Identification of 4,5-Didemethyl-4-O-α-d-glucopyranosylsimmondsin and Pinitol α-d-Galactosides in Jojoba Seed Meal (Simmondsia chinensis)

The isolation and identification of two pinitol α-d-galactosides from jojoba meal are described. The products were isolated by a combination of preparative HPLC on silica gel and TLC on amino silica gel and were identified by MS, NMR spectroscopy, and chemical derivatization as 5-O-(α-d-galactopyranosyl)-3-O-methyl-d-chiro-inositol or 5-α-d-galactopyranosyl-d-pinitol and 2-O-(α-d-galactopyranosyl)-3-O-methyl-d-chiro-inositol or 2-α-d-galactopyranosyl-d-pinitol. The same preparative HPLC method on silica gel allowed a new simmondsin derivative to be isolated and identified as 4,5-didemethyl-4-O-α-d-glucopyranosylsimmondsin mainly by NMR spectroscopy and high-resolution mass spectrometry. Keywords: Simmondsia chinensis; jojoba meal; water soluble carbohydrates; pinitol α-d-galactosides; simmondsins