Biomedical subjects
Publications and source records attributed to Valery M Dembitsky.
Tornabeatins A, B, C and D, have been isolated as new natural products from the lichenized ascomycete Tornabea scutellifera, and their structures elucidated using UV, IR, MS, 1D and 2D NMR spectral data and chemical degradation.
Natural arsenolipids are analogues of neutral lipids, like monoglycerides, glycolipids, phospho- and also phosphonolipids. They have been found in microorganisms, fungi, plants, lichens, in marine mollusks, sponges, other invertebrates, and in fish tissues. This review presented structures of natural arsenolipids (and derivatives), their distribution, biogenesis in algae and invertebrates, synthesis, and also biological activity. Arsenolipids are thought to be end products of arsenate detoxification processes, involving reduction and oxidative methylation and adenosylation. The proposed biogenesis of arsenolipids is based on the natural occurrence of arsenic metabolites, and all the intermediates in the proposed pathway have been identified as natural products of algal origin. Different arseno species are shown to be inhibitors of glycerol kinase, bovine carbonic anhydrase, and also is an effective therapy for acute promyelocytic leukemia, and there has been promising activity noted in other hematologic and solid tumors. Arsonoliposomes demonstrated high anti-trypanosomal activity against Trypanosoma brucei and inhibit growth of some types of cancer cells (HL-60,C6 and GH3).
A novel photo protective mycosporine was isolated from the lichenized ascomycete Collema cristatum. Biological activity was measured in terms of protection against UV-B induced membrane destruction and pyrimidine dimer formation in cultured human keratinocytes, and prevention of UV-B induced erythema. It was found that the pure isolated compound prevented UV-B induced cell destruction in a dose-dependent manner, that the compound partially prevented pyrimidine dimer formation and completely prevented UV-B induced erythema when applied to the skin prior to irradiation.
This article describes recent developments in the synthesis and biological activity of alpha-aminoboronic acids, amine-carboxyboranes and their derivatives as potential therapeutic agents. alpha-Amino acid analogues are of considerable interest as inhibitors of enzymes involved in amino acid and peptide metabolism. In particular, alpha-amino alkylphosphonic acids and alpha-amino alkylboronic acids, in which the carboxyl group of amino acids is replaced by a phosphonic acid or boronic acid function, respectively, constitute a unique class of amino acid mimics from which a number of potent enzyme inhibitors have been synthesized. The inhibitory activity mainly stems from the fact that the tetrahedral phosphonic moiety or the tetrahedral adduct of electrophilic boronic acid is a good mimic of the putative tetrahedral transition state or intermediate encountered in the enzymatic hydrolysis or formation of peptides. Since the peptide hydrolysis and formation invariably involves the tetrahedral high energy species in the course of the reaction, these amino acid mimics serve as a general key element for inhibitors of a broad spectrum of proteases and peptide ligases. Serine protease inhibitors provide promising compounds having a P site binding moiety and a boronic acid chelating moiety. The compounds have been shown to have high inhibitory activity.
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The xanthoside composition of the crude extract of Umbilicaria proboscidea (L.) Schrader was characterized using LC-UV diode array detection and LC-atmospheric pressure chemical ionization (APCI) MS methods. The presence of acylated xanthone-O-glucosides was determined by both positive and negative ion LC-APCI-MS methods. Based on UV and MS spectral data and NMR spectroscopy, a total of 14 compounds (6-O-acylated umbilicaxanthosides A and B) were identified in U. proboscidea for the first time. In order to further develop the applicability of LC-MS techniques in phytochemical characterization, the effect of different ionization energy on fragmentation was studied using APCI. The optimal ionization conditions were achieved in positive ion APCI by using ammonium acetate buffer and in negative ion APCI by using formic acid (pH 4).
[reaction: see text] A new method of synthesis of 3-amino-1-alkenylphosphonates is described. It involves the addition of imines to the alkynylphosphonate titanium(II) complexes 2, which are prepared in situ from 1-alkynylphosphonates and Ti(O-i-Pr)(4)/2 equiv of i-PrMgCl. Compounds 4a-i were obtained regio- and stereoselectivily in high yields.
More than 100 novel, unusual and rare fatty acids, lipids and sterols have been isolated from freshwater sponges. The structures, biogenesis, synthesis and bioactivity of some lipid compounds of freshwater sponge species are reviewed.
Two new compounds isolated from an extract of a Central Asian lichen [Umbilicaria proboscidea (L.) Schrader=Syn.: Gyrophora proboscidea (L.) Ach.] are glucosides with mono- and di-prenylated xanthones as the aglycones and a saccharide moiety from two glucoses linked at C-7. The structures were elucidated on the basis of extensive spectroscopic analysis (1D and 2D NMR, MS, IR and UV) and by hydrolysis.
A new trinorsesterterpene glycoside was isolated from the ethanol extract of the American fern Woodwardia virginica having a 3-[6-(4,8-dimethyl-nona-1,3,7-trienyl)-4-hydroxy-2,6-dimethyl-cyclohex-1-enyl]-3-hydroxypropionic acid, as the aglycone and a saccharide moiety linked at C-4 to glucoses, xylose or arabinofuranose. The structure was elucidated using extensive spectroscopic analysis (1D and 2D NMR, MS, IR and UV) including determination of absolute stereochemistry by means of the MTPA and PGME derivatives and also by chemical methods.
New glycosides having multisubstituted cyclohex-2-enones as aglycones and saccharide moieties consisting of three and four glucoses, respectively were isolated from the ethanol extract of the American fern Woodwardia virginica. The structures were elucidated using extensive spectroscopic analysis (1D and 2D NMR, MS, IR, CD and UV) including determination of absolute stereochemistry by chemical methods.
A comprehensive survey has been made of all fatty acids containing halogen atoms covalently bonded to carbon and which are deemed as naturally occurring. Generally thought to be minor components produced by many different organisms, these interesting compounds now number more than 300. Recent research, especially in the marine area, indicates this number will increase in the future. Sources of halogenated fatty acids include microorganisms, algae, marine invertebrates, and higher plants and some animals. Their possible biological significance has also been discussed
Very-long-chain and multibranched polyunsaturated fatty acids of three freshwater sponges, Ephydatia syriaca, Nudospongilla sp., and Cortispongilla barroisi, were studied by silver TLC, GC-MS, UV, IR, HRMS, and NMR methods. One hundred and eighty-five conventional fatty acids were identified by GC-MS, out of which five were new multibranched polyunsaturated fatty acids. The freshwater sponges belonging to the family Spongillidae (class Demospongia) were shown to contain novel di-, tri-, and tetramethyl substituted dienoic, tetraenoic, and hexaenoic fatty acids. The compounds gave positive results in a brine shrimp toxicity assay.
p-Nonylphenol isomers and other aromatic compounds were found in roots and stalks of the plant Cichorium endivia subsp. divaricatum. These compounds were characterized by high-resolution capillary GC-MS.