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

Seven new lactam -kaurane diterpenoids, cafemides A-G ( - ), were isolated from roasted beans of . Their structures were elucidated by extensive spectroscopic analysis including 1D, 2D NMR (heteronuclear single quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), H- H correlat...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2020-06, Vol.68 (22), p.6112-6121
Main Authors: Hu, Gui-Lin, Gao, Ya, Peng, Xing-Rong, Liu, Jun-Hong, Su, Hai-Guo, Huang, Yan-Jie, Qiu, Ming-Hua
Format: Article
Language:English
Subjects:
Chromatography, Liquid
Coffea - chemistry
Diterpenes, Kaurane - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Plant Extracts - chemistry
Seeds - chemistry
Tandem Mass Spectrometry
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Summary:Seven new lactam -kaurane diterpenoids, cafemides A-G ( - ), were isolated from roasted beans of . Their structures were elucidated by extensive spectroscopic analysis including 1D, 2D NMR (heteronuclear single quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), H- H 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 ( - ) subtype II diterpenoids were successfully identified. In addition, a variety of other subtypes of N-containing diterpenoids have been proven in roasted coffee. Compounds , , , , and showed a moderate inhibitory effect on α-glucosidase with an IC 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.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.9b08149