Mixture Of Glycosides Research Articles

Chemical content of Margaretta rosea Oliv. roots. 323. Glycosides and aglycones

AbstractThe roots of Margaretta rosea Oliv., subsp. rosea Bullock contain cardenolides mixed with Kedde negative ester glycosides. 6 Cardenolides were identified by paper chromatography (PC) and thin layer chromatography (TLC). Three of them were free aglycones (uzarigenin (1), corotoxigenin (3) and coroglaucigenin (5), the other three their corresponding 6‐deoxy‐β‐D‐allo‐pyranosides (ascleposide (2), gofruside (4) and frugoside (6). Only two cardenolides (1 and 5) were isolated in crystalline form. The behaviour of the more polar portion of the glycoside mixture shows that D‐gluco derivatives of at least 5 of the 6 cardenolides mentioned were also present.The Kedde. negative glycosides were a complicated mixture containing mainly 2,6‐dideoxysugars linked to esterified polyhydroxy‐pregnanes. After mild acid hydrolysis cymarose, oleandrose and digitoxose could be identified by PC and TLC. From the crude aglycone portion only one cristalline genin (M) could be isolated. This was still a mixture, but its main component according to the mass spectrum was a monobenzoyl derivative C28H38O7. ‐ A small amount of cristalline O‐acetyl‐β‐amyrin was isolated from the least polar components.

Separation of glycosaminoglycan saccharide and glycoside mixtures by gel filtration

Separation of glycosaminoglycan saccharide and glycoside mixtures by gel filtration

Über die beziehungen zwsichen chemischer struktur und chromatographischem verhalten bei herzglykosiden : V. Mitteilung Dünnschichtchromatographische untersuchungen an herzglykosiden und ihren geninen

The relationship between chemical structure and chromatographic behavior of heart glycosides. V. Thin-layer chromatographic investigations of heart glycosides and their genins Thin-layer chromatographic data are presented for about 160- heart glycosides and genins as well as their peracetylated derivatives in four solvent systems with Kieselgel G as the adsorbent. Some special arising from the sue of thin-layer chromatography for chromatographic structure determination ( cf. the following part) are discussed. Chromatography of a test mixture of heart glycosides under widely varying experimental conditions proved Δ R M values to be the only reliable data for any numerical evaluation of chromatography.

The glycosides of Vincetoxicum hirundinaria Medikus. I. Isolation and cleavage product (glycosides and aglycones)

AbstractThe dried roots of Vincetoxicum hirundinaria MEDIKUS, collected in the lake of Garda area, yielded ca. 6% of a crude glycoside mixture, of which 5,16% consisted of relatively weakly polar material. After mild acid hydrolysis of the latter, 7 sugars could be identified through paper and thin layer chromatography, and paper electrophoresis. Of these D‐cymarose, L‐diginose, D‐digitoxose, and a small amount of lilacinobiose could be isolated in crystalline form. Of the other three sugars, D‐oleandrose was characterised as a crystalline derivative, whereas boivinose and canarose could only be identified through paper and thin layer chromatography, and paper electrophoresis.Four crystalline genins (B, D, E, G) and a glycoside (F) were isolated from the genin extract. Of these, D was very unstable and therefore thus was not further investigated. B, E, and F were shown to be 15‐oxasteroids, a type of steroids so far not found in nature. Very probably, G also represents a 15‐oxasteroid. The four substances B, E, G, and F were given the following trivial names: B = anhydrohirundigenin, E = hirundigenin, G = vincetogenin, and F = hirundoside‐A. F is an oleandroside of anhydrohirundigenin. The structures of hirundigenin and anhydrohirundigenin have already been elucidated [35].

