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Mukhamedova, Kh. S.; Glushenkova, Anna I.

doi:10.1023/a:1002804409503

Cited by 63 publications

(14 citation statements)

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“…There are two classes of these compounds-glycerophosphonolipids and sphingophosphonolipids (representative structures are shown in Figure 2). They have been isolated from numerous organisms including humans, mammals (sheep, goats, and rats), egg yolk, fish, insects, sea anemones, sponges, numerous species of freshwater and marine mollusks, seeds of plants, protozoa, and bacteria [3,[43][44][45][46]. Usually they are a small fraction of the total lipids present, and their isolation and exact identification/characterization are difficult and cumbersome.…”

Section: Ciliatine (Aep 2-aminoethylphosphonic Acid)mentioning

confidence: 99%

Phosphonates: Their Natural Occurrence and Physiological Role

Kafarski¹

2020

Contemporary Topics About Phosphorus in Biology and Materials

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The first natural compound containing carbon-to-phosphorus bond-ciliatine was discovered 60 years ago, and for four decades, phosphonates were considered simply as a biological curiosity. Finding the importance of these compounds in biogeochemical phosphorus cycling, their role in methane production, as well as discovery of numerous phosphonates and phosphonopeptides of promising antibacterial and antifungal activities has stimulated the development of studies on this class of compounds, especially on their metabolism and biochemistry. These studies are driven by the use of 31 P NMR and by a clever combination of genomics and innovative chemistry by using the method of selective labeling of metabolites. These studies revealed unusual and interesting chemistry of these compounds.

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Section: Ciliatine (Aep 2-aminoethylphosphonic Acid)mentioning

confidence: 99%

Phosphonates: Their Natural Occurrence and Physiological Role

Kafarski¹

2020

Contemporary Topics About Phosphorus in Biology and Materials

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“…Along with phospholipids, CAEP has been characterized from a wide variety of marine invertebrates [66,67]. The key precursor of CAEP is 2-aminoethylphosphonate, which can be incorporated into lipid molecules by a pathway similar to that for PE biosynthesis [68].…”

Section: Discussionmentioning

confidence: 99%

Comparative lipidomic analysis of phospholipids of hydrocorals and corals from tropical and cold-water regions

2019

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To expand our knowledge of lipid and fatty acid (FA) biosynthesis in marine cnidarians, polar lipidomes of hydrocorals were studied for the first time and then compared with those of soft corals from tropical and boreal regions. The structure and content of FAs and molecular species of ethanolamine, choline, serine, and inositol glycerophospholipids (PE, PC, PS, and PI, respectively), and ceramide aminoethylphosphonate (CAEP) in tropical hydrocorals ( Millepora platyphylla , M . dichotoma ) and the cold-water hydrocoral Allopora steinegeri were determined by chromatography and mass spectrometry. All soft corals and cold-water hydrocorals are characterized by a considerable amount of C 20 polyunsaturated FAs (PUFAs) elongated into C 22 PUFAs. In the Millepora species, the high level of 22:5n-6 and 22:6n-3 against the background of the extremely low level of C 20 PUFAs may be explained by a high activity of rare Δ4 desaturase. In contrast to hydrocorals, soft corals are able to elongate and further desaturate C 22 PUFAs into C 24 PUFAs. Allopora and soft corals use C 20 PUFAs mainly for the synthesis of PE and PC. The molecular species of PS of soft corals concentrate C 24 PUFAs, while in Allopora and Millepora the PS molecules are mainly based on 22:4n-6 and 22:5n-6 acyl groups, respectively. Short acyl groups (C 14 ) dominate the CAEP molecules of Allopora . In all the animals compared, most molecular species of PE and PC are ether lipids, but diacyl molecular species dominate PI. Hydrocorals and tropical soft corals contain diacyl and ether PS molecules, respectively, whereas cold-water soft corals contain a mixture of these PS forms. The high similarity of the alkyl/acyl compositions indicates a possible biosynthetic relationship between PS and PI in hydrocorals. The data obtained in our study will provide a resource to further investigate the lipid metabolism in marine invertebrates.

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“…The amount of phosphonolipids in organisms varies depending on the species, tissue, or the location of the cell. For example, vertebrates have sphingophosphonolipids as components of sphingomyelin in neural tissue, whereas at invertebrates often contain high levels of these lipids as components of the outer membrane (Figure 56) [176][177][178]. Phosphonopeptides of natural origin.…”

Section: Natural Organophosphorus Compounds With P-c Bondmentioning

confidence: 99%

Phosphorus Compounds of Natural Origin: Prebiotic, Stereochemistry, Application

Kolodiazhnyi

2021

Symmetry

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Organophosphorus compounds play a vital role as nucleic acids, nucleotide coenzymes, metabolic intermediates and are involved in many biochemical processes. They are part of DNA, RNA, ATP and a number of important biological elements of living organisms. Synthetic compounds of this class have found practical application as agrochemicals, pharmaceuticals, bioregulators, and others. In recent years, a large number of phosphorus compounds containing P-O, P-N, P-C bonds have been isolated from natural sources. Many of them have shown interesting biological properties and have become the objects of intensive scientific research. Most of these compounds contain asymmetric centers, the absolute configurations of which have a significant effect on the biological properties of the products of their transformations. This area of research on natural phosphorus compounds is still little-studied, that prompted us to analyze and discuss it in our review. Moreover natural organophosphorus compounds represent interesting models for the development of new biologically active compounds, and a number of promising drugs and agrochemicals have already been obtained on their basis. The review also discusses the history of the development of ideas about the role of organophosphorus compounds and stereochemistry in the origin of life on Earth, starting from the prebiotic period, that allows us in a new way to consider this most important problem of fundamental science.

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Cited by 63 publications

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Phosphonates: Their Natural Occurrence and Physiological Role

Phosphonates: Their Natural Occurrence and Physiological Role

Comparative lipidomic analysis of phospholipids of hydrocorals and corals from tropical and cold-water regions

Phosphorus Compounds of Natural Origin: Prebiotic, Stereochemistry, Application

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