Triterpene glycosides ofAstragalus and their genins. XXII. Cycloorbicoside A fromAstragalus orbiculatus

The quantitatively main glycoside — cycloorbicoside A — has been isolated from the epigeal parts of the plantAstragalus orbiculatus, and on the basis of chemical transformations and spectral characteristics its structure has been established as (23R,24S)-16,23:16,24-diepoxycycloartane-3,7,25-triol 3-0--D-xylopyranoside.Institute of the Chemistry of Plant Substances Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 719–726, November–December, 1986.     

Cardenolides of the seeds ofCoronilla glauca and ofC. scorpioides. New glycosides alloglaucoside and scorpiosidol

Two new glycosides have been isolated from the seeds ofCoronilla glauca L. and C. scorpioides Koch: 3-(0-D-glucopyranosyloxy)-14. 15-dihydroxy-19-oxo-5-card-20(22)-enolide (alloglaucoside) and 3-(-D-gluco-ucofuranosyloxy)-5,14,19-trihydroxy-5-card-20(22)-enolide (scorpiosidol), together with a glycoside previously unknown for theCoronilla genus — 3-(-D-glucopyranosylo)g)-14-hydroxy-5-card-20(22)-enolide (desglucouzarin) and known aglycons (corotoxigenin, alloglaucotoxigenin, coroglaucigenin) and glycosides (glucocorotoxigenin, coronillobioside, glucocoroglaucigenin, coronillobiosidol and scorpioside).Ukraine Pharmaceutical Academy, Kharkov–2. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 372–376, May–June, 1996. Original article submitted August 14, 1995.     

Evonogenin

Conclusions The structure of a new cardiac aglycone, evonogenin, isolated from the seeds ofEvonymus europaea auct. has been established. Evonogenin is 1, 3, 5, 14-tetrahydroxycard-20(22)-enolide.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 5, pp. 386–389, 1969     

Astragalus triterpene glycosides and their genins. I. Structures of cycloalpigenin and cycloalpioside

Another two methylsteroids of the cycloartane series have been isolated from the epigeal part ofAstragalus alopecurus. The structures of the compounds isolated, cycloalpigenin and cycloalpioside, have been established as (20R,24R)-16,24:20, 24-diepoxycycloartane-3,7,25-triol and (20R,24R)-16, 24:20,24-diepoxycycloartane-3,7, 25-triol 3-O--D-xylopyranoside, respectively, on the basis of chemical transformations and spectral characteristics. The structure of cycloalpigenin has been confirmed by chemical correlation with that of cycloalpigenin D.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 700–708, September–October, 1995. Original article submitted February 1, 1995.     

Enantiomer separations with chromatographic supports based on β-cyclodextrin polymers immobilized on porous silica. Role of the polymer structure in separating ability

Summary Two -cyclodextrin (-CD)-containing polymers have been prepared either by condensation of -CD molecules with a bifunctional reagent or by grafting a -CD derivative on to a linear polymer (polyvinylimidazole). HPLC stationary phases were obtained by adsorption of the -CD polymers on to silica. The ability of these chromatographic supports to resolve racemic mixtures of organic compounds such as amino acid derivatives, phenylhydantoins, barbiturates, and hydroxycoumarin derivatives has been investigated. Results were found to depend on the chemical structure of the -CD polymers     

Alkaloids of far-eastern species ofThalictrum. IV

Summary The alkaloid composition of four far-eastern species ofThalictrum — Th. amurense, Th. contortum, Th. filamentosum, andTh. minus — have been studied, for the first time in the case of the first three species.Th. amurense contains -allocryptopine and thalictrisine, andTh. contortum contains -allocryptopine. Glaucine and thalicsimidine have been found inTh. filamentosum, and argemonine has been isolated fromTh. minus for the first time.Institute 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. 6, pp. 788–791, November–December, 1976.     

