Prenylated flavonoids or prenylflavonoids are a sub-class of

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

s. They are widely distributed throughout the plant kingdom. Some are known to have

phytoestrogen A phytoestrogen is a plant-derived xenoestrogen (a type of estrogen produced by organisms other than humans) not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it ...

ic or

antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...

properties. They are given in the list of

adaptogen Adaptogens, or adaptogenic substances, are used in herbal medicine for the purported stabilization of physiological processes and promotion of homeostasis. The concept of adaptogens is not accepted in mainstream science and is not approved as a ...

s in herbalism. Chemically they have a

prenyl Prenylation (also known as isoprenylation or lipidation) is the addition of hydrophobic molecules to a protein or a biomolecule. It is usually assumed that prenyl groups (3-methylbut-2-en-1-yl) facilitate attachment to cell membranes, similar to ...

group attached to their

backbone. It is usually assumed that the addition of

hydrophobic In chemistry, hydrophobicity is the chemical property of a molecule (called a hydrophobe) that is seemingly repelled from a mass of water. In contrast, hydrophiles are attracted to water. Hydrophobic molecules tend to be nonpolar and, thu ...

prenyl groups facilitate attachment to cell membranes.

Prenylation Prenylation (also known as isoprenylation or lipidation) is the addition of hydrophobic molecules to a protein or a biomolecule. It is usually assumed that prenyl groups (3-methylbut-2-en-1-yl) facilitate attachment to cell membranes, similar to ...

may increase the potential activity of its original flavonoid. Monoprenyl isoflavone epoxidase is a key enzyme in fungal ''

Botrytis cinerea ''Botrytis cinerea'' is a necrotrophic fungus that affects many plant species, although its most notable hosts may be wine grapes. In viticulture, it is commonly known as "botrytis bunch rot"; in horticulture, it is usually called "grey mould" ...

'' metabolism of prenylated flavonoids. Many prenylflavonoids appear to have anticancer activity

in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...

. Prenylchalcones, prenylflavones, prenylflavonols and prenylflavanones are classes of prenylflavonoids.

Examples

6-Prenylnaringenin, 6-geranylnaringenin, 8-prenylnaringenin and isoxanthohumol can be found in hops and

beer Beer is an alcoholic beverage produced by the brewing and fermentation of starches from cereal grain—most commonly malted barley, although wheat, maize (corn), rice, and oats are also used. The grain is mashed to convert starch in the ...

. Of the prenylflavonoids, 8-prenylnaringenin is the most potent phytoestrogen known. Australone A can be found in ''

Morus australis Morus may refer to: People * Alexander Morus (1616–1670), Franco-Scottish Protestant preacher * Henryk Moruś (1943–2013), Polish serial killer * Huw Morus (1622–1709), Welsh poet * Thomas More or Morus (1478–1535), English philosopher * ...

''. 6,8-Diprenyleriodictyol, dorsmanin C and dorsmanin F can be found in '' Dorstenia mannii''. '' Epimedium wushanense'' contains a number of flavanoids. 37 compounds were characterized from the underground and aerial parts of the plant. Among them, 28 compounds were prenylflavonoids. The predominant prenylated flavonoid, epimedin C, ranged from 1.4 to 5.1% in aerial parts and 1.0 to 2.8% in underground parts. ''

Artocarpus nobilis ''Artocarpus nobilis'', the Ceylon breadfruit, is a tree species in the family Moraceae. It is endemic to south western regions of Sri Lanka. It is known as "Wal dhel - වල් දෙල්" , "Baedi dhel - බැදි දෙල්" or as "Hi ...

'' contains prenylated flavonoids in its root bark. 8-Prenylkaempferol can be found in '' Sophora flavescens''.

Cannflavin Cannflavins are a group of chemical compounds found in ''Cannabis sativa''. Chemically, they are prenylflavonoids and are unrelated to THC and other cannabinoids. Cannflavins A and B were first identified in the 1980s and cannflavin C was identif ...

s are prenylflavonoids found in ''

Cannabis sativa ''Cannabis sativa'' is an annual Herbaceous plant, herbaceous flowering plant. The species was first classified by Carl Linnaeus in 1753. The specific epithet ''Sativum, sativa'' means 'cultivated'. Indigenous to East Asia, Eastern Asia, the pla ...

''.

Prenylated isoflavonoids

A number of bio-active chemicals have been reported from '' Millettia pachycarpa'' including several prenylflavonoids. Several chemical analyses have yielded a number of novel prenylated

isoflavone Isoflavones are a type of naturally-occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans. Although isoflavones and closely-related phytoestrogens ar ...

s including erysenegalensein E, euchrenone b10, isoerysenegalensein E, 6,8-diprenylorobol, furowanin A and B, millewanins-F, G and H, warangalone, and auriculasin from the leaves. 7-O-Methylluteone is a

prenylated Prenylation (also known as isoprenylation or lipidation) is the addition of hydrophobic molecules to a protein or a biomolecule. It is usually assumed that prenyl groups (3-methylbut-2-en-1-yl) facilitate attachment to cell membranes, similar to ...

isoflavone. It can be found in the bark of '' Erythrina burttii''. Luteone is another prenylated isoflavone found in the pods of ''

Laburnum anagyroides ''Laburnum anagyroides'' ( syn. ''Cytisus laburnum''), the common laburnum, golden chain or golden rain, is a species of flowering plant in the subfamily Faboideae, and genus ''Laburnum''. '' Laburnum alpinum'' is closely related. It is native ...

''. Wighteone (6-prenylgenistein), isowighteone (3′-prenylgenistein), and lupiwighteone (8-prenylgenistein) are

genistein Genistein (C15H10O5) is a plant-derived, aglycone isoflavone. Genistein has the highest content of all isoflavones in soybeans and soy products, such as tempeh. As a type of phytoestrogen, genistein has estrogenic activity in vitro; consequ ...

prenylated derivatives.

References

External links

* {{Xenoestrogens Humulus