Identification of 4,5-didemethyl-4-O-alpha-D-glucopyranosylsimmondsin and pinitol alpha-D-galactosides in jojoba seed meal (Simmondsia chinensis).
The isolation and identification of two pinitol alpha-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-(alpha-D-galactopyranosyl)-3-O-methyl-D-chiro-inositol or 5-alpha-D-galactopyranosyl-D-pinitol and 2-O-(alpha-D-galactopyranosyl)-3-O-methyl-D-chiro-inositol or 2-alpha-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-alpha-D-glucopyranosylsimmondsin mainly by NMR spectroscopy and high-resolution mass spectrometry.
Van Boven
M
M
Laboratory of Toxicology and Food Chemistry, Katholieke Universiteit Leuven, Van Evenstraat 4, B-3000 Leuven, Belgium. maurits.vanboven@farm.kuleuven.ac.be
Leyssen
T
T
Busson
R
R
Holser
R
R
Cokelaere
M
M
Flo
G
G
Decuypere
E
E
D000097:Acetonitriles / Q000032:analysis / Q000302:isolation & purification; D000821:Animal Feed / Q000032:analysis*; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003510:Cyclohexanes; D005697:Galactosides / Q000032:analysis / Q000302:isolation & purification*; D005960:Glucosides / Q000032:analysis / Q000302:isolation & purification; D006131:Growth Inhibitors / Q000032:analysis / Q000302:isolation & purification*; D007294:Inositol / Q000031:analogs & derivatives / Q000032:analysis / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D058428:Silica Gel; D012822:Silicon Dioxide; D014885:Waxes / Q000737:chemistry*
D000097:Acetonitriles; D003510:Cyclohexanes; D005697:Galactosides; D005960:Glucosides; D006131:Growth Inhibitors; D014885:Waxes; C021730:pinitol; D007294:Inositol; D058428:Silica Gel; C034743:jojoba wax; D012822:Silicon Dioxide; C089377:simmondsin