Structure of psolusoside B — A nonholostane triterpene glycoside of the holothurian genus Psolus

The structure of psolusoside B — a minor triterpene oligoglycoside from the holothurianPsolus fabricii and the main glycoside fromPsolus sp. has been determined by the methods of partial acid hydrolysis, methylation,¹³C NMR, and FAB mass spectrometry as 20S-acetoxy-3-{2-O-[O--D-glucopyranosyl-(1 4)-O--D-glucopyranosyl]-4-O-(6-O-sulfato--D-glucopyranosyl)--D-xylo-pyranosyloxy}holosta-7,25-diene-18,16-carbolactone. 3-[O-(3-O-Methyl-6-O-sulfato--D-glucopyranosyl)-(1 3)-O-(6-O-sulfato--D-glucopyranosyl)-(1 4)-O--D-quinovopyranosyl-(12)--D-xylopyranosyloxy]holosta-9(11),25-dien-16-one (psolusoside A), known previously forPsolus fabricii, has been identified in a holothurian —Psolus sp. — from Kraternaya Bay (island of Ushishir).Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 361–368, May–June, 1989.     

Physico-chemical transformations during heating of phosphorites

The thermal behaviour of phosphorites in an oxygen or helium atmosphere was studied by means of simultaneous TG-DTG-DTA-gas titrimetric EGA. Thermal oxidation and/or decomposition steps of the contaminating organic materials, carbonate minerals and pyrite, and of the fluorocarbonate-apatite were identified. The evolution of CO₂ from the latter has its maximum at 750–850 °C and is accompanied by an increase in the lattice parametera ₀.

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Zusammenfassung Das thermische Verhalten von Phosphoriten in Sauerstoff- oder Heliumatmosphäre wurde durch simultane TG-DTG-DTA-EGA (mittels Gastitrimetrie) untersucht. Thermische Oxidations- und/oder Zersetzungsschritte der Verunreinigungen (organische Materialien, Carbonatminerale und Pyrit) und des Calcium-fluoro-carbonat-apatit wurden identifziert. Die CO₂-Abspaltung aus dem letzteren hat ihr Maximum bei 750–850 °C, sie ist begleitet von einer Vergrösserung des Gitterparametersa ₀.

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, , - . ( , , . 750–850° ₀.

     

Triterpene glycosides of the holothurian Eupentacta pseudoquinquisemita

The holothurianEupentacta pseudoquinquisemita Deichmann collected in Kraternaya Bay, Ushishir Islands has yielded two triterpene pentaosides — the previously known cucumarioside C₂, and cucumarioside H, which is a new glycoside. With the aid of¹³C NMR spectroscopy and solvolytic desulfation its structure has been determined as 6-acetoxy-3-([3-O-methyl--D-xylopyranosyl-(1 3)--D-glucopyranosyl-(1 4)] [-D-xylopyranosyl-(1 4)] [-D-xylopyranosyl-(1 2)]--D-quinovopy-ranosyl-(1 2)-(4-O-sulfato--D-xylopyranosyloxy)holosta-7,22,24(trans)-triene. Cucumarioside H was also identified inEupentacta (=Cucumaria)fraudatrix from Posyet Bay, Sea of Japan.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 221–225, March–April, 1988.     

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 2, 3, 11, 14, 20R, 24-hexahydroxy-5-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.     

Triterpene glycosides of Hedera taurica X. Structures of compounds F4, I, and J from the leaves of Crimean ivy

Echinocystic acid 3-sulfate and new 3-sulfates — of the 28-O-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)--D-glucopyranosyl esters of oleanolic and echinocystic acids have been isolated from the leaves of Crimean ivyHedera taurica Carr. (fam. Araliaceae).M. P. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 683–686, November–December, 1992.     

Triterpene glycosides of the leaves of Digitalis ciliata

Two new terpene glycosides have been isolated from the leaves of the foxgloveDigitalis ciliata Trautv.: -D-glucopyranosyl oleanolate 3-O-[O--D-xylopyranosyl-(1 4)--L-rhamnopyranoside] and oleanolic acid 3-O-[O--D-xylopyranosyl-(1 4)--L-rhamnopyranoside].I. G. Kutateladze Institute of Pharmacochemistry Academy of Sciences of the Georgian SSR, Tbilisi. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 246–251, March–April, 1991.     

