Covering: up to July 2020Naturally occurring chalcones carrying up to three modified or unmodified C5-, C10-, and C15-prenyl moieties on both rings A and B as well as at the α- and β-carbons are widely distributed in plants of the families of Fabaceae, Moraceae, Zingiberaceae and Cannabaceae. Xanthohumol and isobavachalcone being the most investigated representatives, exhibit diverse and remarkable biological and pharmacological activities. The present review deals with their structural characters, biological activities and occurrence in the plant kingdom. Biosynthesis of prenylated chalcones and metabolism of xanthohumol are also discussed.