A novel cyclopropyl-containing fatty acid glucoside from the seeds of Litchi chinensis

3,12-Dihydroxy-cis-3,4-methylenedodecanoic acid 3-O-β-d-glucopyranoside, trivially named litchioside C (1), the first cyclopropyl-containing fatty acid glycoside, was isolated along with three previously uncharacterized galactosylacylglycerols from the seeds of Litchi chinensis. Its structure was established on the basis of spectroscopic analysis including HRESIMS and 2D NMR spectra. Its antioxidant and antibacterial activities were evaluated and its biogenetic pathway was discussed.

Graphical AbstractLitchioside C (1), the first cyclopropyl-containing fatty acid glycoside, together with (2S)-1-O-(9Z,12Z-octadecadienoyl)-3-O-β-d-galactopyranosylglycerol (2), (2S)-1-O-hexadecanoyl-3-O-[α-d-galactopyranosyl(1→6)-β-d-galactopyranosyl]glycerol (3), and gingerglycolipid C (4) was isolated from the seeds of Litchi chinensis for the first time. Compounds 1–4 showed weak antioxidant activity in ferric reducing antioxidant power (FRAP) assay.Figure optionsDownload full-size imageDownload as PowerPoint slide