An unusual lipid a from a marine bacterium Chryseobacterium scophtalmum CIP 104199T

Vorob’eva, E. V.; Красикова, И. Н.; Dmitrenok, Andrey S.; Dmitrenok, Pavel S.; Исаков, В. В.; Nedashkovskaya, Olga I.; Соловьева, Т. Ф.

doi:10.1134/s1068162006050128

Cited by 7 publications

(7 citation statements)

References 34 publications

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“…Therefore, we supposed that marine bacteria, whose habitat is typically cold with high pressure and an elevated content of inorganic salts [3], could become a source of structural variants of lipid A that are interesting from a pharmacological viewpoint. However, information on the structure and biological activity of lipid A from marine gram-negative bacteria are available for a limited number of microorganisms [4][5][6].We studied the structure of lipid A from a bacterium of the genus Pseudoalteromonas, P. nigrifaciens IAM 13010 T . This is an aerobic, heterotrophic, gram-negative bacterium [7] and widely distributed obligate marine microorganism that is easily isolated from littoral waters and from the open sea and requires seawater in the growth medium.…”

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Structure of lipid A from the marine gram-negative bacterium Pseudoalteromonas nigrifaciens IAM 13010T

et al. 2007

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The structure of lipid A from the marine γ-proteobacterium Pseudoalteromonas nigrifaciens IAM 13010 T that was prepared by hydrolysis of the corresponding lipopolysaccharide by acetic acid (1%) was determined by chemical analysis, 13 C NMR spectroscopy, and MALDI/TOF and LSIMS mass spectrometry. It was shown that lipid A is a β-1,6-bonded disaccharide of glucosamine that is substituted by two phosphoric acids (in the C1 and C4′ positions), two (R)-3-hydroxyalkanoic (normal and branched) acids with ester bonding (at the C3 and C3′-positions), and (R)-3-hydroxydodecanoic and (R)-3-dodecanoyloxydodecanoic acids (both with amide bonding at C2′ and C2, respectively). It was hypothesized that this type of structure is typical of lipid A from bacteria of the genus Pseudoalteromonas in general.Key words: marine gram-negative bacteria, Pseudoalteromonas nigrifaciens, LPS, lipid A, 13 C NMR spectroscopy, MALDI/TOF and LSIMS mass spectrometry.Gram-negative bacteria contain an unusual glycophospholipid called lipid A in addition to classical lipids constructed from glycerine.It is well-known that variations in the structure of lipid A are largely determined by the cultivation conditions of the microorganisms [1, 2]. Therefore, we supposed that marine bacteria, whose habitat is typically cold with high pressure and an elevated content of inorganic salts [3], could become a source of structural variants of lipid A that are interesting from a pharmacological viewpoint. However, information on the structure and biological activity of lipid A from marine gram-negative bacteria are available for a limited number of microorganisms [4][5][6].We studied the structure of lipid A from a bacterium of the genus Pseudoalteromonas, P. nigrifaciens IAM 13010 T . This is an aerobic, heterotrophic, gram-negative bacterium [7] and widely distributed obligate marine microorganism that is easily isolated from littoral waters and from the open sea and requires seawater in the growth medium.The most common method for preparing lipid A is hydrolysis by AcOH (1%) of lipopolysaccharide (LPS) [8], which is in turn obtained by extraction of defatted cells by hot aqueous phenol (45%) by the Westphal method [9]. Using this approach, lipid A was isolated from P. nigrifaciens and contained glucosamine (GlcN), phosphorus, and FA according to total chemical analysis.The principal FA were 3-hydroxydodecanoic (3-OH-12:0, 36.1 mass %), a part of which (3.4%) occurred as the iso-form; dodecanoic (12:0, 12.8%); 3-hydroxyundecanoic (3-OH-11:0, 7.9%); 3-hydroxytetradecanoic (3-OH-14:0, 6.2%); 3-hydroxytridecanoic (3-OH-13:0, 5.0%); and 3-hydroxydecanoic (3-OH-10:0, 2.6%). Thus, lipid A from P. nigrifaciens, like lipid A from other bacteria of this genus [10], is highly heterogeneous with respect to the composition of 3-hydroxyalkanoic acids.According to TLC, lipid A from P. nigrifaciens is a rather complex mixture of homologs with differing degrees of phosphorylation and acylation. This significantly complicates its further structural characterization. In order to ...