Die Pregnanderivate der Samen von Dregea abyssinica (HOCHST.) K. Schum. (Asclepiadaceae). I. Isolierungen Glykoside und Aglykone, 304. Mitteilung

AbstractThe seeds of Dregea abyssinica (HOCHST.) K. Schum. are very rich in glycosides. These consist of a complicated mixture of ester glycosides, cardenolides are absent. All these glycosides are derived from only the two known pregnane derivatives drevogenin P and Drevogenin D. In the glycosides the latter are esterified with different acids (acetic, isovaleric, α‐hydroxyisovaleric and tiglic acid) and glycosidically linked to different 2‐deoxy‐sugars which in part carry 3‐O‐methyl‐6‐deoxy‐D‐allose and terminal D‐glucose. After mild acidic hydrolysis 5 crystalline sugars and 6 crystalline aglycones could be isolated. The sugars were identified as D‐cymarose, asclepobiose, pachybiose, drebyssobiose and «sugar T» (formerly found in Dregea volubilis). The following aglycones were obtained: drevogenin A, drevogenin B, and four new compounds called drebyssogenin F, G, J and K. The latter was a mixture of two components (K1 and K2). From the original mixture four genuine glycosides could be isolated (the drebyssosides 1, 2, 3 and 4). Of these the drebyssosides 1 and 3 were obtained crystalline, drebyssoside 2 in amorphous but pure form and drebyssoside 4 as a mixture of mainly two closely related components. The probable structures of the new substances (drebyssobiose, sugar T, the four drebyssogenins and the four drebyssosides) are reported in the following publication.

Studies on the constituents of cimicifuga spp. IV. Constituents of Cimicifuga acerina. (4). Structure of methyl cimigenol

Methylcimigenol (II), mp 218-219°, [α] D+39.25°, C31H50O5, is isolated by chromatographic treatment of the product formed by hydrolysis with 50% acetic acid of a mixture of glycosides obtained from the whole herb of Cimicifuga acerina (Japanese name Ohbashoma). Acetylation of II with acetic anhdride and pyridine gives a monoacetate (III), mp 177-178°, [α] D+42.70°, C33H52O6, and a diacetate (IV), mp 206-207°, [α] D+42.65°, C35H54O7. Oxidation of II with chromium trioxide and pyridine produces a monoketone (V), mp 203-204°, C31H48O5, and a diketone (VI), mp 216-217°, C31H46O5. Comparative examination of various properties of these derivatives with those of the derivatives of cimigenol (I) suggests the formula II for methyl cimigenol. This structure was proved chemically by derivation of I to II by treatment with methanolic sulfuric acid.

The glycosides of the roots from Kanahia laniflora (Forssk.) R. Br. 1. Isolation

AbstractThe roots of Kanahia laniflora (FORSSK.) R. BR. contain, in addition to small quantities of cardenolides, a large amount of ester glycosides which are difficulty separable from one another. However, two of these ester glycosides were obtained in a nearly pure form. The crude mixture of ester glycosides, after mild acidic hydrolysis, gave a mixture of acyl‐genins and three sugars: D‐oleandrose, D‐digitoxose and D‐canarose, all of which were obtained in crystalline form. Acetic acid, benzoic acid and another unidentified acid were obtained on alkaline hydrolysis of the mixture of acyl‐genins along with 17‐isolineolon, lineolon, deacetylmetaplexigenin and a small amount of sarcostin‐ketone. Besides these known genins, three probably new genins (α, τ, λ) were obtained in small, but crystalline amounts.

Constituents of asclepiadaceae plants. XVII. Components of Cynanchum wilfordi Hemsley.

The roots of Cynanchum wilfordi HEMSLEY were found to contain a glycoside mixture. The glycosides showed a positive Keller-Kiliani reaction, suggesting the presence of a 2-deoxysugar. The sugar portion of the glycoside was found to be D-cymarose. The aglycone was shown to be an ester. Alkaline hydrolysis of the ester aglycone afforded three kind of pregnane compounds, sarcostin (I), deacylcynanchogenin (II), and deacylmetaplexigenin (III). Cinnamic acid was found in the acidic fractions.

