Berberis alkaloids. XXIII. Structure of turcberine

Berberine, magnoflorine, palmatine, columbamine, jatrorhizine, epiberberine, berbamine, O-methylisothalicberine, armepavine, corypalline, glaucine, and corydine and the new alkaloid turcberine have been isolated fromBerberis turcomanica Kar., and the structure of turcberine has been established. Apart from berberine, this is the first time that any of these alkaloids have been isolated from this species of barberry, while this is the first time that corydine and armepavine have been isolated from the genusBerberis.Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences. Tashkent. Andizhan State Medical Institute. Translated from Khimiya Prirodnykh Soedeninii, No. 1, pp. 77–81, January–February, 1993.     

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.     

Structure of alkaloid L-5 fromColchicum luteum

Conclusions FromColchicum luteum Baker collected in the gorge of the Sazan-Ata River in the Chimkent region have been isolated the known alkaloids colchamine, 3-desmethylcolchamine, 3-desmethyl--lumicolchicine, colchicine, 2-desmethylcolchicine, -lumicolchicine, N-desacetyl-N-formylcolchicine, and luteidine, and the new alkaloids L-5 and L-6. The first three bases have been obtained from this plant for the first time.Paper chromatography showed the presence of another three new alkaloids with R _f 0.38, 0.40, and 0.86. On the basis of UV, IR, and NMR spectroscopy and chemical reactions, the structure of 2-desmethylcolchiceine has been proposed for the alkaloid L-5.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 1, pp. 82–88, 1970     

Severine N-oxide and korsemine fromKorolkowia sewerzowii

Korsevine and the new alkaloids severine N-oxide and korsemine have been isolated from the combined alkaloids ofKorolkowia sewerzowii Regel. On the basis of the results of a study of the IR and NMR spectra of the alkaloids and also of a correlation with korseveriline and korsevine it has been established that base (I) is severine N-oxide and korsemine has the structure of korsevine 3-D-glucopyranoside.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 823–826, November–December, 1979.     

Structure of convosine

From the roots of the plantConvolvulus subhirsutum Regel et Schmalh. have been isolated seven known alkaloids and one new one, for which, on the basis of spectral characteristics, a comparative study with known alkaloids of the tropane series, and synthesis, the structure of (+)-N-isopropyl-3-veratroyloxynortropane has been established.Institute of the Chemistry of Plant Substances of the Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 618–620, September–October, 1986.     

Obtusifolin — A new coumarin from roots of Haplophyllum obtusifolium

From the neutral fraction of a methanolic extract of the roots ofHaplophyllum obtusifolium Ledeb. (family Rutaceae) have been isolated the lignan diphyllin, the alkaloids skimmianine and -fagarine, and a new coumarin with mp 179–180°C the structure of which has been established as 3-(,-dimethylallyl)-7-methoxy-8(3-methylbuta-1,3-diethyl)coumarin.Institute of Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 187–189, March–April, 1988.     

Alkaloids of the epigeal part ofAconitum karakolicum structure of karasamine and of 1-benzoylkarasamine

The known alkaloids phenyl--naphthylamine, karakoline, neoline, delsosine, monticamine, songorine, napelline acetylnapelline, napelline-n-oxide, and isoboldine and two new alkaloids, which have been called karasamine (I) and 1-benzoylkarasamine (II), have been isolated from the epigeal part ofAconitum karakolicum Rapaics. The structure of the new alkaloids have been shown by the preparation of the mono- and triacetates (IV) and (VI) of karasamine and its carbinolamine derivative (V), and also by the direct passage from karakoline (III) to karasamine (I) and 1-bezoylkarasamine (II) and by a study of their spectral characteristics.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 207–210, March–April, 1986.     

In vitro Reactions of Alkaloids I: Decarbalkoxylation of Some Esters with Quinine Monohydrate and Perloline Hydrochloride

We wish to describe the decarbalkoxylation of selected esters with the alkaloids quinine monohydrate (1) and perloline hydrochloride (2). Quinine has been effectively used for medicinal purposes and is the most important constituent of two Rubiaceous genera, Cinchona and Remijia ¹. Perloline² occurs in several species of grass and has been found to be inhibitory to seed germination, root elongation, protozoa mobility and cellulytic activity³. The stimulation of volatile fatty acid production by the alkaloid perloline is particularly noteworthy³.     

A study of the herb Aerva lanata. III. Alkaloids

Four new alkaloids — aervine (10-hydroxycanthin-6-one), methylaervine (10-methoxycanthin-6-one), aervoside (10--D-glucopyranosyloxycanthin-6-one), and aervolanine (3-(6-methyoxy--carbolin-1-yl)propionic acid), and also the known alkaloids canthin-6-one and 3-(-carbolin-1-yl)propionic acid have been isolated from the herbAerva lanata Juss. Their structures have been established on the basis of chemical and spectral characteristics.All-Union Scientific-Research Institute of Medicinal Plants Scientific Production Combine, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 388–394, May–June, 1991.     

Alkaloids ofGentiana. Structure of gentianadine and gentianamine

Summary 1. Gentianine and the three new alkaloids gentiananine, gentianadine, and gentianamine have been isolated fromGentiana turkestanorum andG. olivieri; gentianadine is identical with synthetic 4-(2-hydroxyethyl) nicotinic lactone.2. Gentianamine has the structure 5-vinyl-4-(1-hydroxymethyl-2-hydroxyethyl) nicotinic lactone.3. Dihydrogentianine has been converted into dihydrogentianamine.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 182–187, 1967     

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.     

