Furanocoumarin: Difference between revisions

Latest revision as of 00:44, 9 December 2024

Chemical compounds found in plants

Furanocoumarins are a class of organic chemical compounds produced by a variety of plants. These compounds are known for their role in plant defense mechanisms and their effects on human health, particularly their phototoxic and photochemotherapeutic properties.

Structure and Classification[edit]

Furanocoumarins are derived from the fusion of a furan ring with a coumarin structure. The basic structure consists of a benzopyrone core with a furan ring attached. They are classified into two main types based on the position of the furan ring:

Linear furanocoumarins: In these compounds, the furan ring is attached at the 6,7-position of the coumarin. Examples include psoralen, bergapten, and xanthotoxin.
Angular furanocoumarins: Here, the furan ring is attached at the 7,8-position. Examples include angelicin and pimpinellin.

Biosynthesis[edit]

Furanocoumarins are synthesized in plants through the phenylpropanoid pathway. The biosynthesis begins with the amino acid phenylalanine, which is converted into cinnamic acid by the enzyme phenylalanine ammonia-lyase (PAL). Subsequent enzymatic reactions lead to the formation of umbelliferone, which is then modified to produce various furanocoumarins.

Occurrence[edit]

Furanocoumarins are found in several plant families, including Apiaceae, Rutaceae, and Moraceae. Notable plants containing these compounds include celery, parsley, citrus fruits, and figs.

Biological Activity[edit]

Furanocoumarins have several biological activities:

Phototoxicity: When exposed to ultraviolet (UV) light, furanocoumarins can form covalent bonds with DNA, leading to cell damage and apoptosis. This property is utilized in PUVA therapy (psoralen + UVA) for treating skin conditions like psoriasis and vitiligo.
Inhibition of Cytochrome P450: Some furanocoumarins, such as bergamottin found in grapefruit, can inhibit cytochrome P450 enzymes, affecting drug metabolism and leading to potential drug interactions.

Health Implications[edit]

While furanocoumarins have therapeutic applications, they can also pose health risks. Consumption of foods high in furanocoumarins, like grapefruit, can interfere with the metabolism of certain medications, leading to increased drug levels and potential toxicity. Additionally, handling plants containing furanocoumarins can cause phytophotodermatitis, a skin condition characterized by redness, blistering, and hyperpigmentation upon exposure to sunlight.

Also see[edit]

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-'''Furanocoumarins''' are a class of organic chemical compounds produced by a variety of plants. They are a type of [[coumarin]] with a furan ring fused to the coumarin. The furan may be fused in different ways producing several isomers.
+[[File:Psoralen.svg|thumb]] [[File:Angelicin.png|thumb]] {{Short description|Chemical compounds found in plants}}
+{{Use dmy dates|date=October 2023}}
-==Chemistry==
+'''Furanocoumarins''' are a class of organic chemical compounds produced by a variety of plants. These compounds are known for their role in plant defense mechanisms and their effects on human health, particularly their phototoxic and photochemotherapeutic properties.
-Furanocoumarins are made of a furan ring fused with coumarin. The different isomers, including [[psoralen]], are defined by the fusion of the furan ring and the position of the carbonyl group. They are colorless, crystalline compounds which occur abundantly in nature.
+==Structure and Classification==
+Furanocoumarins are derived from the fusion of a furan ring with a coumarin structure. The basic structure consists of a benzopyrone core with a furan ring attached. They are classified into two main types based on the position of the furan ring:
+* '''Linear furanocoumarins''': In these compounds, the furan ring is attached at the 6,7-position of the coumarin. Examples include [[psoralen]], [[bergapten]], and [[xanthotoxin]].
+* '''Angular furanocoumarins''': Here, the furan ring is attached at the 7,8-position. Examples include [[angelicin]] and [[pimpinellin]].
 ==Biosynthesis==
-Furanocoumarins are biosynthesized from [[phenylalanine]] and [[malonyl-CoA]] by a series of enzymes. The process involves the conversion of phenylalanine into [[umbelliferone]] through a series of steps involving [[trans-cinnamate]] and [[p-coumarate]]. Umbelliferone then undergoes a series of transformations to yield the final furanocoumarin product.
+Furanocoumarins are synthesized in plants through the phenylpropanoid pathway. The biosynthesis begins with the amino acid [[phenylalanine]], which is converted into [[cinnamic acid]] by the enzyme [[phenylalanine ammonia-lyase]] (PAL). Subsequent enzymatic reactions lead to the formation of umbelliferone, which is then modified to produce various furanocoumarins.
-==Biological effects==
+==Occurrence==
-Furanocoumarins have the ability to absorb ultraviolet light, which leads to a variety of biological effects. They are known to cause [[phytophotodermatitis]], a severe skin inflammation in humans. When the skin containing the furanocoumarins is exposed to UVA light, the compounds are excited to an active state and can form covalent bonds with DNA, leading to skin cell death.
+Furanocoumarins are found in several plant families, including [[Apiaceae]], [[Rutaceae]], and [[Moraceae]]. Notable plants containing these compounds include [[celery]], [[parsley]], [[citrus fruits]], and [[figs]].
-==Medical uses==
+==Biological Activity==
-Some furanocoumarins are used in the treatment of [[psoriasis]] and [[vitiligo]]. Psoralen, a type of furanocoumarin, is used in PUVA therapy for the treatment of psoriasis, eczema, and vitiligo. It is applied topically or taken orally, followed by exposure to UVA light to activate the compound.
+Furanocoumarins have several biological activities:
-==Food sources==
+* '''Phototoxicity''': When exposed to ultraviolet (UV) light, furanocoumarins can form covalent bonds with DNA, leading to cell damage and apoptosis. This property is utilized in [[PUVA therapy]] (psoralen + UVA) for treating skin conditions like [[psoriasis]] and [[vitiligo]].
-Furanocoumarins are found in many species of plants. They are particularly high in the families [[Apiaceae]] (including carrots, parsley, and celery) and [[Rutaceae]] (including grapefruit and oranges). They are also found in some fungi and bacteria.
+* '''Inhibition of Cytochrome P450''': Some furanocoumarins, such as [[bergamottin]] found in [[grapefruit]], can inhibit cytochrome P450 enzymes, affecting drug metabolism and leading to potential drug interactions.
-[[File:Furanocoumarin.png|thumb|right|Chemical structure of a furanocoumarin]]
+==Health Implications==
+While furanocoumarins have therapeutic applications, they can also pose health risks. Consumption of foods high in furanocoumarins, like grapefruit, can interfere with the metabolism of certain medications, leading to increased drug levels and potential toxicity. Additionally, handling plants containing furanocoumarins can cause [[phytophotodermatitis]], a skin condition characterized by redness, blistering, and hyperpigmentation upon exposure to sunlight.
-==See also==
+==Also see==
 * [[Coumarin]]
 * [[Psoralen]]
+* [[PUVA therapy]]
 * [[Phytophotodermatitis]]
-* [[Psoriasis]]
+* [[Cytochrome P450]]
-* [[Vitiligo]]
+{{Organic chemistry}}
+{{Pharmacology}}
 [[Category:Organic compounds]]
-[[Category:Medicinal chemistry]]
+[[Category:Phytochemicals]]
-[[Category:Pharmacology]]
+[[Category:Photosensitizing agents]]
-{{medicine-stub}}