Effect of allixin, a phytoalexin produced by garlic, on mutagenesis, DNA-binding and metabolism of aflatoxin B1

Yamasaki, Takahiro; Teel, Robert W.; Lau, Benjamin H.S.

doi:10.1016/0304-3835(91)90171-d

Cited by 42 publications

(20 citation statements)

References 16 publications

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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%

“…[11][12][13][14][15] There was no previous study relating to the pharmacokinetics of allixin, though several biological properties of allixin were investigated in both in vitro and in vivo systems as described above. Therefore, we investigated the pharmacokinetic behavior of allixin because it is well known that pharmacokinetic behaviors, parameters and metabolites of drugs are important factors for studying the action mechanisms and /or development of new drugs.…”

Section: Discussionmentioning

confidence: 99%

“…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.…”

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confidence: 99%

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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: 99%

mentioning

confidence: 99%

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Pharmacokinetic Study of Allixin, a Phytoalexin Produced by Garlic.

et al. 2002

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“…16 In-vitro studies confirmed the coupling of aflatoxin to DNA, forming aflatoxin-DNA adducts. 17,18 Damage to the genetic material at both the gene and chromosome levels may lead to obvious abnormalities in sperm in man. 19 The toxicity of dietary aflatoxin in mammals has been extensively studied 20,21 and several factors have been adduced to contribute to aflatoxin tissue toxicity.…”

Section: Discussionmentioning

confidence: 99%

A Study on the Impact of Aflatoxin on Human Reproduction

Uriah¹,

Ibeh²,

Oluwafemi³

2001

African Journal of Reproductive Health

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Infertility among couples in Nigeria is causing increasing concern. Investigations have shown a relationship between abnormalities in spermatozoa/semen parameters and the incidence of male factor mediated fertility problems in couples. However, the factors responsible for the sudden increase in semen/spermatozoa abnormalities are not fully understood. In this study, blood and semen samples were collected from fifty-five adult Nigerians comprising 30 infertile and 25 fertile control individuals, and screened for the presence of aflatoxin using solvent extraction and quantitation by high performance liquid chromatography. Semen parameters such as volume, viscosity, pH, fructose, spermatozoa count, morphology, and motility were determined. Blood and semen aflatoxin levels in infertile men ranged from 700 to 1392ng/ml and 60 to l48ng/ml respectively and these values were significantly higher than the concentrations of the toxin in fertile men (p <0.05). Deviation from normal in semen parameters showed a definite pattern in infertile men. About 37% of the infertile men had aflatoxin in their blood and semen suggesting that aflatoxins may be a contributory factor to the incidence of infertility in Nigerians since the toxin has been shown to produce deleterious effect on the reproductive system.

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“…Allixin, 3-hydroxy-5-methoxy-6-methyl-2-penthyl-4H-pyrane-4-one, is the first phytoalexin compound isolated from garlic, and this compound showed several unique biological properties, 3) such as anticancer promoting activity, 4) inhibition of aflatoxin B1 DNA binding activity 5) and neurotrophic activity. 6) It is said that phytoalexin is produced by continuous stress conditions which are induced by chemical or biological agents, such as mercury chloride, hydrogen peroxide, or the invasion of microorganisms.…”

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confidence: 99%