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Auraptene and umbelliprenin are among the most abundant naturally occurring prenyloxy umbelliferone derivatives. Both have been mainly isolated from plants belonging to numerous genera of the Rutaceae (in particular auraptene in Citrus spp.) and Apiaceae (in particular umbelliprenin in Ferula spp.) families, comprising different and widely used medicinal plants and in general plants having beneficial effects to human welfare as well as edible fruits and vegetables. Although known for quite a long time (nearly a century for auraptene and 50 years for umbelliprenin), only in the last two decades the two title natural compounds were revealed to possess valuable and promising pharmacological properties as dietary feeding active cancer chemopreventive, antibacterial, anti-protozoal, anti-fungal, anti-inflammatory, neuroprotective, and anti-oxidant agents among the activities best detailed in the recent literature. The aim of this comprehensive review is to outline in detail the effects described in the very last years for auraptene and umbelliprenin and what has been reported about the mechanisms of action underlying the observed pharmacological activities of these oxyprenylated secondary metabolites. In view of the herein described data suggestions on how to address the future research about both natural products in the best ways according to Authors will be also provided.

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7-Isopentenyloxycoumarin is among the most widespread naturally occurring prenyloxy umbelliferone derivatives. This secondary metabolite of mixed biosynthetic origin has been typically isolated from plants belonging to several genera of the Rutaceae and Apiaceae families, comprising widely used medicinal plants and in general plants with beneficial effects on human welfare, as well as edible fruits and vegetables. Although known for quite a long time (more than 50 years), only in the last two decades has this natural compound been revealed to exert powerful and promising pharmacological properties, such as active cancer chemopreventive, antibacterial, antiprotozoal, antifungal, anti-inflammatory, neuroprotective, and antioxidant properties, among the activities best outlined in the recent literature. The aim of this comprehensive miniature review article is to detail the novel natural sources and the effects described during the last decade for 7-isopentenyloxycoumarin and what has been reported on the mechanisms of action underlying the observed biological activities of this oxyprenylated secondary metabolite. In view of the herein described data, suggestions on how to address future research on the abovementioned natural product and structurally related derivatives in the best ways according to the authors will be also provided.