Analysis of Molecular Species of Glycolipids in Fruit Pastes of Red Bell Pepper (Capsicum annuum L.) by High-Performance Liquid Chromatography−Mass Spectrometry

Abstract

Five major glycolipid classes (acylated steryl glucoside, steryl glucoside, monogalactosyldiacylglycerol, digalactosyldiacylglycerol, and glucocerebroside) from fruit pastes of red bell pepper were separated by silica gel column chromatography. The molecular species of each glycolipid were separated and characterized by reversed-phase high-performance liquid chromatography coupled with on-line mass spectrometry using atmospheric pressure chemical ionization. The molecular species of steryl glucoside were beta-sitosteryl and campesteryl glucosides, and those of the acylated steryl glucoside were their fatty acid esters. The dilinolenoyl species was predominant in monogalactosyldiacylglycerol in addition to small amounts of another five molecular species, whereas digalactosyldiacylglycerol consisted of seven molecular species varying in their degree of unsaturation. The glucocerebroside class contained at least seven molecular species, which were characterized by proton nuclear magnetic resonance spectroscopy.

<i>Drymaria cordata</i> (Linn.) Willd (Caryophyllaceae): Ethnobotany, Pharmacology and Phytochemistry

“…This chemical composition is quite close to that of the red Bell Pepper (Capsicum annuum) [26]. Edible plant glycolipids are believed to play a role in human diet as nutrients.…”

Bioassay directed isolation of a novel anti-inflammatory cerebroside from the leaves of Aerva sanguinolenta

“…The general features of the 1 H and 13 C NMR spectra containing typical peaks for a b-glucoside (d H 4.94,d,J = 7.8 Hz;d C 62.9,71.8,75.5,78.8,78.9,105.9), an amide (d C 176.0, d H 8.58d), and several other oxygenated (d C 70.8, 72.7(2), 76.2) or N-substituted (d C 52.0) carbon atoms besides a di-substituted double bond (d C 131.0, 131.2; d H 5.52 m) and long-chain aliphatic moieties (d C 14.6-35.9) suggest the possible identification of this molecule as a cerebroside. The molecular formula deduced from the above Mass and NMR spectral data was already reported for a constituent of Capsicum annuum L. by Yamauchi et al (2001) and of several Euphorbia species by Cateni et al (2003aCateni et al ( , b, 2008. But our sample (ASE-1) showed typical peaks for the allylic carbons of a 'trans' olefin rather than 'cis' (d C 33-34 ppm and not 27-28 ppm).…”

Generic Characterization of Apolar Metabolites in Red Chili Peppers (Capsicum frutescens L.) by Orbitrap Mass Spectrometry.

“…Yamauchi et al 9 previously reported the detection of free phytosterols and phytosterol glucoside derivatives in chili pepper by performing consecutive prefractionations before analysis. During this study, a single generic sample preparation protocol was applied to extract all of the compounds reported in this paper.…”

“…The fatty acid moieties that were found to be part of the galactosyldiacylglycerol lipids consisted of C18:3, C18:2, C18:1, C18:0, C16:3, C16:2, C16:1, and C16:0, which corresponds with previous findings. 9 Relative abundances were calculated for the monogalactosyldiacylglycerol and digalactosyldiacylglycerol families with the acetate adducts obtained in negative APCI mode. Monogalactosyldiacylglycerol (18:3/18:3), digalactosyldiacylglycerol (18:3/18:3), digalactosyldiacylglycerol (18:3/16:0), and digalactosyldiacylglycerol (18:3/18:0) were the most abundant galactosyl diacylglycerol lipids present in the chili pepper accessions, as previously found.…”