Über Alliin, die genuine Muttersubstanz des Knoblauchöls. 1. Mitteilung über Allium‐Substanzen

Stoll, A.; Seebeck, E.

doi:10.1002/hlca.19480310140

Cited by 168 publications

(22 citation statements)

References 14 publications

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“…All other chemicals and reagents were of the highest quality commercially available. NASAC was synthesized as described by Stoll and Seebeck (1948). Briefly, SAC (0.7 mmol) was dissolved in 2.8-ml ice-cold 1N NaOH and placed on ice.…”

Section: Methodsmentioning

confidence: 99%

Sulfoxides as Urinary Metabolites ofS-Allyl-l-Cysteine in Rats: Evidence for the Involvement of Flavin-Containing Monooxygenases

Krause¹,

Glocke²,

Elfarra³

2002

Drug Metab Dispos

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ABSTRACT:S-Allyl-L-cysteine (SAC), a component of garlic and a metabolite of allyl halides, is a known substrate for multiple flavin-containing monooxygenases (FMOs). In the current study, we characterize the in vivo SAC metabolism by investigating the presence of SAC, N-acetyl-S-allyl-L-cysteine (NASAC), and their corresponding sulfoxides in the urine of rats given SAC (200 or 400 mg/kg i.p.). In some experiments, rats were given aminooxyacetic acid (AOAA), an inhibitor of cysteine conjugate ␤-lyase, or methimazole, an alternative FMO substrate, 30 min prior to treatment with 200 mg/kg SAC. Nearly 40 to 50% of the dose was recovered in the 24-h collection period. In all treatment groups, the majority of the metabolites were excreted within 8 h. The major metabolites detected were NASAC and NASAC sulfoxide (NASACS; nearly 30-40% and 5-10% of the dose, respectively). Only small amounts of the dose (approximately 1.5%) were recovered as SAC and SAC sulfoxide (SACS). Methimazole pretreatment significantly reduced amounts of both SACS and NASACS detected in the urine when compared with rats given SAC only, whereas AOAA pretreatment had no effect. In vitro assays using rat liver microsomes were also carried out to compare the sulfoxidation rates of SAC and NASAC. The results showed that SAC was much more readily oxidized than NASAC. Collectively, the results provide evidence for the involvement of FMOs in the in vivo metabolism of SAC and that SAC is a much better substrate for FMOs than its corresponding mercapturic acid. (SAC 1 ) is a significant water-soluble allyl sulfur component in garlic preparations (Weinberg et al., 1993), a component which has been shown to have antioxidant and anticancer properties in animals (Sumiyoshi and Wargovich, 1990;Hatono et al., 1996;Ho et al., 2001). SAC has been shown to have antiproliferative effects on neuroblastoma (Welch et al., 1992), melanoma (Takeyama et al., 1993), and prostate carcinoma cells (Pinto et al., 1997). However, the mechanisms of the anticancer properties of SAC are unclear. S-Allyl-L-cysteineSAC is also a known metabolite of allyl halides and allyl esters, including allyl chloride, allyl bromide, sodium allyl sulfate, and allyl nitrate (Kaye et al., 1972;Kaye, 1973). It results from the formation of the glutathione conjugate of the allyl halide or ester. The glutamate and glycine moieties of S-allyl-glutathione are then cleaved by ␥-glutamyl transpeptidase and dipeptidases to yield SAC.Our laboratory has previously shown that SAC is a substrate for multiple rabbit and human flavin-containing monooxygenases (FMOs). FMOs are microsomal enzymes that catalyze the NADPHdependent oxidation of many compounds that contain sulfur, nitrogen, selenium, and phosphorus (Ziegler, 1993). Previously, we have shown that SAC is metabolized to the greatest extent by cDNA-expressed rabbit FMO3 followed by FMO1 and then FMO2, but SAC showed no activity with rabbit FMO5 (Ripp et al., 1997). More recently and using cDNA-expressed human FMOs, SAC has been shown to be a good substr...

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Section: Methodsmentioning

confidence: 99%

Sulfoxides as Urinary Metabolites ofS-Allyl-l-Cysteine in Rats: Evidence for the Involvement of Flavin-Containing Monooxygenases

Krause¹,

Glocke²,

Elfarra³

2002

Drug Metab Dispos

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“…for deodorization. After Moore et al,1] the Duolite C-25 adsorbed fraction (21 g) was put on a Dowex 50x8 column (100-200 mesh, DowChem. Co., 5 x 140cm, pre-equilibrated with 0.2n sodium citrate buffer (pH 3.0)) and chromatographed with four sodium citrate buffers ((1) 0.2 n (pH 3.0), 6.01 (2) 0.2n (pH 3.25), 3.01 (3) 0.2n (pH 4.25), 3.01 40.35n (pH 5.26), 6.5 1) and 2% ammonia (101).…”

Section: Methodsmentioning

confidence: 99%

Characteristic flavor constituents in water extract of garlic.

Ueda

SAKAGUCHI

Hirayama

et al. 1990

Agricultural and Biological Chemistry

110

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The flavoring effects of a water extract of garlic (Allium sativum L.) being added to common soups (Chinese soup and curry soup) were examined by a sensory evaluation. Whena small amount (0.1 or 0.4% w/v) of the extract was added to the soups, it showed characteristic kokumi flavors (continuity, mouthfulness, and thickness), and other tests revealed that this effect was clearly recognized in the umami solution composed of 0.05 % w/v of monosodium glutamate and 0.05 %w/v of disodium inosinate. To find the key compoundswhich gave rise to the effect, the water extract was chromatographed on Duolite C-25 and the adsorbed fraction showed the activity. Further chromatographic studies of the fraction showed that the key compounds were sulfur-containing components, such as alliin, (+)-5methyl-L-cysteine sulfoxide, and y-L-glutamyl-iS-allyl-L-cysteine. Garlic (Allium sativum L.) is cultivated as an important seasoning material in many countries. It is used as a seasoning and also a healthful food on account of its virtue as medicine. The character of its odor, which comes up when its raw material is crushed, has been investigated for a long time. The

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“…(1) and (2) as shown in Table II. The extract and the fraction showed no influence on the intensities of umami of the solutions but added the kokumi flavors to them.…”

Section: Preparation Of Duolite C-25 Fractionmentioning

confidence: 97%

“…(3) and (4) were stronger than those in solns. (1) or (2). These screening methods were very simple and seemed to be useful, so we used soln.…”

Section: Preparation Of Duolite C-25 Fractionmentioning

confidence: 99%

Characteristic Flavor Constituents in Water Extract of Garlic

Ueda

Sakaguchi

Hirayama

et al. 1990

Agricultural and Biological Chemistry

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Über Alliin, die genuine Muttersubstanz des Knoblauchöls. 1. Mitteilung über Allium‐Substanzen

Cited by 168 publications

References 14 publications

Sulfoxides as Urinary Metabolites ofS-Allyl-l-Cysteine in Rats: Evidence for the Involvement of Flavin-Containing Monooxygenases

Sulfoxides as Urinary Metabolites ofS-Allyl-l-Cysteine in Rats: Evidence for the Involvement of Flavin-Containing Monooxygenases

Characteristic flavor constituents in water extract of garlic.

Characteristic Flavor Constituents in Water Extract of Garlic

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