Transformations of solasodine

Solasodine (I) has been subjected to a number of transformations. The following compounds have been obtained from it by described procedures: 3-acetoxypregna-5,16-dien-20-one (II), 3-acetoxypregn-5-en-20-ol (III), and 3-acetoxypregn-5-en-20-ol (IV). The oxidation of (III) and (IV), the formation of an oxime, and the reduction of the oxime with sodium in ethanol, followed by Hess methylation, has led to 20-dimethylaminopregn-5-en-3-ol (IX) and to 20-dimethylaminopregn-5-en-3-ol (X). From compounds (IX) and (X), by analogy with (III) and (IV) by their oxidation and the preparation of oximes, which were then reduced and methylated, the following were obtained: 3,20-bisdimethylaminopregnane (XVII) and 3,20-bisdimethylaminopregnane (XVIII), and also quaternary salts of the latter.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 370–374, May–June, 1980.     

Unsaturated esters of N-(β-hydroxyethyl) lactams

A general method is developed for synthesizing methacrylic esters with a 5-, 6-, or 7-membered lactam ring to the carboxyl group, by reacting the sodio-derivatives of the lactams with -chloroethyl methacrylate. The esters synthesized are prone to thermal polymerization, and able to copolymerize with other monomers in the presence of azodiisobutyronitrile. The following copolymers are prepared; -(N-pyrrolidonyl) ethyl acrylate with methyl acrylate, -(N-pyrrolidonyl) ethyl, -(N-2-oxotetramethyleneimino) ethyl, and -(N-2-oxopentamethyleneimino) ethyl methacrylates withmethyl methacrylate.     

Synthesis of tetra- and pentacarbocyanine dyes with alkoxy groups in the β,β′ positions of the polymethine chain

Previously unknown symmetrical and unsymmetrical , '-dialkoxytetracarbocyanine and , '-dialkoxypentacarbocyanine dyes have been synthesized by the condensation of -alkoxy-substituted hexamethine and octamethine hemicyanines with quaternary salts of -alkoxypropenyl derivatives of heterocyclic bases. Tetracarbocyanines with a symmetrical structure have also been obtained by the direct interaction of quaternary salts of -alkoxypropenyl derivatives of heterocyclic bases with malonaldehyde dianil.     

Triterpene glycosides ofSalsola micranthera. I. Structures of salsolosides C and D

New triterpene glycosides — salsolosides C and D — have been isolated from the epigeal part ofSalsola micranthera Botsch. On the basis of chemical transformations and physicochemical measurements, salsoloside C has been assigned the structure of oleanolic acid 28-0--D-glucopyranoside 3-0-[0--D-xylopyranosyl-(1 4)--D-glucuropyranoside], and salsoloside D has the structure of hederagenin 28-0--D-glucopyranoside 3-0-[0--D-xylopyranosyl-(1 4)--D-glucuropyranoside].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 727–732, November–December, 1983.     

Structure of subchrysin

A new sesquiterpene lactone having the structure 3-acetoxy-1-hydroxy-6, 7(H)-germacra-4,10(14), 11(13)-trien-6, 12-olide has been isolated fromArtemisia subchrysolepis Filat. and has been called subchrysin. Its stereochemistry has been established by x-ray structural analysis.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 176–180, March–April, 1998.     

Steroid glycosides from the starfish Crossaster papposus

Two new steroid glycosides have been isolated from an ethanolic extract of the starfishCrossaster papposus — crossasterosides P₁ and P₂. On the basis of chemical transformations and spectral characteristics, the structure of crossasteroside P₁ has been established as (24R)-24-ethyl-5-cholestane-3,6,8,15,16,29-hexaol 29-O-[2-O-methyl--D-xylopyranosyl-(1 2)--D-galactofuranoside]. Crossasteroside P₂ is its 4-hydroxy analogue.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 669–673, September–October, 1989.     

