Chemical structure and immunobiological activity of lipid A from Serratia marcescens LPS

2007 ◽  
Vol 56 (11) ◽  
pp. 1440-1446 ◽  
Author(s):  
Yutaka Makimura ◽  
Yasuyuki Asai ◽  
Akiko Sugiyama ◽  
Tomohiko Ogawa
Keyword(s):  
Serratia Marcescens ◽  
Chemical Structure ◽  
Lipid A ◽  
Biological Activities ◽  
Gel Filtration ◽  
Peritoneal Macrophages ◽  
Weak Acid ◽  
Active Centre ◽  
Necrosis Factor Alpha ◽  
Phenol Water

The chemical structure and immunobiological activities of Serratia marcescens lipid A, an active centre of LPS, were investigated. LPS preparations of S. marcescens were extracted using a hot phenol/water method, after which purified lipid A specimens were prepared by weak acid hydrolysis, followed by normal phase and gel filtration chromatographic separation. The lipid A structure was determined by MS to be a diglucosamine backbone with diphosphates and five C14 normal chain acyl groups, including two acyloxyacyl groups at the 2 and 3 positions of the non-reducing side. S. marcescens lipid A and Escherichia coli-type synthetic lipid A (compound 506) exhibited definite reactivity in Limulus amoebocyte lysate assays. The lethal toxicity of S. marcescens lipid A was nearly comparable to that of compound 506, and both induced nuclear factor-κB activation in murine cells via Toll-like receptor (TLR)4/MD-2 but not TLR2, as well as various inflammatory cytokines in peritoneal macrophages of C3H/HeN mice but not C3H/HeJ mice. Furthermore, S. marcescens lipid A induced nearly the same amounts of tumour necrosis factor alpha, interleukin-6, and nitric oxide production by the murine alveolar macrophage cell line MH-S as compared with compound 506. These results indicate that S. marcescens possesses a penta-acylated lipid A, which is nearly identical to E. coli lipid A in regard to biological activities, while it also may be a crucial virulence factor of the bacterium.

scholarly journals Relationship of Structure and Biological Activity of Monosaccharide Lipid A Analogues to Induction of Nitric Oxide Production by Murine Macrophage RAW264.7 Cells

1998 ◽  
Vol 66 (12) ◽  
pp. 5792-5798 ◽  
Author(s):  
Keiji Funatogawa ◽  
Motohiro Matsuura ◽  
Masayasu Nakano ◽  
Makoto Kiso ◽  
Akira Hasegawa
Keyword(s):  
Nitric Oxide ◽  
Time Course ◽  
Lipid A ◽  
Biological Activities ◽  
Suppressive Effect ◽  
No Production ◽  
Murine Macrophage ◽  
Necrosis Factor Alpha ◽  
Tnf Α ◽  
Relationship Of

ABSTRACT Lipid A is the active center of bacterial lipopolysaccharide (LPS), which exhibits diverse biological activities via the production of various mediators. We investigated the production of nitric oxide (NO), one of the mediators, by a murine macrophage cell line, RAW264.7, upon stimulation with a series of monosaccharide lipid A analogues to elucidate the relationship of structure and activity in NO production. The production of other representative mediators, such as tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6), was also investigated to compare the structural requirements for the production of these cytokines with those for the production of NO. Structure-activity relationships in NO production correlated well with those in the production of TNF-α and IL-6. Among the lipid A analogues possessing different numbers of acyl groups on a 4-O-phosphono-d-glucosamine backbone, compounds like GLA-60 that possess three tetradecanoyl (C14) groups exhibited stronger activities in the production of the mediators than compounds possessing four or two C14 groups. Time course study of the production of these mediators showed that production of NO started and peaked later than those of TNF-α and IL-6. Neither neutralization of TNF-α activity by antibody nor suppression of TNF-α production by pentoxifylline showed a significant suppressive effect on production of NO and IL-6 upon stimulation with LPS or lipid A analogues. Neutralization of IL-6 activity by antibody showed no significant suppressive effect on production of NO and TNF-α. A monosaccharide lipid A analogue (GLA-58) which exhibited no detectable agonistic activity showed a suppressive effect on the production of all three mediators upon stimulation with LPS or lipid A analogues. These results indicate that signals for NO production by LPS agonists in murine macrophages are transduced in good correlation with those for production of TNF-α and IL-6, although they are not transduced via production of those cytokines.

scholarly journals Modification of the Structure and Activity of Lipid A in Yersinia pestis Lipopolysaccharide by Growth Temperature

