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.
Highlights
Garcinia oblongifolia Champ. ex Benth. (Clusiaceae), a tree or medium-sized shrub with edible fruits, is widely distributed in tropical regions of southern mainland China and northern Vietnam
A series of new prenylated benzoylphloroglucinols, oblongifolins J–U were isolated from the bioacitve petroleum ether-soluble part of the acetone extract of G. oblongifolia leaves by bioassay-guided fractionation, in which two compounds exhibited significant anti-EV71 activity3
In follow-up work, UPLC-photodiode-array detection (PDA)-QTOFMS-guided fractionation led to the isolation of two new prenylated xanthones, oblongixanthones D and E [1,2], six new prenylated benzoylphloroglucinol derivatives, oblongifolins V–Z [3,4,5,6,7] and oblongifolin AA [8], as well as a known compound, oblongifolin L [9] from this fraction (Fig. 1)
Summary
Garcinia oblongifolia Champ. ex Benth. (Clusiaceae), a tree or medium-sized shrub with edible fruits, is widely distributed in tropical regions of southern mainland China and northern Vietnam. The EtOAc-soluble fraction of the acetone extract of the leaves of Garcinia oblongifolia and its subfractions were analyzed by UPLC-PDA-QTOFMS in positive mode to screen and characterize potentially new compounds.
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