Comparative structural study of the lipopolysaccharides of Y. enterocolitica serovars 0:7.8 and 0:19.8

The lipopolysaccharides ofYersinia enterocolitica, serovars 0:7.8 (strain 106) and 0:19.8 (strain 842), isolated from the microbial mass by phenol-water extraction, contained residues of L-fucose, 6-deoxy-D-gulose, D-mannose, D-galactose, D-glucose, D- and L-glycero-D-mannoheptoses, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, and 2-keto-3-deoxyoctonic acid (KDO). The polysaccharides obtained by mild acid hydrolysis of the lipopolysaccharides followed by gel filtration on Sephadex G-50 were a mixture of the O-specific polysaccharide and the core, which could not be separated even by repeated rechromatography because of the comparability of their molecular masses. On the basis of the results of monosaccharide analysis, methylation, Smith degradation, and partial hydrolysis, a structure has been suggested for the repeating unit of the O-specific polysaccharides of the lipopolysaccharides ofY. enterocolitica of the serovars studied.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 763–770, November–December, 1989.     

Structural investigation of the lipopolysaccharide ofYersinia enterocolitica serovar 0:8

The lipopolysaccharide ofYersinia enterocolitica serovar 0:8 (strain 161) isolated from the microbial mass by aqueous-phenol extraction contains residues of L-fucose-6-deoxy-D-gulose, D-mannose, D-galactose, D-glucose, D- and L-glycero-D-mannoheptoses, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, and 2-keto-3-deoxyoctonic acid (KDO). The polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide followed by gel filtration on Sephadex G-50. On the basis of the results of monosaccharide analysis, methylation, Smith degradation, and partial hydrolysis the following structure is suggested for the repeating unit of the O-specific polysaccharide of the LPS ofYersinia enterocolitica, serovar 0:8:     

Lipopolysaccharides of the pseudotuberculosis microbe Yersinia pseudotuberculosis

This review generalizes the results of structural investigations of the polysaccharides of the O-specific side chains, of the core oligosaccharides, and of the lipid A of the pseudotuberculosis microbeYersinia pseudotuberculosis which causes Far-Eastern scarlatina-like fever. The complete structures of the repeating units of the specific polysaccharides from the lipopolysaccharides of serovars I A, I B, III, IV A, V A, V B, and VI which are responsible for the O-antigenic specificity of the microorganism are given. For the majority of serovars the repeating unit is represented by a branched pentasaccharide. Exceptions are the lipopolysaccharides of serovars I A and III which have a tetrasaccharide repeating unit. The presence of an aminosugar residue at the reducing end, by which the O-specific chain is attached to the oligosaccharide of the core, is common and characteristic for the lipopolysaccharides isolated from all the serovars. The structures of the core oligosaccharide and of lipid A, which are common for all serovars ofYersinia pseudotuberculosis, are given.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 163–171, March–April, 1988.     

Structural investigation of the lipopolysaccharide ofYersinia enterocolitica serovar 0:8

The lipopolysaccharide ofYersinia enterocolitica serovar 0:8 (strain 161) isolated from the microbial mass by aqueous-phenol extraction contains residues of L-fucose-6-deoxy-D-gulose, D-mannose, D-galactose, D-glucose, D- and L-glycero-D-mannoheptoses, N-acetyl-D-glucosamine, N-acetyl-D-galactosamine, and 2-keto-3-deoxyoctonic acid (KDO). The polysaccharide was obtained by mild acid hydrolysis of the lipopolysaccharide followed by gel filtration on Sephadex G-50. On the basis of the results of monosaccharide analysis, methylation, Smith degradation, and partial hydrolysis the following structure is suggested for the repeating unit of the O-specific polysaccharide of the LPS ofYersinia enterocolitica, serovar 0:8:Pacific Ocean Institute of Bioorganic Chemistry of the Far-Eastern Scientific Center of the USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedenenii, No. 5, pp. 657–664, September–October, 1987.     

Chemical and immunochemical characterization of the lipopolysaccharides of Yersinia kristensenii serovars 0:12,25; 0:12,26; and 0:25,35

A comparative and immunochemical characterization of the lipopolysaccharides of three serovars ofY. kristensenii has been performed and the ratios of the monosaccharides have been established. The results of the immunochemical investigations confirmed the serotyping of the microorganisms.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 335–338, May–June, 1988.     

