A 2H-NMR analysis of 6α-hydroxy-3-oxo-pinguis-5(10)-ene-11,6-olide produced by axenic culture of liverwort Aneura pinguis in the presence of [4-2H2]-labeled mevalonate clarified the presence of a 1,2-hydride shift and retention of deuterium at the C-4 position in the biosynthesis of pinguisane-type sesquiterpenes from FPP.
