Quantitative determination of triterpenoids of the dammarane series by the densitometry of thin-layer chromatograms

Summary Using the optical densitometry of thin-layer chromatograms, the amounts of triterpenoids of the dammarane series have been determined in the unsaponifiable fractions of ethereal extracts from the leaves of Far Eastern species of birch:Betula costata, B. mandshurica, B. dahurica, B. platyfolia, andB. kamtschatica. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, USSR, Vladivostok Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 349–353, May–June, 1977.     

New quinone from a marine sponge of the order dictyoceratida

Two pigments of quinoid nature, one of which has been identified as ilimaquinone, have been isolated from a hexane extract of a marine spongeHyatella sp., family Spongiidae, order Dictyoceratida. The second was a new benzoquinone of the drimane series with the composition C₂₂H₃₂O₅, which has been called hyatoquinone. Its structure has been established on the basis of spectral characteristics and chemical transformations.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 793–796, November–December, 1987.     

Determination of the positions of the sulfate groups in sulfated polysaccharides

Summary 1. The possibility has been shown of using a method proposed by us previously to determine the positions of the sulfate groups in sulfated polysaccharides.2. The positions of the sulfate groups in the following sulfated polysaccharides have been determined: fucan and pelvecyan fromPelvetia wrightii and sargassan fromSargassum pallidum.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center of the Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 573–577, September–October, 1976.     

Structures of four new triterpene glycosides from the holothurian Cucumaria japonica

Four new triterpene glycosides of the holostane series have been isolated from an alcoholic extract of the economically important Pacific Ocean holothurianCucumaria japonica: cucumariosides A₁-2 (I), A₂-3 (II), A₂-4 (III), and A₄-2 (IV). The structures of these substances have been established by the methods of carbohydrate chemistry and¹³C NMR spectroscopy.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 787–793, November–December, 1990.     

Investigation of the protein component of the lipopolysaccharide-protein complex ofYersinia pseudotuberculosis

It has been established by electrophoresis in polyacrylamide gel that the protein component of the lipopolysaccharide-protein complex ofYersinia pseudotuberculosis consists of two poly-peptides with molecular weights of 42,000–45,000 and 18,000–20,000. These polypeptides have been detected in the cell wall ofY. pseudotuberculosis as the main components. Protein fractions B-2 and B-3, differing with respect to solubility in phenol, were isolated from the LPPC ofY. pseudotuberculosis by extraction with hot 45% phenol. These protein fractions had the same polypeptide composition, which is characteristic for membrane proteins. B-3 included the LPS component and B-2 contained lipid A or fragments of it as impurity. Fractions B-3 and B-2 precipitated with antiserum to the LPPC.Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 92–97, January–February, 1980.     

New derivatives of (?)-neocembrene from the soft coral Sarcophyton trocheliophorum

A hexane extract of the soft coralSarcophyton trocheliophorum has yielded two new diterpenoids for which the structures of 13S-hydroxy-(–)-neocembrene and 13S-hydroxy-11,12-epoxy-(–)-neocembrene have been established.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 535–540, July–August, 1988.     

An thraquin one pigments of the starfish Echinaster echinophorus. IV

Summary 1. Anthraquinone pigments forming derivatives of 1,6,8-trihydroxy-9,10-anthraquinone have been found in the starfishEchinaster echinophorus (Lamarck).2. The structures of the pigments isolated are identical with those of pigments of sea lilies.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center of the Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 636–640, September–October, 1977.     

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.     

N-acylphosphatidylethanolamine in the fish brain

It has been shown that a minor phospholipid isolated from the brain of the mackerelHexagrammos octogrammus is a N-acylphosphatidylethanolamine a considerble part of which is present in the plasmalogen form. This lipid was detected with the aid of a specially developed method of high-performance micro-TLC in the brains of 15 species of bony fishes, but it could not be detected in the brains of the shark and the ray.Institute of Marine Biology, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 326–329, May–June, 1985.     

Avarol and isoavarol from a Pacific Ocean sponge Dysidea sp.

Two hydroquinone-group-containing terpenoids have been isolated from a Pacific Ocean spongeDysidia, sp. One of them has been identified by physicochemical methods as the previously known avarol. The second, isoavarol, obtained for the first time, differs from avarol by the 4(11)-position of the double bond.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 358–361, May–June, 1990.     

Lipids and lipopolysaccharides of the genusFlavobacterium

The fatty acid compositions of the free lipids of three strains and the monosaccharide compositions of the lipopolysaccharides of four strains of new species of microorganisms of the genusFlavobacterium have been studied. The acidic nature of the polysaccharides of the LPSs of the microorganisms studied has been shown.Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center of the USSR Academy of Sciences, Vladivostok, and Institute of Microbiology of the USSR Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 564–567, September–October, 1986.     