Synthesis of natural triisopentenylated flavanone, euchrenone a2

Euchrenone a₂ (7) isolated from the roots ofEuchresta japonica has been synthesised from 3-prenylphloroacetophenone (1) by other workers. We carried out its cyclodehydrogenation with dichloro dicyano quinone (DDQ) to obtain 6-acetyl-5,7-dihydroxy-2,2-dimethylchromene (2) which was ethoxymethylated in the 7-position to give 6-acetyl-7-ethoxymethoxy-5-hydroxychromene (3). Chalcone condensation of3 and 4-ethoxymethoxy-3-C-prenylbenzaldehyde (4) gave 4,6′-bisethoxymethoxy-2′-hydroxy-6″, 6″-dimethyl-3-C-prenylpyrano (2″, 3″–4,3) chalcone (5) which cyclised with methanolic sodium acetate to give protected 5,4′-bisethoxymethoxy-6″, 6″-dimethyl-3′-C-prenylpyrano (2″, 3″–7,8) flavanone (6). Deprotection of6 with 4% methanolic HCl yielded (7) with melting point and spectral data identical to that of the natural compound.     

Lipid complex of Peganum harmala

The lipid complex of the seeds ofPeganum harmala (fam. Zygophyllaceae) has been investigated. The qualitative and quantitative compositions of the neutral lipids and the phospholipids have been studied. The fatty acid compositions of the acyl-containing lipids have been determined and it has been shown that in the triacylglycerols and phosphatidylethanolamines the sn-2 position is esterified mainly by linoleic acid. Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 625–627, November–December, 1992.     

Lignans of the bark of Syringa volgaris

Two lignans have been isolated from the bark ofSyringa vulgaris and identified: (+)-lariciresinol 4-β-D-glucopyranoside (I) and -olivil 4-β-D-glucopyranoside (II). This is the first time that glycoside (9) has been described. All-Union Scientific-Research Institute of Medicinal Plants Scientific-Production Association, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 768–771, November–December, 1991.     

Phytoecdysteroids of Rhaponticum carthamoides. II. Rhapisterone B

A new ecdysteroid (rhapisterone B) has been isolated from the seeds ofRhaponticum cathamoides (Willd.) Iljin. (familyCompositae). It has been shown that it is 2β, 3β, 11α, 14α, 20R, 24ξ-hexahydroxy-5β-cholest-7-en-6-one. Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 806–808, November–December, 1991.     

Lipids of the seeds of Cynoglossum officinale

The compositions of the lipids and fatty acids of the seeds ofCynoglossum officinale, familyBoraginaceae have been established. The bulk of the lipids consisted of netural compounds (95.2%), while the amounts of glycolipids and phospholipids were 3.1 and 1.7%, respectively. Among the fatty acids, in addition to the usual components, acids characteristic for theBoraginaceae family have been found: 18:3 (6, 9, 12), 18:3 (9, 12, 15), 18:4 (6, 9, 12, 15), 20:1 (11), 22:1 (13), and 24:1 (15). Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. South Urals Reservation, Bashkir. Institute of Chemistry, Bashkir Scientific-Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 758–762, November–December, 1991.     

Triterpene glycosides of Astragalus and their genins XXXIX. Cycloaraloside D from Astragalus amarus

The structure of a triterpene glycoside of the cycloartane series — cycloaraloside D, isolated from the roots ofAstragalus amarus Pall. (Leguminosae) — has been established on the basis of chemical transformations and spectral characteristics. Cycloaraloside D is 20R, 24S-epoxycycloartane-3β, 6α, 16β, 25-tetraol 3-0-[0-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranoside]. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 526–528, July–August, 1991.     

A sesquiterpene glucoside from cultivated cells of Scorzonera hispanica

A sesquiterpene glucoside has been isolated from a tissue culture ofScorzonera hispanica, and its structure has been established by mass spectrometry and two-dimensional NMR as 6,9-dihydroxy-4,10,14,15-tetradehydroguaian-6,12-olide 9-O-β-D-glucopyranoside. Irkursk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 640–645, November–December, 1992.     

