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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 ...
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Angelicin
Angelicin is the parent compound in a family of naturally occurring organic compounds known as the angular furanocoumarins. Structurally, it can be considered as benzapyra-2-one fused with a furan moiety in the 7,8-position. Angelicin is commonly found in certain Apiaceae and Fabaceae plant species such as ''Bituminaria bituminosa''. It has a skin permeability coefficient (Log''Kp'') of -2.46. The maximum absorption is observed at 300 nm. The 1HNMR spectrum is available; the infrared and mass spectra of angelicin can be found in thidatabase The sublimation of angelicin occurs at 120 °C and the pressure of 0.13 Pa. Angelicin is a coumarine. History and etymology Humans have used plants rich in angelicin for centuries. The earliest known record dates back to 3000 BC when ancient Egyptians applied the oil and sap of local ''Apiaceae'' species exposing their skin to sunlight to cure vitiligo. In meantime, tribes in India used ''Psoralea corylifolia'' which contained psora ...
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Angelicin
Angelicin is the parent compound in a family of naturally occurring organic compounds known as the angular furanocoumarins. Structurally, it can be considered as benzapyra-2-one fused with a furan moiety in the 7,8-position. Angelicin is commonly found in certain Apiaceae and Fabaceae plant species such as ''Bituminaria bituminosa''. It has a skin permeability coefficient (Log''Kp'') of -2.46. The maximum absorption is observed at 300 nm. The 1HNMR spectrum is available; the infrared and mass spectra of angelicin can be found in thidatabase The sublimation of angelicin occurs at 120 °C and the pressure of 0.13 Pa. Angelicin is a coumarine. History and etymology Humans have used plants rich in angelicin for centuries. The earliest known record dates back to 3000 BC when ancient Egyptians applied the oil and sap of local ''Apiaceae'' species exposing their skin to sunlight to cure vitiligo. In meantime, tribes in India used ''Psoralea corylifolia'' which contained psora ...
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Bergapten
Bergapten (5-methoxypsoralen) is a naturally-occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus '' Heracleum'' in the family Apiaceae. Cited by Mitchell and Rook (1979). In the family Rutaceae, various ''Citrus'' species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange. Bergapten belongs to a class of chemical compounds known as the furanocoumarins. In 1834, Kalbrunner isolated 5-methoxypsoralen from bergamot essential oil, hence the common name "bergapten". It was the first furanocoumarin to be isolated and identified. Toxicity Bergapten is a derivative of psoralen, the parent compound of a family of naturally-occurring organic compounds known as the linear furanocoumarins (so called since they exhibit a linear chemical ...
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Phytophotodermatitis
Phytophotodermatitis, also known as berloque dermatitis or margarita photodermatitis, is a cutaneous phototoxic inflammatory reaction resulting from contact with a light-sensitizing botanical agent followed by exposure to ultraviolet light (from the sun, for instance). Symptoms include erythema, edema, blisters (Skin condition#Vesicle, vesicles and/or Skin condition#Bulla, bullae), and delayed hyperpigmentation. Heat and moisture tend to exacerbate the reaction. A reaction may be elicited in any person who has been exposed to adequate amounts of both a photosensitizing, photosensitizer and ultraviolet light. Phytophotodermatitis is not an Immunology, immunologic response; no prior exposure to the photosensitizing agent is required. The photosensitizing substances found in phototoxic plants belong to a class of chemical compounds called the furanocoumarins, which are activated by long-wavelength ultraviolet (UVA) light. The most toxic of these organic compounds are the linear furan ...
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Psoralen
Psoralen (also called psoralene) is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. It is structurally related to coumarin by the addition of a fused furan ring, and may be considered as a derivative of umbelliferone. Psoralen occurs naturally in the seeds of ''Psoralea corylifolia'', as well as in the common fig, celery, parsley, West Indian satinwood, and in all citrus fruits. It is widely used in PUVA (psoralen + UVA) treatment for psoriasis, eczema, vitiligo, and cutaneous T-cell lymphoma; these applications are typically through the use of medications such as Methoxsalen. Many furanocoumarins are extremely toxic to fish, and some are deposited in streams in Indonesia to catch fish. Uses Psoralen is a mutagen, and is used for this purpose in molecular biology research. Psoralen intercalates into DNA and on exposure to ultraviolet (UVA) radiation can form monoadducts and covalent interstrand cross-links (ICL) w ...
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Psoralen
Psoralen (also called psoralene) is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. It is structurally related to coumarin by the addition of a fused furan ring, and may be considered as a derivative of umbelliferone. Psoralen occurs naturally in the seeds of ''Psoralea corylifolia'', as well as in the common fig, celery, parsley, West Indian satinwood, and in all citrus fruits. It is widely used in PUVA (psoralen + UVA) treatment for psoriasis, eczema, vitiligo, and cutaneous T-cell lymphoma; these applications are typically through the use of medications such as Methoxsalen. Many furanocoumarins are extremely toxic to fish, and some are deposited in streams in Indonesia to catch fish. Uses Psoralen is a mutagen, and is used for this purpose in molecular biology research. Psoralen intercalates into DNA and on exposure to ultraviolet (UVA) radiation can form monoadducts and covalent interstrand cross-links (ICL) w ...