Mass spectra of tetrahydroquinazoline and tetrahydroquinazolin-4-one derivatives

Summary 1. From the combined alkaloids of the epigeal part ofKorolkowia sewertsovii Rgl. collected at Saryagach we have isolated sevkorine, korseveriline, korseveridine, korseverinine, a base with mp 212–214°C, and the new alkaloid severtizidine.2. On the basis of a study of the chemical and physical characteristics of the alkaloids itself and the products of its transformations, the most probable structure and configuration of severtzidine has been established as 3,6,14-trihydroxycevanine.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 367–371, May–June, 1976.     

Reverse Phase Isolation of Pyrrolizidine Alkaloids

Abstract

A new liquid chromatography method for the isolation of pyrrolizidine alkaloids has been developed. The use of reverse phase high pressure liquid chromatography with a methanol - .01 M KH₂ PO₄ (pH 6.3) solvent system is discussed. Pyrrolizidine alkaloids from Senecio vulgaris, S. longilobus, and S. jacobaea have been isolated and identified.     

Cardenolides and coumarins ofCoronilla varia, C. cretica, etc.

Conclusions The cardenolide and coumarin composition ofC. varia L. and the closely related speciesC. hyrcana Pril.,C. cretica L., andC. orientalis Müll have been investigated. It has been shown that they all contain the cardiac glycoside hyrcanoside, with the exception ofC. orientalis, in which another, unidentified, glycoside, has also been found.A comparative study of some properties of hyrcanogenin (⁴-strophanthidin) and pachygenin (⁵-strophanthidin) connected with conformational features has been carried out.In the species studied, no less than five coumarins have been found of which umbelliferone, scopoletin, and daphnoretin have been isolated.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 3, pp. 141–144, 1969     

Alkaloids of Korolkowia sewerzowii. Structure of korselidine

Two new alkaloids have been isolated from the combined alkaloids of the epigeal part ofKorolkowia sewerzowii Regel.: a base with mp 272–274°C (methanol) and the alkaloid korselidine. As a result of a study of the chemical and physical properties of the alkaloid itself and of the products of its transformation, the structure and partial configuration of 3, 6, 20-trihydroxy-27-methylcevanine has been established for korselidine.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 34–36, January–February, 1989.     

The β-Methoxyethoxymethyl Protecting Group in Alkaloid Synthesis. Synthesis of Abresoline

The isolation of abresoline (1), the only seco-Lythraceae alkaloid, is one of the few pieces of evidence for the proposed oxidative coupling pathway for the biosynthesis of the Type I Lythraceae alkaloids.¹ We required compound 2 for our study of oxidative ary1 coupling as a synthetic route to these alkaloids. The similarity between 1 and 2 prompted the investigation of the synthesis of abresoline as a model for the preparation of 2 and related compounds.     

Alkaloids ofZygadenus sibiricus. The structure of verazinine

The alkaloids verazine, veratoylzygadenine, a base with mp 224–226°C, and a new alkaloid verazinine have been isolated fromZygadenus sibiricus (L). A. Gray. It has been established by chemical and spectral methods that verazinine is verazine 3-O--D-glycopyranoside.Eastern Siberian Technological Institute, Ulan-Ude. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 368–369, May–June, 1985.     

Alkaloids of Haplophyllum leptomerum. I. The structure of leptomerine

From the epigeal part of the plantHaplophyllum leptomerum Lincz. et Vved. growing in the mountains of Babatag, Tadzhik SSR, which has not been studied previously, have been isolated -sitosterol, the known alkaloids -fagarine, skimmianine, and N-methyl-2-phenyl-4-quinolone, and the new alkaloid leptomerine. On the basis of spectral characteristics, the structure of N-methyl-2-propyl-4-quinolone has been established for leptomerine.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 84–86, January–February, 1986.     

Pinusolide, a new diterpenoid from Pinus sibirica and P. korsensis

Conclusions From the neutral fraction of the oleoresin ofPinus sibirica R. Mayr andP. koraensis Sieb. et Zucc. a new diterpenoid has been isolated which we have called pinusolide, whose structure has been shown to be that of methyl labd-8(20)-1,3-dien-16,15-olid-19-oate.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 541–545, September–October, 1970.     

The Analysis of Cell Contents of Some Papaveraceous Plants by Newly Devised Automated Histochemical Chromatography

Abstract

Contents of the colored cells (alkaloidal cells¹) found in Macleaya cordata root and Sanguinaria canadensis rhizome were analysed quantitatively by histochemical chromatography (HC) with the help of newly modified automated micromanipulator.

These were found to have 4 alkaloids viz protopine type protopine(1) and allocryptopine(2) and benzo- [c]phenanthridine type (sanguinarine(3) and cheleryth-rine(4)) in both the plants. Quantitatively the pro-topine alkaloids were 10-40 ng per cell while the benzo-[c]phenanthridines (as chlorides) were only 1-6 ng per cell in M. cordata root. However, in S. canadensis rhizome the relative quantities of the 4 alkaloids (1), (2), (3) and (4) were found to be 10, 13, 137 and 68 ng per cell respectively.