Steroids of the spirostan and furostan series from plants of the genus Allium. XXVI. Structure of anzurogenin and anzuroside from the collective fruits of Allium suvorovii and Allium stipitatum

A new steroid glycoside of the spirostan series, anzuroside, has been isolated from the collective fruits of the cocultivatedAllium suvorovii Rgl. andA. stipitatum Rgl. (family Liliaceae, local name anzur). Enzymatic cleavage of the glycoside has given the previously undescribed steroid sapogenin anzurogenic C, which has the structure of (24S, 25S)-2,3,5,24-tetrahydroxy-5-spirostan-6-one. Anzuroside is the 24-O--D-glucopyranoside of anzurogenin C.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 505–510, July–August, 1989.     

Chemical investigation of the bitter substances of the fruit of Lonicera caerulea

Esters of malic and citric acids have been isolated from an ethyl acetate fraction of an ethanolic extraction ofLonicera caerulea L.: dibutyl malate (I), 4-butyl 1-methyl malate (II), 1-butyl 4-methyl malate (III), tributyl citrate (IV), 1,5-dibutyl citrate (V), 1,1-dibutyl citrate (VI), 1,5-dibutyl 1-methyl citrate (VII), 1,1-dibutyl 5-methyl citrate (VIII), 1-butyl citrate (IX), 1-butyl citrate (X), 1-butyl 1,5-dimethyl citrate (XI), and 1-butyl 1,5-dimethyl citrate (XII). Compounds (I-IV, VII, VIII, XI, and XII) had a bitter taste and were the main components of the bitter substances of the fruit ofLonicera caerulea. The structures of compounds (I-XII) were established on the basis of their¹H and¹³C NMR spectra, by FAB mass spectrometry and chromato-mass spectrometry.Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Sverdlovsk Institute of the National Economy. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 338–342, May–June; 1989.     

A further study of the substrate specificity in the reduction of 20-oxosteroids with a culture ofActinomyces roseochromogenus

Conclusions A culture ofActinomyces roseochromogenus ATCC 3347 reduces 17-hydroxy- and 16, 17-epoxy-20-oxopregnenes to the corresponding 20-alcohols, but is incapable of reducing 17-acetoxy-, 17-methyl-, and 16-methylprogesterones or 17-unsubstituted 20-oxopregnenes. The results obtained show that the presence of the side chain in a conformation favorable for the formation of 20-alcohols in the reduction of 20-oxosteroids with complex metal hydrides is in itself insufficient for the reduction of the 20-oxosteroids by a culture ofActinomyces roseochromogenus, which also reduces the 20-oxo group of 17-pregnenes.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 38–47, 1970     

Triterpene glycosides of alfalfa. IV. Medicoside J

A new triterpene glycoside has been isolated from the roots ofMedicago sativa L. (family Fabaceae) — medicoside J, and its structure has been established as a medicagenic acid 3-O--D-glucopyranoside 28-O-[O--D-xylopyranosyl-(1 4)-O--L-rhamnopyranosyl-(1 2)--L-arabinopyranoside].Institute of the Chemistry of Plant Substances of the Uzbek Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 610–613, September–December, 1986.     

Saponins ofDioscorea polystachya

Summary A new water-soluble saponin, dioscinin, consisting of a glucoside-dirhamnoside-glucoside of 25D-22-spirost-5-en-3-ol has been isolated from the rhizomes ofDioscorea polystachya. In addition to dioscin and dioscinin, the rhizomes ofDioscorea polystachya contain a small amount of gracillin and the kikuba-saponin corresponding to it.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 155–158, 1967     

Steroids of the spirostan and furostan series from nolina microcarpa III. Structure of nolinofurosides G and H

Two new glycosides which have been called nolinofurosides G(I) and H(III), have been isolated from the leaves ofNolina microcarpa. Nolinofuroside G is the sodium salt of 26--D-glucofuranosyloxy-(25S)-furost-5,20(22)-diene-1, 3-diol 1-sulfate, and nolinofuroside H is the sodium salt of 1--D-fucopyranosyloxy-26--D-glucopyranosyloxy-(25S)-furost-5,20(22)-dinen-1-3-ol 3-sulfate.M. V. Frunze Simferopol' State University. Institute of the Chemistry of Plant Substances, Uzbek. Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 801–806, November–December, 1991.     

New glycosides from plants of the genus Phlojodicarpus

From plants of the genusPhlojodicarpus have been isolated the new coumarins umbelliferone -D-apiosyl (1 6)--D-glucopyranoside (I) and 8-(2,3-dihydroxy-3-methylbutyl)umbelliferone 7-O--D-glucopyranoside (II) and also the flavone glycoside diosmetin 7-O--D-glucopyranoside (III). The result of IR, UV, PMR, and¹³C NMR spectroscopy are given.Institute of Chemistry, Academy of Sciences of the Mongolian Peoples' Republic, Ulan-Bator; Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 36–39, January–February, 1986.     

