Heliciopsides A-E, Unusual Macrocyclic and Phenolic Glycosides from the Leaves of Heliciopsis terminalis and Their Stimulation of Glucose Uptake

从Heliciopsis terminalis叶片中分离得到的Heliciopsis AE、不寻常的大环酚类糖苷及其对葡萄糖吸收的刺激作用

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Abstract

Ten phenolic constituents, including three new macrocyclic glycosides (1-3), a new phenolic glycoside (5), a new biphenyl glycoside (6), and five known compounds (4, 7-10), were isolated from a 70% MeOH extract of the leaves of Heliciopsis terminalis by liquid chromatography-tandem mass spectrometry (LC-MS/MS)-guided molecular networking. The chemical structures of new compounds 1-3, 5 and 6 were established based on comprehensive spectroscopic data analysis, including 1D and 2D NMR and HRESIMS techniques. All isolated compounds (1-10) were evaluated for their stimulation of glucose uptake in differentiated 3T3-L1 adipocytes using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-d-glucose (2-NBDG) as a fluorescent glucose analog. Compounds 3, 6 and 8 showed stimulatory effects on the uptake of 2-NBDG in 3T3-L1 adipocyte cells. Among them, compounds 3 and 6 activated the AMPK signaling pathway in differentiated C2C12 myoblasts.

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