13C and1H NMR spectra of spiropiperidine alkaloids of Nitraria

A detailed interpretation is given of the¹³C and¹H NMR spectroscopy of the spiropiperidine alkaloids of the nitramine group, and the results are generalized. The assignment has been made of the carbon-13 resonance lines in the spectra of five natural compounds. A dependence of the parameters on the spatial structures of the compounds of this series has been found. The overall PMR spectra of seven natural alkaloids and some of their derivatives are discussed. The conformations of acyl derivatives have been established.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 82–91, January–February, 1988.     

NMR investigation of alkaloids I.13C NMR spectra and stereochemistry of pentacyclic oxindole alkaloids of the heteroyohimbine group of the epiallo and allo series

The¹³C NMR spectra of pentacyclic oxindole alkaloids of the heteroyohimbine group of the allo and epiallo series have been studied and an assignment has been made of the CSs of the carbon atoms. Characteristic differences have been noted in the¹³C CSs of the C₂, C₃, C₇, C₁₄, C₁₅, and C₁₉ carbon atoms that may be useful for solving stereochemical problems in new bases of this series from their¹³C NMR spectra.Communicated at the All-Union Conference on Recent Advances in High-resolution NMR spectroscopy, Tashkent, September, 1979 [1].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 217–224, March–April, 1980.     

Applications of1H and13C NMR spectroscopy in structural investigations of Vinca indole alkaloids

This review considers the laws connecting the parameters of the¹H and¹³C NMR spectra with the structure of the substances and the use of these laws for solving structural and stereochemical problems of theVinca indole alkaloids and other compounds of closely related structure. For each type of alkaloids, characteristic features of the PMR and¹³C NMR spectra are given that permit the structures of similar bases to be established and their stereochemical identification to be performed.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 3–15, January–February, 1986.     

13C NMR spectra of some coumarins of Haplophyllum obtusifolium

Coumaris ofHaplophyllum obtusifolium Ledeb. — obtusinin, capensin, and fraxetin 7-O--D-glucopyranoside — have been investigated by¹³C NMR spectroscopy. Several distinctive features of their NMR spectra have been observed. A complete assignment of the¹³C NMR spectra of these coumarins has been made and their structures have been confirmed.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 796–799, November–December, 1987.     

An investigation by the NMR method of the structure of the alkaloid sophorine fromSophora alopecuroides

A new base — sophorine, with mp 59–60°C, [] _D ²³ -18.9° (c 0.98; ethanol) — has been isolated from the epigeal part of the plantSophora alopecuroides L. Its IR spectrum and the nature of its mass spectrometric composition have permitted sophorine to be assigned to the quinolizidine alkaloids. The¹³C NMR spectrum has shown the presence of 19 carbon atoms. The analysis of several of the carbon signals has confirmed the results of IR and mass spectroscopy. Additional details of the structure of sophorine have been obtained from its PMR spectrum.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 604–608, September–October, 1981.     

The NMR investigation of alkaloids. VII.13C NMR spectra and structure of “kopsanone” and kopsinilam

On the basis of a study of the¹³C NMR spectra of a base fromVinca erecta previously regarded as kopsanone, and the known alkaloid kopsinilam, it has been shown that the former is 5,22-dioxokopsane.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 344–346, May–June, 1984.     

The NMR investigation of alkaloids. IX.13C NMR spectra and stereochemistry of convolvine,convolamine, convoline,convolidine, subhirsine,and 6-hydroxyhyoscyamine

On the basis of the results of a study of the¹³C NMR spectra, a correlation has been made of the CSs of the¹³C carbon nuclei with the structure and stereochemistry of the tropane alkaloids convolvine, convolamine, convoline, convolidine, subhirsine, and 6-hydroxyhyoscyamine. It has been established that the N-CH₃ group in convolamine and the N-OH group in convoline are oriented equatorially, and the N-CH₃ in hydroxyhyoscyamine axially.Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 80–84, January–February, 1986.     

The structure of luteidine

Summary On the basis of UV,¹³C NMR, and mass spectra, it has been established that luteidine belongs to the group of homoproaporphine alkaloids.The IR, PMR, and¹³C NMR spectra of luteidine and the products of its transformations have permitted the structure of 1-hydroxy-2,13-dimethoxy-11-oxo-9,10-dihydrohomoproaporphine to be proposed for this base.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 354–359, May–June, 1976.     

The NMR study of alkaloids. VI. A comparison of the stereochemistries of pseudocopsinine and 14,15-dihydrovindolinine by13C NMR spectroscopy

On the basis of a comparative study of the¹³C NMR spectra of the natural alkaloid pseudocopsinine and its synthetic analog 14,15-dihydrovindolinine it has been shown that their stereochemistries are not identical.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 334–337, May–June, 1984.     

