Crystal and molecular structure of the sesquiterpene humulane ester juniferdin

The spatial structure of the sesquiterpene humulane ester juniferdin, isolated fromFerula juniperina, has been established by the x-ray structural method. An analysis is given of the 11-membered humulane ring in comparison with the conformation observed in fexerol and juniferol.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Institute of Crystallography, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinii, No. 4, pp. 494–499, July–August, 1991.     

Crystal and molecular structure of the sesquiterpene humulane alcohol juniferol

The spatial structure of the sesquiterpene humulane alcohol juniferol, which is represented in the crystal by two conformers, IA and IB, differing by the conformation of the C2...C9 section, has been established by the x-ray structural method. The strain energies of the conformers have been calculated by the method of molecular mechanics. The barrier to the interconversion of the conformers by rotation of the C2...C9 section has been calculated; it amounts to 7–8 kcal/mole. This value of the transformation barrier permits the assumption that the two conformers also exist in solution, their interconversion being hindered. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Institute of Crystallography, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 757–762, November–December, 1990.     

Molecular and crystal structure of the germacranolide argolide from Artemisia glabella

The new germacranolide argolide has been isolated from the epigeal part ofArtemisia glabella, and its structure has been shown by its conversion into oxopelenolide B. From the results of an x-ray investigation it is suggested that argolide has the spatial structure of 3-oxo-4α,7α,6β(H)-germacra-1(10),11(13)-dien-6,12-olide. Institute of Organic Synthesis and Coal Chemistry, Kazakh Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Organometallic Chemistry, Russian Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–657, September–October, 1991.     

Triterpene glycosides of Astragalus and their genins XXXII. Cyclocarposide from Astragalus coluteocarpus

A new triterpene glycoside of the cycloartane series, which has been called cyclocarposide, has been isolated from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). The structure of cyclocarposide has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3β,6α,16β,25-tetraol 6-0-α-L-rhamnopyranoside 3-0-α-D-xylopyranoside. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pamir Biological Institute, Academy of Sciences of the Tadzhik SSR, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–656, September–October, 1990.     

Biodegradation of aromatic compounds by the yeast-like fungus Trichosporon cutaneum

The biodegradation reactions of veratryl- and guaiacylpropane compounds modeling structural fragments of the lignin macromolecule by the yeast-like fungusTrichosporon cutaneum D-46 have been investigated. It has been shown that the enzyme complex ofT. cutaneum is capable of catalyzing a series of reactions of the biotransformation of arylpropane substrates, namely: oxidation, the cleavage of the C_α-C_β bond of the propane chain, demethylation, and decarboxylation. The action of the enzymes was shown most actively in the case of substrates having an unsubstituted phenolic hydroxy group. Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk. Institute of Microbiology, Belorussian Academy of Sciences, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 558–564, September–October, 1992.     

Leuconine — A new alkaloid from Aconitum leucostomum and A. septentrionale

A new alkaloid — leuconine — has been isolated from the epigeal parts ofAconitum leucostomum andA. septentrionale, and its structure has been established on the basis of spectral characteristics. Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 538–540, September–October, 1992.     

Lipids of the seeds of Cynoglossum officinale

The compositions of the lipids and fatty acids of the seeds ofCynoglossum officinale, familyBoraginaceae have been established. The bulk of the lipids consisted of netural compounds (95.2%), while the amounts of glycolipids and phospholipids were 3.1 and 1.7%, respectively. Among the fatty acids, in addition to the usual components, acids characteristic for theBoraginaceae family have been found: 18:3 (6, 9, 12), 18:3 (9, 12, 15), 18:4 (6, 9, 12, 15), 20:1 (11), 22:1 (13), and 24:1 (15). Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. South Urals Reservation, Bashkir. Institute of Chemistry, Bashkir Scientific-Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 758–762, November–December, 1991.     

Insect pheromones and their analogues XLII. Synthesis of 2,6-dimethyloct-1-yl formate — A mimic of the aggregation pheromone of flour beetles

2-6-Dimethyloctan-1-ol, the formate of which is a mimic of the aggregation pheromone of the flour beetlesTribolium confusum andT. castaneum, has been synthesized by the hydroboration of 2,6-diemthyloct-1-ene, obtained from β-methylvaleric acid. Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 571–573, September–October, 1992.     

Insect pheromones and their analogues. XXII. Methyl-branched pheromones based on 4-methyltetrahydropyran. Synthesis of racemic 2-acetoxy-3,7-dimethylpentadecane (diprionyl acetate)

A synthesis is proposed of racemic 2-acetoxy-3,7-dimethylpentadecane — the sex attractant (diprionyl acetate) of plane sawflies of the generaDiprion andNeodiprion on the basis of the regioselective transformation of bifunctional products of the cleavage of 4-methyltetrahydropyran. Institute of Chemistry, Bashkir Scientific Center, Urals Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 573–576, July–August, 1989.     

