New glycosides from the holothurian Cucumaria japonica

Four new compounds have been isolated from the fraction of weakly polar triterpene glycosides of the holothurianCucumaria japonica: cucumariosides A₁-2 (I), A₀-1 (II), A₀-2 (III), and A₀-3 (IV). The structures of these substances have been established by chemical and physical methods.Deceased.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 242–248, March–April, 1993.     

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.     

Triterpene glycosides from the holothurian Cucumaria frondosa

Two triterpene glycosides have been isolated from an alcoholic extract of the holothurianCucumaria frondosa collected in the Kola littoral, Barents Sea: the main component of the glycoside fraction — frondoside A (I) — and a minor component — frondoside A₁ (II).Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Murmansk Marine Biological Institute. Russian Academy of Sciences, Dal'nie Zelentsy, Murmansk province. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 260–263, March–April, 1993.     

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.     

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.     

Determination of stichoposides in the body of the holothurianStichopus japonicus

A method has been developed for the quantitative determination of triterpene glycosides — stichoposides — in the tissues of the Far Eastern holothurianStichopus japonicus Selenka. The quantitative determination of the combined triterpene glycosides was based on the isolation of a glycosidic fraction from an ethanolic extract on a column of Polikhrom-1 with subsequent spectrophotometry at 268 nm of the product formed as the result of the reaction of the glycosides with 1 N NaOH. The quantitative determination of the individual glycosides is based on the densitometry of slides or thin-layer chromatography in silica gel with the aid of a Lyuman-IUF-1 luminescence microscope.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Pacific Ocean Institute of Oceanography and Fisheries. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 56–59, January–February, 1984.     

Mass spectrometry of pennogenin glycosides

The electron-impact mass spectra of five unesterified pennogenin glycosides, which contain the M⁺ or (M - H₂O)⁺ peaks, have been obtained. The characteristic features of the fragmentation of these compounds have been studied. In addition to ions characterizing the successive elimination of carbohydrate units, fragments have been detected which show the breakdown of the terminal pyranose ring. Five new directions of the fragmentation of the spirostanol skeleton due to the presence of an OH group at C-17 have been found.Institute of the Chemistry of Plant Substance, Academy of Sciences of the Uzbek SSR, Tashkent. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Science Center of the Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 337–341, May–June, 1986.     

Secondary-ion mass spectra of pennogenin glycosides

LSIMS mass spectra of pennogenin glycosides have been studied; the most characteristic ions are (M+H–H₂O)⁺ (with glycerol as the liquid matrix) and (M+Na)⁺ (with glycerol +NaCl as matrix). In both cases the peaks of ions formed as the result of the successive elimination of the carbohydrate units, the breakdown of the bonds of the terminal pyranoses, the cleavage of the bonds of the rings D and E, and the peaks of the ions Agl⁺ and (Agl–H₂O)⁺ were observed.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. All-Union Scientific-Research Institute for Agricultural Biotechnology, All-Union Academy of Agricultural Sciences, Moscow. Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 523–525, July–August, 1991.     

Steroid glycosides of the roots ofCapsicum annuum. I. The structure of capsicosides A1, B1, and C1

Three new steroid glycosides of the spirostan series — capsicosides A₁, B₁, and C₁ — have been isolated from a methanolic extract of the roots of red pepper. In an investigation of the products of complete acid hydrolysis of these glycosides, a single aglycon — gitogenin — was identified. The complete chemical structure of each of the capsicosides has been shown with the aid of complete and partial acid hydrolysis, methylation and methanolysis, and periodate oxidation, and also by physicochemical methods of investigation.Institute of Chemistry, Academy of Sciences of the Moldavian SSR, Kishinev. Institute of Ecological Genetics, Academy of Sciences of the Moldavian SSR, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 708–712, November–December, 1986.     

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.     

Alkaloids ofThalictrum sachalinense. V

Summary Glaucine, N-methylnantenine, thalrugosine, magnoflorine, berberine, and the unidentified bases (II) and (III) have been obtained from the roots and rhizomes ofThalictrum sachalinense. The main alkaloid in the combined bases of the roots and rhizomes was magnoflorine.Intitute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. 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. 594–597, September–October, 1978.     

Sulfated derivatives from marine organisms

Sulfated steroid alcohols from marine invertebrates of the classHolothurioidea have been isolated and characterized for the first time.Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center of the Academy of Sciences of the USSR, Vladivostok, and National Institute of Oncology and Radiobiology of the Cuban Ministry of Public Health, Havana. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 585–586, September–October, 1981.     

Synthesis of polybrominated diphenyl ethers of marine origin

Polybrominated diphenyl ethers — antimicrobial metabolites of the marine spongeDysidea fragilis — have been obtained by the reaction of 2,3,5-tribromonitrobenzene with 3,5-dibromo-2-methoxyphenol and the reaction of brominated diphenyliodonium salts with brominated phenols.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 352–354, May–June, 1993.     

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.     

Optimization of the method of isolating (25R)-spirost-5-ene-3β,17α-diol (pennogenin) from plant material

The method for the acid hydrolysis of pennogenin glycosides with the aim of isolating the native aglycon has been optimized. The highest yield of pennogenin (49.5% of its amount in the plant material) is given by hydrolysis with 1 N H₂SO₄ in 96% ethanol at 100°C for 3 h.Pacific Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 115–119, January–February, 1987.     

Polysaccharides ofAloe arborescens

Summary An acidic polysaccharide belonging to the class of pectin substances has been isolated from the leaves ofAloe arborescens.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center of the Academy of Sciences of the USSR. Academician A. B. Fomin Botanical Garden. T. G. Shevchenko Kiev State University. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 3–5, January–February, 1975.     

First example of the formation of highly ordered supermolecular structures in a series of gibberellin derivatives

The 3-O-palmitate and 3-O-tridecanoate of gibberellin A₃ have been synthesized and monomolecular Langmuir-Blodgett films have been obtained from them.Novosibirsk Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 793–795, November–December, 1994.     

Trisulfated glycosides from the holothurianCucumaria japonica

Three new triterpene glycosides have been isolated from an alcoholic extract of the Pacific Ocean commercial holothurian Cucumaria japonica: cucumariosides A _T 1 (I), A _T 2 (II), and A _T 3 (III). The structures of these glycosides have been established by chemical and physical methods.     

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.