Aporphine alkaloids

The review gives information on aporphine alkaloids and their oxo and dehydro derivatives and discusses the characteristic features of the chemical and spectral properties of these alkaloids.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 279–312, May–June, 1980.     

Alkaloids of the epigeal part ofAconitum karakolicum

The dynamics of the accumulation of alkaloids in the epigeal part ofAconitum karakolicum according to vegetation periods has been studied. It has been established that the highest content of alkaloids is found in the early period. On separating the combined alkaloids, the aporphine alkaloid isoboldine has been isolated from this plant for the first time and a new base has been obtained — napelline N-oxide, the structure of which has been shown on the basis of the results of a study of spectral characteristics and direct transition to napelline.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 826–829, November–December, 1979.     

Alkaloids ofLiriodendron tulipifera

The alkaloids of the tulip treeLiriodendron tulipifera L., family Magnoliaceae, are considered. More then 20 alkaloids have been isolated during different vegetation periods from various organs of the plant growing in Uzbekistan, and these have been assigned to the aporphine alkaloids and their dehydro, oxo, and 7-hydroxy derivatives; only two alkaloids proved to be derivatives of proaphorphine and of tetrahydroberberine. On the basis of the results of a comparative study of the NMR spectra of aporphines unsubstituted in ring D and some chemical transformations, the structure and configuration of the (R)-3-hydroxy-1,2-dimethoxyaporphine have been proposed for the new alkaloid lirinine. The absolute configurations, possible biogenetic interconnections, and mutual transitions of the alkaloids ofL. tylipifera that are derivatives of aporphine, oxoaporphine, and dehydroaporphine are discussed. A summery table is given which includes 41 alkaloids found in this plant.     

Mass-spectrometric study of the new alkaloids from plants of the family Liliaceae

A review is given of the mass spectra of alkaloids isolated from plants of the generaColchicum L.,Merendera ramond, family Liliaceae that are derivatives of homoproaporphine, homoaporphine, homomorphine, and allochlchiceine. The basic fragmentation pathways and the analytical indications of individual structural types and differences due to the mutual positions of the functional groups, substituents, and the unsaturation of individual rings are given.Yuldash Akhunbabaev Institute of Textiles and Light Industry, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 3–11, January–February, 1985.     

Alkaloids ofThalictrum isopyroides

Summary 6,7-Dimethoxy-2-methyl-1,2-dihydroisoquinolin-1-one and the new aporphine base 9-hydroxy-1,2,3,10-tetramethoxyaporphine, which has been called thalisopynine, have been isolated fromThalictrum for the first time.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnyk Soedinenii, No. 4, pp. 472–474, July–August, 1978.     

Alkaloids ofPapaver orientale

Continuing the separation of the total alkaloids of the plantPapaver orientale L., collected in the flowering phase in the region of Lake Sevan, orientalidine, mecambridine, isothebaine, and bracteoline have been isolated, together with new alkaloids — oreintine, O-methylisothebaine, and orientidine, the structures of which 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. 81–83, January–February, 1984.     

Alkaloids ofCorydalis stricta

The alkaloids of the epigeal part and roots ofCorydalis stricta have been studied. Of the 23 alkaloids isolated, N-methylcorypalline proved to be new, and its structure has been determined. Stilopine hydroxymethylate and pycnarrhine have been isolated from the genusCorydalis for the first time, and cheilanthiofoline isocorypalmine, scoulerine, isoboldine, reticuline, N-methylcoclaurine, coreximine, juziphine, pancorydine, corypalline, wilsonirine, stilopine, adlumidine, dihydrosanguinarine, adlumine, and bicucculine have been isolated from this species of plant for the first time.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 490–493, July–August, 1983.     

Alkaloids ofColchicum luteum

The paper gives a review of the alkaloids ofColchium luteum Baker from various growth sites. The structure of luteidine — one of the main alkaloids of the plant — has been established. In addition, two new alkaloids have been isolated from the plant and the structure of one of them has been established as collutine N-oxide.M. I Kalinin Turkmen Agricultural Institute, Ashkhabad, and V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 810–815, November–December, 1985.     

Alkaloids ofRhinopetalum stenantherum. Structure of stenanzidine

Three new alkaloids have been isolated from the combined alkaloids of the epigeal part ofRhinopetalum stenantherum: stenanzidine, stenanzidinine, and stenanzamine.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 341–344, May–June, 1984.     

Alkaloids ofGlaucium fimbrilligerum. II

The alkaloids of the epigeal part and roots of the plantGlaucium fimbrilligerum have been studied. A total of 18 alkaloids has been isolated, of which epiglaufidine proved to be new, and its structure has been established. Columbamine has been isolated from the genusGlaucium for the first time, and magnoflorine and stilopine -hydroxymethylate from this species of plant for the first time.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Purkinje University, Brno, Czechoslovakia. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 493–496, July–August, 1983.     

