Low-molecular Bioregulators Research Articles

Conversions of seven-membered terpene lactones towards low-molecular bioregulators

The review describes the low-temperature reduction of (-)-mentholactone with diisobutylaluminum hydride in methylene chloride studied by the authors. It was found that, depending on the reaction conditions, it proceeds with the formation of three products: 7 S -isopropyl-4 R -methyloxepan-2 S -ol [(-)-mentholactol], 8-hydroxy-2,6 R -dimethyloctan-3-one or 2 S -isobutoxy-7 S -isopropyl-4 R -methyloxepane, for each of which the probable routes are given and the conditions for selective formation are selected. A new reaction in the chemistry of organoaluminum compounds has been discovered - the formation of isobutyl acetals of 2-oxepanols during low-temperature (-70°C) reduction of 7-membered lactones with two-fold or more molar amounts of diisobutylaluminum hydride in methylene chloride. On the basis of (-)-mentholactol, its aluminate, and 8-hydroxy-2,6R-dimethyloctan-3-one, a number of low molecular weight bioregulators, including optically active pheromones of insect pests in agriculture and forestry, have been synthesized.

Semi-synthesis of Cytotoxic Molecules From Cycloartane Type Sapogenols

Semi-synthetic anticancer drug-discovery programs focusing on saponins mainly engaged with commercially available triterpenoids such as oleanolic acid and ursolic acid (1,2,3), not including less common miscellaneous aglycons such as cycloartanes, lanostanes and hopanes. Cycloartanes occupy a special position among low molecular bioregulators because they are produced by photosynthesizing organisms only, and one from the initial representatives of this range, cycloartenol, serves as the key link in the biosynthesis of different phytosterols (4). In general, the plants of Astragalus genera proved to be the richest source of this class of compounds.

Особливості обміну аргініну й синтезу оксиду азоту в юнаків при адаптації до фізичних навантажень у тренувальному та змагальному періодах

A survey of 29 trained and untrained youths in the age of 18-20 years was carried out. It is shown that the optimal level of adaptation of the body to prolonged and intensive physical activity is provided by multi-dominance nonoxidizing arginase metabolism and its oxidative metabolism by constitutively calcium dependent NO-synthase (eNOS and nNOS). Nonoxidizing arginase metabolism results in formation of several important low-molecular bioregulators and antioxidants (urea, polyamines, GABA). Significant reduction of functionality of the trained body at the end of the competitive period and consequently disadaptation correlates with Ca(2+)-independent NO synthesis which does not compensate the organism needs in NO.

Biologically active metabolites of marine actinobacteria

This review systematically data on the chemical structure and biological activity of metabolites of obligate and facultative marine actinobacteria, published from 2000 to 2007. We discuss some structural features of the five groups of metabolites related to macrolides and compounds containing lactone, quinone and diketopiperazine residues, cyclic peptides, alkaloids, and compounds of mixed biosynthesis. Survey shows a large chemical diversity of metabolites actinobacteria isolated from marine environment. It is shown that, along with metabolites, identical to previously isolated from terrestrial actinobacteria, marine actinobacteria synthesize unknown compounds not found in other natural sources, including micro organisms. Perhaps the biosynthesis of new chemotypes bioactive compounds in marine actinobacteria is one manifestation of chemical adaptation of microorganisms to environmental conditions at sea. Review stresses the importance of the chemical study of metabolites of marine actinobacteria. These studies are aimed at obtaining new data on marine microorganisms producers of biologically active compounds and chemical structure and biological activity of new low-molecular bioregulators of natural origin.

Natural products: Designing Russian medications.

The study of natural products (low-molecular bioregulators) is an important research area that lies on the boundary of biology and chemistry. It involves searching, isolating, and identifying the structure and studying the biological functions of such substances, as well as investigating their chemical conversions, especially those that lead to highly active products. These research efforts play an important part in deepening biological and chemical knowledge and build the scientific groundwork for designing new drugs and biologically active food additives. Some results of the study of natural compounds were discussed in a paper read at a session of the RAS Presidium and are published below.

Unsaturated sugars in enantiospecific synthesis of natural low-molecular bioregulators and their structural analogues

The review of works of the authors devoted to the synthesis of low-molecular bioregulators with the use of unsaturated sugars is presented. The schemes of synthesis of insect pheromones and acetogenins and glycosphingolipids on the basis of glycals are discussed. The pathways of synthesis of triterpene 2-deoxy-alpha-glycosides are shown. The synthesis of prostanoids from levoglucosenone is considered.

Ozonolysis in the chemistry of low-molecular bioregulators

Numerous records in the chemistry of pheromones, juvenile hormone analogues (juvenoids), ecdysteroids, tocopherols and related compounds demonstrate the effectiveness and, in many cases, the uniqueness of ozonolysis in the synthesis of low-molecular biologically active compounds.

What to synthesize? From Emil Fischer to peptidomics.

The driving forces, incentives and strategic targets of peptide synthesis have undergone considerable evolution during the centenary following the pioneer work of Emil Fischer. In those days peptide synthesis was considered as a way of confirming the polypeptide theory of protein structure. The scientific community also expected (naively) that the synthesis would eventually lead to the creation of artificial living organisms. Only in the 1950s, when the first exact amino acid sequences were established did peptide chemistry obtain firmer ground and clearly defined targets. The total synthesis of peptide hormones and antibiotics became possible, providing valuable material for elucidating structure-functional relationships and the mechanisms of biological action. In the following years the number of peptides isolated from various biological sources grew with impressive speed and peptides became known as the most abundant, ubiquitous group of low molecular bioregulators. The design and synthesis of novel peptide based pharmaceuticals became an important area of peptide chemistry. At present we are facing the challenge of analysing the structures and bioactivities of total sets of peptides, i.e. peptidoms, present in concrete tissues or groups of cells. The results obtained along these lines at the IBCH RAS Institute of Bioorganic Chemistry are briefly considered in the review.

Synthesis and Properties of Aminophosphonic Acids and Phosphonopeptides

Abstract In recent years phosphorous analogues of amino acids (aminophosphonic, aminophosphinic and aminophosphonous acids) have attracted growing attention of investigators. Among these compounds are the first natural ones containing P-C bond and produced by living organisms.1 As mimetics of natural amino acids they are potential bioregulators. These compounds were found to be substrates and inhibitors of enzymes, to possess plant growth regulating and herbicidal properties, to display antibacterial, antitumoral and neuronal activities.2 Studies of aminophosphonic and aminophosphinic acids (APA) in our laboratory have been directed towards development of APA synthesis methods, obtaining of new APA, investigation of their properties, evaluation of structure-bioactivity relations and design of APA-based low-molecular bioregulators. The chemical aspects of our studies are described here.