found in perfume, used as a flavoring or as a solvent, and also for consumption. The Seville orange variety is used in the ... [...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] |
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