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乳清 - 贝壳杉烷二萜:存在于烘烤咖啡豆中的新一类二萜类化合物。

Lactam -Kaurane Diterpene: A New Class of Diterpenoids Present in Roasted Beans of .

机构信息

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, People's Republic of China.

University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.

出版信息

J Agric Food Chem. 2020 Jun 3;68(22):6112-6121. doi: 10.1021/acs.jafc.9b08149. Epub 2020 May 18.

Abstract

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.

摘要

从烘烤咖啡豆中分离得到了 7 个新的内酰胺-贝壳杉烷二萜类化合物 cafemides A-G(-)。通过广泛的光谱分析,包括 1D、2D NMR(异核单量子相关 (HSQC)、异核多键相关 (HMBC)、H-H 相关光谱 (COSY) 和旋转框架 Overhauser 效应光谱 (ROESY))、高分辨电喷雾电离质谱 (HRESIMS) 和红外光谱,阐明了它们的结构。根据结构将它们分为亚型 I-III。此外,借助基于液相色谱-串联质谱 (LC-MS/MS) 的分子网络,成功鉴定了 7 种 (-) 亚型 II 二萜类化合物。此外,已证明在烘烤咖啡中存在多种其他含氮二萜类化合物。化合物 、 、 、 、和 对 α-葡萄糖苷酶表现出中等抑制作用,IC 值分别为 8.28 ± 0.62 μM、38.23 ± 8.87 μM、28.94 ± 1.42 μM、12.44 ± 1.37 μM 和 22.2 ± 5.34 μM。据我们所知,这是首次在咖啡中报道含氮二萜类化合物。

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