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Molecules 2015, 20(1), 1731-1750; doi:10.3390/molecules20011731

Glutathione-Garlic Sulfur Conjugates: Slow Hydrogen Sulfide Releasing Agents for Therapeutic Applications

1
Department of Chemical Sciences and Technologies, University of Rome Tor Vergata, via della Ricerca Scientifica, Rome 00133, Italy
2
Department of Professional Chemistries and Pharmacognosy, University of Medicine, Tirana, Str. "Dibra", Nr. 371, Tirana 1000, Albania
*
Author to whom correspondence should be addressed.
Academic Editors: Noriyuki Nagahara and Maria Wrobel
Received: 13 December 2014 / Revised: 31 December 2014 / Accepted: 13 January 2015 / Published: 20 January 2015
(This article belongs to the Special Issue Sulfur Atom: Element for Adaptation to an Oxidative Environment)
View Full-Text   |   Download PDF [2121 KB, uploaded 20 January 2015]   |  

Abstract

Natural organosulfur compounds (OSCs) from Allium sativum L. display antioxidant and chemo-sensitization properties, including the in vitro inhibition of tumor cell proliferation through the induction of apoptosis. Garlic water- and oil-soluble allyl sulfur compounds show distinct properties and the capability to inhibit the proliferation of tumor cells. In the present study, we optimized a new protocol for the extraction of water-soluble compounds from garlic at low temperatures and the production of glutathionyl-OSC conjugates during the extraction. Spontaneously, Cys/GSH-mixed-disulfide conjugates are produced by in vivo metabolism of OSCs and represent active molecules able to affect cellular metabolism. Water-soluble extracts, with (GSGaWS) or without (GaWS) glutathione conjugates, were here produced and tested for their ability to release hydrogen sulfide (H2S), also in the presence of reductants and of thiosulfate:cyanide sulfurtransferase (TST) enzyme. Thus, the TST catalysis of the H2S-release from garlic OSCs and their conjugates has been investigated by molecular in vitro experiments. The antiproliferative properties of these extracts on the human T-cell lymphoma cell line, HuT 78, were observed and related to histone hyperacetylation and downregulation of GAPDH expression. Altogether, the results presented here pave the way for the production of a GSGaWS as new, slowly-releasing hydrogen sulfide extract for potential therapeutic applications. View Full-Text
Keywords: garlic; hydrogen sulfide; allyl sulfur compounds; sulfurtransferase; tumor cells; extraction; sulfur conjugates garlic; hydrogen sulfide; allyl sulfur compounds; sulfurtransferase; tumor cells; extraction; sulfur conjugates
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bhuiyan, A.I.; Papajani, V.T.; Paci, M.; Melino, S. Glutathione-Garlic Sulfur Conjugates: Slow Hydrogen Sulfide Releasing Agents for Therapeutic Applications. Molecules 2015, 20, 1731-1750.

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