Triterpene glycosides ofHedera helix II. Determination of the structure of glycoside L-6d from common ivy leaves

A new hederagenin pentaoside — glycoside L-6d — has been isolated from the leaves of common ivyHedera helix L., fam. Araliaceae, and its structure has been determined by using various NMR-spectroscopic methods. Glycoside L-6d is hederagenin 3-O-[O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl-(14)-O--L-rhamnopyranosyl-(12)--L-arabinopyranoside.Simferopol' State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 746–752, November–December, 1994.     

Triterpene Glycosides of Astragalus and Their Genins. LXVI. Cycloorbicoside C, a New Bisdesmoside

The new triterpene glycoside cycloorbicoside C was isolated from the aerial parts of Astragalus orbiculatus Ledeb. (Leguminosae) and was identified as (23R,24S)-16,23;16,24-diepoxycycloartan-3,25-diol 3-O--D-xylopyranoside 25-O--D-glucopyranoside.     

Rearrangement ofα -trifluoromethyl-β-dialkylamino-β-fluoroacrylic acid N.N-dialkylamides

Conclusions When heated in the presence of a catalytic amount of BF₃ etherate,-trifluoromethyl--diethylamino--fluoroacrylic acid N, N-dimethylamide is reversibly isomerized to-trifluoromethyl--dimethylamino--fluoroacrylic acid N, N-diethylamide. The methyl esters of-trifluoromethyl--diethylammo--fluoroacrylic acid and-trifluoromethyl--phenoxy--fluoroacrylic acid N,N-dimethylamide are not isomerized under the same conditions.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.1, pp.137–141, January, 1976.     

Alkaloids ofThalictrum simplex

Conclusions Eleven alkaloids have been isolated from the roots ofThalictrum simplex L. Thalicmine, thalicminine, -allocryptopine, and magnoflorine have been found in this species for the first time. Thalicmidine and thalictrisine are new alkaloids.The main alkaloids of this species of plant are hernandezine in the tertiary fraction and magnoflorine in the quaternary fraction.     

Triterpene Glycosides and Their Genins from Tragacantha stipulosa. Structure of Cyclostipuloside C

A new cycloartane glycoside of the cyclostipuloside C series, 3-O--D-xylopyranoside-6,16-di-O--D-glucopyranoside-20S-24R-epoxycycloartan-3,6,16,25-tetraol is isolated from aerial organs of Tragacantha stipulosa Boriss.     

Alkaloids of Aconitum kirinense. Structure of akirine

The known alkaloid lepenine and the new diterpene alkaloid akirine have been isolated from the epigeal part ofAconitum kirinense Nakai. To establish the structure of akirine, its spectral characteristics have been studied and an x-ray structural analysis has been made. It is 1,8-dihydroxy-16-methoxy-9,14-methylenedioxy-3,4-epoxy-N-ethylaconitane — the first diterpene alkaloid with a lycoctonine skeleton containing a 9,14-methylenedioxy group and a -oriented substituent at C14.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 534–538, September–October, 1992.     

Iriterpene glycosides of Astragalus and their genins XLIII. Cycloaraloside B from Astragalus amarus

The structure of a new cycloartane glycoside, cycloaraloside B, isolated from the roots ofAstragalus amarus Pall. (Leguminosae) has been established on the basis of chemical transformations and spectral characteristics: it is 20R,24S-epoxycycloartane-3,6,16,25-tetraol 3-O-[O--L-rhamnopyranosyl-(12)-(6-O-acetyl--D-glucopyranoside)].Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 528–531, September–October, 1992.     

Mass spectrometric study of monoalkyl-substituted thiacyclanes

Monosubstituted - and -alkylthiophans and -, -, and -alkylthiacyclohexanes were subjected to a comparative mass spectrometric study. The stability of the M⁺ ion increases on passing from - to -alkylthiophans and from - to - and -alkylthiacyclohexanes. In the case of -alkylthiophans and - and -alkylthia-cyclohexanes the principal process is associated with ejection of the substituent as a whole, whereas a portion of the alkyl substituent, with retention of one CH₂ group in the composition of the charged fragment, is eliminated from the molecular ions of -alkylthiophans and -alkylthiacyclohexanes.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 176–181, February, 1978.