Flavor Precursors and Sensory-Active Sulfur Compounds in Alliaceae Species Native to South Africa and South America

Abstract

Profiles of S-substituted cysteine flavor precursors were determined in 42 Alliaceae species native to South Africa and South America. It was found that the pool of cysteine derivatives present in these plants is remarkably very simple, with S-((methylthio)methyl)cysteine 4-oxide (marasmin) being the principal flavor precursor, typically accounting for 93-100% of the pool. Out of the other cysteine derivatives, only minor quantities of methiin were present in some species. The marasmin-derived thiosulfinate marasmicin (2,4,5,7-tetrathiaoctane 4-oxide), a major sensory-active compound of the freshly disrupted plants, was isolated, and its organoleptic properties were evaluated. Furthermore, sulfur-containing volatiles formed upon boiling of these alliaceous species were studied by GC-MS. The profile of the volatiles formed was relatively simple, with 2,3,5-trithiahexane and 2,4,5,7-tetrathiaoctane being the major components. Despite the traditional belief, ingestion of the marasmin-rich plants was always accompanied by development of a strong "garlic breath". We believe that especially several Tulbaghia species deserve to attract much greater attention from the food industry thanks to their pungent garlicky taste and unusual yet pleasant alliaceous smell.

The effect of storage and processing on antimicrobial activity of Tulbaghia violacea

“…The highest levels of marasmin (1.0-1.7 mg/g fresh weight) are present in T. violacea, T. alliacea, Tulbaghia capensis, Tulbaghia natalensis, and Tulbaghia leucantha, while the other Tulbaghia species contain considerably lower amounts (typically b 0.15 mg/g fresh weight) (Kubec et al, 2013). The presented data suggest that these five marasmin-rich species could be utilized interchangeably for the treatment of microbial infections.…”

“…Marasmicin (2) was isolated from T. violacea rhizomes and purified by preparative HPLC as described by Kubec et al (2013). Allicin (4) was synthesized by oxidation of diallyl disulfide with peroxoacetic acid (0°C, 30 min, CH 2 Cl 2 ) and purified by preparative HPLC.…”

“…2). We previously isolated this compound by preparative HPLC and identified it to be marasmicin (2,4,5,7-tetrathiaoctane-4-oxide, 2) by a combination of spectroscopic methods (Kubec et al, 2002b(Kubec et al, , 2013.…”

“…When Tulbaghia tissue is disrupted, a C-S lyase present in cell vacuoles comes into contact with marasmin and catalyzes its breakdown into the thiosulfinate marasmicin (2,4,5,7-tetrathiaoctan-4-oxide, 2) analogously to the formation of allicin (4) from alliin (3) in garlic ( Fig. 1) (Kubec et al, 2002b(Kubec et al, , 2013.…”

Metabolomic Technologies for Improving the Quality of Food: Practice and Promise

“…Cruciferous crops also contain a small amount of methionine-derived or phenylalanine-derived glucosinolates. The sulfur-containing compounds resulting from the alliin-alliinase system are the result of hydrolysis of nonvolatile alkyl and alkenyl-substituted L-cysteine sulfoxides as a result of the action of the enzyme alliinase following tissue disruption (Kubec et al 2013, Mithen 2006. Tissue disruption and the resulting enzymatic activity produce a large number of sensory-active alliaceous compounds.…”