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.[1]
Generally furanocoumarins are most abundant in plants that have flowered and in ripe seeds and fruits.[1] (An exception is the common fig where furanocoumarins are found chiefly in the milky sap of the leaves and shoots but not the fruits.[2]) During the early stages of plant growth, their presence is not easily detected.
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 isomers. The parent compounds of the most common isomers are psoralen and angelicin. Derivatives of these two compounds are referred to respectively as linear and angular furanocoumarins,[3] so called since they exhibit a linear or angular chemical structure.
Furanocoumarins produced by plants may serve as a defense mechanism against predators such as insects and mammals.[5][6] It is also likely that furanocoumarins are related to a plant's natural defense against fungal attack.[7] In particular, the linear furanocoumarins (psoralen, bergapten, and methoxsalen), which occur naturally in Apiaceae, Rutaceae, and other plant families, are known to be toxic to fungi.[8] Plants that cause phytophotodermatitis usually contain linear furanocoumarins.[7]
Furanocoumarins are found in the sap of plants such as Ammi majus, parsnip, and giant hogweed. At least 36 species of the genus Heracleum in the family Apiaceae are known to contain one or more furanocoumarin compounds.[9]
Medication interactionsedit
Furanocoumarins have other biological effects as well. For example, in humans, bergamottin and 6',7'-dihydroxybergamottin are responsible for the "grapefruit juice effect", in which these furanocoumarins affect certain P450 liver and gut enzymes, such as the inhibition of CYP3A4 which either activates or deactivates many drugs, thus leading to higher or lower levels in the bloodstream.[10] Furanocoumarins have various effects which can specifically increase or decrease (depending on the drug) the blood levels of many pharmaceuticals in ways that can be life-threatening, so FDA-approved drugs include warnings for grapefruit.
^ abPathak, M. A.; Daniels Jr., Farrington; Fitzpatrick, T. B. (September 1962). "The Presently Known Distribution of Furocoumarins (Psoralens) in Plants". Journal of Investigative Dermatology. 39 (3): 225–239. doi:10.1038/jid.1962.106. PMID 13941836.
^Zaynoun, S. T.; Aftimos, B. G.; Abi Ali, L.; Tenekjian, K. K.; Khalidi, U.; Kurban, A. K. (July 1984). "Ficus carica; isolation and quantification of the photoactive components". Contact Dermatitis. 11 (1): 21–25. doi:10.1111/j.1600-0536.1984.tb00164.x. PMID 6744838. Cited in McGovern and Barkley 2000, section Phytophotodermatitis.
^Berenbaum, May (June 14, 2010). "Furanocoumarins as potent chemical defenses".
^Cox, George W. (2004). Alien species and evolution: the evolutionary ecology of exotic plants, animals, microbes, and interacting native species. Island Press. p. 125. ISBN978-1-55963-009-2.
^ abMcGovern, Thomas W.; Barkley, Theodore M. (2000). "Botanical Dermatology". The Electronic Textbook of Dermatology. Internet Dermatology Society. Section Phytophotodermatitis. Retrieved November 29, 2018.
^Camm, E. L.; Wat, C. K.; Towers, G. H. N. (1976). "An assessment of the roles of furanocoumarins in Heracleum lanatum". Can. J. Bot. 54 (22): 2562–2566. doi:10.1139/b76-275.
^Mitchell, John; Rook, Arthur (1979). Botanical Dermatology: Plants and Plant Products Injurious to the Skin. Vancouver: Greengrass. pp. 692–699.
^Kakar, SM; Paine, MF; Stewart, PW; Watkins, PB (2004). "6',7'-Dihydroxybergamottin contributes to the grapefruit juice effect". Clinical Pharmacology and Therapeutics. 75 (6): 569–579. doi:10.1016/j.clpt.2004.02.007. hdl:2027.42/109773. PMID 15179411.