Investigation of the core of the lipopolysaccharides ofYersinia pseudotuberculosis

Lipopolysaccharides have been isolated from two R mutants of the pseudotuberculosis microbeYersinia tuberculosis, serovar VA. Mild acid hydrolysis followed by gel filtration on Sephadex G-25 gave the core oligosaccharides OS I and OS II. Complete acid hydrolysis showed that OS I consisted of residues of D-galactose, G-glucose, two heptoses (D-glycero-D-mannoheptose and L-glycero-D-mannoheptose), and D-glucosamine in a ratio of 1:2.5:4:1, while OS II consisted of residues of D-glucose, heptoses, and D-glucosamine in a ratio of 1:2.5:0.2. On the basis of the results of monosaccharide analysis, methylation, Smith degradation, etc., a partial structure of the core oligosaccharide of the LPS ofY. pseudotuberculosis has been put forward.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 751–755, November–December, 1985.     

Synthesis of antigenic bacterial polysaccharides and their fragments

Conclusions The free trisaccharide-D-mannopyranosyl(1-4)--L-rhamnopyranosyl(1 3)-D-galactopyranose was obtained, which is the repeating unit of the backbone chain of the O-specific polysaccharides ofSalmonella of serological groups A, B, and D₁.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.1, pp.165–167, January, 1976.     

Determination of glycuronic acids by high-performance anion chromatography with pulsed amperometric detection

Summary Acid hydrolysis (0.25M H₂SO₄) coupled with enzyme catalysis (pectolyase and β-D-glucuronidase) were employed to extract galacturonic and glucuronic acids from microbial polysaccharides, plant residues, animal wastes, sewage sludge and soil. The glycuronic acids were separated by high-performance anion chromatography (HPAC) on a strong anion-exchange column using 0.1M sodium hydroxide with 0.25M sodium acetate as the mobile phase and determined by pulsed amperometric detection (PAD). HPAC-PAD was found to be superior to high-performance liquid chromatography with ultra-violet (UV) detection in terms of resolution and sensitivity of glycuronic acids. HPAC-PAD was not subject to interferences present with low UV detection (210 nm) and was highly selective for glycuronic acids. Enzymatic hydrolysis after treatment with mild acid (0.25M H₂SO₄) released galacturonic acids from orange peel and pectin, while glucuronic acid was released from Acacia powder. Large amounts of glycuronic acids were also extracted from plant materials. Low levels of uronic acids were detected in poultry manure, sewage sludge and organic-amended soils.     

Triterpene glycosides of alfalfa. V. Medicoside H

A new triterpene glycoside — medicoside H — has been isolated from the roots ofMedicago sativa L. (Fabaceae), and on the basis of chemical transformations and spectral characteristics its structure has been established as medicagenic acid 3-O-β-D-glucopyranoside 28-O-[O-α-L-rhamnopyronosyl-(1 → 2)-β-L-arabino-pyranoside]. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 673–677, September–October, 1989.     

Investigation of natural compounds by the HPLC method II. HPLC fingerprint method for the epigeal organs of Ferula kuhistanica and F. tenuisecta

A microcolumn HPLC fingerprint method has been developed for the epigeal organs ofFerula kuhistanica andF. tenuisecta. The possibility has been shown of control by the microcolumn HPLC method of the qualitative and quantitative yields of ferutinin in the initial plant raw material and in preparations extracted from it, and also at each stage of the isolation of the desired product. The method is universal and does not depend on species and chemical composition of the plant. Institute of the Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 635–636, November–December, 1992.     

Molecular and crystal structure of jurineolide — A germacrane lactone from Jurinea multiflora

By extraction with chloroform, followed by treatment of the total extractive substances with hexane and chromatography of the resulting precipitate, the epigeal part ofJurinea multiflora has yielded a sesquiterpene lactone of the germacrolide type, jurineolide. The following spatial structure is proposed for jurineolide: 8α-(4′-hydroxytigloyloxy)-6β,7α(H)-germacra-trans-1(10),trans-4(5),11(13)-trien-6,12-olide. Institute of Organic Synthesis and Coal Chemistry, Central Kazakhstan Branch, Academy of Sciences of the Kazakh SSR. Translated from Khimiya Prirodnykh Soedinii, No. 4, pp. 490–494, July–August, 1991.     

The flavonoids of the milk vetches

Summary 1. A new flavonoid glycoside that we have calledastragaloside has been isolated from the flowers ofAstragalus publiflorus D.C.; it has the structure of isorhamnetin 3-(-D-glucosyl-6--D-glucoside).2. Stepwise acid hydrolysis and enzymatic hydrolysis withAspergillus oryzae has given a flavonol glycoside, isorhamnetin 3--D-glucoside.3. The carbohydrate component is O-6--D-glucosyl-D-glucose.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 6, pp. 394–399, 1966