Hyperelatosides A-E, biphenyl ether glycosides from Hypericum elatoides, with neurotrophic activityElectronic supplementary information (ESI) available: 1D NMR, 2D NMR, and HRESIMS of 1-6; chemical structures of 7-15. See DOI: 10.1039/c8ra05322g

Five new biphenyl ether glycosides, hyperelatosides A-E ( 1-5 ), one new benzoate glycoside, hyperelatoside F ( 6 ), along with nine known phenolic compounds ( 7-15 ), were isolated from the aerial parts of Hypericum elatoides . Their structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS, as well as chemical derivatization. This is the first report of the identification of biphenyl ether glycosides as plant metabolites and their possible biosynthetic pathway is proposed. Except for 3 , the new phenolic metabolites exhibited significant neurotrophic activities to enhance nerve growth factor-induced neurite outgrowth in PC12 cells. In addition, the anti-neuroinflammatory and antioxidant activities of compounds 1-15 were preliminarily evaluated in vitro . Five new biphenyl ether glycosides, hyperelatosides A-E, one new benzoate glycoside, hyperelatoside F, were isolated from Hypericum elatoides . Hyperelatosides A, B, and D-F significantly enhanced NGF-induced neurite outgrowth in PC12 cells.