title: UPLC-PDA-QTOFMS-guided isolation of prenylated xanthones and benzoylphloroglucinols from the leaves of Garcinia oblongifolia and their migration-inhibitory activity.
abstract: A UPLC-PDA-QTOFMS-guided isolation strategy was employed to screen and track potentially new compounds from Garcinia oblongifolia. As a result, two new prenylated xanthones, oblongixanthones D and E (1-2), six new prenylated benzoylphloroglucinol derivatives, oblongifolins V-Z (3-7) and oblongifolin AA (8), as well as a known compound oblongifolin L (9), were isolated from the EtOAc-soluble fraction of an acetone extract of the leaves of Garcinia oblongifolia guided by UPLC-PDA-QTOFMS analysis. The structures of the new compounds were elucidated by 1D- and 2D-NMR spectroscopic analysis and mass spectrometry. Experimental and calculated ECD spectra were used to determine the absolute configurations. The results of wound healing and transwell migration assay showed that oblongixanthones D (1), E (2), and oblongifolin L (9) have the ability to inhibit cancer cell migration in lower cytotoxic concentrations. Western blotting results showed that these compounds exhibited an anti-metastasis effect mainly through downregulating RAF protein levels. In addition, 2 and 9 could inhibit phospho-MEK and phospho-ERK at downstream. Moreover, 1, 2, and 9 could inhibit snail protein level, suggesting that they could regulate the EMT pathway.
authors: School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P.R. China.|Engineering Research Centre of Shanghai Colleges for TCM New Drug Discovery, Shanghai, 201203, P.R. China.
authors: Hong
authors: H
authors: Zhang
authors: School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P.R. China.
authors: Dan
authors: D
authors: Zheng
authors: School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P.R. China.
authors: Zhi-Jie
authors: ZJ
authors: Ding
authors: School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P.R. China.|Engineering Research Centre of Shanghai Colleges for TCM New Drug Discovery, Shanghai, 201203, P.R. China.
authors: Yuan-Zhi
authors: YZ
authors: Lao
authors: School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P.R. China.|Engineering Research Centre of Shanghai Colleges for TCM New Drug Discovery, Shanghai, 201203, P.R. China.
authors: Hong-Sheng
authors: HS
authors: Tan
authors: School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, P.R. China.|Engineering Research Centre of Shanghai Colleges for TCM New Drug Discovery, Shanghai, 201203, P.R. China.
authors: Hong-Xi
authors: HX
authors: Xu
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002464:Cell Migration Inhibition / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D004354:Drug Screening Assays, Antitumor; D058750:Epithelial-Mesenchymal Transition / Q000187:drug effects; D029760:Garcinia / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D020935:MAP Kinase Signaling System / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D018515:Plant Leaves / Q000737:chemistry; D054876:Prenylation; D021241:Spectrometry, Mass, Electrospray Ionization; D044004:Xanthones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D044004:Xanthones; D010696:Phloroglucinol