Structure of aerugine from Pseudomonas aeruginosa

A new optically active phenolic alkaloid with the composition C₁₀H₁₁NO₂S, mp 85–88°C, [α]_D +28° (c 1.0; chloroform) (I) has been isolated from the microorganismPseudomonas aeruginosa (strain 590) and has been called aerugine. The action of diazomethane gave an O-methyl derivative (II). On the basis of the formation of ortho-cresol by the hydrogenolytic desulfuration reaction, a study of the IR, mass, and PMR spectra and (I) and its acetyl derivative (III), and also the¹³C NMR spectrum of (I), the structure of 4-hydroxymethyl-2-(o-hydroxyphenyl)-2-thiazoline has been established for aerugine. The spectral characteristics of the compounds mentioned are given.     

Alkaloids ofArundo donas VII. A spectroscopic and X-ray structural investigation of arundinine—A new dimeric alkaloid from the epigeal part ofArundo donax

FromArundo donax L. we have isolated the new dimeric alkaloid arundinine, with the composition C₂₃H₂₈N₄O, the structure of which has been established on the basis of its physicochemical characteristics and¹H and¹³C NMR spectroscopy, including 1D and 2D experiments in both homo- and heteronuclear regimes. The proposed structure—3a-(3′-dimethylaminoethylindol-5′-yloxy)-1-methylpyrrolidino[1a,3a-b]indoline — has been confirmed by x-ray structural analysis (XSA). Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (371) 120 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 790–795, November–December, 1998.     

Bisquaternary salts of alkaloids of the heliotridane series and some products of their transformation

Summary The reaction of ,-dibromoalkanes with trachelanthimidine and its derivatives and of bis (4-chlorobutyl) ether with the alkaloids lindelofine and viridiflorine have yielded bisquaternary salts of the pyrrolizidine series.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 368–371, May–June, 1977.     

VI. The structure of donine

A new dimeric alkaloid donine with the composition C₁₉H₂₂N₂O₄ has been isolated from the epigeal part of Arundo donax. On the basis of chemical transformations and UV, IR, mass, PMR, and¹³C NMR spectra the structure of diethyl NN-methylenebis(4-aminobenzoate) is proposed for this alkaloid.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. 2, pp. 221–224, March–April, 1996. Original article submitted October 2, 1995.     

Folipidine,a New Type Quinoline Alkaloid from Plants of the <Emphasis Type="Italic">Haplophyllum</Emphasis> Genus

The new quinoline alkaloid folipidine, the structure of which was established by chemical transformations and spectral data (UV, IR, mass, NMR) using APT, 2D ¹H-¹H COSY, NOESY, and ¹H-¹³C HSQC, HMBC, was isolated from two plants of the Haplophyllum genus. Folipidine is the first representative of a new type of quinoline alkaloids that contain a heteroaromatic skeleton of [3,4-b] conjugated pyrrole and quinoline fragments. The total alkaloids of these plants exhibit antitumor activity. Folipidine does not possess such activity.__________Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 49–52, January–February, 2005.     

N-ALLYLISONITRARINE AND NARCISSIN FROM PLANTS OF THE Nitraria GENUS

The new alkaloid N-allylisonitrarine was isolated from the aerial part ofNitraria schoberiL. Its structure was established using spectral data and chemical transformations. Leaves ofNitraria komaroviicontain the flavonoid narcissin. Its ¹ H and ¹³ C NMR spectra were studied.     

Withasteroids ofPhysalis. V. A study of the1H and13C NMR spectra of the withasteroids visconolide and 28-hydroxywithaperuvin C

The PMR and¹³C NMR spectra of new withasteroids — visconolide and 28-hydroxywithaperuvin C, isolated fromPhysalis viscosa L. — have been investigated. A detailed analysis of the spectral characteristics obtained is given. For visconolide is proposed the structure of 4,12,17,28-pentahydroxy-1-oxo-5, 6-epoxy-22R-witha-2,24-dienolide, and for 28-hydroxywithaperuvin C that of 6,14,17,20R, 28-pentahydroxy-l-oxo-22R-witha-2, 4, 24-trienolide.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 657–663, September–October, 1985.     

Amount of sterols and triterpenoids in leaves and petioles of leaf-shedding and standard lines of cotton plant

The amount of free and bound sterols and triterpenoids in the leaf blades and petioles of the variety Tashkent-1 and the deciduous lines L-275 and L-470 in the budding-flowering, maturing, and leaf-fall phases have been compared. In the leaf blades, the maximum accumulation of free sterols in the deciduous lines is observed in an earlier phase than in the variety Tashkent-1, and this is most characteristic for sterols saturated in the C-17 side chain. The dynamics of the change in the content of unsaturated sterols is individual for each line. The nature of the change in the amount of free sterols in the petioles is typical for each line and does not depend on the nature of the sterol for the variety Tashkent-1 this index falls sharply in the leaf-fall phase while for L-275 the process is retarded between the second and third phases, and for L-470 in the same period the amount of these substances rises sharply. In the leaf blades, as a rule, the level of sterol esters changes in parallel with the levels of free sterols, and in the petioles in the antiparallel direction between the first and second phases. In all the samples free and bound amyrin was detected. The dynamics of the change in the amounts of these substances in the three lines were different.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Institute of Experimental Plant Biology, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, pp. 796–805, November–December, 1989.     

Berberis alkaloids XXXV. The structure of nummularine

The new N-benzyltetrahydroisoquinoline alkaloid nummularine has been isolated from the leaves ofBerberis nummularia. On the basis of a study of its spectral characteristics (PMR, IR, and mass spectra), the structure of nummularine has been established as 6-hydroxy-N-(3-hydroxy-4-methoxybenzyl)-7-methoxy-1-methyltetrahydroisoquinoline.Translated from Khimiya Prirodnykh Soedinenii, Vol. 33, No. 1, pp. 91–93, January–February, 1997.