Comparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and Phase 2 enzyme induction in vivo

Munday, Rex; Munday, John S.; Munday, Christine M.

doi:10.1016/s0891-5849(03)00144-8

Cited by 126 publications

(107 citation statements)

References 54 publications

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“…2 for chemical structures). A similar structure-activity correlation has been observed for the cancer-preventative effects of garlicderived organic polysulfides (25,26). The facile formation of H 2 S from the reaction of DADS with GSH indicates that this reaction proceeds at least in part by a different mechanism from the more common thiol/disulfide exchange because the exchange reaction does not produce H 2 S (Fig.…”

Section: Discussionsupporting

confidence: 70%

Hydrogen sulfide mediates the vasoactivity of garlic

Benavides

Squadrito

Mills

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

759

647

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The consumption of garlic is inversely correlated with the progression of cardiovascular disease, although the responsible mechanisms remain unclear. Here we show that human RBCs convert garlic-derived organic polysulfides into hydrogen sulfide (H2S), an endogenous cardioprotective vascular cell signaling molecule. This H2S production, measured in real time by a novel polarographic H2S sensor, is supported by glucosemaintained cytosolic glutathione levels and is to a large extent reliant on reduced thiols in or on the RBC membrane. H2S production from organic polysulfides is facilitated by allyl substituents and by increasing numbers of tethering sulfur atoms. Allyl-substituted polysulfides undergo nucleophilic substitution at the ␣ carbon of the allyl substituent, thereby forming a hydropolysulfide (RSnH), a key intermediate during the formation of H2S. Organic polysulfides (R-Sn-R; n > 2) also undergo nucleophilic substitution at a sulfur atom, yielding RSnH and H2S. Intact aorta rings, under physiologically relevant oxygen levels, also metabolize garlic-derived organic polysulfides to liberate H2S. The vasoactivity of garlic compounds is synchronous with H2S production, and their potency to mediate relaxation increases with H2S yield, strongly supporting our hypothesis that H2S mediates the vasoactivity of garlic. Our results also suggest that the capacity to produce H2S can be used to standardize garlic dietary supplements.Allium ͉ aorta ͉ polysulfides ͉ red blood cells ͉ vasorelaxation

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Section: Discussionsupporting

confidence: 70%

Hydrogen sulfide mediates the vasoactivity of garlic

Benavides

Squadrito

Mills

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

759

647

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“…Some authors have suggested a direct effect of naringenin (the aglycone fraction of naringin), which can chelate the ferrous ion needed to form the central core of the haemoglobin, making it unavailable (Gnanamani et al, 2008;Renugadevi and Milton Prabu, 2009). Other authors, with similar results after feeding flavonoids to animals, have suggested a lipoperoxidation of blood cell membranes resulting in haemolysis and removal of damaged erythrocytes by the cells of the reticulo-endothelial system (Munday et al, 2003;Ostrowska et al, 2004). Nevertheless, in this study, the lack of significant differences in plasma Fe values and MCHC do not support the idea that naringin may cause haemolysis.…”

Section: Antioxidant Parameterscontrasting

confidence: 79%

Naringin dietary supplementation at 0.15% rates does not provide protection against sub-clinical acidosis and does not affect the responses of fattening lambs to road transportation

López-Campos

Bodas

Prieto

et al. 2010

Animal

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Forty Assaf fattening lambs (initial age 13 to 15 weeks) offered a diet of barley straw and a commercial concentrate were used to assess the effect of naringin (a type of citrus flavonoid with proven antioxidant, antimicrobial and anti-inflammatory properties in monogastric animals) at a dose of 1.5 g/kg per dry matteron plasma lipid peroxidation thiobarbituric acid reactive substances (TBARS), immune response, ruminal bacterial community and protection provided by the ruminal wall against subclinical acidosis. After 49 days of the experimental diets, lambs were subjected to a 4-h transportation stress period. As expected, TBARS values were significantly increased in all the lambs just after the transportation period, but no effect of naringin was observed. Although naringin lowered red blood cell count, neither the total white blood cells counts nor the production of IFN-g were affected by naringin. No anti-inflammation activity preventing rumenitis was detected, but a clear effect on ruminal bacterial community was observed in lambs consuming naringin. Further experiments, using different doses of naringin might show health benefits of naringin supplementation in lambs, but a clear beneficial effect on health was not readily apparent in this study.

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“…Din-propyl-disulphide (H 7 C 3 S 2 C 3 H 7 ) and allyl propyl disulphide (H 5 C 3 S 2 C 3 H 7 ) have been implicated in onion-induced haemolytic anaemia (Kay, 1983;Fenwick and Hanley, 1985;Houston and Myers, 1993;Gault et al, 1995;Talcott, 2004;Sebastian, 2007) but, recently, more active oxidizing sulphur-containing compounds have been discovered and proposed as causative agents, either in onion (Munday et al, 2003) or in garlic (Yamato et al, 2003) poisoning episodes. The susceptibility to onion intoxication depends on several factors (Talcott, 2004), the hereditary condition resulting in erythrocytes with high concentrations of reduced glutathione and potassium probably being the most studied (Yamato and Maede, 1992;Yamato et al, 1999).…”

Section: Discussionmentioning

confidence: 99%

Heinz body anaemia in two dogs after Catalan spring onion ("calcot") ingestion: a case report

Guitart¹,

Mateu²,

Agullo³

et al. 2008

Vet. Med. - Czech

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Catalan spring onions, or "calcots", are a very popular kind of vegetables obtained by special agronomic practices that avoid photosynthesis and subsequent metabolism by the Allium cepa plants. They have been considered for more than a century harmless for pets, as pleasant odour and sweet taste differ so largely from any other onion that can be ingested by children and adults in huge quantities, up to ~3% body weight, without problems being observed. However, the organosulphur chemicals responsible for oxidative damage to canine red blood cells found in this plant species seem to remain present, as two dogs were confirmed to be poisoned after eating left-over "calcots". Both patients presented haemolytic anaemia with Heinz body formation, and eccentrocytosis. Veterinarians and owners should be aware of the dangers associated with this particular onion variety and type, as it is highly palatable to pets and no effective treatment is currently available.

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Comparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and Phase 2 enzyme induction in vivo

Cited by 126 publications

References 54 publications

Hydrogen sulfide mediates the vasoactivity of garlic

Hydrogen sulfide mediates the vasoactivity of garlic

Naringin dietary supplementation at 0.15% rates does not provide protection against sub-clinical acidosis and does not affect the responses of fattening lambs to road transportation

Heinz body anaemia in two dogs after Catalan spring onion ("calcot") ingestion: a case report

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