Bioavailability of Sulphur-Containing Ingredients of Garlic in the Rat

Zi-Jing, Guo; Müller, Daniela; Pentz, R.; Kress, George H.; Siegers, C P

doi:10.1055/s-2006-961372

Cited by 18 publications

(16 citation statements)

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“…11,16) Synthesized allixin-d 11 was used as the internal standard for the analysis of allixin content in blood samples. The yield of allixin and allixin-d 11 protons in the n-pentyl group of allixin were replaced with deuterium on the synthesis of allixin-d 11 using 1-bromopentane-d 11 3.89 (3H, s, -OMe), 6.1-6.35 (1H, br, -OH), 13 C-NMR (CDCl 3 ) d: 13.94 (C-5Ј), 15.06 (-Me), 22.33 (C-4Ј), 26.39 (C-1Ј), 28.31 (C-2Ј), 31.26 (C-3Ј), 60.14 (-OMe), 141.84 (C-3, C-5), 150.15 (C-2), 158.09 (C-6), 169.48 (CϭO). Allixin-d 11 ), in water was 301, according to Eq.…”

Section: Resultsmentioning

confidence: 99%

“…The bioavailability of allixin itself in mice was low, but combining allixin with the administration substance improved its solubility in aqueous solution when the inclusion compound was prepared with Mb-Cyd. However, the bioavailability of allixin was about two times higher than that of alliin (16.5%), 26) which is a wellknown sulfur-containing compound in intact garlic. In the preliminary administration study using an inclusion compound, allixin was not detected in rat plasma at a dose of 0.5, 5 or 10 mg/kg upon peroral administration, while allixin was detected in intravenous administration, even at dose of 0.5 mg/kg (data not shown, intact allixin in saline solution was used at a dose of 0.5 mg/kg).…”

Section: Discussionmentioning

confidence: 97%

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Pharmacokinetic Study of Allixin, a Phytoalexin Produced by Garlic.

et al. 2002

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Intact constituents or transformation compounds derived from garlic (Allium sativum L.) have been investigated for more than 60 years, and numerous compounds have been isolated and investigated to reveal the relationship between the compounds and biological activities of garlic.1,2) Sulfur-containing compounds, such as allicin, diallylsulfides, dithiins, alliin and S-allylcysteine, have been well investigated by numerous researchers because garlic is rich in sulfur and its sulfur containing compounds were believed to be responsible for many biological activities of garlic.1,2) S-Allylcysteine has been investigated comprehensively, including its physical, chemical and biological properties. [1][2][3][4][5][6] On the other hand, other compounds such as saponins, proteins or maillard reaction products derived from garlic, which are non-sulfur containing compounds, have also been investigated to reveal the biological properties of garlic. 1,2,[7][8][9][10] Allixin (3-hydroxy-5-methoxy-6-methyl-2-penthyl-4H-pyran-4-one), a non-sulfur containing compound having a gpyrone skeleton structure (Fig. 1), was the first compound isolated from garlic as a phytoalexin, a product induced in plants by continuous stress.11) This compound has been shown to have unique biological properties, such as anti-oxidative effects, 11) anti-microbial effects, 11) anti-tumor promoting effects, 12) inhibition of aflatoxin B 2 DNA binding, 13) and neurotrophic effects.14) Allixin showed an anti-tumor promoting effect in vivo, inhibiting skin tumor formation by TPA in DMBA initiated mice.12) Analogs of this compound have exhibited anti tumor promoting effects in in vitro experimental conditions. 15) Herein, allixin and/or its analogs may be expected useful compounds for cancer prevention or chemotherapy agents for other diseases.Analysis of the biological mechanism of action of allixin is important for the study of cancer prevention or other biological properties, and also for drug development. Nishino et al. has reported that allixin interacts with the Ca 2ϩ -calmodulin complex.12) This in vitro study suggests that allixin may play an important role in signal transduction or regulation. However, the pharmacokinetic behavior of this compound has not been evaluated, and this is an important factor for in vivo studies. Therefore, this paper presents the pharmacokinetic behavior and identified metabolites of allixin. Result Preparation of Allixin and Allixin-d 11Allixin and allixin-d 11 were prepared as previously reported.16) The chemical structure of the obtained materials were confirmed by NMR and MS comparison with previous reporteds.11,16) Synthesized allixin-d 11 was used as the internal standard for the analysis of allixin content in blood samples. The yield of allixin and allixin-d 11 was 20% and 9%, respectively. Here, all The pharmacokinetic behavior of allixin (3-hydroxy-5-methoxy-6-methyl-2-penthyl-4H-pyran-4-one) was investigated in an experimental animal, mice. Allixin was administered using an inclusion compound because the solubili...

