Lactam ent-Kaurane Diterpene: A New Class of Diterpenoids Present in Roasted Beans of Coffea arabica

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.