Structures of montticamine and monticoline

The new C₁₈ diterpene alkaloids monticamine and monticamine have been isolated from the epigeal part ofAconitum monticola Steinb. Their structures have been established on the basis of the results of¹H and¹³C NMR, IR, and mass spectra and also of chemical transformations.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 466–470, July–August, 1981. Original article submitted February 10, 1981.     

Alkaloids of a new type fromSophora alopecuroides L.

Summary The structures of aloperine and allylaloperine (fromSophora alopecuroides L.) — alkaloids of a new structural type for the genusSophora — have been established by chemical and spectral methods. A number of parameters, NMR spectra, and mass spectra characterizing this class of compounds has been obtained. The partial synthesis of allylaloperine has been performed.All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 30–37, January–February, 1975.     

NMR investigation of alkaloids

On the basis of a study of the spin-spin coupling constants J_CH and the¹³C chemical shifts of haplophyllidine an assignment has been made of the signals of the carbon atoms of the 5,6,7,8-tetrahydrofuranoquinoline alkaloids haplophyllidine, perforine, anhydroperforine, their derivative (IV), and the furanoquinoline base -fagarine.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 25–30, January–February, 1989.     

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.     

The structure of regeline

Summary On the basis of a study of spectra and chemical transformations the structure of 11-hydroxy-2,12-dimethoxy-1,12-epoxyhexahydrohomoproaporphine has been proposed for regeline — a base fromColchicum kesselringii Rgl.The homoproaporphine carbon-nitrogen skeleton and the complete structure of regeline have been confirmed by a study of its¹³C NMR spectrum.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 783–787, November–December, 1976.     

Studies of Erythrina alkaloids: VII—13C NMR spectral studies of some Erythina alkaloids

A variety of alkaloids have been isolated from the seeds of a range of Erythrina species, including dienoid, alkenoid and lactonic derivatives. The ¹³C NMR spectra of these compounds have been assigned by internal comparisons within this series of related compounds and also by the use of model compounds.     

NMR investigation of alkaloids. III.13C NMR spectra and reconsideration of the stereochemistry of herbamine and herbadine

The stereochemistry previously proposed for herbamine (V) and herbadine (II) as C₂-H has been reconsidered on the basis of a comparative study of the¹³C NMR of these compounds and of vincamajine, quebrachidine, ajmaline, vincamajoreine, and majoridine, and it has been established unambiguously that herbamine and herbadine belong to the dihydroindole alkaloids with C₂-H, herbamine being C₃-hydroxyvincamajine, and herbadine C₆-hydroxyquebrachidine.For Communication II, see [1].Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 731–735, November–December, 1982.     

Gaigranin and gaigrandin — New sesquiterpene lactones fromGaillardia grandiflora

Two new sesquiterpene lactones — gaigranin and gaigrandin — have been isolated from the epigeal part ofGaillardia grandiflora, and their structures have been established on the basis of spectral (IR, PMR,¹³C NMR, and mass) characteristics and x-ray structural analysis.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 79–85, January–February, 1995. Original article submitted October 7, 1994.     

Synthesis and spectral and luminescent properties of 3-formyl-7-dialkylaminocoumarins

By means of the Vilsmeier reaction, starting with various 4-substituted 7-dialkylaminocoumarins having an open position 3, the corresponding 3-formyl derivatives have been obtained, and their spectral and luminescence characteristics have been studied. The ¹³C NMR spectra and acid—base properties of a number of the synthesized compounds have been examined.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1480–1487, November, 1991.     

1H and13C NMR spectra and the structure of a new coumarin, C-glycoside dauroside D, fromHaplophyllum dauricum

On the basis of chemical transformations,¹H and¹³C NMR spectra, the structure of dauroside D isolated fromHaplophyllum dauricum has been established as 6-C--D-glucopyranosyl-5,7-dihydroxycoumarin. Some interesting features of the¹H NMR spectra of its acetate have been reported and an assignment of the signals in its¹H and¹³C NMR spectra has been made. Dauroside D is the first natural coumarin C-glycoside.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 441–445, July–August, 1983.     

Photochemical isomers of tropolone alkaloids

This review, which covers the literature up to 1989, generalizes advances in the field of the study of the photochemical isomers of colchicine and tropolone alkaloids related to it. Information is given on their natural sources, methods of isolation, structure, and configuration, and photochemical and thermal interconversions. Characteristics distinguishing them from the topolone alkaloids in their UV, IR, mass, and²H and¹³C NMR spectra of the photochemical isomers are pointed out.Deceased.Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 147–165, March–April, 1990.