Seven new lactam ent-kaurane diterpenoids, cafemides
A–G (1–7), were isolated from
roasted beans of Coffea arabica. Their structures
were elucidated by extensive spectroscopic analysis including 1D,
2D NMR (heteronuclear single quantum correlation (HSQC), heteronuclear
multiple bond correlation (HMBC), 1H–1H correlation spectroscopy (COSY), and rotating frame Overhauser
effect spectroscopy (ROESY)), high-resolution electrospray ionization
mass spectrometry (HRESIMS), and IR spectra. They were divided into
subtype I–III according to the structure. Further, with the
aid of liquid chromatography–tandem mass spectrometry (LC–MS/MS)
based molecular network, seven (8–14) subtype II diterpenoids were successfully identified. In addition,
a variety of other subtypes of N-containing diterpenoids have been
proven in roasted coffee. Compounds 1, 2, 3, 5, and 7 showed a moderate
inhibitory effect on α-glucosidase with an IC50 value
of 8.28 ± 0.62 μM, 38.23 ± 8.87 μM, 28.94 ±
1.42 μM, 12.44 ± 1.37 μM, and 22.2 ± 5.34 μM,
respectively. To the best of our knowledge, this is the first time
that N-containing diterpenoids have been reported in coffee.