2002 ◽  
Vol 70 (8) ◽  
pp. 4092-4098 ◽  
Author(s):  
Kazuyoshi Kawahara ◽  
Hiroko Tsukano ◽  
Haruo Watanabe ◽  
Buko Lindner ◽  
Motohiro Matsuura
Keyword(s):  
Yersinia Pestis ◽  
Cell Lines ◽  
Lipid A ◽  
Biological Activities ◽  
Human Macrophage ◽  
Necrosis Factor Alpha ◽  
Acyl Lipid ◽  
Tnf Α ◽  
Factor Alpha ◽  
The Difference

ABSTRACT Yersinia pestis strain Yreka was grown at 27 or 37°C, and the lipid A structures (lipid A-27°C and lipid A-37°C) of the respective lipopolysaccharides (LPS) were investigated by matrix-assisted laser desorption ionization-time-of-flight (MALDI-TOF) mass spectrometry. Lipid A-27°C consisted of a mixture of tri-acyl, tetra-acyl, penta-acyl, and hexa-acyl lipid A's, of which tetra-acyl lipid A was most abundant. Lipid A-37°C consisted predominantly of tri- and tetra-acylated molecules, with only small amounts of penta-acyl lipid A; no hexa-acyl lipid A was detected. Furthermore, the amount of 4-amino-arabinose was substantially higher in lipid A-27°C than in lipid A-37°C. By use of mouse and human macrophage cell lines, the biological activities of the LPS and lipid A preparations were measured via their abilities to induce production of tumor necrosis factor alpha (TNF-α). In both cell lines the LPS and the lipid A from bacteria grown at 27°C were stronger inducers of TNF-α than those from bacteria grown at 37°C. However, the difference in activity was more prominent in human macrophage cells. These results suggest that in order to reduce the activation of human macrophages, it may be more advantageous for Y. pestis to produce less-acylated lipid A at 37°C.

scholarly journals Biological Properties of Lipid A Isolated fromFlavobacterium meningosepticum

2001 ◽  
Vol 8 (3) ◽  
pp. 522-527 ◽  
Author(s):  
Ken-Ichi Tanamoto ◽  
Hitomi Kato ◽  
Yuji Haishima ◽  
Satoko Azumi
Keyword(s):  
Lipid A ◽  
Structural Similarity ◽  
Peritoneal Macrophages ◽  
Biological Properties ◽  
Moderate Activity ◽  
Necrosis Factor Alpha ◽  
Tnf Α ◽  
Specific Antagonist ◽  
Factor Alpha ◽  
High Level

ABSTRACT The biological properties of the lipid A from Flavobacterium meningosepticum, which we recently isolated and whose complete chemical structure has been determined (H. Kato, T. Iida, Y. Haishima, A. Tanaka, and K. Tanamoto. J. Bacteriol. 180:3891–3899, 1998), were studied. The lipid A exhibited generally moderate activity compared toSalmonella enterica subsp. enterica serovar abortus equi lipopolysaccharide (LPS) used as a control in the assay systems tested; lethal toxicity in galactosamine-sensitized mice, mitogenicity in mouse spleen cells, induction of tumor necrosis factor alpha (TNF-α) release from mouse peritoneal macrophages and J774-1 mouse macrophage-like and human THP-1 line cells, nitric oxide induction activity from J774-1 cells, and Limulus gelation activity. The moderate activity of the F. meningosepticumlipid A may be explained by its unique fatty acid composition and the lack of a phosphate group in position 4′. It is noteworthy that the lipid A apparently induced TNF-α release from peritoneal macrophages in LPS-unresponsive C3H/HeJ mice and that the activation was suppressed by the LPS-specific antagonist, succinylated lipid A precursor. Significant splenocyte mitogenicity in C3H/HeJ mice was also observed with the lipid A. Taken together with the previous results concerningPorphyromonas gingivalis lipid A, which has a high level of structural similarity to the lipid A of F. meningosepticum, and the induction of TNF-α release in macrophages from C3H/HeJ mice, the lipid A of F. meningosepticum, which has novel fatty acids, may possibly play an role for the activation of C3H/HeJ macrophages.

scholarly journals Chemical Structure and Biological Activities of Porphyromonas gingivalis Lipid A.

