Glycosyl glycerides from the aerial parts of Malva verticillata and their chemopreventive effects

[Display omitted] •A new glycosyl glyceride and 12 known ones were isolated from Malva verticillata.•1 and 2 contained a unique sugar, (6-deoxy-6-sulfo)-α-d-glucopyranose.•1 and 2 have never been isolated from natural sources.•Structure of 1 and 2 was determined using NMR experiment for the first time.•Some compounds showed cytotoxicity and apoptosis on human cancer cells. A new glycosyl glyceride (5) along with twelve known ones (1–4 and 6–13) including two sulfoquinovosyl glycerides (1 and 2) were isolated from the aerial parts of Malva verticillata. Based on several spectroscopic methods, compound 5 was identified to be (2S)-1-O-β-d-galactopyranosyl-3-O-isostearoyl glyceride, and named malvaglycolipid A. Compounds 1 and 2 contained a unique sugar, (6-deoxy-6-sulfo)-α-d-glucopyranose, which very rarely occurs in natural sources. This is the first report for the isolation of compounds 1 and 2 from natural sources and the structure determination using NMR experiment. It was also of note that no glycosyl glyceride has previously been isolated from the family of Malvaeae. Most glycosyl glycerides showed cytotoxicity to HepG2, AGS, HCT-15, and A549 human cancer cells. Especially, compounds 1, 2, and 11 exhibited significant cytotoxicity to AGS cells, with IC50 values of 33.7 ± 0.64 μM, 11.1 ± 0.07 μM, and 10.6 ± 0.10 μM, respectively. The n-BuOH fraction and compounds 1, 2, and 11 increased the number of apoptotic cells in the Tali assay and had a significant effect on the levels of proteins related to apoptosis including PARP, caspase-3, Bcl-2, Bax, and β-actin.