Isolation of the galactan ofPhyllophora nervosa and characterization of its structure

Summary 1. The chemical composition of the galactan of the Black-Sea algaPhyllophora nervosa has been established and its structure has been studied. The polysaccharide is linear and is constructed of D-galactose residued connected by 1 3 glycosidic bonds and of 3,6-anhydro-D-galactose residues connected by 1 4 bonds:-(4-0--D-Galp-13--D-3,6-AhGalp-1)-.2. The ester nature of the bond of the sulfuric acid residues with the primary and secondary carbon atoms of the galactose residues has been shown.M. V. Lomonosov Odessa Technological Institute of the Food Industry. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 693–698, November–December, 1976.     

Steroid glycosides from the starfish Crossaster papposus

The following have been isolated from the starfishCrossaster papposus and characterized: the new glycoside (24S)-5-cholestane-3,4,6,8,15,24-hexaol 24-O-[O-(2,4-di-O-methyl--D-xylopyranosyl)-(1 5)--L-arabinofuranoside] (crossasteoside P₄) and the previously known attenuatoside B-1.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 257–260, March–April, 1993.     

Coumarin composition of Seseli grandivittatum

Summary From the roots ofSeseli grandivittatum, together with -sitosterol and (–)-3R-decursinol, found in nature for the first time, and its angelate, we have isolated two new compounds which we have called grandivittin and grandivittinol.On the basis of IR, PMR, and mass spectra and chemical transformations, the structure of 3-senecioyloxy-3,4-dihydro-3R-xanthyletin is proposed for grandivittin, and 7-hydroxy-6-(3-hydroxy-2-senecioyloxyisopentyl) coumarin for grandivittinol.Leningrad Sanitary-Hygienic Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 640–646, September–October, 1977.     

Triterpene glycosides of Hedera taurica. IV. Structure of hederosides A1, A2, D1, and D2 from the berries of Crimean ivy

New triterpene glycosides have been isolated from the berries of Crimean ivyHedera taurica Carr. (family Araliaceae) — hederoside A₁ (methyl ester of 3-O--D-glucopyranosylhederagenin) and hederoside D₁ 3-O-[O--D-glucopyranosyl]-(12)--D-glucopyranosyl]hederagenin and also the known glycosides 3-O--D-glucopyranosyloleanolic acid and 3-O-[O--D-glucopyranosyl-(12)--L-arabinopyranosyl]hederagenin. The structures of these compounds were established on the basis of the results of chemical methods and¹H and¹³C NMR spectroscopy.M. V. Frunze Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 228–230, March–April, 1990.     

Coumarins of theLibanotis buchtormensis

Conclusions From the roots ofLibanotis buchtormensis (Fisch.) D.C. have been isolated the furocoumarins bergapten, isoimperatorin, a pyranocoumarin, xanthogallol, and a new coumarin buchtormin C₁₉H₂₀O₅, for which the structure (+)-3-(,-dimethylacryloxy)-2,2-dimethyl-3, 4-dihydropyrano-5, 6:8, 7-coumarin has been proposed and confirmed by synthesis.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 3, pp. 145–149, 1968     

Triterpene glycosides ofSilphium perfoliatum. IV. Structure of siliphioside C

The epigeal part ofSilphium perfoliatum has a yielded a new triterpene glycoside, silphioside C — C₅₀H₈₀O₁₉, mp 207–210°C (from aqueous methanol), []_D ²⁵ +19.3 ± 2°C (c 0.88; methanol). On the basis of acid hydrolysis, mild alkaline saponification, and the results of GLC and of IR, mass, and¹H and¹³C spectroscopy the structure of silphioside C had been established as 28--D-glucopyranosyl 3-O-[O--D-glucopyranosyl-(12)-(6-O-acetyl--D-glucopyranosyl)oleanolate.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pyatigorsk Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii. No. 4, pp. 519–522, July–August, 1985.     

Kinetics of the alkaline hydrolysis of flavonoid glycosides

Summary 1. In a study of the kinetics of the alkaline hydrolysis of flavone glycosides it has been found that derivatives of 3,3,4,5,7-pentahydroxyflavone hydrolyze faster than derivatives of 3,4,5,7-tetrahydroxyflavone and of 3,4,5,7-tetrahydroxy-3-methoxyflavone.2. In the hydrolysis of diglycosides of 3,3,4,5,7-pentahydroxyflavones the maximum amount of intermediate product is formed after 2 min (3,4,5,7-tetrahydroxyflavone glycoside), and in the case of 3,4,5,7-tetrahydroxy-3-methoxyflavone glycosides after 120–150 min.I. V. Kutateladze Institute of Pharmacochemistry, Academy of Sciences of the Georgian SSR, Tbilisi. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 646–649, September–October, 1977.