Hydrogen sulfide mediates the vasoactivity of garlic
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 sig...
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| Published in | Proceedings of the National Academy of Sciences - PNAS Vol. 104; no. 46; pp. 17977 - 17982 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
National Academy of Sciences
13.11.2007
National Acad Sciences |
| Series | From the Cover |
| Subjects | |
| Online Access | Get full text |
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| Abstract | 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 glucose-maintained 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 α 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. |
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| AbstractList | 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 (H 2 S), an endogenous cardioprotective vascular cell signaling molecule. This H 2 S production, measured in real time by a novel polarographic H 2 S sensor, is supported by glucose-maintained cytosolic glutathione levels and is to a large extent reliant on reduced thiols in or on the RBC membrane. H 2 S 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 α carbon of the allyl substituent, thereby forming a hydropolysulfide (RS n H), a key intermediate during the formation of H 2 S. Organic polysulfides (R-S n -R′; n > 2) also undergo nucleophilic substitution at a sulfur atom, yielding RS n H and H 2 S. Intact aorta rings, under physiologically relevant oxygen levels, also metabolize garlic-derived organic polysulfides to liberate H 2 S. The vasoactivity of garlic compounds is synchronous with H 2 S production, and their potency to mediate relaxation increases with H 2 S yield, strongly supporting our hypothesis that H 2 S mediates the vasoactivity of garlic. Our results also suggest that the capacity to produce H 2 S can be used to standardize garlic dietary supplements. Allium aorta polysulfides red blood cells vasorelaxation 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 (...), an endogenous cardioprotective vascular cell signaling molecule. This ... production, measured in real time by a novel polarographic ... sensor, is supported by glucose-maintained cytosolic glutathione levels and is to a large extent reliant on reduced thiols in or on the RBC membrane. ... 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 (...), a key intermediate during the formation of ... Organic polysulfides (R-S...-R'; n > 2) also undergo nucleophilic substitution at a sulfur atom, yielding ... and ... Intact aorta rings, under physiologically relevant oxygen levels, also metabolize garlic-derived organic polysulfides to liberate ... The vasoactivity of garlic compounds is synchronous with ... production, and their potency to mediate relaxation increases with ... yield, strongly supporting our hypothesis that ... mediates the vasoactivity of garlic. Our results also suggest that the capacity to produce ... can be used to standardize garlic dietary supplements. (ProQuest: ... denotes formulae/symbols omitted.) 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 (H 2 S), an endogenous cardioprotective vascular cell signaling molecule. This H 2 S production, measured in real time by a novel polarographic H 2 S sensor, is supported by glucose-maintained cytosolic glutathione levels and is to a large extent reliant on reduced thiols in or on the RBC membrane. H 2 S 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 α carbon of the allyl substituent, thereby forming a hydropolysulfide (RS n H), a key intermediate during the formation of H 2 S. Organic polysulfides (R-S n -R′; n > 2) also undergo nucleophilic substitution at a sulfur atom, yielding RS n H and H 2 S. Intact aorta rings, under physiologically relevant oxygen levels, also metabolize garlic-derived organic polysulfides to liberate H 2 S. The vasoactivity of garlic compounds is synchronous with H 2 S production, and their potency to mediate relaxation increases with H 2 S yield, strongly supporting our hypothesis that H 2 S mediates the vasoactivity of garlic. Our results also suggest that the capacity to produce H 2 S can be used to standardize garlic dietary supplements. 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 (H(2)S), an endogenous cardioprotective vascular cell signaling molecule. This H(2)S production, measured in real time by a novel polarographic H(2)S sensor, is supported by glucose-maintained cytosolic glutathione levels and is to a large extent reliant on reduced thiols in or on the RBC membrane. H(2)S 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 alpha carbon of the allyl substituent, thereby forming a hydropolysulfide (RS(n)H), a key intermediate during the formation of H(2)S. Organic polysulfides (R-S(n)-R'; n > 2) also undergo nucleophilic substitution at a sulfur atom, yielding RS(n)H and H(2)S. Intact aorta rings, under physiologically relevant oxygen levels, also metabolize garlic-derived organic polysulfides to liberate H(2)S. The vasoactivity of garlic compounds is synchronous with H(2)S production, and their potency to mediate relaxation increases with H(2)S yield, strongly supporting our hypothesis that H(2)S mediates the vasoactivity of garlic. Our results also suggest that the capacity to produce H(2)S can be used to standardize garlic dietary supplements. 