Isolation and Identification of a New Cysteine Sulfoxide and Volatile Sulfur Compounds from Allium Subgenus Melanocrommyum

Journal of Agricultural and Food Chemistry
2010.0

Abstract

A new cysteine sulfoxide containing a pyridyl residue was identified in bulbs of Allium L. species belonging to the subgenus Melanocrommyum section Megaloprason. One of these species, Allium stipitatum, is widely used as a crop plant and in folk medicine in Central Asia. The new cysteine sulfoxide was identified as L-(+)-S-(2-pyridyl)-cysteine sulfoxide. Aside from this cysteine sulfoxide, several pyridyl compounds could be identified, which were formed out of cysteine sulfoxides by the action of alliinase. Found cysteine sulfoxides and their metabolites are chemically unstable; thus, the analysis is rather difficult. By combining high-performance liquid chromatography (HPLC), HPLC tandem mass spectrometry, NMR, IR, and photometric methods, full structure elucidation of the cysteine sulfoxide was possible. Alliinase reaction products were mainly determined by various MS techniques. The achieved results give new insights in the chemistry of Allium crop plants and are probably useful for chemotaxonomical classification of the subgenus Melanocrommyum.

Knowledge Graph

Similar Paper

Isolation and Identification of a New Cysteine Sulfoxide and Volatile Sulfur Compounds from <i>Allium</i> Subgenus <i>Melanocrommyum</i>
Journal of Agricultural and Food Chemistry 2010.0
Isolation and Identification of a Red Pigment from <i>Allium</i> Subgenus <i>Melanocrommyum</i>
Journal of Agricultural and Food Chemistry 2008.0
Isolation of<i>S</i>-<i>n</i>-Butylcysteine Sulfoxide and Six<i>n-</i>Butyl-Containing Thiosulfinates from<i>Allium siculum</i>
Journal of Natural Products 2002.0
Isolation ofS-n-Butylcysteine Sulfoxide and Sixn-Butyl-Containing Thiosulfinates fromAllium siculum
Journal of Natural Products 2002.0
Distribution of <i>S</i>-Alk(en)ylcysteine Sulfoxides in Some <i>Allium</i> Species. Identification of a New Flavor Precursor:  <i>S</i>-Ethylcysteine Sulfoxide (Ethiin)
Journal of Agricultural and Food Chemistry 2000.0
<i>S</i>-Alkenyl Cysteine Sulfoxide and Its Antioxidant Properties from <i>Allium cepa</i> var. <i>tropeana</i> (Red Onion) Seeds
Journal of Natural Products 2008.0
<i>S</i>-Alkenyl Cysteine Sulfoxide and Its Antioxidant Properties from <i>Allium cepa</i> var. <i>tropeana</i> (Red Onion) Seeds
Journal of Natural Products 2008.0
HPLC of<i>S</i>-Alk(en)yl-<scp>L</scp>-cysteine Derivatives in Garlic including Quantitative Determination of (+)-<i>S</i>-Allyl-<scp>L</scp>-cysteine Sulfoxide (Alliin)
Planta Medica 1989.0
Chemical Characterization of <i>Allium ursinum</i> L. Depending on Harvesting Time
Journal of Agricultural and Food Chemistry 2005.0
Cysteine sulfoxide derivatives in Petiveria alliacea
Phytochemistry 2001.0