Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Abstract

Prenyloxycoumarins and prenyloxyfuranocoumarins (isopentenyloxy-, geranyloxy-, linear and cyclic sesquiterpenyloxy compounds and their biosynthetic derivatives) represent a family of secondary metabolites that have been considered for years just as intermediates of other coumarin-based compounds. Only in the last two decades these secondary metabolites have been recognized as interesting and valuable biologically active natural products. Up to now more than 160 compounds have been isolated from plants mainly belonging to the families of Rutaceae and Umbelliferae, comprising common edible vegetables and fruits like lemons, oranges and grapefruits. In view of the biological activity of some natural prenyloxycoumarins, very recently syntheses of structurally related analogs aimed to establish detailed structure-activity relationships have also been carried out. Many of the isolated prenyloxy- and prenyloxy-furanocoumarins and their semisynthetic derivatives were shown to exert in vitro and in vivo remarkable anti-tumoral, anti-inflammatory and anti-viral effects. The object of this review is to examine in detail the different types of prenyloxycoumarins and prenyloxyfuranocoumarins from the chemical, phytochemical and biological point of view.

Microwave-Assisted Synthesis of Bioactive Six-Membered Heterocycles and Their Fused Analogues

“…Benzopyrones are an important class of oxygenated heterocycles, widely distributed in plants, including edible vegetables and fruits [79] and many of them have broad and interesting ranges of biological activities [80][81][82][83]. The two more important benzopyrone derivatives are the chromones and coumarins.…”

Rapid Assembly of Polycyclic Structures via Sigmatropic Rearrangement of S-Propargyl Xanthates

“…8 Chromene subunits are present in several classes of bioactive compounds and are found in numerous plants and edible vegetables. 9 Synthetic analogues are known to be pharmacologically important, having anti-fungal and anti-microbial activities. 10 Furthermore, the 1,3-dithiolen-2-one motifs in the cycloadducts are interesting in their own right, as they furnish tetrathiafulvenes upon reductive coupling with phosphines or phosphites.…”

Coumarins of Haplopappus Multifolius and Derivative as Inhibitors of Lox: Evaluation in-Vitro and Docking Studies

“…Simple prenyl coumarins like osthole are moderate and selective 5-LOX inhibitors 11 . Finally, prenylated coumarins such as auraptene 12 and umbelliprenin exhibit remarkable and potent inhibition against 15-sLOX 13 .…”