Environmental aspects of methylenedioxyphenyl and related derivatives

Fishbein, Lawrence; Falk, Hans L.

doi:10.1016/0013-9351(69)90033-4

Cited by 23 publications

(3 citation statements)

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“…Isolation of Myristicin from Nutmeg. Myristicin was isolated from nutmeg because this chemical is present at a concentration of 1% w/w (Fishbein and Falk, 1969) and nutmeg is available as a commercial product. For isolation purposes, 500 g of powdered nutmeg were extracted by refluxing with 800 mL of chloroform for 90 min.…”

Section: Chemicalsmentioning

confidence: 99%

“…Myristicin is known to occur in nutmeg, mace, black pepper, and several members of the plant family Umbelliferae including parsnip, parsley, celery, dill, and carrots (Hall, 1973). Nutmeg is used in baked goods (2000 ppm), to these foods and flavorings, essential oils containing myristicin are used in soaps, hair tonics, perfumes, dentifrices, and tobacco flavoring (Fishbein and Falk, 1969). d-Carvone has been isolated from dill, caraway, and mandarin peel (Merck Index, 1968).…”

mentioning

confidence: 99%

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Effects of naturally occurring food plant components on insecticide degradation in rats

Tw¹,

Lichtenstein²,

Fw³

1978

J. Agric. Food Chem.

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Section: Chemicalsmentioning

confidence: 99%

mentioning

confidence: 99%

Effects of naturally occurring food plant components on insecticide degradation in rats

Tw¹,

Lichtenstein²,

Fw³

1978

J. Agric. Food Chem.

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“…For instance, the P450-mediated metabolism of some chemicals can generate carbenes which lead to the inhibition of enzymes and further undesired effects such as drug–drug interactions and hepatotoxicity in the human body. ,, Methylenedioxyphenyl (MDP) derivatives are the best-known examples for the MBI of P450s. , MDP is an integral part of the chemical structure of several drugs, pesticides, and flavoring agents (Scheme ). − The highly reactive intermediate of oxidized MDP (a carbene molecule) produces a MIC with the heme-iron, which leads to a quasi-irreversible inhibition of the enzyme. For instance, it has been revealed that tadalafil and paroxetine (see Scheme ) selectively inhibit the activity of CYP3A4 and CYP2D6, respectively.…”

Section: Inhibitors Classificationmentioning

confidence: 99%

Mechanism-Based Inactivation of Cytochrome P450 Enzymes: Computational Insights

Mirzaei

Ivanov

Mirzaei

2021

Chem. Res. Toxicol.

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Mechanism-based inactivation (MBI) refers to the metabolic bioactivation of a xenobiotic by cytochrome P450s to a highly reactive intermediate which subsequently binds to the enzyme and leads to the quasi-irreversible or irreversible inhibition. Xenobiotics, mainly drugs with specific functional units, are the major sources of MBI. Two possible consequences of MBI by medicinal compounds are drug–drug interaction and severe toxicity that are observed and highlighted by clinical experiments. Today almost all of these latent functional groups (e.g., thiophene, furan, alkylamines, etc.) are known, and their features and mechanisms of action, owing to the vast experimental and theoretical studies, are determined. In the past decade, molecular modeling techniques, mostly density functional theory, have revealed the most feasible mechanism that a drug undergoes by P450 enzymes to generate a highly reactive intermediate. In this review, we provide a comprehensive and detailed picture of computational advances toward the elucidation of the activation mechanisms of various known groups with MBI activity. To this aim, we briefly describe the computational concepts to carry out and analyze the mechanistic investigations, and then, we summarize the studies on compounds with known inhibition activity including thiophene, furan, alkylamines, terminal acetylene, etc. This study can be reference literature for both theoretical and experimental (bio)chemists in several different fields including rational drug design, the process of toxicity prevention, and the discovery of novel inhibitors and catalysts.

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