Beta-bitter acids of hops (lupulones) revealed sedative and antidepressant-like effects in animal studies. Transformation of β-acids during beer brewing leads to the formation of tricyclic transformation products, which have a close structural analogy to hyperforin. The latter compound is responsible for the antidepressant activity of St. John's wort by activation of TRPC6 cation channels in neuronal-like cells leading to Ca influx. In this study, nortricyclolupones, dehydrotricyclolupones, and tricyclolupones were isolated from a wort-boiling model and their structures were elucidated by UHPLC-DAD, UHPLC-ESI-MS/MS and 1D/2D-NMR spectroscopy. Beta-bitter acids and their transformation products induced Ca influx in PC12 cells to the same extent as hyperforin. Application of a Ca-free environment abolished the Ca elevation, indicating that the increase is mediated by influx across the plasma membrane. Thus, activation of neuronal-like Ca-channels by lupulones and tricyclolupones represent a novel mechanism contributing to the antidepressant activity of hops.
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