13C NMR spectra of the aminoglycoside antibiotics streptomycin and dihydrostreptomycin. Complete assignment of the signals

On the basis of the results of a study of the dependence of the chemical shifts of the¹³C NMR spectra streptomycin and dihydrostreptomycin over a wide pH range (from 1.0 to 10.0) and a comparison with the spectrum of streptidine in an acid medium, a complete assignment of the spectra of the antibiotics investigated has been made. The optimum pH values of solutions at which the clearest separation of the resonance signals in the spectra of streptomycin and dihydrostreptomycin have been determined (pH 1.0–7.0 and pH ≤ 8.6, respectively). All-Union Scientific-Research Institute of Antibiotics, Moscow. I. M. Sechinov 1st Moscow Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 695–700, September–October, 1980.     

Transannular cyclization of the E,E-germacradienolide hanphyllin

The results are reported of the interaction of the trans,trans-germacradienolide hanphyllin with m-chloroperbenzoic acid and with 50% sulfuric acid. This leads to a cyclization reaction with the formation of eudesmanolides: 1β-hydroxy-3-oxo-1,4,5,7α(H),6β(H)-eudesm-11(13)-en-6,12-olide, ridentin B, and 3β-hydroxy-5,7α(H),6β(H)-eudesma-4(15),11(13)-dien-6,12-olide; and also products of the opening of the lactone ring as a consequence of transesterification. The structures of the compounds obtained are discussed on the basis of spectral results (IR, PMR, and mass spectra) and of x-ray structural analysis. Institute of Organic Synthesis and Coal Chemistry, Kazakhstan Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 508–517, September–October, 1992.     

Structure of the alkaloids of Aerva lanata

By the NOE method using¹³C NMR and UV spectra we have confirmed the structures of four new alkaloids isolated previously: 10-hydroxycanthin-6-one (ervine), 10-methoxycanthine-6-one (methylervine), 10-β-D-glucopyranosyloxycanthin-6-one (ervoside), and 6-methoxy-β-carbolin-l-ylpropionic acid (ervolanine). All-Union Scientific-Research Institute of Drugs Scientific-Production Association, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 821–824, November–December, 1991.     

Secondary metabolites of Ulocladium chartarum. Ulocladols A and B — New phytotoxins of terpenoid nature

Ulocladols A and B — new exometabolites having a mixed sesquiterpenoid-polyketide nature that are structurally close to the host-specific toxins ofAlternaria citri — have been isolated from the deuteromyceteUlocladium chartarum. Both substances inhibit the growth of cotton seeds. All-Union Scientific Research Institute of Phytopathology, Moscow Province, Golitsyno. M. V. Lomonosov Moscow State University. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 642–648, September–October, 1991.     

Branched polycyclic tetrazole systems. 1. Synthesis and structure of 2-(5-tetrazolyl)ethyl derivatives of some CH-, OH-, and NH-acids

The cycloaddition of dimethylammonium azide to the nitrile groups of 2-cyanoethyl derivatives of CH-, OH-, and NH-acids leads to open-chain branched structures containing terminal NH-tetrazolyl groups. An x-ray diffraction structural analysis of tris[2-(5-tetrazolyl)ethyl]nitromethane revealed steric access of the equivalent NH-tetrazolyl rings of the branched system. In going from the branched nitrile substrates to the corresponding tetrazoles, the PMR spectra show a breakdown in the resolution of the multiplet components, which had not been observed previously for monocyclic 5-substituted tetrazoles. A dependence was found for the¹³C NMR chemical shifts on the pK_a values, reflecting the NH-acidity of the branched polycyclic tetrazoles in water. Dedicated to the memory of I. N. Goncharova. St. Petersburg State Technological Institute, 198013 St. Petersburg. V. A. éngel'gart Institute of Molecular Biology, Russian Academy of Sciences, 117984 Moscow. L. Ya. Karpov Physics and Chemistry Research Institute, 103062 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1494–1501, November, 1997.     