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Structure of lipid A from the marine gram-negative bacterium Pseudoalteromonas nigrifaciens IAM 13010T

et al. 2007

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“…Finally, the Endozoicomonas sp. HEX 311 lipid A was found to possess uncommon features, such as the odd‐numbered fatty acids reported for other marine bacteria, including Shewanella pacifica KMM 3772, Arenibacter certesii KMM 3941 T , Pseudoalteromonas haloplanktis ATCC 14393 T , Chryseobacterium scophtalmum CIP 104199 T , or Thermomonas hydrothermalis . The occurrence of both odd‐numbered and very short acyl chains ( iso ‐9:0) might also have a role in the establishment of the symbiotic process because it was previously demonstrated that, not only the amount, but also the length of the fatty acids is required for proper TLR4/MD‐2 activation, with a minimum length of eight and an optimal length of ten carbon atoms …”

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The Lipid A Structure from the Marine Sponge Symbiont Endozoicomonas sp. HEX 311

et al. 2018

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Endozoicomonas sp. HEX311 is a Gram-negative bacterium known to establish a commensal interaction with the marine demosponge Suberites domuncula. The molecular bases of the sponge-microbe interaction events are still poorly defined. Nevertheless, it has been proved that S. domuncula possesses an innate immune system with similarities to the mammalian one and is able to recognize the main component of the Gram-negative bacteria cell wall: the lipopolysaccharide. Whether this recognition occurs in a structure-dependent manner, which is typical for mammalian immune system receptors, is still under investigation. Herein, we report the Endozoicomonas sp. HEX311 lipid A structure obtained by a combination of data attained from chemical, MALDI MS, and MS approaches. The lipid A is a complex family of species decorated by pyrophosphate and phosphate units and carrying (R)-3-hydroxydodecanoic acid, (R)-3-hydroxytetradecanonic acid, iso-2-hydroxyundecanoic acid, iso-(R)-3-hydroxyundecanoic acid, and iso-nonanoic acid as acyl chains.

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“…Later studies revealed a few special features of the lipid A molecules, the most pronounced of which is a penta-acyl type of structure [15]. We conducted systematic studies of lipid A from 13 wild strains of marine Proteobacteria belonging to the families of Alteromonadaceae ( Alteromonas , Idiomarina , and Pseudoalteromonas genera [16,17,18]) and Vibrionaceae ( Shewanella and Vibrio genera [16]) and the genera of Marinomonas [19,20,21] and Chryseobacterium [22]. The marine lipid As molecules were shown to be characterized by significant structural diversities (Figure 3).…”

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“…( a ) Lipid А of P. haloplanktis АТСС 14399 Т bacteria [17], where R = 3-OH-11:0, 3-OH-12:0, 3-OH-13:0, 3-OH- iso -11:0, 3-OH- iso -12:0 acid; ( b ) Lipid A of M. сommunis ATCC 27118 T [21] (I), M. vaga ATCC 27119 T [20] (II) and M. mediterranea АТСС 700492 Т [24] (III) bacteria, where (I) −R = C12:0 acid; (II) −R = С10:0, С12:0 or С12:1 acids; (III) −R = 3-ОН-С10:0 acid; С4′ atom in the molecule of this lipid A is replaced with the residue of phosphoric acid; ( c ) Lipid A C. scophthalmum CIP 104199 Т [22] and C. indoltheticum CIP 103168 Т [24]. …”

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Marine Compounds with Therapeutic Potential in Gram-Negative Sepsis

et al. 2013

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This paper concerns the potential use of compounds, including lipid A, chitosan, and carrageenan, from marine sources as agents for treating endotoxemic complications from Gram-negative infections, such as sepsis and endotoxic shock. Lipid A, which can be isolated from various species of marine bacteria, is a potential antagonist of bacterial endotoxins (lipopolysaccharide (LPSs)). Chitosan is a widespread marine polysaccharide that is derived from chitin, the major component of crustacean shells. The potential of chitosan as an LPS-binding and endotoxin-neutralizing agent is also examined in this paper, including a discussion on the generation of hydrophobic chitosan derivatives to increase the binding affinity of chitosan to LPS. In addition, the ability of carrageenan, which is the polysaccharide of red alga, to decrease the toxicity of LPS is discussed. We also review data obtained using animal models that demonstrate the potency of carrageenan and chitosan as antiendotoxin agents.

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An unusual lipid a from a marine bacterium Chryseobacterium scophtalmum CIP 104199T

Cited by 7 publications

References 34 publications

Structure of lipid A from the marine gram-negative bacterium Pseudoalteromonas nigrifaciens IAM 13010T

Structure of lipid A from the marine gram-negative bacterium Pseudoalteromonas nigrifaciens IAM 13010T

The Lipid A Structure from the Marine Sponge Symbiont Endozoicomonas sp. HEX 311

Marine Compounds with Therapeutic Potential in Gram-Negative Sepsis

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