Alkaloids ofNitraria komarovii nitraricine and nitrarizine nitrarizine

Two new alkaloids — nitraricine and nitraricine — have been isolated from the epigeal part ofNitraria komarovii.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. 1, pp. 95–99, January–February, 1995. Original article submitted October 10, 1994.     

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.     

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.     

Berberis alkaloids XXXVI. Turcomanidine — A new alkaloid fromBerberis turcomanica

The alkaloid composition of the leaves ofBerberis turcomanica has been studied. Together with known 1-benzylisoquinoline alkaloids, we isolated a new one — turcomanidine, the structure of which has been established by chemical transformations and a study of spectral characteristics. Of the known alkaloids, N-methylcorydaldine has been detected in plants of the Berberis genus for the first time.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 885–888, November–December, 1996. Original article submitted March 4, 1996.     

NMR study of alkaloids. V.13C NMR spectra and reconsideration of the structures of 11- and 10-hydroxypleiocarpamines and the structures of new alkaloids fromVinca erecta

The structures of phenolic alkaloids isolated previously fromVinca erecta Rgl. et Schmalh. have been reconsidered on the basis of the results of a study of their¹³C NMR spectra, and it has been shown that a base with mp 228–229° has the structure of 11-hydroxystrictamine and an amorphous base of the same composition isomeric with it is 10-hydroxystrictamine. The structures of two new indolenine alkaloids — ercinamine and ercinaminine — have been determined from an analysis of¹³C NMR spectra, and also on the basis of PMR and IR spectra and 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. 483–488, July–August, 1983.     

Alkaloids ofGlaucium fimbrilligerum

From the epigeal part and roots ofGlaucium fimbrilligerum 22 alkaloids have been isolated, of which three have proved to be new — d-isocorytuberine, dehydrocorydine, and corydine N-oxide.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 224–228, March–April, 1980.     

Alkaloids ofNitraria komarovii. XV. Vasicinone and deoxyvasicinone N-oxides

Two new alkaloids have been isolated from the epigeal part ofNitraria komarovii — the N-oxides of vasicinone and of deoxyvasicinone. Their structures have been established on the basis of spectral results and chemical transformations.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 580–582, July–August, 1993.     

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 ofNitraria komarovii XVII. Peganine N-oxide, N-allylschoberine, and dehydronitramidine

Three new alkaloids have been isolated from the epigeal part ofNitraria komarovii — peganine N-oxide, N-allylschoberine, and dehydronitramidine. Their structures have been determined on the basis of chemical transformations and spectral results.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. 6, pp. 780–783, November–December, 1994.     

Alkaloids ofNitraria komarovii. IV. Total synthesis of komarovine and komarovidine

Two alkaloids of a new type — komarovine and komarovidine — have been isolated from the epigeal part of theNitraria komarovii. Their structures — 3-(quinolin-8'-yl)--carboline and 3-(quinolin-8'-yl)-5,6-dihydro--carboline, respectively — have been established by synthesis.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 192–195, March–April, 1981.     

Quaternary benzophenanthridine alkaloids 9,10-demethylene derivatives of sanguinarine

Summary In the isolation and purification of the benzophanthridine alkaloids sanguinarine and chelerythrine two minor bases — 9,10-demethylenesanguinarine and 9,10-demethylene-9,10-dehydrosanguinarine — were isolated, and it was shown that the former is an artefact produced from sanguinarine in the process of isolation and also when the sulfates of the alkaloids are subjected to prolonged storage.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 764–767, November-December, 1978. Original article submitted August 10, 1978.     

Umbrofine and 6-acetylumbrofine — New C18-diterpene alkaloids from Aconitum umbrosum

Two new alkaloids — umbrofine and 6-acetylumbrofine — have been isolated fromAconitum umbrosum, and their structures have been established on the basis of spectral characteristics.Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedenini, No. 1, pp. 73–77, January–February, 1993.     

Ionization constants of a number of alkaloids used in medicine

The pK_a values of a number of alkaloids in water or in aqueous ethanol have been measured by the potentiometric titration method: nuphleine — 4.59, 6.98; brevicolline — 5.17, 8.02; chelidonine — 6.40; sanguinarine — 7.32; chelerythrine — 7.53; stepharine — 8.48; d-pseudoephedrine — 9.49. For nuphleine and brevicolline, each of which has two nitrogen atoms capable of protonation, assignments have been made of pK_a values to the corresponding atoms on the basis of the results of UV spectroscopy.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 337–341, May–June, 1984.     

Corumdephine — A new alkaloid fromDelphinium corumbosum

The epigeal part ofDelphinium corumbosum Rgl., collected in the flowering phase in the environs of Pokatilovka (Dzhungarian Ala-Tau) has yielded — in addition to the known alkaloids methyllycaconitine, lycoctonine, delcorine, deoxydelcorine, delcoridine, dehydrodelcorine, dephatine, browniine, dictysine, and dictysine acetonide — a new diterpene alkaloid with the composition C₂₅H₃₉NO₆ (I), which has been called corumdephine. The structure of corumdephine has been established on the basis of a passage from (I) to deoxydelcorine and spectral characteristics.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 95–98, January–February, 1985.     

Alkaloids ofPetilium eduardi. Petine and petine N-oxide

Two new alkaloids — petine and petine N-oxide — have been isolated from the bulbs of Petilium eduardi. Their structures have been established on the basis of spectral characteristics and chemical transformations.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. 4, pp. 524–528, July–August, 1994.     

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.     

HPLC-Analytik hochpolarer Pyridoxyl-Alkaloide im S?ugerblut

Summary A HPLC-method for the determination of pyridoxyl alkaloids — endogenous condensation products of vitamin B₆ and biogenic amines, resp. amino acids — is presented. On the basis of ion-pair assisted reversed-phase HPLC, conditions were found for the first time that allow an efficient separation and detection of these — partially extremely polar — heterocycles even from complex biofluids like mammalian blood and urine. The method allows to investigate the condensation kinetics in vitro, and — in combination with radiochemical methods — to prove the formation of pyridoxyl alkaloids in vivo. In single cases, the analysis is hampered by other constituents of blood or urine; the detection limit (S/N = 2) for a 250 l test volume under optimum conditions is 1–2 ng.

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Teil 5: Bringmann G, Hille A, Zsika M (1987) Heterocycles, im Druck

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Diese Arbeit ist Herrn Professor Dr. Helmut Dörfel, BASF AG, Ludwigshafen, zum 60. Geburstag gewidmet.     

Alkaloids of Merendera iolantae

Summary The alkaloids ofMerendera iolantae E. Czerniak have been studied for the first time. The total alkaloids consist of tropolone compounds and bases without a tropolone ring. From this plant we isolated the known alkaloids colchicine, colchamine, -lumicolchicine, colchameine, and 2-demethylcolchiceine, and four new, nontropolone, bases — MI-1 (iolantamine), MI-2, MI-3, and MI-4. The presence of colchiceine, 3-demethylcolchamine, and two unknown bases with R _f 0.49 and 0.53 was shown by chromatographic methods.A developed formula has been put forward for iolantamine on the basis of its spectral characteristics.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 487–493, July–August, 1972.