Determination of beeswax and some impurities by IR spectroscopy

Summary Analysis of the IR spectra of waxes isolated from samples of paints from paintings dating from the Ist to VIIth centuries of our era and fragments of archaeological antique murals has shown that in some cases the wax isolated is pure beeswax and in others it contains as impurities what are presumably resin acids, and also salts of fatty acids. The IR spectrum of pure beeswax extracted from a fragment buried for 2000 yr is absolutely identical with the spectrum of modern beeswax, which shows the extreme chemical stability of the wax.All-Union Central Scientific-Research Laboratory for Conservation and Restoration, Moscow. Scientific-Research Institute of Organic Intermediates and Dyes, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 271–275, March–April, 1977.     

Chemical ionization mass spectra of natural monohydroxy- and monoacyloxy-substituted dihydropyranocoumarins and dihydrofurocoumarins

Summary The chemical ionization mass spectra of ten compounds of the group of natural monohydroxy and monoacyloxy derivatives of dihydropyranocoumarins and dihydrofurocoumarins have been studied. Their difference from the electron impact mass spectra has been shown. The structural-analytical possibilities of the method of chemical ionization for this series of substances has been determined.M. V. Lomonosov Moscow State University. Patrice Lumumba International Friendship University, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 508–512, July–August, 1977.     

Phenolic lipid from Azotobacter chroococcum

Summary From the total cell lipids of the nitrogen-fixing bacteriumAzotobacter chroococcum 92 a previously unknown lipid has been isolated which has been identified as a 1-alkyl-3,5-dihydroxybenzene. The alkyl chains of the main components of the lipid fraction have a normal structure and contain 19 and 21 carbon atoms.M. M. Shemyakin Institute of Bioorganic Chemistry, USSR, Moscow, All-Union Scientific-Research Institute of Microbiological Agents for Plant Protection and Bacterial Preparations, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 494–499, July–August, 1977.     

Heteroadamantanes and their derivatives 26. Synthesis of derivatives of hydroxybenzyldiazahomoadamantane

Summary 1-(4-Hydroxy-3-nitrobenzyl)-3,6-diazahomoadamantan-9-one was obtained by the nitration of hydroxybenzyldiazahomoadamantanone. The behavior of the carbonyl group of this ketone and of its nitro derivative has been studied. The structures of the functional derivatives obtained were confirmed by data of IR, PMR, and mass spectra.For part 25 see [1].M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, Moscow 117571. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 391–394, March, 1995.Original article submitted December 29, 1994.     

Low-molecular-weight metabolies of wheat. I. Components of an ethereal extract of wheat leaves

The chromatographic separation of the components of an ethereal extract of the leaves of Mironovskaya 808 wheat has been performed. The presence in wheat of phthalic acid and its dimethyl, diethyl, and dibutyl esters has been shown for the first time. Substituted benzoic and cinnamic acids, p-hydroxybenzaldehyde, vanillin, 6-methoxybenzoxazolone, tricin, and aconitic and fumaric acids have also been isolated. The structures of the compounds isolated have been confirmed by IR, UV, mass, and NMR spectra.M. M. Shemyakin Institute of Bioorganic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 783–789, November–December, 1981.     

Mass-spectrometric study of the sesquiterpene lactone germanin-A and its derivatives

Summary The mass spectra of the sesquiterpene lactone germanin-A and 11 of its derivatives and deuterium analogs have been studied. A scheme has been put forward for the decomposition of germanin-A under the action of electron impact. It has been established that the elimination of a molecule of acid from position 8 in the dissociative ionization of germanin-A and of tetrahydrogermanin-A involves the hydrogen atom of the carboxy group present in position 10 of the sesquiterpene ring. On this basis, a suggested conformation of the germanin-A molecule has been put forward.M. V. Lomonosov Moscow State University. All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 337–345, May–June, 1978.     

