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Isolation and structure determination of sulfonoquinovosyl dipalmitoyl glyceride, a P-selectin receptor inhibitor from the alga Dictyochloris fragrans.

Bioassay-guided fractionation of the marine alga Dictyochloris fragrans led to the isolation and identification of sulfonoquinovosyl dipalmitoyl glyceride (1). The structure of 1 was determined by a combination of spectroscopic methods. On the basis of P-selectin inhibition assays (i.e., P-selectin-IgG ELISA, cell binding assay of receptor globulin, and platelet:HL60 adhesion, it was demonstrated that 1 selectively blocks the P-selectin-ligand interaction in vitro and could be considered a lead compound for synthetic modification in order to design more potent inhibitors of cell adhesion processes that play important roles in development of inflammatory-mediated disease states.

Cell Adhesion↗

Glyceride-cysteine lipoproteins and secretion by Gram-positive bacteria.

The membrane penicillinases of Bacillus licheniformis and Bacillus cereus are lipoproteins with N-terminal glyceride thioether modification identical to that of the Escherichia coli outer membrane lipoprotein. They are readily labeled with [3H]palmitate present during exponential growth. At the same time, a few other proteins in each organism become labeled and can be detected by fluorography after sodium dodecyl sulfate-polyacrylamide gel electrophoresis of total membrane proteins. We distinguish these proteins from the O-acyl proteolipids by demonstrating the formation of glyceryl cysteine sulfone after performic acid oxidation and hydrolysis of the protein. By this criterion, B. licheniformis and B. cereus contain sets of lipoproteins larger in average molecular weight than that of E. coli. Members of the sets probably are under a variety of physiological controls, as indicated by widely differing relative labeling intensity in different media. The set in B. licheniformis shares with membrane penicillinase a sensitivity to release from protoplasts by mild trypsin treatment, which suggests similar orientation on the outside of the membrane. At least one protein is the membrane-bound partner of an extracellular hydrophilic protein, the pair being related as membrane and exopenicillinases are. We propose that the lipoproteins of gram-positive organisms are the functional equivalent of periplasmic proteins in E. coli and other gram-negative bacteria, prevented from release by anchorage to the membrane rather than by a selectively impermeable outer membrane.

Bacillus↗

Ethnic differences in in vitro glyceride synthesis in subcutaneous and omental adipose tissue.

Considerable evidence suggests that there are ethnic differences in lipid metabolism between African American and Caucasian women, which may result in increased synthesis of fat in adipose tissue. The purpose of this study was to measure the in vitro rates of [14C]glucose incorporation into the glyceride-glycerol backbone of triglycerides (TG) and diglycerides (DG) in abdominal subcutaneous (SAT) and omental adipose tissue (OAT). Morbidly obese [African American (n = 15): body mass index (BMI) = 45 +/- 2.3; Caucasian (n = 18): BMI = 51 +/- 2.3] and preobese [African American (n = 7): BMI = 27 +/- 1.0; Caucasian (n = 7): BMI = 25 +/- 1.0] women were examined in this study. There were no significant differences in the rates of synthesis of either TG or DG in SAT of either preobese or obese women. On the other hand, both preobese and obese African American women had higher rates of synthesis of TG in OAT compared with their Caucasian counterparts. This increase in TG synthesis in OAT was not due to differences in cell size or rates of reesterification. Thus African American woman have an increased capacity to synthesize TG in OAT compared with Caucasian women, which may contribute to the higher prevalence of obesity in African American women.

Adipose Tissue↗

Chemical structures of mono-, di-, tri-, and tetraglycosyl glycerides in rice bran.

1. Monoglycosyl monoglyceride, mono-, di-, tri- and tetraglycosyl diglycerides were isolated from rice bran and characterized for their chemical structures. 2. Monoglycosyl monoglycerides were characterized as Gal(beta 1' leads to 3)-1- or 2-monoacyl-sn-glycerol and Glc(beta 1' leads to 3)-1- or 2-monoacyl-sn-glycerol. 3. The structures of monoglycosyl diglyceride were Gal(beta 1' leads to 3)-1,2-diacyl-sn-glycerol and Glc(beta 1' leads to 3)-1,2diacyl-sn-glycerol. Epimeric separation of the galactosyl and glucosyl glycerides was for the first time achieved by thin-layer chromatography. 4. The main diglycosyl diglyceride was shown to be Gal(alpha 1'' leads to 6')-Gal(beta 1' leads to 3)-1,2-diacyl-sn-glycerol. 5. The major structure of triglycosyl diglyceride was characterized as Gal(alpha 1''' leads to 6'')-Gal(alpha 1'' leads to 6')-Gal(beta 1' leads to 3)-1,2-diacyl-sn-glycerol. 6. The representative structure of tetraglycosyl diglyceride was for the first time established as Gal(alpha 1'''' leads to 6''')-Gal(alpha 1''' leads to 6'')-Gal(a-pha 1'' leads to 6')-Gal(beta1' leads to 3)-1,2-diacyl-sn-glycerol.

Chemical Phenomena↗