Studies on the constituents of asclepiadaceae plants. XIX. Components of Metaplexis japonica Makino. IV.

The roots of Metaplexis japonica MAKINO contain a complex glycoside mixture. The alkaline hydrolysate of the crude ester-aglycone mixture showed the presence of sarcostin (I), deacylmetaplexigenin (IIa), deacylcynanchogenin (IVa), utendin (VI), and three other new aglycones. The structure of one of these new aglycones, named pergularin, was found to be closely related to utendin.

STUDIES ON THE CONSTITUENTS OF ASCLEPIADACEAE PLANTS. XIV. STRUCTURE OF TOMENTOGENIN.

The stems of Marsdenia tomentosa contain a glycoside mixture. The alkaline hydrolysate of the crude aglycones showed the presence of sarcostin and two new aglycones. The structures of those two new materials, tomentogenin and dehydrotomentogenin has been proved. Tomentogenin was shown to be identical with 5α-dihydroutendin and dehydrotomentogenin with utendin. The structures of these latter materials were determined about the same time as this work by Reichstein.

STUDIES ON THE CONSTITUENTS OF ASCLEPIADACEAE PLANTS. XV. ON THE COMPONENTS OF METAPLEXIS JAPONICA MAKINO. II.

The roots of Metaplexis japonica MAKINO has proved to contain a glycoside mixture. The acidic hydrolysates of the crude glycoside showed the presence of metaplexigenin and two new aglycones. The structure of metaplexigenin was determined.

Polyoxyethylene ethers of some polyol glycosides and their fatty esters

AbstractStarch heated with a polyol, such as ethylene glycol, propylene glycol, or glycerol, in the presence of an acid catalyst undergoes transglycosidation and forms a mixture of polyol glycosides. This mixture is sufficiently heat‐stable to permit polyetherification with ethylene oxide. The preparation and properties of a number of glycoside polyoxyethylene ethers are described.Nonionic emulsifying agents were prepared by reacting glycoside polyethers with either saturated or unsaturated long‐chain fatty acids and linseed oil. In general, the esterified glycoside polyethers exhibited good emulsifying action, and the unsaturated esters of the polyethers possessed film‐forming properties.

STUDIES ON THE CONSTITUENTS OF ASCLEPIADACEAE PLANTS. XII. ON THE COMPONENTS OF PERGULARIA EXTENSA N.E. BR. (DAEMIA EXTENSA R. BR.).

The whole plant of Perugularia extensa N. E. Br. was proved to contain a glycoside mixture which showed strong Keller-Kiliani reaction, suggesting the presence of a 2-deoxy-sugars in the sugar part. The sugar fraction obtained by acid hydrolysis was found to contain D-cymarose, D-sarmentose, L-oleandrose, and D-glucose by a paper chromatographic comparison with authentic specimens. Uzarigenin and a new glycoside (m.p. 244∼248°) were found.

The slow reacting substance of anaphylaxis: Its identification as a mixture of glycosides of neuraminic acid

The slow reacting substance of anaphylaxis: Its identification as a mixture of glycosides of neuraminic acid

Studies on the Constituents of Asclepiadaceae Plants. VIII. On the Components of <I>Metaplexis japonica</I> MAKINO.1

The stems and leaves of Metaplexis japonica MAKINO were proved to contain glycoside mixture. The glycoside showed the Keller-Kiliani reaction, suggesting the presence of 2-desoxy-sugar. The sugar portion of the glycoside was found to be D-cymarose and D-digitoxose by paper partition chromatography when compared with the authentic specimen. Five kinds of crystal, such as crystal No, 1, m. p.194-196°, crystal No.2, m. p.248/154°, crystal No.3, m. p.234-237°, crystal No.4, m. p.245°, and crystal No.5, m. p.264°, were isolated by adsorption chromatography using alurnina, and partition chromatography over Celite as a carrier. Crystal No.2 was identified to be sarcostin by the mixed melting point determination and the paper chromatography.

