Lipids of the fruit of Rumax paulsenianus

The lipids of the fruit ofRumex paulsenianus have been investigated. The lipid content of the seeds was 7.8% and of the perianths 0.58%. Of the 18 classes of lipids detected, 16, including anthraquinone pigments, were identified by CC and TLC and by UV and IR spectroscopies and mass spectrometry. The low-molecular-mass triacylgly-cerols dimyristoylacetin, dimyristoylcaproin, myristoylcaproylacetin, and hydroxylipids have been detected in the fruit of plants of the Polygonaceae family 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. 5, pp. 604–611, September–October, 1990.     

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.     

Lipid complex of Peganum harmala

The lipid complex of the seeds ofPeganum harmala (fam. Zygophyllaceae) has been investigated. The qualitative and quantitative compositions of the neutral lipids and the phospholipids have been studied. The fatty acid compositions of the acyl-containing lipids have been determined and it has been shown that in the triacylglycerols and phosphatidylethanolamines the sn-2 position is esterified mainly by linoleic acid. Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 625–627, November–December, 1992.     

Isolation of preparations with a high content of eicosapentaenoic acid from the red marine alga Palmaria stenogona

The composition is given of the fatty acids of the red marine algaPalmaria stenogona. The amount of eicosapentaenoic acid (EPA) in the alga was 69.9–77.0% of the total fatty acids. The procedure for isolating EPA of 80–90% purity from the alga is described which includes the saponification of the algal lipids, the selective extraction of the unsaponifiable lipids, the isolation of the free fatty acids, and their separation by the method of crystallizing inclusion complexes of the fatty acids with urea. Institute of Marine Biology, Far Eastern Branch, USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 330–333, May–June, 1990.     

New hydroxy fatty acids of Acanthopanax sessiliflorus

The structures of six new hydroxy fatty acids from the hydroxyacyldiacylglycerols of the fruit ofAcanthopanax sessiliflorus (Rupr. et amaxim.) Seem. (family Araliaceae have been established as 6-hydroxyhexadeca-12Z-enoic, 6-hydroxyhexadeca-9Z,12Z-dienoic, and the isomeric 6- and 7-hydroxyoctadeca-12-Z-enoic, and 6- and 7-hydroxyoctadeca-9Z,12Z-dienoic acids and their quantitative amounts have been determined with the aid of spectral, chromatographic, and chemical methods of analysis. Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 616–619, September–October, 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.     

Lipids of the fruit ofAcanthopanax sessiliflorus

In the lipids of the seeds and pericarp of the introduced speciesAcanthopanax sessiliflorus (Rupr. et Maxim.) Seem (familyAraliaceae), 23 classes of compounds have been detected, of which 19 have been identified. Sixteen of the classes have been studied. The lipids of the pericarp contain a more complex set of components than the seeds. Hydroxyacyldiacylglycerides, fatty acid methyl esters, and a complex group of pthalicacidesters have been detected in the familyAraliaceae for the first time. The fatty acid compositions of the seed and pericarp lipids are characterized by a high level of petroselinic acid.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 760–766, November–December, 1985.     

Secondary metabolites of Pyricularia oryzae II. Polyketide metabolites

A number of exometabolites have been isolated from the deuteromycetePyricularia oryzae Cav., of which harman and O-demethyldiaporthin have been isolated from this species for the first time. The latter is the first example of a hexaketide from fungi of the genusPyricularia, for which only penta- and heptaketides have previously been described. All-Union Scientific-Research Institute of Phytopathology, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 471–475, July–August, 1991.     

Crystal and molecular structure of 20S,24S-dihydroxydammar-25-en-3-one

The complete spatial structure of 20S,24S-dihydroxydammar-25-en-3-one — a triterpenoid isolated from the leaves of a Far-Eastern species of birch,Betula mandschurica — has been established. Intermolecular cooperative hydrogen bonds that are unusual for a triterpenoid system have been detected in crystals of 20S,24S-dihydroxydammar-25-en-3-one, with the participation of both hydroxy groups in one chain of bonds and an orientation of the associated molecules that is characteristic for a bimolecular layer. Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 667–672, September–October, 1991.     

GC-MS analysis of total diterpene alkaloids from roots of Aconitum septentrionale

For the first time, using a MS 25RF chromato-mass spectrometer with a Carlo Erba 5160 chromatograph and a packed column, the possibility of the partial separation of the mixture of diterpene alkaloids of various types from the roots ofAconitum septentrionale has been shown. From their chromatographic parameters and mass-spectral characteristics 18 bases have been detected, including a new one with M⁺ 407 which was probably deoxydelcorine, while 6-O-methyldelcorine and 6-O-methyleldelidine have been found in plants for the first time. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodynkh Soedinenii, No. 4, pp. 538–543, July–August, 1989.     

