[Indole derivatives in vegetables of the family Cruciferae].

Abstract

The chemical background of the biological activities of vegetables of the Cruciferae family is considered. These vegetables contain alkaloids of the glucobrassicin group that are decomposed by the enzyme myrosinase (thioglucosidase, EC 3.2.3.1) released upon damage to the plant cells. This results in several indole derivatives, with ascorbigen and indole-3-carbinol predominating. In the gastrointestinal tract, these compounds form 5H,11H-indolo[3,2-b]carbazole, natural ligand of the aromatic hydrocarbon receptor (Ah receptor) and a functional analogue of 2,3,7,8-tetrachlorodibenzo-p-dioxin, a dangerous xenobiotic. The indolocarbazole-Ah receptor complex activates the gene of CYP1A1, an isoenzyme of cytochrome P450-dependent monoamine oxidase, which enhances the 2-hydroxylation (inactivation) of estrogens. In its turn, the resulting lowered level of estrogens inhibits the growth of hormone-dependent tumors or prevents their appearance. The mechanism of xenobiotic inactivation, underlying the anticarcinogenic action of food products including vegetables of Cruciferae family and some homogeneous indole compounds, is similar. Some other effects of nutrient indole compounds, e.g., the inhibition of expression of the cyclin-dependent kinase 6 (CDK6) by indole-3-carbinol that leads to the cell cycle arrest in G1 phase, are also considered. Analysis of the biological effects of the Cruciferae diet has helped start clinical studies of indole-3-carbinol as an antitumor and anticarcinogenic remedy for patients with a high risk of tumor diseases.

• Authors: M N Preobrazhenskaia, A M Korolev
• Journal: Bioorganicheskaia khimiia (Bioorg Khim) Vol. 26 Issue 2 Pg. 97-111 (Feb 2000) ISSN: 0132-3423 [Print] Russia (Federation)
• Vernacular Title: Indol'nye soedineniia v ovoshchakh semeĭstva Krestotsvetnykh (Cruci ferae)
• PMID: 10808405 (Publication Type: English Abstract, Journal Article, Review)

Chemical References

• Indoles

Topics

• Brassicaceae (metabolism)
• Indoles (chemistry, metabolism)