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Ammi Majus
''Ammi majus'', commonly called bishop's flower, false bishop's weed, laceflower, bullwort, etc., is a member of the carrot family Apiaceae. The plant, which has white lace-like flower clusters, has a large distribution through Southern Europe, North Africa and West and Central Asia, though it is hypothesized to be native to the Nile River Valley. Nomenclature The plant is called by various common names: bishop's flower or bishop's weed (false bishop's weed); laceflower, lady's lace or false Queen Anne's lace; bullwort (large bullwort); white dill and greater ammi. It is known in Arabic as ''hirz al-shayateen'' () or ''khella/khilla shaitani'' (). The plant is also introduced into China, where it is called ''da a min qin'' ( zh, 大阿米芹) and cultivated in medicinal farms. Description ''Ammi majus'' is a herbaceous annual, or rather a biennial that behaves like an annual in cultivation. The lower leaves are 1-2-pinnate, upper leaves 2(-3)-pinnate with serrate lobes. Th ...
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Common Fig
The fig is the edible fruit of ''Ficus carica'', a species of small tree in the flowering plant family Moraceae. Native to the Mediterranean and western Asia, it has been cultivated since ancient times and is now widely grown throughout the world, both for its fruit and as an ornamental plant.''The Fig: its History, Culture, and Curing'', Gustavus A. Eisen, Washington, Govt. print. off., 1901 ''Ficus carica'' is the type species of the genus ''Ficus'', containing over 800 tropical and subtropical plant species. A fig plant is a small deciduous tree or large shrub growing up to tall, with smooth white bark. Its large leaves have three to five deep lobes. Its fruit (referred to as syconium, a type of multiple fruit) is tear-shaped, long, with a green skin that may ripen toward purple or brown, and sweet soft reddish flesh containing numerous crunchy seeds. The milky sap of the green parts is an irritant to human skin. In the Northern Hemisphere, fresh figs are in season from l ...
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Apiaceae
Apiaceae or Umbelliferae is a family of mostly aromatic flowering plants named after the type genus ''Apium'' and commonly known as the celery, carrot or parsley family, or simply as umbellifers. It is the 16th-largest family of flowering plants, with more than 3,700 species in 434 generaStevens, P.F. (2001 onwards)Angiosperm Phylogeny Website Version 9, June 2008. including such well-known and economically important plants as ajwain, angelica, anise, asafoetida, caraway, carrot, celery, chervil, coriander, cumin, dill, fennel, lovage, cow parsley, parsley, parsnip and sea holly, as well as silphium, a plant whose identity is unclear and which may be extinct. The family Apiaceae includes a significant number of phototoxic species, such as giant hogweed, and a smaller number of highly poisonous species, such as poison hemlock, water hemlock, spotted cowbane, fool's parsley, and various species of water dropwort. Description Most Apiaceae are annual, biennial or perennial ...
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Methoxsalen
Methoxsalen, sold under the brand name Oxsoralen among others, is a medication used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to ultraviolet (UVA) light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. Levels of individual patient PUVA exposure were originally determined using the Fitzpatrick scale. The scale was developed after patients demonstrated symptoms of phototoxicity after oral ingestion of methoxsalen followed by PUVA therapy. Chemically, methoxsalen belongs to a class of organic natural molecules known as furanocoumarins. They consist of coumarin annulated with furan. It can also be injected and used topically. Natural sources In 1947, methoxsalen was isolated (under the name "ammoidin") from the plant ''Ammi majus'', bishop's weed. In 1970, Nielsen extracted 8-methoxypsoralen from four species of the genus '' Heracleum'' in the ...
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Giant Hogweed
''Heracleum mantegazzianum'', commonly known as giant hogweed, is a monocarpic perennial herbaceous plant in the carrot family Apiaceae. ''H. mantegazzianum'' is also known as cartwheel-flower, giant cow parsley, giant cow parsnip, or hogsbane. In New Zealand, it is also sometimes called wild parsnip (not to be confused with ''Pastinaca sativa'') or wild rhubarb. Giant hogweed is native to the western Caucasus region of Eurasia. It was introduced to Britain as an ornamental plant in the 19th century, and has also spread to other areas in Western Europe, the United States, and Canada. Its close relatives, Sosnowsky's hogweed and Persian hogweed, have similarly spread to other parts of Europe. The sap of giant hogweed is phototoxic and causes phytophotodermatitis in humans, resulting in blisters and scars. These serious reactions are due to the furanocoumarin derivatives in the leaves, roots, stems, flowers, and seeds of the plant. Consequently, it is considered to be a no ...
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Parsnip
The parsnip (''Pastinaca sativa'') is a root vegetable closely related to carrot and parsley, all belonging to the flowering plant family Apiaceae. It is a biennial plant usually grown as an annual. Its long taproot has cream-colored skin and flesh, and, left in the ground to mature, it becomes sweeter in flavor after winter frosts. In its first growing season, the plant has a rosette of pinnate, mid-green leaves. If unharvested, in its second growing season it produces a flowering stem topped by an umbel of small yellow flowers, later producing pale brown, flat, winged seeds. By this time, the stem has become woody and the tap root inedible. The parsnip is native to Eurasia; it has been used as a vegetable since antiquity and was cultivated by the Romans, although some confusion exists between parsnips and carrots in the literature of the time. It was used as a sweetener before the arrival of cane sugar in Europe. Parsnips are usually cooked, but can also be eaten raw. T ...
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