Chemical structure of8-prenylnaringenin, a prenylated flavanone found in hops
Prenylated flavonoids orprenylflavonoids are a sub-class offlavonoids. They are widely distributed throughout the plant kingdom. Some are known to havephytoestrogenic orantioxidant[1] properties. They are given in the list ofadaptogens in herbalism. Chemically they have aprenyl group attached to theirflavonoid backbone. It is usually assumed that the addition ofhydrophobic prenyl groups facilitate attachment to cell membranes.Prenylation may increase the potential activity of its original flavonoid.[2]
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]
^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.
^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.PMID10418944.
^Stevens, Jan F; Page, Jonathan E (2004). "Xanthohumol and related prenylflavonoids from hops and beer: To your good health!".Phytochemistry.65 (10):1317–30.doi:10.1016/j.phytochem.2004.04.025.PMID15231405.
^Dhooghe, Liene; Naessens, Tania; Heyerick, Arne; De Keukeleire, Denis; Vlietinck, Arnold J.; Pieters, Luc; Apers, Sandra (2010). "Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards".Talanta.83 (2):448–56.doi:10.1016/j.talanta.2010.09.041.PMID21111159.
^Li, Hui-Fang; Guan, Xiang-yu; Ye, Min; Xiang, Cheng; Lin, Chang-hu; Sun, Chao; Guo, De-an (2011). "Qualitative and quantitative analyses of Epimedium wushanense by high-performance liquid chromatography coupled with diode array detection and electrospray ionization tandem mass spectrometry".Journal of Separation Science.34 (12):1437–46.doi:10.1002/jssc.201000899.PMID21560245.
^Jayasinghe, U.L.B.; Samarakoon, T.B.; Kumarihamy, B.M.M.; Hara, N.; Fujimoto, Y. (2008). "Four new prenylated flavonoids and xanthones from the root bark of Artocarpus nobilis".Fitoterapia.79 (1):37–41.doi:10.1016/j.fitote.2007.07.014.PMID17855020.
^Barrett, M. L.; Scutt, A. M.; Evans, F. J. (1986). "Cannflavin A and B, prenylated flavones fromCannabis sativa L".Experientia.42 (4):452–453.doi:10.1007/BF02118655.PMID3754224.S2CID19652191.
^Singhal, Ashok K.; Sharma, Ram P.; Thyagarajan, Gopalakrishna; Herz, Werner; Govindan, Serengolam V. (1980). "New prenylated isoflavones and a prenylated dihydroflavonol fromMillettia pachycarpa".Phytochemistry.19 (5):929–34.doi:10.1016/0031-9422(80)85140-5.
^Ye, Haoyu; Chen, Lijuan; Li, Yanfang; Peng, Aihua; Fu, Afu; Song, Hang; Tang, Minghai; Luo, Houding; Luo, Youfu; Xu, Yongbin; Shi, Jianyou; Wei, Yuquan (2008). "Preparative isolation and purification of three rotenoids and one isoflavone from the seeds of Millettia pachycarpa Benth by high-speed counter-current chromatography".Journal of Chromatography A.1178 (1–2):101–7.doi:10.1016/j.chroma.2007.11.060.PMID18082754.
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