Effects of Mace and Nutmeg on Human Cytochrome P450 3A4 and 2C9 Activity

Kimura, Yuka; Ito, Hideyuki; Hatano, Tsutomu

doi:10.1248/bpb.33.1977

Cited by 46 publications

(27 citation statements)

References 35 publications

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“…Finally, the furan ring was absolutely formed by the remaining three degrees of unsaturation. This is strongly supported by the comparison of 13 C chemical shifts between 1 and a known furan fatty acid, 3¢-methyl-5¢-pentyl-furylarylic acid, isolated from a plant (Kimura et al, 2010). Overall, the structure of 1 proved to be a new furan fatty acid (Fig.…”

Section: Structure Elucidation Of Mumiamicin (1)mentioning

confidence: 61%

“…Several furan fatty acids have been isolated as secondary metabolites from various organisms, including plants (Kimura et al, 2010), fungi (Ma et al, 2016) and fish (Hammann et al, 2015). They have displayed various biological activities, such as antioxidative (Teixeira et al, 2013) and anti-inflammatory (Wakimoto et al, 2011) prop-erties.…”

Section: Discussionmentioning

confidence: 99%

“…Additionally, this is the first report about secondary metabolites from the genus Mumia. A similar compound with a shorter aliphatic chain than 1 was only reported as a plant metabolite, and was devoid of any biological activity (Kimura et al, 2010).…”

Section: Discussionmentioning

confidence: 99%

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Mumiamicin: Structure and bioactivity of a new furan fatty acid from <i>Mumia</i> sp. YSP-2-79

Kimura

Tajima

Inahashi

et al. 2018

J. Gen. Appl. Microbiol.

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Section: Structure Elucidation Of Mumiamicin (1)mentioning

confidence: 61%

Section: Discussionmentioning

confidence: 99%

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Mumiamicin: Structure and bioactivity of a new furan fatty acid from <i>Mumia</i> sp. YSP-2-79

Kimura

Tajima

Inahashi

et al. 2018

J. Gen. Appl. Microbiol.

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Section: )mentioning

confidence: 99%

“…[2][3][4] In vitro screening assays with beverages and foods such as beer, red wine, black and herbal tea, garlic, spices, mace, nutmeg, fruits, and fruit juices have all shown the ability to inhibit enzyme-mediated drug metabolism. [5][6][7][8][9][10] CYP3A4 is the most important drug metabolizing enzyme, in that it metabolizes more than 50% of all clinical drugs.11) It is expressed as the most abundant constituent in the human liver CYP enzyme system 12) and is also expressed at substantial levels in the intestinal epithelial cells to metabolize and limit absorption of orally administered CYP3A4 substrate drugs.13) Grapefruit juice is an extensively studied dietary substance that is shown to irreversibly inhibit enteric CYP3A in a mechanism-based manner. [14][15][16] Mechanism-based inhibition (MBI) of CYP3A4 is characterized by nicotinamide adenine dinucleotide phosphate (NADPH)-, time-, and concentration-dependent enzyme inactivation that occurs when some substrates are converted by CYPs into reactive metabolites.…”

mentioning

confidence: 99%

Mechanism-Based Inhibition of Recombinant Human Cytochrome P450 3A4 by Tomato Juice Extract

Sunaga

Ohkawa

Nakamura

et al. 2012

Biological & Pharmaceutical Bulletin

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This study investigates whether tomato juice can inhibit cytochrome P450 (CYP) 3A4-mediated drug metabolism. Three commercially available, additive-free tomato juices, along with homogenized fresh tomato, were analyzed for their ability to inhibit testosterone 6β-hydroxylation activity using human recombinant CYP3A4. Results were compared to that of grapefruit juice. Ethyl acetate extracts of the tomato juices moderately reduced residual activity of CYP3A4 testosterone 6β-hydroxylation activity by 19.3-26.2% with 0-min preincubation. Residual activity was strongly reduced by 69.9-83.5% at 20-min preincubation, a reduction similar to that of grapefruit juice extract, known to contain constituents of mechanism-based inhibitors. One juice extract (tomato juice C) showed irreversible dose-and preincubation time-dependent and partial nicotinamide adenine dinucleotide phosphate (NADPH)-dependent inhibition of CYP3A4 activity. Furthermore, we examined whether the CYP3A4 inhibitory effect of tomato juice was substrate dependent by examining midazolam 1′-hydroxylation activity and nifedipine oxidation activity, in addition to testosterone 6β-hydroxylation activity. Tomato juice showed a potent inhibitory effect on nifedipine oxidation activity, which was comparable to that on testosterone 6β-hydroxylation activity; however, it showed a weak inhibitory effect on midazolam 1′-hydroxylation activity. We conclude that tomato juice contains one or more mechanism-based and competitive inhibitor(s) of CYP3A4. Additionally, significant CYP3A4 inhibitory activity did not result from lycopene, a major compound in tomato. Although the active compound was uncertain, a strong CYP3A4 inhibitory activity was observed in other solanaceous plants, i.e., potato, eggplant, sweet pepper, and capsicum. Therefore, responsible compounds in tomato are likely commonly shared among solanaceous vegetables.Key words tomato juice; mechanism-based inhibition; food-drug interaction; human recombinant cytochrome P450 3A4 Many foods and/or beverages have recently been found to influence drug metabolism or transport, sometimes resulting in clinically important drug interactions. This food-drug interaction is a critical aspect of pharmacotherapy. Food-drug interaction can be viewed in terms of pharmacokinetics and pharmacodynamics. Pharmacokinetic interactions can involve enzymes and transporters that are implicated in drug absorption, distribution, metabolism, or excretion. Pharmacodynamic interactions involve the pharmacological effect of a drug or physiologic effect of a dietary constituent. 1)Foods that inhibit drug metabolism enzymes, such as cytochrome P450 (CYP), elevate the blood concentration of co-administered drugs, resulting in a food-drug interaction, which sometimes causes adverse effects. [2][3][4] In vitro screening assays with beverages and foods such as beer, red wine, black and herbal tea, garlic, spices, mace, nutmeg, fruits, and fruit juices have all shown the ability to inhibit enzyme-mediated drug metabolism. [5][6][7][8][9][10] CYP...

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Purification and Isolation Techniques for Enrichment of Bioactive Phytochemicals from Herbs and Spices

Aznar

Dilip

2020

Herbs, Spices and Medicinal Plants

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Effects of Mace and Nutmeg on Human Cytochrome P450 3A4 and 2C9 Activity

Cited by 46 publications

References 35 publications

Mumiamicin: Structure and bioactivity of a new furan fatty acid from <i>Mumia</i> sp. YSP-2-79

Mumiamicin: Structure and bioactivity of a new furan fatty acid from <i>Mumia</i> sp. YSP-2-79

Mechanism-Based Inhibition of Recombinant Human Cytochrome P450 3A4 by Tomato Juice Extract

Purification and Isolation Techniques for Enrichment of Bioactive Phytochemicals from Herbs and Spices

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