Synthesis of 24-ethylcholesta-7, 22E-diene-3β, 5β-triol — A natural trihydroxysteroid from the bryozoan Myriapora truncata

24-Ethylcholesta-7, 22E-diene-3β,5α,6β-triol — a natural trihydroxysteroid from the bryozoanMyriapora truncata — has been synthesized from stigmasterol. Institute of Bioorganic Chemistry, Academy of Sciences of the Belorussian SSR, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 664–669, September–October, 1989.     

A sesquiterpene glucoside from cultivated cells of Scorzonera hispanica

A sesquiterpene glucoside has been isolated from a tissue culture ofScorzonera hispanica, and its structure has been established by mass spectrometry and two-dimensional NMR as 6,9-dihydroxy-4,10,14,15-tetradehydroguaian-6,12-olide 9-O-β-D-glucopyranoside. Irkursk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 640–645, November–December, 1992.     

Phytoecdysteroids of Rhaponticum carthamoides. II. Rhapisterone B

A new ecdysteroid (rhapisterone B) has been isolated from the seeds ofRhaponticum cathamoides (Willd.) Iljin. (familyCompositae). It has been shown that it is 2β, 3β, 11α, 14α, 20R, 24ξ-hexahydroxy-5β-cholest-7-en-6-one. Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 806–808, November–December, 1991.     

Insect phermones and their analogues XXXVIII. Synthesis of (±)-3-methylheneicosan-2-one and (±)-2-acetoxy-3,7-dimethylpentadecane using the reductive β-vinylation of α-olefins

Schemes are proposed for the synthesis of (±)-3-methylheneicosan-2-one and (±)-2-acetoxy-3,7-dimethylpentadecane — racemic analogues of the sex pheromones of the common cockroach (Blatella germanica) and of plane sawflies of the generaDiprion andNeodiprion, respectively, using the reductive β-vinylation of α-olefins. Institute of Chemistry of the Bashkir Scientific Center, Urals Division of the Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 567–571, September–October, 1992.     

Natural antioxidants. Furanoeremophilanes from Cacalia roots

Sesquiterpene compounds of the furanoeremophilane series have been isolated from extracts of the roots ofCacalia sp. growing in the Soviet Far East. The presence of antioxidant and antiradical activities in two representatives of the series has been established. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 643–646, September–October, 1989.     

Vasoactive peptides from venom of the wasp Polistes gallicus. Isolation and physicochemical and functional properties

Six vasoactive peptides have been isolated in the homogeneous form from the venom of the waspPolistes gallicus. Their physicochemical characteristics have been investigated. The wasp kinins exhibit myotropic and hypotensive effects. One of the kinins shows a prolonged hypotensive action. A. S. Sadykov Institute of Bioorganic Chemistry, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 564–568, July–August, 1989.     

Components of Matricaria discoidea — Geranyl isovalerate,trans-β-farnesene,and herniarin

In a study of the components of theMatricaria discoidea DC. growing in Estonia, three individual compounds have been isolated from the essential oil. On the basis of spectral characteristics, their structures have been shown as geranyl isovalerate, trans-β-farnesene, and herniarin. Tartu State University, and Institute of Chemical and Biological Physics, Academy of Sciences of the Estonian SSR, Tallin. Translated from Khimiya Prirodynkh Soedinenii, No. 6, pp. 804–806, November–December, 1988.     

Alkaloids of Aconitum coreanum. III. 13-Acetyl-14-hydroxy-2-isobutyrylhetisine N-oxide

It has been established by the x-ray structural method that a new alkaloid isolated from the epigeal part ofAconitum coreanum has the structure of 13-acetyl-14-hydroxy-2-isobutyrylhetisine N-oxide. This is the first time that a N-oxide has been isolated among the hetisine alkaloids. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 378–383, May–June, 1990.     

α- and β-scopodonnines from Datura inoxia seeds

A mixture of two alkaloids, d, ℓ-α- and β-scopodonnines, known earlier as synthetic products, has been isolated for the first time from the seed ofDatura inoxia. The spatial structure of β-scopodonnine dimethiodide has been established by the x-ray structural method. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 532–537, July–August, 1991.     

Mass-spectrometric method of analyzing mixtures of diterpene bases from plants of the genus Aconitum

The qualitative composition of the mixture of diterpene alkaloids from the roots ofAconitum septentrionale from various growth sites has been studied. Twenty-one bases have been detected. The mass-spectrometric method of multipeak monitoring has been used for the rapid checking of the amounts of the main component and seven subsidiary components. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 532–536, July–August, 1989.     

Investigation of natural compounds by the HPLC method II. HPLC fingerprint method for the epigeal organs of Ferula kuhistanica and F. tenuisecta

A microcolumn HPLC fingerprint method has been developed for the epigeal organs ofFerula kuhistanica andF. tenuisecta. The possibility has been shown of control by the microcolumn HPLC method of the qualitative and quantitative yields of ferutinin in the initial plant raw material and in preparations extracted from it, and also at each stage of the isolation of the desired product. The method is universal and does not depend on species and chemical composition of the plant. Institute of the Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 635–636, November–December, 1992.