Monoprenylierte acylphloroglucine

Polycyclic Polyprenylated Acylphloroglucinols

“…Early labeling experiments provided evidence for a polyketide-type biosynthesis for bitter acids that involves one acyl-CoA and three malonyl-CoA units (Scheme 2). 57,81 Similarly, numerous enzymologic studies showed that the biosynthesis of acylphloroglucinols involves condensation of three molecules of malonyl-CoA and one molecule of acyl-CoA. The product, a tetraketide, is subsequently cyclized by Dieckmann condensation into an acylphloroglucinol.…”

Polyprenylated Phloroglucinols and Xanthones

“…α-Acids are responsible for the flavor and bitter taste of beer [25] while β-acids show, among other properties, free radical scavenger activity [7,26]. Labeling and enzymological experiments have provided evidence that bitter acids are biosynthesized via condensation of three malonyl-CoA and one acyl-CoA, such as isobutyryl-CoA (9) (Scheme 12.1) [27][28][29][30]. The intermediate polyketide 10 can then cyclize via an intramolecular Dieckmann condensation to produce acylphloroglucinol 11 [31,32].…”