Field desorption mass spectra of flavonoid acylglycosides. I. Natural acetyl derivatives

The field desorption mass spectra (FD spectra) of 17 natural flavonoid acetylglycosides have been studied. In the spectra of each of the 0-monoglycosides the molecular ion (M or M + H) appears as the main peak and it is accompanied by the ions of the aglycone (A or A + H) and of the acylated anhydrosugar (S). The intensity of the latter peak is largely connected with the structure of the substance. In the FD spectra of flavone 0-biosides, fragment S is absent but its mass can be calculated from the difference (M – A). Useful information for establishing the position of the acetyl group is given by the fragments S₁ and (M – S₁) corresponding to the detachment of the terminal sugar residue. The FD spectra of flavone C-glycosides differ greatly from the spectra of the 0-glycosides: In them the main peak is that of the ion (M), but peaks (A) and (S) are absent and the ions present resemble the fragmentation of the C-glycosides under the action of electron impact.All-Union Scientific-Institute of Medicinal Plants, Moscow. L. Ya. Karpov Scientific-Research Institute of Physical Chemistry, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 573–582, September–October, 1984.     

Low-voltage mass spectra of monohydroxy-and monoacyloxydihydropyranocoumarins and -dihydrofurocoumarins

Summary With the aid of the low-voltage mass spectra of 16 compounds belonging to the monohydroxy- and monoacyloxydihydropyranocoumarins and -dihydrofurocoumarins and their deuterium analogs it has been shown the relative intensities of the ions with m/e 176 and 175 is an analytical magnitude both for the dihydropyranocoumarins and the dihydrofurocoumarins which enables linear and angular isomers in these series of substances to be distinguished.Patrice Lumumba International Friendship University, Moscow, M. V. Lomonosov Moscow State University. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 212–215, March–April, 1977.     

Polysaccharides ofEremurus. X. Characteristics of the polysaccharides ofEremurus lactiflorus andE. luteus

Water-soluble polysaccharides have been isolated from two species ofEremurus — E. lactiflorus andE. luteus — with yields of 13.5% and 20.5%, respectively. They contained mainly glucose and mannose in ratios of 1:5 and 1:3.1. The polysaccharides ofE. lactiflorus were separated from a column of DEAE-cellulose. The yield of neutral fraction was 10.3%. Gel filtration of the polysaccharides on Sephadex G-200 showed their polydispersity. Homogeneous fractions were obtained by fractional precipitation with ethanol. They have been characterized with respect to monosaccharide composition, molecular weight, and IR spectra.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 604–608, September–October, 1979.     

Mass-spectrometric study of some derivatives of furo- and dihydrofurocoumarins

Summary The mass spectra of eight compounds beloning to the class of linear furo- and dihydrofurocoumarins have been studied. A scheme of the fragmentation of these substances under the action of electron impact has been proposed. It has been shown that the mass-spectrometric method permits acyl derivatives of oreoselone to be distinguished reliably from acyl derivatives of dihydrooreoselol and the latter series of substances from derivatives isomeric with them belonging to the class of dihydrofuro- and dihydropyranocoumarins.M. V. Lomonsov Moscow State University. All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 560–568, September–October, 1974.     

Mass-spectrometric distinction of linear and angular 2,2'-dimethyl-3'-oxo-dihydropyranocoumarins

Summary The mass spectra of linear and angular 2,2-dimethyl-3-oxodihydropyranocoumarins and their deuterium analogs have been studied. A basic mass-spectrometric difference between these substances has been found which consists in the greater stability of the fragment (M - CO)⁺. for the linear isomer than for the angular isomer. A hypothesis has been put forward on the most probable route for the formation of the ion (M - 2CO - H)⁺ in the mass spectra of the compounds mentioned.M. V. Lomonosov Moscow State University. Patrice Lumumba International Friendship University, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 664–668, September–October, 1977.     

A study of the products of the reduction of the antibiotic reumycin (6-methylpyrimido [5,4-e][1,2,4]triazine-5,7-dione)

The structures of the products of the reduction of the antibiotic reumycin (I), which is a specific autooxidizable acceptor of reducing equivalents from certain flavin dehydrogenases of the respiratory chain of the mitochondria of yeast and animal tissues, have been established with the aid of physicochemical methods (UV, IR, and PMR spectroscopy and mass spectrometry). In the determination of the structures of five reduction products of reumycin effective use has been made of high-resolution mass spectrometry and a consideration of the spectra of metastable ions (the DADI technique). It has been shown that only the asym-triazine ring in the initial (I) undergoes reduction and ring-opening.All-Union Scientific-Research Institute of Antibiotics, Moscow Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 85–95, January–February, 1981.     