A study of the herb Aerva lanata II. Feruloylamines

All-Union Scientific-Research Institute of Medicinal Plants, Scientific Production Combine, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 694–695, September–October, 1990.     

Determinationation of kanamycin by square-wave cathodic adsorptive stripping voltammetry

A square-wave cathodic adsorptive stripping voltametric (SWCASV) method for the determination of kanamycin was developed on a thin-film mercury electrode (TFME). The optimal working conditions for the application of the method were found to be pH 8.0, provided by a Britton-Robinson (B.R.) buffer, and an adsorption potential of +0.30 V during 300 s. The equilibration time was applied during 10 s, and potential scans were performed at a scan rate of 40 mV/s, with a square-wave frequency of 100 Hz. The measuring-system response was linear over the kanamycin concentration range from 1.2 × 10⁻⁹ to 5.0 × 10⁻⁸ M and the detection limit achieved was 4.8 × 10⁻¹⁰ M. The relative error and relative standard deviation obtained were 1.20 and 4.67%, respectively. The voltammetric procedure was applied successfully to give a rapid and precise assay of kanamycin in kanamycin sulfate injection form. Published in Elektrokhimiya in Russian, 2008, Vol. 44, No. 12, pp. 1433–1437. The text was submitted by author in English     

NMR investigation of alkaloids. XI.13C NMR spectra and structure of codonopsine and codonopsinine

An assignment of the signals in the¹³C NMR spectra of the alkaloids codonopsinine and codonopsine has been made on the basis of selective double heteronuclear resonance experiments. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 536–538, July–August, 1989.     

Selective binary mobile phase for high-performance liquid chromatography of 12, 13-epoxytrichothec-9-en-8-ones

M. V. Lomonosov Moscow State University. All-Union Scientific-Research Institute of Veterinary Medicine, Moscow. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, pp. 861–863, November–December, 1989.     

Dimeric stilbenes of the wood of Maackia amurensis

Dimeric stilbenes have been isolated from the wood of Amur maackia for the first time. Two of them have been identified as the known scirpusins A and B. The structure of a new dimeric stilbene with a dioxane linkage, which has been called maackinin, has been established. The PMR and¹³C NMR spectra of the substances isolated have been studied in detail. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 468–476, September–October, 1992.     

Synthesis,structure, and action of some gossypol derivatives on the peroxidation of the lipids of biosubstrates

The synthesis has been effected of new gossypol derivatives using piperidino-and morpholinoethylamines. According to their PMR spectra, these substances exist in the keto-amine form. Their action on the peroxidation of lipids (POL) of various biosubstrates has been studied. Gossypol bis(piperinoethylimine) and bis(morpholinoethylimine) in concentrations of 1·10⁻⁷–5·10⁻⁶ mM exert a pronounced antioxidant action on human blood serum and rat brain synaptosomes. In the same concentrations, these substances suppressed the POL in enzymatic and nonenzymatic systems of the oxidation of rat liver microsomes. A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Institute of Hematology and Blood Transfusion, Ministry of Health of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 707–712, September–October, 1989.     

X-ray and quantum chemical study of the electronic structure of glycine and its metal complexes

OK_α spectra of glycine and some transition metal complexes with glycine ligands were obtained. The electronic structure of the glycine zwitterion is calculated by a quantum chemical method, and a theoretical X-ray spectrum of the glycine molecule is constructed. The nature of the metal-ligand bond in the compounds is discussed on the basis of experimental spectra and theoretical calculations. Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences. Moscow State Academy of Light Industry, Novosibirsk Branch. Moscow State Academy of Light Industry. Novosibirsk State University. Translated fromZhurnal Strukturnoi Khimii, Vol. 34, No. 4, pp. 112–116, July–August, 1994. Translated by L. Smolina     

Molecular and crystal structure of the germacranolide argolide from Artemisia glabella

The new germacranolide argolide has been isolated from the epigeal part ofArtemisia glabella, and its structure has been shown by its conversion into oxopelenolide B. From the results of an x-ray investigation it is suggested that argolide has the spatial structure of 3-oxo-4α,7α,6β(H)-germacra-1(10),11(13)-dien-6,12-olide. Institute of Organic Synthesis and Coal Chemistry, Kazakh Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Organometallic Chemistry, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–657, September–October, 1991.     

