Hemolytic Properties of Synthetic Glycosides

Segal, Ruth; Shud, Frieda; Milo-Goldzweig, Ilana

doi:10.1002/jps.2600671123

Cited by 7 publications

(2 citation statements)

References 26 publications

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“…The close adhesion and/or destruction of the organism may expose the host cells to the CGs. It has been observed that steryl glycosides possess hemolytic properties (32). In this work, the CG of H. pylori showed hemolytic activities.…”

Section: Discussionmentioning

confidence: 50%

Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis

et al. 1995

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A chloroform-methanol-extracted lipid of Helicobacter pylori was studied. Three kinds of glycolipids, accounting for about 25% (wt/wt) of the total lipid, were detected and identified to be cholesteryl glucosides. The structures of two of them were determined to be cholesteryl-␣-D-glucopyranoside and cholesteryl-6-O-tetradecanoyl-␣-D-glucopyranoside, and the plausible structure of the third one was identified as cholesteryl-6-Ophosphatidyl-␣-D-glucopyranoside. Cholesteryl glucosides are very rare in animals and bacteria. Furthermore, those in H. pylori had an ␣-glycosidic linkage, which is rather unusual for natural glycosides, and a phosphatelinked cholesteryl glycoside like the cholesteryl-6-O-phosphatidyl-␣-D-glucopyranoside has not been reported previously. As the cholesterol glucosides were detected in strains obtained from diverse geographical locations, the presence of cholesteryl glucosides in H. pylori is a very unique and a characteristic feature of the species. These findings add a new facet to the physiology and biochemistry, especially the cholesterol and glucose metabolism, of H. pylori. Furthermore, the cholesteryl glucosides of H. pylori showed hemolytic activities.Helicobacter pylori is a curved gram-negative bacterium which was first reported in 1983 (21, 35). The organism is now recognized as a primary cause of active chronic gastritis and is reported to be associated with peptic ulcer disease, gastric adenocarcinoma, and low-grade B-cell gastric lymphoma of mucosa-associated lymphoid tissue (4,14,36).The organism can colonize in and under the mucus layer of the human gastric mucosa without the copresence of other bacterial species. It, living in the unique gastric environment, is likely to have features distinct from other bacteria. Furthermore, it has been found to possess a unique urease having a very low K m value, which hydrolyzes urea efficiently even at the low urea concentration found in the gastric mucosa (13,24).On the other hand, the lipid composition of microorganisms can adapt in response to alterations of environmental conditions (15, 25), and those living in unique environments may have special lipids (5). It is likely that H. pylori living in the gastric niche may have a distinct lipid composition or structure. The fatty acid composition of H. pylori has been studied extensively (9, 10, 19), and it has been shown that the cellular fatty acids 3-OH C 16:0 and 3-OH C 18:0 are unique to this organism. However, little is known about the polar lipid composition of H. pylori.Therefore, we studied the lipid composition of H. pylori and detected three kinds of glycolipids, which were identified as cholesteryl glucosides (CGs). Additionally, the molecular structures of these CGs have been determined. MATERIALS AND METHODSBacterial strains and growth conditions. H. pylori NCTC 11638 was mainly used in this study. H. pylori ATCC 43504 and two clinical isolates of H. pylori obtained from Japan and Bangladesh were used for comparison. These were grown in brain heart infusion broth (Difco, D...

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Section: Discussionmentioning

confidence: 50%

Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis

et al. 1995

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“…In general, therapeutic application of saponins is very limited because of either the poor absorbance from the intestine when taken orally or the toxicity induced by marked hemolysis when administered by injection, especially i.v. (Segal et al, 1978). Better understanding of the efficacy and safety of saikosaponins requires the elucidation of their biologic fates in the body.…”

Section: Introductionmentioning

confidence: 99%

Metabolism of Saikosaponin a in Rats: Diverse Oxidations on the Aglycone Moiety in Liver and Intestine in Addition to Hydrolysis of Glycosidic Bonds

Guoqiang

Tian

et al. 2013

Drug Metabolism and Disposition

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The main objective of the present study was to completely characterize the metabolites of the triterpenoid saikosaponin a (SSa) in rats. To this aim, we compared the metabolites in plasma, bile, urine, and feces samples following oral and i.v. routes of administration using liquid chromatography-diode array detector coupled with hybrid ion trap-time-of-flight mass spectrometry. As a result, besides 2 known metabolites, prosaikogenin f and saikogenin f, 15 new metabolites were detected in all. It was found that SSa is metabolized mainly in phase I manner, i.e., hydration and monooxidation on the aglycone moiety and hydrolysis of the b-glucosidic bond in the liver, and sequential hydrolysis of b-glucosidic and b-fucosidic bonds followed by dehydrogenation, hydroxylation, carboxylation, and combinations of these steps on the aglycone moiety in the intestinal tract. Both the renal and biliary routes were observed for the excretion of SSa and its metabolites. Further, a clear metabolic profile in rats was proposed in detail according to the results from the in vivo animal experiment after different routes of administration. Our results update the preclinical metabolism and disposition data on SSa, which is not only helpful for the future human metabolic study of this compound but also provides basic information for better understanding of the efficacy and safety of prescriptions containing saikosaponins.

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Structure—activity relationships of synthetic diosgenyl monoglycosides

Takechi

Tanaka

1991

Phytochemistry

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Hemolytic Properties of Synthetic Glycosides

Cited by 7 publications

References 26 publications

Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis

Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis

Metabolism of Saikosaponin a in Rats: Diverse Oxidations on the Aglycone Moiety in Liver and Intestine in Addition to Hydrolysis of Glycosidic Bonds

Structure—activity relationships of synthetic diosgenyl monoglycosides

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