Six new prenylated acylphloroglucinols
with menthane moieties,
hypascyrins A–E (1–5) and ent-hyphenrone J (6), together with four known
analogues, were isolated from Hypericum ascyron roots.
Detailed spectroscopic data analyses resulted in the assignment of
their structures. The absolute configuration of 1 was
deduced by experimental and calculated ECD data, while those of 2–6 were assigned by ECD data analyses
as well as chemical conversions. Hypascyrins A (1), C
(3), and E (5) and ent-hyphenrone
J (6) exhibited antimicrobial activity against MRSA (MIC50 values of 4.0, 8.0, 2.0, and 4.0 μM, respectively)
and Bacillus subtilis (MIC values of 4.0, 4.0, 2.0,
and 4.0 μM, respectively).