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.     

Conformation of δ-cadinol in solution

An assignment of the signals in the¹³C and¹H NMR spectra of the natural sesquiterpene alcohol δ-cadinol has been made by the NMR method (INADEQUATE, 2D-INADEQUATE, two-dimensional C-H correlation on¹J_CH constants, two-dimensional homonuclear J-spectroscopy) and the spin-spin coupling constants¹J_CC and some J_HH constants have been determined. By comparing the experimental and calculated values of the spin-spin coupling constants J_HH it has been shown that the predominant conformation of the δ-cadinol molecule in solution is that in which ring A has the half-chair form and ring B the chair form with an equatorial arrangement of the hydroxy and isopropyl groups. Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 635–638, September–October, 1990.     

Solubility of the proteins and phytates of cottonseed meal in the presence of metal ions

The solubility of the proteins and phytates of cotton seeds in the presence of metal ions (Ca²⁺, Fe³⁺, Zn²⁺) at various pH values of the medium has been studied. It has been shown that complete precipitation of the protein by phytin from solution (C_protein)=1.5%), sets in at a mass ratio of phytin to protein of 1:15, pH 1.5. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, FAX (3712) 62 73 48. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 421–424. May–June, 1994.     

Polysaccharides of saponin-bearing plants. V. Structural investigation of glucans A,B, and C and their oligosaccharides fromBiebersteinia multifida plants

The partial acid hydrolysis of glucans A, B, and C has given five linear oligosaccharides consisting of α-(1→6)-bound glucopyranose residues, and their structures have been investigated by reduction, peroxidate oxidation, methylation, mass spectrometry, and¹³C NMR spectrometry. Chemical structures are proposed for glucans A, B, and C. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 891475. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 709–714, November–December, 1994.     

Structure of a new phenol aldehyde from the leaves of Eucalyptus viminalis

A new terpenoid phenol aldehyde has been isolated from an alcoholic extract of the leaves of the ribbon eucalyptus by column chromatography on silica gel, and on the basis of the results of¹H and¹³C NMR spectroscopy and mass spectrometry the structure of 4-[1-(3,5-diformyl-2,4,6-trihydroxyphenyl)-3-methylbutyl]-ledol is proposed for it. The relative configurations of the substituents in the terpenoid moiety of the molecule have been determined. All-Union Scientific-Research Institute of Medicinal Plants and Production Association, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 789–795, November–December, 1991.     

Complete 1H and 13C NMR assignments for kanamycin A,kanamycin B and penta-N-acetyl-kanamycin B

The complete ¹H and ¹³C NMR assignments for kanamycin A, kanamycin B and penta-N-acetylkanamycin B were made by a combination of 1D- and 2D     

Simulation and interpretation of the vibrational spectra of heterofullerenes

This paper reports on a computer simulation of the vibrational spectra of C₅₉B, C₅₉N, C₅₉BN, and C₅₉HN. The modes whose frequencies are most sensitive to carbon substitution by heteroatoms are revealed. It is shown that the new bands at 818, 839, and 845 cm⁻¹ in the experimental IR spectrum of C₅₉HN arise from changes in selection rules and by removal of degeneracies due to a reduction in the symmetry of the molecule and force field perturbation. In the Raman spectrum of C₅₉HN, the shifts of the 1460 and 491 cm⁻¹ bands to the low-frequency region by 7 and 3 cm⁻¹, respectively, relative to two A_g modes of C₆₀ are explained by the perturbation induced by the N and C(H) atoms in the force field of adjacent CC bonds not containing these atoms. Institute of Spectroscopy, Russian Academy of Sciences (Troitsk, Moscow Region). Scientific and Production Association “Complex.” Scientific and Production Association “Tekhon.” Translated fromZhurnal Strukturnoi Khimii, Vol. 39, No. 3, pp. 401–411, May–June, 1998.