1997 ◽  
Vol 52 (2) ◽  
pp. 475-483
Author(s):  
Toshio UMEMOTO ◽  
Hidefumi KUMADA ◽  
Kiyoko WATANABE
Keyword(s):  
Porphyromonas Gingivalis ◽  
Chemical Structure ◽  
Lipid A ◽  
Biological Activities

scholarly journals Structural and Biological Diversity of Lipopolysaccharides from Burkholderia pseudomallei and Burkholderia thailandensis

2009 ◽  
Vol 16 (10) ◽  
pp. 1420-1428 ◽  
Author(s):  
Vidhya Novem ◽  
Guanghou Shui ◽  
Dongling Wang ◽  
Anne K. Bendt ◽  
Siew Hoon Sim ◽  
...  
Keyword(s):  
Burkholderia Pseudomallei ◽  
Molecular Mechanisms ◽  
Lipid A ◽  
Biological Diversity ◽  
Biological Activities ◽  
Immune Recognition ◽  
Necrosis Factor Alpha ◽  
Burkholderia Thailandensis ◽  
Low Level

ABSTRACT Burkholderia pseudomallei, the etiological agent of melioidosis, is a facultative intracellular pathogen. As B. pseudomallei is a gram-negative bacterium, its outer membrane contains lipopolysaccharide (LPS) molecules, which have been shown to have low-level immunological activities in vitro. In this study, the biological activities of B. pseudomallei LPS were compared to those of Burkholderia thailandensis LPS, and it was found that both murine and human macrophages produced levels of tumor necrosis factor alpha, interleukin-6 (IL-6), and IL-10 in response to B. pseudomallei LPS that were lower than those in response to B. thailandensis LPS in vitro. In order to elucidate the molecular mechanisms underlying the low-level immunological activities of B. pseudomallei LPS, its lipid A moiety was characterized using mass spectrometry. The major lipid A species identified in B. pseudomallei consists of a biphosphorylated disaccharide backbone, which is modified with 4-amino-4-deoxy-arabinose (Ara4N) at both phosphates and penta-acylated with fatty acids (FA) C14:0(3-OH), C16:0(3-OH), and either C14:0 or C14:0(2-OH). In contrast, the major lipid A species identified in B. thailandensis was a mixture of tetra- and penta-acylated structures with differing amounts of Ara4N and FA C14:0(3-OH). Lipid A species acylated with FA C14:0(2-OH) were unique to B. pseudomallei and not found in B. thailandensis. Our data thus indicate that B. pseudomallei synthesizes lipid A species with long-chain FA C14:0(2-OH) and Ara4N-modified phosphate groups, allowing it to evade innate immune recognition.

scholarly journals Peptidogalactomannan from Histoplasma capsulatum yeast cell wall: role of the chemical structure in recognition and activation by peritoneal macrophages

2021 ◽  
Author(s):  
Giulia Maria Pires dos Santos ◽  
Gustavo Ramalho Cardoso dos Santos ◽  
Mariana Ingrid Dutra da Silva Xisto ◽  
Rodrigo Rollin-Pinheiro ◽  
Andréa Regina de Souza Baptista ◽  
...  
Keyword(s):  
Cell Wall ◽  
Yeast Cell ◽  
Chemical Structure ◽  
Histoplasma Capsulatum ◽  
Peritoneal Macrophages ◽  
Yeast Cell Wall

scholarly journals A Further Comprehensive Review on the Phytoconstituents from the Genus Erythrina

2020 ◽  
Vol 23 (1) ◽  
pp. 65-77 ◽  
Author(s):  
Mohammad Musarraf Hussain
Keyword(s):  
Chemical Structure ◽  
Biological Activities ◽  
Chemical Constituents ◽  
Pharmaceutical Journal ◽  
Significant Source ◽  
Comprehensive Review ◽  
Chemical Structures ◽  
Previous Review

Erythrina is a significant source of phytoconstituents. The aim of this review is to solicitude of classification, synthesis, and phytochemicals with biological activities of Erythrina. In our previous review on this genus (Hussain et. al., 2016a) fifteen species (Erythrina addisoniae, E. caribeae, E. indica, E. lattisima, E. melanacantha, E. mildbraedii, E. poeppigiama, E. stricta, E. subumbrans, E. veriagata, E. vespertilio, E. velutina, E. zeberi, E. zeyheri and E. americana) have been studied and 155 molecules with chemical structures were reported. A further comprehensive review was done upon continuation on the same genus and thirteen species (E. abyssinica, E. arborescens, E. berteroana, E. burttii, E. caffra, E. coralloids, E. crista-galli, E. fusca, E. herbaceae, E. lysistemon, E. mulungu, E. speciosa and E. tahitensis) of Erythrina have been studied and 127 compounds are reported as phytoconstituents with their chemical structure in this review. Erythrina crista-galli and E. lysistemon consist of highest number of chemical constituents. Bangladesh Pharmaceutical Journal 23(1): 65-77, 2020

Sign in / Sign up

Export Citation Format

Share Document