January 01, 1970
furanocoumarin, furanocoumarins, furocoumarins, class, organic, chemical, compounds, produced, variety, plants, most, plant, species, found, contain, furanocoumarins, belong, handful, plant, families, families, apiaceae, rutaceae, include, largest, numbers, pl. 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 1 PsoralenAngelicinTwo furanocoumarin isomers Generally furanocoumarins are most abundant in plants that have flowered and in ripe seeds and fruits 1 An exception is the common fig where furanocoumarins are found chiefly in the milky sap of the leaves and shoots but not the fruits 2 During the early stages of plant growth their presence is not easily detected Contents 1 Structure 2 Biosynthesis 3 Effects 3 1 Direct toxicity 3 2 Medication interactions 4 See also 5 ReferencesStructure editThe 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 isomers The parent compounds of the most common isomers are psoralen and angelicin Derivatives of these two compounds are referred to respectively as linear and angular furanocoumarins 3 so called since they exhibit a linear or angular chemical structure Biosynthesis editThe compounds are biosynthesized partly through the phenylpropanoid pathway and the mevalonate pathway which is biosynthesized by a coupling of dimethylallyl pyrophosphate DMAPP and 7 hydroxycoumarin umbelliferone Effects editDirect toxicity edit Many furanocoumarin compounds are toxic The phytochemicals enter the nucleus of epithelial cells and form a bond crosslinking with the DNA when exposed to UV which causes cell death and causes inflammation via activation of the arachidonic acid cascade The result is known as phytophotodermatitis a serious skin inflammation 4 Furanocoumarins produced by plants may serve as a defense mechanism against predators such as insects and mammals 5 6 It is also likely that furanocoumarins are related to a plant s natural defense against fungal attack 7 In particular the linear furanocoumarins psoralen bergapten and methoxsalen which occur naturally in Apiaceae Rutaceae and other plant families are known to be toxic to fungi 8 Plants that cause phytophotodermatitis usually contain linear furanocoumarins 7 Furanocoumarins are found in the sap of plants such as Ammi majus parsnip and giant hogweed At least 36 species of the genus Heracleum in the family Apiaceae are known to contain one or more furanocoumarin compounds 9 Medication interactions edit Furanocoumarins have other biological effects as well For example in humans bergamottin and 6 7 dihydroxybergamottin are responsible for the grapefruit juice effect in which these furanocoumarins affect certain P450 liver and gut enzymes such as the inhibition of CYP3A4 which either activates or deactivates many drugs thus leading to higher or lower levels in the bloodstream 10 Furanocoumarins have various effects which can specifically increase or decrease depending on the drug the blood levels of many pharmaceuticals in ways that can be life threatening so FDA approved drugs include warnings for grapefruit See also editPyranocoumarin NaringinReferences edit a b Pathak M A Daniels Jr Farrington Fitzpatrick T B September 1962 The Presently Known Distribution of Furocoumarins Psoralens in Plants Journal of Investigative Dermatology 39 3 225 239 doi 10 1038 jid 1962 106 PMID 13941836 Zaynoun S T Aftimos B G Abi Ali L Tenekjian K K Khalidi U Kurban A K July 1984 Ficus carica isolation and quantification of the photoactive components Contact Dermatitis 11 1 21 25 doi 10 1111 j 1600 0536 1984 tb00164 x PMID 6744838 Cited in McGovern and Barkley 2000 section Phytophotodermatitis IUPAC Compendium of Chemical Terminology 2nd ed the Gold Book 1997 Online corrected version 2006 furanocoumarins doi 10 1351 goldbook F02558 IUPAC Compendium of Chemical Terminology 2nd ed the Gold Book 1997 Online corrected version 2006 furocoumarins doi 10 1351 goldbook F02562 Baugh WP September 8 2016 Phytophotodermatitis Medscape Retrieved February 19 2020 Berenbaum May June 14 2010 Furanocoumarins as potent chemical defenses Cox George W 2004 Alien species and evolution the evolutionary ecology of exotic plants animals microbes and interacting native species Island Press p 125 ISBN 978 1 55963 009 2 a b McGovern Thomas W Barkley Theodore M 2000 Botanical Dermatology The Electronic Textbook of Dermatology Internet Dermatology Society Section Phytophotodermatitis Retrieved November 29 2018 Camm E L Wat C K Towers G H N 1976 An assessment of the roles of furanocoumarins in Heracleum lanatum Can J Bot 54 22 2562 2566 doi 10 1139 b76 275 Mitchell John Rook Arthur 1979 Botanical Dermatology Plants and Plant Products Injurious to the Skin Vancouver Greengrass pp 692 699 Kakar SM Paine MF Stewart PW Watkins PB 2004 6 7 Dihydroxybergamottin contributes to the grapefruit juice effect Clinical Pharmacology and Therapeutics 75 6 569 579 doi 10 1016 j clpt 2004 02 007 hdl 2027 42 109773 PMID 15179411 Retrieved from https en wikipedia org w index php title Furanocoumarin amp oldid 1212535964, wikipedia, wiki, book, books, library,
