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 (see estrogen) not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonster ...

ic or

antioxidant Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubrica ...

properties. They are given in the list of adaptogens 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 ...

group attached to their

backbone. It is usually assumed that the addition of

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

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 ...

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" or ...

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

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

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

Examples

6-Prenylnaringenin, 6-geranylnaringenin, 8-prenylnaringenin and

isoxanthohumol Isoxanthohumol is a prenylflavonoid, and it is a phytoestrogen. It is abbreviated as IX or IXN. 8-Prenylnaringenin can be produced from isoxanthohumol by flora in the human intestine, and by fungi in cell cultures. This prenylflavonoid is found ...

can be found in hops and

beer Beer is one of the oldest and the most widely consumed type of alcoholic drink in the world, and the third most popular drink overall after water and tea. It is produced by the brewing and fermentation of starches, mainly derived from ce ...

. Of the prenylflavonoids, 8-prenylnaringenin is the most potent phytoestrogen known. Australone A can be found in '' Morus australis''. 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'' contains prenylated flavonoids in its root bark. 8-Prenylkaempferol can be found in ''

Sophora flavescens ''Sophora flavescens'', the shrubby sophora, is a species of plant in the genus '' Sophora'' of the family Fabaceae. This genus contains about 52 species, nineteen varieties, and seven forms that are widely distributed in Asia, Oceania, and the ...

''. Cannflavins are prenylflavonoids found in ''

Cannabis sativa ''Cannabis sativa'' is an annual herbaceous flowering plant indigenous to Eastern Asia, but now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history, used as a source of industrial fibe ...

''.

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 isoflavones 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 prenylated derivatives.

References

External links

* {{Xenoestrogens Humulus