Metabolism of the proximate carcinogen 1′-hydroxysafrole and the isomer 3′-hydroxyisosafrole

Peele, James; Oswald, E.O.

doi:10.1007/bf01685816

Cited by 12 publications

(3 citation statements)

References 6 publications

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“…(1971) reported that the major basic urinary metabolites of safrole were dimethylamino and piperidyl aminopropiophenones. Peele and Oswald (1978) reported similar findings for animals fed 1'-hydroxysafrole. Attempts to correlate the carcinogenicity of safrole with mutagenic activity have led t o mixed results using the Safrnonellu/mammalian-microsome mutagenicity test (Ames e t al.…”

Section: Fig 1 Safrolesupporting

confidence: 63%

“…Wislocki et al (1977) suggested that 2',3'-epoxysafrole (safrole-2',3'-oxide) or l'-hydroxy-2',3'-epoxysafrole ( 1 ' -hydroxysafrole-2',3'-oxide) may be the ultimate carcinogenic metabolites of safrole. Peele and Oswald (1978) suggested that 1 ' -hy droxysafrole is further metabolized to form 1'-oxosafrole, 3'-hydroxysafrole, and 1 '-hydroxyeugenol. Benedetti et al (1977) examined the absorption and excretion of safrole in humans and rats.…”

Section: Fig 1 Safrolementioning

confidence: 99%

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Toxicity of Spices Containing Methylenedioxybenzene Derivatives: A Review

Buchanan

1978

Journal of Food Safety

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Section: Fig 1 Safrolesupporting

confidence: 63%

Section: Fig 1 Safrolementioning

confidence: 99%

Toxicity of Spices Containing Methylenedioxybenzene Derivatives: A Review

Buchanan

1978

Journal of Food Safety

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“…The major toxicity of safrole is caused by its metabolite character. Safrole is oxidized into 1-hydroxysafrole in human body, which is carcinogenic (Peele Jr. & Oswald, 1978). The maximum dose of safrole as stated by UK and French governments is 1 mg/day (European Commission, 2002).…”

Section: Introductionmentioning

confidence: 99%

Determination of Safrole in Ethanol Extract of Nutmeg (Myristica fragrans Houtt) Using Reversed-Phase High Performance Liquid Chromatography

Saputri¹,

Mutakin²,

Lestari³

et al. 2014

IJC

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Dehydrodiisoeugenol (DDIE), myristicin, and safrole are chemical compounds contained in fruit and seed of nutmeg (Myristica fragrans Houtt). DDIE shows antidiabetic activity on PPARγ receptor, while myristicin is hallucinogenic agent. Of the three compounds, safrole is the most toxic substance due to its carcinogenic activity. In this work, we developed an analytical method to determine safrole in ethanol extract of nutmeg. Reversed-Phase High Performance Liquid Chromatography (Dionex Ultimate 3000) using C-18 LiChroCART 250-4, LiChrospher 100 RP 18e (5 µm) 250 mm column as stationary phase, was selected as the method of analysis. A mixture of methanol:water (73:27) at flow rate 1 mL/min was used as mobile phase. Detection was done at 282 nm. Using such conditions, retention time for safrole was 10.45 minutes. The recovery was 101.421%, while the value of CV was 0.838%. LOD and LOQ were 0.668 µg/mL and 2.023 µg/mL, respectively. Mean concentration of safrole in the nutmeg seed extract was 10.979%.

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Metabolism of isosafrole and dihydrosafrole in the rat

Klungsøyr

Scheline

1982

Biol. Mass Spectrom.

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The urinary metabolites of isosafrole (1,2-methylenedioxy-4-propenylbenzene) and dihydrosafrole (1,2-methylenedioxy-4-propylbenzene) in the rat were identified using gas chromatographic mass spectrometric methods. Additionally, the amounts of the individual metabolites excreted were determined gas chromatographically. Metabolite excretion was 89% (isosafrole) and 97% (dihydrosafrole) of the dose in 72 h. Although isosafrole was metabolized by allylic hydroxylation and via the epoxide-diol pathway, demethylenation leading mainly to 1,2-dihydroxy-4-propenylbenzene was by far the most prominent reaction. This was similarly true with dihydrosafrole which was metabolized mainly to 1,2-dihydroxy-4-(1-propyl) benzene. The total amount of demethylenated metabolites formed were 92% (isosafrole) and 95% (dihydrosafrole) of the identified material.

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Metabolism of the proximate carcinogen 1′-hydroxysafrole and the isomer 3′-hydroxyisosafrole

Cited by 12 publications

References 6 publications

Toxicity of Spices Containing Methylenedioxybenzene Derivatives: A Review

Toxicity of Spices Containing Methylenedioxybenzene Derivatives: A Review

Determination of Safrole in Ethanol Extract of Nutmeg (Myristica fragrans Houtt) Using Reversed-Phase High Performance Liquid Chromatography

Metabolism of isosafrole and dihydrosafrole in the rat

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