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7. New Derivatives of 3,4-Dihydroisoquinoline-3-carboxylic Acid with Free-Radical Scavenging, D-Amino Acid Oxidase, Acetylcholinesterase and Butyrylcholinesterase Inhibitory Activity

Author

Solecka, Jolanta, primary, Guśpiel, Adam, additional, Postek, Magdalena, additional, Ziemska, Joanna, additional, Kawęcki, Robert, additional, Łęczycka, Katarzyna, additional, Osior, Agnieszka, additional, Pietrzak, Bartłomiej, additional, Pypowski, Krzysztof, additional, and Wyrzykowska, Agata, additional

Published
2014
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9. Characterization and Optimization of Biosynthesis of Bioactive Secondary Metabolites Produced by Streptomycessp. 8812

Author

RAJNISZ, ALEKSANDRA, GUŚPIEL, ADAM, POSTEK, MAGDALENA, ZIEMSKA, JOANNA, LASKOWSKA, ANNA, RABCZENKO, DANIEL, and SOLECKA, JOLANTA

Abstract

The nutritional requirements and environmental conditions for a submerged culture of Streptomycessp. 8812 were determined. Batch and fed-batch Streptomycessp. 8812 fermentations were conducted to obtain high activity of secondary metabolites. In the study several factors were examined for their influence on the biosynthesis of the active metabolites-7-hydroxy-6-oxo-2,3,4,6-tetrahydroisoquinoline-3-carboxyl acid (C10H9NO4) and N-acetyl-3,4-dihydroxy-l-phenylalanine (C11H13NO5): changes in medium composition, pH of production medium, various growth phases of seed culture, amino acid supplementation and addition of anion exchange resin to the submerged culture. Biological activities of secondary metabolites were examined with the use of dd-carboxypeptidase 64–575 and horseradish peroxidase. Streptomycessp. 8812 mycelium was evaluated under fluorescent microscopy and respiratory activity of the strain was analyzed. Moreover, the enzymatic profiles of the strain with the use of Api®ZYM test were analyzed and genetic analysis made. Phylogenetic analysis of Streptomycessp. 8812 revealed that its closest relative is Streptomyces capoamusJCM 4734 (98%), whereas sequence analysis for 16S rRNA gene using NCBI BLAST algorithm showed 100% homology between these two strains. Biosynthetic processes, mycelium growth and enzyme inhibitory activities of these two strains were also compared.

Published
2016
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10. INTRACELLULAR ANTIOXIDANT ACTIVITY OF A STREPTOMYCES SP. 8812 SECONDARY METABOLITE, 6,7-DIHYDROXY-3,4-DIHYDROISOQINO- LINE-3-CARBOXYLIC ACID, AND ITS SYNTHETIC DERIVATIVES.

Author

Guśpiel A, Ziemska J, Cześcik A, Kawecki R, and Solecka J

Subjects
Animals, Chlorocebus aethiops, Chromans chemical synthesis, Free Radical Scavengers chemistry, Humans, Reactive Oxygen Species analysis, Vero Cells, Antioxidants pharmacology, Chromans pharmacology, Streptomyces chemistry
Abstract

The aim of this study was to determine the antioxidant properties of 6,7-dihydroxy-3,4-dihydroiso- quinoline-3-carboxylic acid (1) and its derivatives in living cells against reactive forms of oxygen and nitrogen, i.e., hydrogen peroxide and nitric oxide. Four of tested compounds scavenged the reactive form of nitrogen more efficiently or similarly to Trolox (EC50 = 55.80 µM). Two compounds exhibited antioxidant activity against reactive oxygen species better than Trolox (EC50 = 51.88 µM). The most active derivative of 1 was the compound containing an iodine atom at position 8 (6,7-dihydroxy-8-iodo-3,4-dihydroisoquinoline-3-carboxylic acid). Our studies showed that some of the derivatives had the ability to cross the cell membrane and scavenge free radicals inside living cells. Thus, they are able to protect DNA and other cellular structures from the dam- aging effects of reactive oxygen and nitrogen species. In addition, some molecular descriptors of the tested compounds were determined with the use of ICM Pro (Molsoft L.L.C.).

Published
2016

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