Biosynthesis of alkaloids in Sophora alopecuroides

Summary The interconversions of the alkaloids of Sophora alopecuroides L. have been studied by feeding the plants with tritium-labelled alkaloids ([³H]sophoridine, [³H]pachycarpine, [³H]cytisine, [³H]isosophoridine, [³H]allomatrine, and [³H]N-methylcytisine). It has been established that the conformationally stable isomers of the alkaloids — isosophoridine and allomatrine — do not take part actively in the metabolism of the alkaloids. It has also been shown that the alkaloids of the sparteine group are converted into martrine alkaloids in the development of the plant. The methylation of cytisine to N-methylcytisine and the reverse transition have been shown experimentally in the plant organism.V. I. Lenin Tashkent State University. Institute of Plant Biochemistry, Academy of Sciences of the GDR, Halle. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 244–247, March–April, 1977.     

Dynamics of the accumulation of alkaloids in the epigeal part ofAconitum leucostomum

The dynamics of the accumulation of alkaloids in the epigeal part ofAconitum leucostromum Worosch. from various growth sites according to the vegetation periods have been studied. It has been shown that in all cases in the early period of development of the plant diterpene bases predominate in the total material, and in the fruit-bearing period isoquinoline bases.Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 805–808, November–December, 1980.     

Berberis alkaloids. XV. Structure of bargustanine

Bargustanine (I), belonging to a new type of isoquinoline alkaloids, has been isolated from the phenolic fraction of the total alkaloids from the roots ofBerberis vulgaris L. Its structure has been established by chemical and spectral methods.Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Andizhan State Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–47, January–February, 1993.     

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.     

Berberis alkaloids. XVII. Investigation of the alkaloids of Berberis heteropoda

The alkaloid composition of young shoots and leaves ofBerberis heteropoda Schrenk has been studied. In addition to known alkaloids, two new ones have been isolated — N-methyldihydroberberine and 8-oxoberberrubine, the structures of which were established by chemical transformations and a study of spectral properties. Of known alkaloids, berbamunine, aromoline, glaucine, thalicmidine, isocorydine, and reticuline have been found in this plant for the first time. Pseudopalmitine and laudanosine have been found for the first time in plants of the genusBerberis.Andizhan State Medical Institute. Institute of the Chemistry of Plant Substances of Uzbek Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 53–59, January–February, 1993.     

Alkaloids ofDicentra

Methanolic extraction ofDicentra spectabilis L., collected in the flowering period in the botanical garden of Pyatigorsk Pharmaceutical Institute, has yielded 0.17% of combined alkaloids from the epigeal part and 0.25% from the roots. By the separation of these materials, dihydrosanguinarine, sanguinarine, scoulerine, cheilanthifoline, corydine, and protopine have been obtained.Dicentra peregrina Rudolph, collected in the flowering period on the island of Sakhalin, has yielded 1.8% of combined alkaloids from the epigeal part and 1.51% from the roots. From these combined materials have been isolated isocorydine, corydine, dicentrine, protopine, dihydrosanguinarine, sanguinarine, cheilanthifoline, bicuculline, lederine, scoulerine, isoboldine, predicentrine, reticuline, and allocryptopine.Institute of the Chemistry of Plant Substances. Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 79–81, January–February, 1984.     

Alkaloids of Papaver fugax

Papaver fugax growing on the shore of Lake Kazenoi Am in the Checheno-Ingushskii ASSR at the boundary with the Dagestan ASSR has yielded 0.39% of alkaloids. Seven alkaloids have been isolated, of which cheilanthifoline, scoulerine, and reticuline have been detected in this species for the first time, while it is the first time that d-remeroline has been found in a plant of thePapaver genus.Pyatigorsk Pharmaceutical Institute. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 559–562, July–August, 1988.     

Alkaloids ofPapaver orientale

Summary From the combined alkaloids ofPapaver orientale we have isolated isothebaine, oripavine, thebaine, mecambridine, orientalidine, alpinigenine, protopine, bracteoline, oripavidine, and the new alkaloid isothebaidine, the structure of which has been established.Institute of the Chemistry of Plant Substances, Tashkent. Pyatigorsk Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 474–475, July–August, 1978.     

An investigation of the alkaloids of Lolium cuneatum

Summary In addition to three known alkaloids, the seeds ofL. cuneatum have yielded N-formylloline, N-acetylnorloline, and the new alkaloids N-methylloline and N-formylloline methiodide.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 60–63, January–February, 1976.