Prenylflavonoid

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

Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant[1] properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition 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.

  1. ^ Dufall, K.G.; Ngadjui, B.T.; Simeon, K.F.; Abegaz, B.M.; Croft, K.D. (2003). "Antioxidant activity of prenylated flavonoids from the West African medicinal plant Dorstenia mannii". Journal of Ethnopharmacology. 87 (1): 67–72. doi:10.1016/S0378-8741(03)00108-9. PMID 12787956.
  2. ^ Shen; Huhman, D.; Lei, Z.; Snyder, J.; Sumner, L. W.; Dixon, R. A.; et al. (March 2012). "Characterization of an Isoflavonoid-Specific Prenyltransferase from Lupinus albus" (PDF). Plant Physiology. 159 (1): 70–80. doi:10.1104/pp.112.195271. PMC 3375986. PMID 22430842.
  3. ^ Tanaka, Mitsuharu; Tahara, Satoshi (1997). "Fad-dependent epoxidase as a key enzyme in fungal metabolism of prenylated flavonoids". Phytochemistry. 46 (3): 433–9. doi:10.1016/S0031-9422(97)00322-1.
  4. ^ Miranda, C.L.; Stevens, J.F.; Helmrich, A.; Henderson, M.C.; Rodriguez, R.J.; Yang, Y.-H.; Deinzer, M.L.; Barnes, D.W.; Buhler, D.R. (1999). "Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines". Food and Chemical Toxicology. 37 (4): 271–85. doi:10.1016/S0278-6915(99)00019-8. PMID 10418944.