Secondary metabolites of Ulocladium chartarum. Ulocladols A and B — New phytotoxins of terpenoid nature

Ulocladols A and B — new exometabolites having a mixed sesquiterpenoid-polyketide nature that are structurally close to the host-specific toxins ofAlternaria citri — have been isolated from the deuteromyceteUlocladium chartarum. Both substances inhibit the growth of cotton seeds. All-Union Scientific Research Institute of Phytopathology, Moscow Province, Golitsyno. M. V. Lomonosov Moscow State University. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 642–648, September–October, 1991.     

Vapor-phase hydrogenation in the GLC analysis of sesquiterpene lactones of the eudesmane series

The GLC analysis has been carried out of the products of the vapor-phase hydrogenation of the unsaturated lactoens ofInula helenium L. Tetrahydroalantolactone has been detected for the first time in elecampane rhizones and roots. During the vapor-phase hydrogenation of the compounds being analyzed in the presence of a Ni catalyst, a migration of the exocyclic double bond of isoalantolactone and of dihydroisoalantolactone was observed. All-Union Scientific-Research Institute of Drug Chemistry and Technology, Kharkov. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 797–801, November–December, 1991.     

Extraction of the total alkaloids from the epigeal part of Aconitum orientale

The process of extracting the total alkaloids fromAconitum orientale with aqueous solutions of a number of electrolytes has been investigated. It has been established that it is most desirable to use 2% solutions of H₂SO₄ and 5% solutions of CH₃COOH. The optimum parameters of the process have been found, under which the degree of extraction of the total alkaloids averages 96%. I. G. Kutateladze Institute of Pharmacochemistry, Georgian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 816–821, November–December, 1991.     

Insect pheromones and their analogues XLIII. Chiral pheromones from (S)-(+)-3,7-dimethylocta-1,6-diene 3. Synthesis of (4R)-4-methylnonan-1-OL — Sex pheromone of Tenebrio molitor and its racemic analogue

Starting from the readily available enantiomerically enriched (S)-(+)-3,7-dimethylocta-1,6-diene (ee ≃ 50%), we have synthesized (4R)-4-methylnonan-1-ol — the sex pheromone of the yellow mealworm bettleTenebrio molitor L. A scheme for synthesizing the racemic analogue of the pheromone from 4-methyltetrahydropyran has been developed. Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 711–714, November–December, 1992.     

Lignans of the bark of Syringa volgaris

Two lignans have been isolated from the bark ofSyringa vulgaris and identified: (+)-lariciresinol 4-β-D-glucopyranoside (I) and -olivil 4-β-D-glucopyranoside (II). This is the first time that glycoside (9) has been described. All-Union Scientific-Research Institute of Medicinal Plants Scientific-Production Association, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 768–771, November–December, 1991.     

Synthesis of natural triisopentenylated flavanone, euchrenone a2

Euchrenone a₂ (7) isolated from the roots ofEuchresta japonica has been synthesised from 3-prenylphloroacetophenone (1) by other workers. We carried out its cyclodehydrogenation with dichloro dicyano quinone (DDQ) to obtain 6-acetyl-5,7-dihydroxy-2,2-dimethylchromene (2) which was ethoxymethylated in the 7-position to give 6-acetyl-7-ethoxymethoxy-5-hydroxychromene (3). Chalcone condensation of3 and 4-ethoxymethoxy-3-C-prenylbenzaldehyde (4) gave 4,6′-bisethoxymethoxy-2′-hydroxy-6″, 6″-dimethyl-3-C-prenylpyrano (2″, 3″–4,3) chalcone (5) which cyclised with methanolic sodium acetate to give protected 5,4′-bisethoxymethoxy-6″, 6″-dimethyl-3′-C-prenylpyrano (2″, 3″–7,8) flavanone (6). Deprotection of6 with 4% methanolic HCl yielded (7) with melting point and spectral data identical to that of the natural compound.     

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.     

Analysis of oligospirostanosides in a suspension culture of Dioscorea deltoidea cells by high-performance liquid chromatography

A method has been developed for the quantitative determination of oligospirostanosides in a culture ofDioscorea deltoidea cells with the aid of HPLC on a LiChrosorb RP-18 column. Elution was performed with acetonitrile-water (50–75%) with detection at 207 nm. A. N. Bakh Institute of Biochemistry, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 549–551, July–August, 1988.     

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.