Studies on the Constituents of Asclepiadaceae Plants. IX. On the Components of <I>Cynanchum caudatum</I> MAX

The stems and leaves of Cynanchum caudatum MAX. were proved to contain a glycoside mixture. The sugar portion of the glycoside was found to be D-cymarose by paper partition chromatogoraphy comparing with an authentic specimen.Six kinds of aglycone, such as deacylcynanchogenin, sarcostin, crystal, m. p.215-220°, and other 3 spots were found by paper partition chromatography. They were isolated by adsorption chromatography using alumina, and partition chromatography over Celite as a carrier.

Studies on the Constituents of Asclepiadaceae Plants. VI. On the Components of <I>Marsdenia tomentosa</I> DECNE

The whole plant of Marsdenia tomentosa DECNE. was proved to contain a glycoside mixture which showed strong Keller-Kiliani reaction, suggesting the presence of 2-desoxy sugars. The suger part which was obtained by acid hydrolysis was found to be glucose and cymarose by the paper chromatography compared with the authentic specimens. The aglycones were presumed to be esters. Their alkaline hydrolysis afforded two kinds of crystals, tomentogenin, a new aglycone (m.p. 247-249°) and sarcostin (m.p. 150°/245-250°) and from acidic portions tiglic acid, isovaleric acid, and acetic acid were found.

A clinical study of gitalin.

VARIOUS purified fractions of digitalis leaf have been prepared in the hope of improving its effectiveness in the management of cardiac decompensation. Better standardization has been afforded by crystalline derivatives. Variations in rapidity of action and excretion have been achieved, and the preparations developed for intravenous administration have proved most useful when rapid digitalization is desired. However, in spite of these newer developments, opinions concerning the most satisfactory digitalis preparation are widely divergent. In general, familiarity with the drug used and its judicious administration have appeared more important in most cases than the actual product used. It is probably true that a well-standardized digitalis leaf preparation is as efficacious as any of the purified products in the treatment of the average case of cardiac decompensation. Recently the studies of Batterman and associates 1 have initiated a revival of the use of gitalin, a water-soluble amorphous mixture of glycosides first isolated

Observations upon the resistance of the rat to consecutive injections of strychnine

A series of the protected alkyl glycosides 5a/5b–12a/12b was synthesized from the parent isomeric alcohols (insect juvenile hormone bioanalogs; juvenoids), 4-[4′-(2″-hydroxycyclohexyl)methylphenoxy]-3-methyl-but-2-enoic acid ethyl ester (1a/1b–4a/4b; racemic structures) and (1a–4a; enantiopure structures). Cadmium carbonate was used as a promoter of this Koenigs–Knorr reaction, and the products were obtained in 82–92% yields. Deprotection of the carbohydrate functionality of 5a/5b–12a/12b was carefully performed using ethanolysis in the presence of zinc acetate, due to the presence of another ester functionality in the aglycone part of the molecule of protected alkyl glycosides. Resulting alkyl glycosides 13a/13b–20a/20b (diastereoisomeric mixtures) and 13a–20a (enantiopure compounds), biochemically activated hormonogenic compounds (juvenogens), were obtained in 82–93% yields. Finally, chiral HPLC separation of the diastereoisomeric mixtures of alkyl glycosides was applied to get sufficient quantities of the respective enantiomers 13b–20b of the alkyl glycosides for their structure elucidation and 13C chemical shift assignment by 1H and 13C NMR spectroscopy. Partial introductory entomological screening tests of the target alkyl glycosides 13a/13b–20a/20b were performed on the red firebug (Pyrrhocoris apterus). The results of this biological testing clearly demonstrated the time-extended effect of several juvenogens on P. apterus due to their biochemical activation, i.e., hydrolysis of the juvenogen molecule, which results in liberation of the biologically active juvenoid in the insect organism.