A study of the conformational states of cyclopeptide systems

Summary 1. An empirical method for the quantitative determination of the number of NH groups of different types in peptides based on measurements of the integral intensity of the amide A bands in the IR spectra has been developed.2. The IR spectra of the diastereomeric cyclohexaalanyls in CHCl₃ solutions have been studied; they indicate the participation of an average of four NH groups in IMBHs.3. On the basis of a theoretical conformational analysis and of dipole-moment measurements, the system of IMHBs and the type of dominant conformation of the cyclohexapeptides in nonpolar solvents have been established.M. M. Shemyakin Institute of the Chemistry of Natural Compounds of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 347–357, May–June, 1971.     

Nature of the transformations of oleanolic acid in an acid medium

3-Trifluoroacetoxyoleanolic acid and 3-trifluoroacetoxyolean-13(18)-en-28-oic acid have been isolated from the mixture of the products of the transformation of oleanolic acid in a trifluoroacetic acid medium, and their structures have been established with the aid of IR, PMR and mass spectra. The formation of these products indicates an unambiguous route of the stabilization of the intermediate carbocation with the charge on the C-13 atom. The hydroxy group at C-3 is esterified by the trifluoroacetic acid.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 320–323, May–June, 1986.     

Solid-phase synthesis of oligonucleotides representing fragments of trp promoters

The self-complementary oligonucleotides AACTAGTT and AGTTAACT, which are homologs of functionally important sections of trp promoters of three related bacteria, have been synthesized by the solid-phase method. A new block variant of synthesis on a polymer has been worked out and has been used for obtaining the octanucleotides AACTAGTTp and AGTTAACTp.M. V. Lomonosov Moscow State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 362–369, May–June, 1984.     

Synthesis of ephedrine (dialkyl phosphorothioate)s. Crystallographic structure of ephedrine (diethyl phosphorothioate)

The synthesis of ephedrine (dialkyl phosphorothioate)s has been effected. The method of their preparation and their properties are described. The IR and PMR spectra of ephedrine (dialkyl phosphorothioate)s and some results of an x-ray structural investigation of the spatial structure of ephedrine (diethyl phosphorothioate) are given.Institute of Organic Synthesis and Coal Chemistry, Kazakh SSR Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 88–91, January–February, 1989.     

Configuration of stereoisomers of naringenin 5-glucoside present in flamin

The configurations of the C-2 chiral centers of the stereoisomers of naringenin 5-glucoside isolated from flamin by HPLC have been established by the method of circular dichroism. One of the stereoisomers is (–)-2S-naringenin 5-glucoside and the other has been characterized as a molecular compound containing the 5-glucosides of (+)-2R- and (–)-2S-naringenins in a ratio of 2:1.1st I. M. Sechenov Moscow Medical Institute. M. V. Lomonosov Moscow State University. All-Union Scientific-Research Institute of Drug Chemistry and Technology, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 185–188, March–April, 1989.     

The sesquiterpene lactones ofStizolophus balsamita

Summary From the epigeal part ofStizolophus balsamita (Lam.) Cass. ex Takht. a new sesquiterpene lactone balsamin has been isolated with the composition C₂₀H₂₆O₆, mp 242–244°C (from ethanol), [] _D ¹⁷ –45.70° (c 1.9; chloroform). Do the basis of the basis of the IR, UV, and PMR spectra of balsamin and its acetate, a stereochemical structure has been proposed for balsamin, and the structures of stizolin and stizolicin isolated previously from the same plant have also been supplemented by stereochemistry.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 467–472, July–August, 1976.     

Identification of aliphatic 2- and 3-hydroxy acids in the form of cyclic phenylboronates by GLC-mass spectrometry

A method is prepared for identifying aliphatic 2- and 3-hydroxy acids which is based on the GLC-mass spectrometry of the corresponding phenylboronates. The phenyl-boronates are sufficiently volatile for analysis with the aid of GLC and give simple and informative mass spectra.M. M. Shemyakin Institute of Bioorganic Chemistry, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 283–288, May–June, 1981.     

Chemical investigation of biomass of a culture of ginseng cells III. Polysaccharides of a callus culture of ginseng

A water-soluble polysaccharide fraction has been isolated from a callus culture of ginseng with a yield of 16–20%. It has been shown that it included starch a and acidic polysaccharides — arabinogalactans and a xyloglucan.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, USSR Academy of Sciences, Vladivostok, All-Union Scientific Research Institute of Biochemical Machinery Design, USSR Ministry of the Medical Industry, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 771–772, November–December, 1989.