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 97%

Pharmacokinetic Study of Allixin, a Phytoalexin Produced by Garlic.

et al. 2002

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“…Studies of Guo et al conducted on mice demonstrated that shortly after orally administration of alliin, this compound was observed in the stomach, intestine and liver without the production of allicin-derived compounds [Guo et al, 1990]. This allows for conclusion that alliin is not metabolized to respective organosulfur compounds without an appropriate enzyme (allinase).…”

Section: Metabolism Of Garlic and Garlic-derived Organosulfur Compoundsmentioning

confidence: 98%

Biological properties of garlic and garlic‐derived organosulfur compounds

Iciek

Kwiecień

Włodek

2009

Environ and Mol Mutagen

371

270

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Medicinal properties of garlic (Allium sativum) have been widely known and used since ancient times till the present. Garlic enhances immune functions and has antibacterial, antifungal and antivirus activities. It is known to prevent platelet aggregation, and to have hypotensive and cholesterol- and triglyceride-lowering properties, although the latter features have been questioned. This review is focused on anticancer efficacy of Allium sativum, and attempts to explain the mechanisms of this action. Medicinal properties of garlic rely upon organosulfur compounds mostly derived from alliin. Organosulfur compounds originating from garlic inhibit carcinogen activation, boost phase 2 detoxifying processes, cause cell cycle arrest mostly in G2/M phase, stimulate the mitochondrial apoptotic pathway, increase acetylation of histones. Garlic-derived sulfur compounds influence also gap-junctional intercellular communication and participate in the development of multidrug resistance. This review presents also other little known aspects of molecular action of garlic-derived compounds, like modulation of cellular redox state, involvement in signal transduction and post-translational modification of proteins by sulfane sulfur or by formation of mixed disulfides (S-thiolation reactions).

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“…SACS, which is also known as alliin, is one of the major active compounds in garlic reported to have antioxidant [21], immunomodulatory [22], myocardial protection, and antihyperlipidemic [23] activities. Despite these activities, the bioavailability of SACS is reported to be low (16.5 %) in rats [24]. NASAC and NASACS are major metabolites of SAC and their pharmacological activities are still unknown.…”

Section: Oral Administration Of (S)-allyl-l-cysteine and Aged Garlic mentioning

confidence: 99%

Oral Administration of (S)-Allyl-l-Cysteine and Aged Garlic Extract to Rats: Determination of Metabolites and Their Pharmacokinetics

Park

Lee

et al. 2017

Planta Med

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()-Allyl-l-cysteine is the major bioactive compound in garlic. ()-Allyl-l-cysteine is metabolized to ()-allyl-l-cysteine sulfoxide, -acetyl-()-allyl-l-cysteine, and -acetyl-()-allyl-l-cysteine sulfoxide after oral administration. An accurate LC-MS/MS method was developed and validated for the simultaneous quantification of ()-allyl-l-cysteine and its metabolites in rat plasma, and the feasibility of using it in pharmacokinetic studies was tested. The analytes were quantified by multiple reaction monitoring using an atmospheric pressure ionization mass spectrometer. Because significant quantitative interference was observed between ()-allyl-l-cysteine and -acetyl-()-allyl-l-cysteine as a result of the decomposition of -acetyl-()-allyl-l-cysteine at the detector source, chromatographic separation was required to discriminate ()-allyl-l-cysteine and its metabolites on a reversed-phase C analytical column with a gradient mobile phase consisting of 0.1% formic acid and acetonitrile. The calibration curves of ()-allyl-l-cysteine, ()-allyl-l-cysteine sulfoxide, -acetyl-()-allyl-l-cysteine, and -acetyl-()-allyl-l-cysteine sulfoxide were linear over each concentration range, and the lower limits of quantification were 0.1 µg/mL [()-allyl-l-cysteine and -acetyl-()-allyl-l-cysteine] and 0.25 µg/mL [()-allyl-l-cysteine sulfoxide and -acetyl-()-allyl-l-cysteine sulfoxide]. Acceptable intraday and inter-day precisions and accuracies were obtained at three concentration levels. The method satisfied the regulatory requirements for matrix effects, recovery, and stability. The validated LC-MS/MS method was successfully used to determine the concentration of ()-allyl-l-cysteine and its metabolites in rat plasma samples after the administration of ()-allyl-l-cysteine or aged garlic extract.

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Bioavailability of Sulphur-Containing Ingredients of Garlic in the Rat

Cited by 18 publications

References 0 publications

Pharmacokinetic Study of Allixin, a Phytoalexin Produced by Garlic.

Pharmacokinetic Study of Allixin, a Phytoalexin Produced by Garlic.

Biological properties of garlic and garlic‐derived organosulfur compounds

Oral Administration of (S)-Allyl-l-Cysteine and Aged Garlic Extract to Rats: Determination of Metabolites and Their Pharmacokinetics

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