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

Ten phenolic constituents, including three new macrocyclic glycosides (-), a new phenolic glycoside (), a new biphenyl glycoside (), and five known compounds (, -), were isolated from a 70% MeOH extract of the leaves of by liquid chromatography-tandem mass spectrometry (LC-MS/MS)-guided molecular networking. The chemical structures of new compounds -, and were established based on comprehensive spectroscopic data analysis, including 1D and 2D NMR and HRESIMS techniques. All isolated compounds (-) 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 , and showed stimulatory effects on the uptake of 2-NBDG in 3T3-L1 adipocyte cells. Among them, compounds and activated the AMPK signaling pathway in differentiated C2C12 myoblasts.