Crystal and molecular structures of 1,8-diacetyl-3-methyl-DL-allantoin

DL-Allantoin (I) has been isolated from an alcoholic extract of a marine spongeAxinellidae gen. sp., and derivatives of it have been obtained: 1, 8-diacetyl-DL-allantoin (II) and 1,8-diacetyl-3-methyl-DL-allantoin (III). The crystal and molecular structures of (III) have been established by X-ray structural analysis.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 422–426, May–June, 1988.     

Isoprenoids of various species of the genus Betula

The review contains an analysis of the literature up to 1986, inclusive on the chemical investigation of some species of the genusBetula (family Betulaceae). Attention is devoted mainly to the distribution of the triterpene compounds in various parts of birch trees, and their biological properties and prospects are also discussed. Information (structure, melting point, angle of rotation, source) is given on 33 triterpenoids of the dammarane series isolated from the leaves, catkins, and young twigs of birch trees, and of 23 triterpenoids of the lupane and -amyrin series isolated from the outer bark.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 325–341, May–June, 1988.     

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.     

An investigation of a lipopolysaccharide-protein complex fromYersinia pseudotuberculosis by the light-scattering method

Summary An estimate has been made of the molecular weights and characteristic viscosities of aggregates of the LPPC fromYersinia pseudotuberculosis in water, and also in aqueous solutions of sodium chloride, urea, guanidine hydrochloride, and sodium dodecyl sulfate. It has been shown that a high ionic strength of the solution and the presence of disaggregating agents lead to a considerable decrease in the molecular weight of the LPPC.Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 51–53, January–February, 1979.     

Lipopolysaccharides of marine blue-green algae

The lipopolysaccharides (LPSs) have been isolated from two blue-green algae,Oscillatoria hilderbrandtii andNostoc sp. by the method of phenol-water extraction. The LPSs contain polysaccharide and lipid components. The polysaccharide fraction fromO. hildebrandtii consists predominantly of 1,3-bound rhamnose residues with a substituent in the second position. The rhamnose residues in the polysaccharide fraction ofNostoc are connected by 1,3- and 1,2-glycosidic bonds. The lipid components of the LPSs fromO. hilderbrandtii andNostoc consist of palmitic and steric acids, with glucosamine and glucose.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 493–496, July–August, 1985.     

Mass spectra of polyhydrosysteroids of the starfishPatiria pectinifera

The electron-impact fragmentation of six polyhydroxysteroids from the starfishPatiria pectinifera, including three glycosides, has been studied. In addition to the directions of fragmentation that are characteristic for sterols from other sources and for steroid compounds of other classes, fragments have been found that result from the unusual arrangement of hydroxy groups in the molecules of the samples investigated. Two breakdown pathways of the furanose ring have been found in the spectra of the glycosides.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek, SSR, Tashkent. Pacific Ocean Institute of Bioogranic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 361–367, May–June, 1985.     

Steroid compounds from ophiuroids. I. New steroid sulfate from Ophiura sarsi

The sulfate of a steroid polyol has been isolated from the Far Eastern ophiuroidOphiura sarsi, and its structure has been established by chemical and spectral methods as cholest-5-ene-3,4,21-diol 3-(sodium sulfate). No steroid compounds of such structure from ophiuroids have been described previously.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 375–379, May–June, 1988.     

Cembrenolides of a soft coral Lobophytum sp. (coelenterata, octocorallia, alcyonacea)

The known cembrenolide sarcophin and its new acetoxy derivative — 13-acetoxy-7,8-epoxycembra-1(15),3,11-trien-2,16-olide — have been isolated from the soft coralLobophytum sp.. The compounds isolated are inhibitors of the activity of Na⁺K⁺-ATPase and are membranotropic agents. The structures of the compounds have been shown on the basis of the results of NMR spectroscopy.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 762–765, November–December, 1990.     

Quinoid pigments of echinodermata III. Minor pigments of the sea urchin Strongylocentrotus nudus

Summary 1. 3-Acetyl-2,7-dihydroxy-6-methylnaphthazarin, not previously described, has been isolated from the test and needles of the sea urchinStronglyocentrotus nudus.2. The pigments of this sea urchin have been shown to include 2,7-dihydroxynaphthazarin and spinochrome E.3. A number of minor pigments forming naphthazarin derivatives has been isolated. One of them is connected with spinochrome C by mutual transformations.The subject matter of the present paper was given in part at the All-Union Conference on Biological Resources of the Seas of the Far East (Vladivostok, 1975).Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center of the Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 202–207, March–April, 1977.