Chemical Structure of Lipid A: Recent Advances in Structural Analysis of Biologically Active Molecules

2020 ◽  
pp. 93-114 ◽  
Author(s):  
Ulrich Zähringer ◽  
Buko Lindner ◽  
Ernst T. Rietschel
Author(s):  
Shukla PK ◽  
Singh MP ◽  
Patel R

Indole and its derivatives have engaged a unique place in the chemistry of nitrogen heterocyclic compounds. The recognition of the plant growthhormone, heteroauxin, the significant amino acids, tryptamine & tryptophan and anti-inflammatory drug, indomethacine are the imperativederivatives of indole which have added stimulus to this review work. Isatin (1H-indole-2,3-dione), an indole derivative of plant origin. Althoughit is a naturally occurring compound, but was synthesized by Erdmann and Laurent in 1840 before it was found in nature. Isatin is a versatileprecursor for many biologically active molecules and its diversified nature makes it a versatile substrate for further modifications. It is concernedin many pharmacological activities like anti-malarial, antiviral, anti-allergic, antimicrobial etc; isatin and its derivatives have been also found todemonstrate promising outcomes against various cancer cell lines. This review provides a brief overview on the recent advances and futureperspectives on chemistry and biological aspects of isatin and its derivatives reported in the recent past.


1984 ◽  
Vol 48 (1) ◽  
pp. 251-252 ◽  
Author(s):  
Makoto Kiso ◽  
Hideharu Ishida ◽  
Akira Hasegawa
Keyword(s):  
Lipid A ◽  

1994 ◽  
Vol 1 (3) ◽  
pp. 137-148 ◽  
Author(s):  
N. Qureshi ◽  
K. Takayama ◽  
U. Seydel ◽  
R. Wang ◽  
R.J. Cotter ◽  
...  

2008 ◽  
Vol 3 (10) ◽  
pp. 1934578X0800301 ◽  
Author(s):  
Maria I. Bilan ◽  
Anatolii I. Usov

Sulfated polysaccharides of brown algae (“fucoidans”) constitute a wide variety of biopolymers from simple sulfated fucans up to complex heteropolysaccharides composed of several neutral monosaccharides, uronic acid and sulfate. The increased interest in this class of polysaccharides is explained by their high and versatile biological activities, and hence, by their possible use in new drug design. Structural analysis of several fucoidans demonstrates that their biological properties are determined not only by charge density, but also by fine chemical structure, although distinct correlations between structure and biological activity cannot be formulated at present. The aim of this review is to describe the methods of structural analysis currently used in fucoidan chemistry, and to discuss some new information on the structures of fucoidans presented in recent publications.


1989 ◽  
Vol 12 (8) ◽  
pp. 505-508 ◽  
Author(s):  
G. Passavanti ◽  
E. Buongiorno ◽  
G. De Fino ◽  
D. Fumarola ◽  
P. Coratelli

This study of 20 endotoxemic patients submitted to 70 hemodialyses (HD) found a reduction of the pre-HD limulus amebocyte lysate (LAL) positivity in 50 HD (71%), without appreciable differences in terms of effectiveness between cuprophan and AN 69 membranes. To define the mechanisms responsible for the reduction in LAL positivity during HD, the membranes were used in two in vitro studies, the first of which showed that the LAL positivity of blood containing lipopolysaccharide (LPS), submitted to hemofiltration (HF) for 300 min, remained unchanged and the ultrafiltrate remained constantly LAL negative. These results suggest that the reduction in LAL positivity observed in HD in vivo, an expression of reduced endotoxemia, cannot be attributed either to the filtration of the LPS as such or to its fragmentation following blood-membrane interaction into theoretically less filtrable molecules or to mechanisms of LPS adsorption on the membrane. The in vivo reduction of LAL positivity is more likely due to removal of the filtrable endotoxin fragments already released in the body, like lipid A, the biologically active component of LPS, known to react to LAL. This hypothesis was borne out by the second in vitro study, where the LAL positivity of blood containing lipid A, treated by HF for 80 min, gradually decreased, and dialytic permeability to lipid A was confirmed by the appearance of LAL positivity in the ultrafiltrate.


2007 ◽  
Vol 56 (11) ◽  
pp. 1440-1446 ◽  
Author(s):  
Yutaka Makimura ◽  
Yasuyuki Asai ◽  
Akiko Sugiyama ◽  
Tomohiko Ogawa

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.


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