Über Steroide. (35. Mitteilung). Zur Darstellung von Saccharidderivaten der Steroide

Meystre, Ch.; Miescher, K.

doi:10.1002/hlca.19440270125

Cited by 60 publications

(9 citation statements)

References 8 publications

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“…Cholesterol, campesterol, stigmasterol, fl-sitosterol, and cholesteryl palmitate were purchased from Applied Science Laboratories, Inc., State College, Pa. The synthesis of cholesteryl glucoside was by the method of Meystre and Miescher (13). Five grams of cholesterol and 6 g of silver carbonate were dissolved in 200 ml of benzene.…”

Section: Methodsmentioning

confidence: 99%

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Effects of Free Sterols, Steryl Ester, and Steryl Glycoside on Membrane Permeability

Grünwald

1971

Plant Physiol.

152

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Section: Methodsmentioning

confidence: 99%

“…Five grams of cholesterol and 6 g of silver carbonate were dissolved in 200 ml of benzene. This mixture was brought to boiling under continuous stirring, and 13 HCI. The cholesteryl glucoside precipitated.…”

Section: Methodsmentioning

confidence: 99%

Effects of Free Sterols, Steryl Ester, and Steryl Glycoside on Membrane Permeability

Grünwald

1971

Plant Physiol.

152

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“…Base hydrolysis, however, produced two radioactive sterol products which chromatographed by TLC close to ASG. It is quite possible that the unknown is a steryl glycoside that is acylated at a position other than the C6 of the carbohydrate moiety (18).…”

Section: Discussionmentioning

confidence: 99%

“…Sterol-labeled cholesteryl glucoside was synthesized from [4-'4C]cholesterol by a modified method of Meystre and Miescher (10,18). The product was purified by TLC on Silica Gel G plates.…”

mentioning

confidence: 99%

Acylated Steryl Glycoside Synthesis in Seedlings of Nicotiana tabacum L.

Frasch

Grünwald²

1976

Plant Physiol.

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more radioactivity, and at a faster rate, than did the SG fraction (3). Furthermore, when labeled cholesteryl glucoside was supplied to intact seedlings, only small amounts of the label were found as ASG, but much more radioactivity was found as free sterol. Based on these data, the existence of a second biosynthetic pathway for ASG was suggested (3). Inasmuch as sterols have been shown to be influential in controlling membrane stability and, hence, permeability (10, 11), the possibility of the existence of a second pathway for the synthesis of ASG in intact tobacco is of great interest.This study was designed to elucidate the biosynthesis of ASG in the in vivo system. We isolated a sterol component which was readily converted to ASG and was not SG, indicative of a second biosynthetic pathway for ASG.MATERIALS AND METHODS Plant Material. Tobacco seeds (Nicotiana tabacum L. var. Burley 21) were germinated on Whatman No. 1 filter paper placed on a tray so that both ends of the filter paper were submerged in H20, providing a constant source of moisture. The tray was covered and placed under a constant light source of 1 .1 x 104 ergs/cm2 sec at 27 C. The relative humidity in the tray was between 90 and 100%. The seeds germinated uniformly with radicle protrusion occurring in 2 to 2.5 days..8-D-Cholesteryl-Glucose Synthesis. Sterol-labeled cholesteryl glucoside was synthesized from [4-'4C]cholesterol by a modified method of Meystre and Miescher (10,18). The product was purified by TLC on Silica Gel G plates. The solvent system was chloroform-methanol-acetic acid-water (90:8:1:1, v/v/v/v). Authentic cholesteryl glucoside had an RF value of 0.11 and the corresponding zone was scraped and the radioactive SG eluted with chloroform-methanol (2:1, v/v). After hydrolysis with 0.5% H2SO4 in 95% ethanol for 12 hr, TLC revealed one radioactive spot which corresponded to free cholesterol with an RF of 0.70. Digitonin precipitation of the acid hydrolysate gave a 92% free sterol recovery. ml of dry pyridine was added, dropwise, 400 mg of palmitoyl chloride in 5 ml of dry benzene. This mixture was allowed to stand for 3 hr after which it was acidified with dilute H2S04. The ASG was extracted with chloroform and washed twice with H20. The sample was evaporated to a small volume and purified by TLC with solvent system chloroform-methanol-acetic acid-water (10:8:1:1, v/v/v/v

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“…glycosylated steroids was opened up in 1936 by Lettré and Hagedorn, 8 who prepared cholesterol glucoside tetraacetate in 33% yield by the use of calcium hydride combined with silver oxide in refluxing ether. Schapiro 9 in 1938, and Huebner et al 10 and Meystre et al 11 in 1944 subsequently reported the synthesis of some other steroid glucosiduronates. The same procedure was applied in 1955 by Schneider et al to the synthesis of methyl (21-acetoxy-11,20-dioxo17a-hydroxy-5b-pregnan-3a-yl-2,3,4-tri-O-acetyl-b-Dglucosid)-uronate.…”

Section: Glycosylation Using Glycosyl Bromide and Chloridementioning

confidence: 95%

The glycosylation of steroids

Pellissier

2004

Tetrahedron

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Über Steroide. (35. Mitteilung). Zur Darstellung von Saccharidderivaten der Steroide

Cited by 60 publications

References 8 publications

Effects of Free Sterols, Steryl Ester, and Steryl Glycoside on Membrane Permeability

Effects of Free Sterols, Steryl Ester, and Steryl Glycoside on Membrane Permeability

Acylated Steryl Glycoside Synthesis in Seedlings of Nicotiana tabacum L.

The glycosylation of steroids

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