Hepatic metabolism of diallyl disulphide in rat and man

  title={Hepatic metabolism of diallyl disulphide in rat and man},
  author={Eric Germain and Jo{\"e}lle Chevalier and M. H. Siess and Caroline Teyssier},
  pages={1185 - 1199}
1. The metabolism of diallyl disulphide was investigated in vitro with rat and human liver cell subfractions and ex vivo with an isolated perfused rat liver. 2. Diallyl disulphide was oxidized to diallylthiosulphinate by rat liver microsomes with an apparent Km = 0.86 ± 0.1 mM and an apparent Vmax = 0.47 ± 0.12 nmol min−1 mg−1 protein (mean ± SE). Both cytochrome P450 (CYP) and flavin-containing monooxygenases were involved, with CYP2B1/2 and CYP2E1 being the most active CYP enzymes. 3. In rat… 

Disposition and metabolism of dipropyl disulphide in vivo in rat

The metabolism of dipropyl disulphide, a sulphur compound from onion, was investigated in vivo in the rat by gas chromatography coupled with mass spectrometry in the stomach, intestine, liver, and blood and MPSO2 was the most abundant and persistent of these metabolites.

Metabolism and pharmacokinetics studies of allyl methyl disulfide in rats

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  • Chemistry, Biology
    Xenobiotica; the fate of foreign compounds in biological systems
  • 2019
The transformation mechanism study indicated that AMDS was firstly reduced to allyl mercaptan (AM) in rat erythrocytes, and then methylated toallyl methyl sulfide (AMS) by S-adenosylmethionine (SAM) and S- adenosylhomocysteine (SAH), and finally oxidized to AMSO and AMSO2 by liver microsomes.

Metabolism of Bis(4-fluorobenzyl)trisulfide and Its Formation of Hemoglobin Adduct in Rat Erythrocytes

BFBTS was unstable when it met with thiols, and RBCs were the main site of BFBTS metabolism, and Hb adducts induced by BFB TS could be detected in vitro at high concentration but not in vivo even at high dose.

Cysteine and glutathione mixed-disulfide conjugates of thiosulfinates: chemical synthesis and biological activities.

The prepared conjugates were found to be able to induce quinone reductase (QR) in murine hepatoma cells and to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells, indicating they have potential cancer preventive and anti-inflammatory activities.

Hydrogen sulfide mediates the vasoactivity of garlic

It is shown that human RBCs convert garlic-derived organic polysulfides into hydrogen sulfide (H2S), an endogenous cardioprotective vascular cell signaling molecule, strongly supporting the hypothesis that H2S mediates the vasoactivity of garlic.

A tissue homogenate method to prepare gram-scale Allium thiosulfinates and their disulfide conjugates with cysteine and glutathione.

A simple enzymatic method using Allium tissue homogenates as a reaction system to prepare gram-scale TS, including those enriched in 1-propenyl groups, which are particularly difficult to obtain.

S-alk(en)ylmercaptocysteine: chemical synthesis, biological activities, and redox-related mechanism.

The inhibitory effects of GSH and NAC on the biological activities of CySSR were correlated with a glutaredoxin-dependent intracellular reduction of Cy SSR to generate cysteine and RSH, which were secreted into the extracellular medium.

Diallyl Disulfide-Induced Modulation of a Few Phase I and II Drug Metabolizing Enzymes on Aroclor 1254 Toxicity in Rattus norvegicus Liver and Ventral Prostate

Results suggest that PCBs can be readily metabolized by DADS administration through enhancing phase II enzymes thereby it reduces the toxic effects.

Oxidative species and S‐glutathionyl conjugates in the apoptosis induction by allyl thiosulfate

The studies show that sodium 2‐propenyl‐thiosulfate reacts spontaneously with reduced glutathione at physiological pH, leading to the formation of S‐allyl‐mercapto‐glutathione, radicals and peroxyl species, which are able to induce inhibition of enzymes with cysteine in the catalytic site, such as sulfurtransferases.

Heme oxygenase-1 as a potential therapeutic target for hepatoprotection.

It is interesting to note that induction of HO-1 expression contributes to protection against liver damage induced by several chemical compounds such as acetaminophen, carbon tetrachloride and heavy metals, suggestingHO-1 induction as an important cellular endeavor for hepatoprotection.



In vivo metabolism of diallyl disulphide in the rat: identification of two new metabolites

The aim was to identify and analyse the metabolites produced in vivo after a single oral administration of 200 mg kg -1 DADS to rats, and data indicate that DADS is absorbed and transformed into allyl mercaptan, allyl methyl sulphide, allYL methyl sulphoxide and allylmethyl sulphone, which are detected throughout the excretion period.

Modification of hepatic drug-metabolizing enzymes in rat fed naturally occurring allyl sulphides.

1. The effects of feeding allyl sulphides to rat (2000 ppm of the diet for 15 days) were investigated on various microsomal hepatic drug-metabolizing enzymes by their immunochemical detection and

Metabolism of dipropyl disulfide by rat liver phase I and phase II enzymes and by isolated perfused rat liver.

  • C. TeyssierM. Siess
  • Biology, Chemistry
    Drug metabolism and disposition: the biological fate of chemicals
  • 2000
The metabolism of dipropyl disulfide (DPDS), an Allium sulfur compound, was investigated in rat liver cell subfractions and in an isolated perfused rat liver, and the action of phase II enzymes on DPDS metabolism was studied by incubating DPDS or DPDSO with liver cytosols or microsomes.

Metabolites of diallyl disulfide and diallyl sulfide in primary rat hepatocytes.

  • L. SheenC. C. WuC. LiiS. Tsai
  • Medicine, Biology
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association
  • 1999

Metabolism of ethyl methyl sulphide and sulphoxide in rat microsomal fractions.

  • I. NnaneL. Damani
  • Chemistry, Biology
    Xenobiotica; the fate of foreign compounds in biological systems
  • 1999
1. Gas chromatographic (GC) methods for the analysis of ethyl methyl sulphide (EMS) and its corresponding sulphoxide (EMSO) and sulphone (EMSO2) in rat microsomes and aspects of the in vitro

Cytochrome P450 mediated bioactivation of methyleugenol to 1'-hydroxymethyleugenol in Fischer 344 rat and human liver microsomes.

The rate of 1'-hydroxylation of methyleugenol in vitro in 13 human liver samples varied markedly (by 37-fold), with the highest activities being similar to the activity evident in control rat liver microsomes, which suggests that the risk posed by dietary ingestion of methylesugenol could vary markedly in the human population.

Metabolism of garlic constituents in the isolated perfused rat liver.

Diallyl disulfide and allyl mercaptan were identified as metabolites of allicin, whereby diallyl Disulfide probably is the metabolic precursor of allyl Mercaptan as shown by perfusion with dially l disulfides alone.


The present paper gives a detailed account of the investigations on rabbit liver microsomes and crude microsomal digests, which have led to postulate the hemoprotein nature of the pigment.