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1. (Article ID: 12605)
 
Preobrazhenskaya MN, Korolev AM
Indole derivatives in vegetables of the Cruciferae family
Russian Journal of Bioorganic Chemistry 26(2) (2000) 85-97
 

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, a 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 the 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.

aromatic hydrocarbon receptor, ascorbigen, cytochrome P450 monoamine oxidase, glucobrassicin alkaloids, indole-3-carbinol, indolocarbazole

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2. (Article ID: 12611)
 
Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J
Myrosinase: gene family evolution and herbivore defense in Brassicaceae
Plant Molecular Biology 42(1) (2000) 93-113
 

Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

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3. (Article ID: 12884)
 
Yudina LN, Korolev AM, Reznikova MI, Preobrazhenskaya MN
Investigation of neoascorbigen
Chemistry of Heterocyclic Compounds 36(2) (2000) 144–151
 

The synthesis of N-methoxyascorbigen (neoascorbigen) — a natural substance from plants of the Cruciferae family — and also N-ethoxyascorbigen is described. In an acidic media under drastic conditions N-alkoxyascorbigens undergo transformations with the release of ascorbic acid and the formation of oligomers of 1-alkoxy-3-methyleneindolenine or with opening of the lactone ring, decarboxylation, and dehydration and the formation of 2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enone. Amides of neoascorbigen, 3-O-methylglycoside of N-ethoxyascorbigen, and the product of the reduction of N-ethoxyascorbigen by sodium borohydride were obtained for the first time.

2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enones, neoascorbigen, N-ethoxyascorbigen

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