Prenylflavonoid

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Chemical structure of 8-prenylnaringenin, a prenylated flavanone found in hops

Prenylated flavonoids or prenylflavonoids are a sub-class of

hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid.[2]

Monoprenyl isoflavone epoxidase is a key enzyme in fungal Botrytis cinerea metabolism of prenylated flavonoids.[3]

Many prenylflavonoids appear to have anticancer activity in vitro.[4]

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.[5][6] Of the prenylflavonoids, 8-prenylnaringenin is the most potent phytoestrogen known.

Australone A can be found in Morus australis.[7]

6,8-Diprenyleriodictyol, dorsmanin C and dorsmanin F can be found in Dorstenia mannii.[1]

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,[8] ranged from 1.4 to 5.1% in aerial parts and 1.0 to 2.8% in underground parts.[9]

Artocarpus nobilis contains prenylated flavonoids in its root bark.[10]

8-Prenylkaempferol can be found in Sophora flavescens.[11]

Cannflavins are prenylflavonoids found in Cannabis sativa.[12]

Prenylated isoflavonoids

A number of bio-active chemicals have been reported from

Millettia pachycarpa including several prenylflavonoids.[13][14] 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.[15][16]

7-O-Methylluteone is a prenylated isoflavone. It can be found in the bark of Erythrina burttii.

Luteone is another prenylated isoflavone found in the pods of Laburnum anagyroides.

Wighteone (6-prenylgenistein), isowighteone (3′-prenylgenistein), and lupiwighteone (8-prenylgenistein) are genistein prenylated derivatives.[2]

References

External links