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 (H(2)S), an endogenous cardioprotective vascular cell signaling molecule. This H(2)S production, measured in real time by a novel polarographic H(2)S sensor, is supported by glucose-maintained cytosolic glutathione levels and is to a large extent reliant on reduced thiols in or on the RBC membrane. H(2)S 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 alpha carbon of the allyl substituent, thereby forming a hydropolysulfide (RS(n)H), a key intermediate during the formation of H(2)S. Organic polysulfides (R-S(n)-R'; n > 2) also undergo nucleophilic substitution at a sulfur atom, yielding RS(n)H and H(2)S. Intact aorta rings, under physiologically relevant oxygen levels, also metabolize garlic-derived organic polysulfides to liberate H(2)S. The vasoactivity of garlic compounds is synchronous with H(2)S production, and their potency to mediate relaxation increases with H(2)S yield, strongly supporting our hypothesis that H(2)S mediates the vasoactivity of garlic. Our results also suggest that the capacity to produce H(2)S can be used to standardize garlic dietary supplements.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 (H(2)S), an endogenous cardioprotective vascular cell signaling molecule. This H(2)S production, measured in real time by a novel polarographic H(2)S sensor, is supported by glucose-maintained cytosolic glutathione levels and is to a large extent reliant on reduced thiols in or on the RBC membrane. H(2)S 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 alpha carbon of the allyl substituent, thereby forming a hydropolysulfide (RS(n)H), a key intermediate during the formation of H(2)S. Organic polysulfides (R-S(n)-R'; n > 2) also undergo nucleophilic substitution at a sulfur atom, yielding RS(n)H and H(2)S. Intact aorta rings, under physiologically relevant oxygen levels, also metabolize garlic-derived organic polysulfides to liberate H(2)S. The vasoactivity of garlic compounds is synchronous with H(2)S production, and their potency to mediate relaxation increases with H(2)S yield, strongly supporting our hypothesis that H(2)S mediates the vasoactivity of garlic. Our results also suggest that the capacity to produce H(2)S can be used to standardize garlic dietary supplements. 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 glucose-maintained 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 α 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. 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 glucose-maintained 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 α carbon of the allyl substituent, thereby forming a hydropolysulfide$({\rm RS}_{{\rm n}}{\rm H})$, a key intermediate during the formation of H₂S. Organic polysulfides (${\rm R}\text{-}{\rm S}_{{\rm n}}\text{-}{\rm R}^{\prime}$; n > 2) also undergo nucleophilic substitution at a sulfur atom, yielding${\rm RS}_{{\rm n}}{\rm H}$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. |
| Author | Doeller, Jeannette E Benavides, Gloria A Isbell, T. Scott Kraus, David W Patel, Hetal D Mills, Robert W Squadrito, Giuseppe L Darley-Usmar, Victor M Patel, Rakesh P |
| Author_xml | – sequence: 1 fullname: Benavides, Gloria A – sequence: 2 fullname: Squadrito, Giuseppe L – sequence: 3 fullname: Mills, Robert W – sequence: 4 fullname: Patel, Hetal D – sequence: 5 fullname: Isbell, T. Scott – sequence: 6 fullname: Patel, Rakesh P – sequence: 7 fullname: Darley-Usmar, Victor M – sequence: 8 fullname: Doeller, Jeannette E – sequence: 9 fullname: Kraus, David W |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/17951430$$D View this record in MEDLINE/PubMed |
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| Snippet | The consumption of garlic is inversely correlated with the progression of cardiovascular disease, although the responsible mechanisms remain unclear. Here we... |
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| SubjectTerms | Acetylcysteine - pharmacology Aorta Assembly lines Biological Sciences cardioprotective effect Cardiovascular disease Cardiovascular diseases cardiovascular system Chromatography, High Pressure Liquid Coronary vessels Disulfides Electrochemistry Erythrocytes Erythrocytes - drug effects Erythrocytes - metabolism food intake Garlic Garlic - chemistry Glutathione - blood Glutathione Disulfide - blood Humans Hydrogen Hydrogen sulfide Hydrogen Sulfide - blood Hydrogen Sulfide - pharmacology metabolism organic polysulfides organic sulfur compounds Polysulfides Respirometers Risk factors Sensors Sulfides Sulfur Thiols Vasodilation |
| Title | Hydrogen sulfide mediates the vasoactivity of garlic |
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