Pheromones of insects and their analogs

From cyclohexene and caproaldehyde, using ozonolysis and the Knoevenagel reaction, we have synthesized hexadeca-7Z,11E-dien-l-yl acetate — the sex pheromone ofSitotroga cerealella and a component of the sex pheromone ofPectinophora gossypiella.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 704–707, September–October, 1991.     

Coumarins of Fraxinus mandschurica and F. potamophila

Summary The leaves ofFraxinus mandschurica Rupr. and the bark ofF. potamophila Herd. have yielded esculetin, fraxinol, and a new coumarin C₁₀H₈O₅, mp 228–230°C which we have called isofraxetin. On the basis of NMR and UV spectroscopy it has been established that isofraxetin is 5,7-dihydroxy-7-methoxycoumarin.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Institute of Chemistry, Academy of Sciences of the Turkmen SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 493–497, July–August, 1973.     

Triterpenoid saponins Communication 16. Structure of araloside C

Summary The complete structure of araloside C — a triterpenoid saponin from the roots ofAralia manshurica (Rupr. et Mey) — was established.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimisheskaya, No. 7, pp. 1214–1222, July, 1965     

Neptunium-237 in the marine environment determination in animal and plant species in the English Channel: Biological indicators and trophic relationships

We have studied the uptake of²³⁷Np in marine plants and animals belonging to several phyla, and collected samples from the end of January 1986 to March 1986, in a sampling station situated near the outlet of the irradiated fuel reprocessing plant at La Hague.We determined the²³⁷Np by neutron activation analysis. This method is very sensitive, with a limit of detection of 5×10^–10 mg, 1.3×10^–2 mBq. The method consists of the following steps:Reduction of the neptunium to the tetravalent state by treatment with a mixture of hydrazine sulfate and ferrous iron-chromatographic separations on Dowex 1×10 resin in a nitric medium, then in a hydrochloric medium-neutron irradiation in a nuclear reactor-purification of the neptunium by chromatography on Dowex 1×10 resin in a nitric then hydrochloric medium-measurement of the isotope²³⁸Np by gamma ray spectrometry using a Ge(Li) detector. The species were collected at Goury, at the northwest extremity of the Cotentin Peninsula, 5 km from the outlet of the reprocessing plant at La Hague. The levels of²³⁷Np were as follows: red algaeCorallina officinalis 64 mBq kg^–1 wet weight; andChondrus crispus 18 mBq kg^–1 wet weight; the spongeHalichondria panicea 14 mBq kg^–1 wet weight; the ascidianDendrodoa grossularia 12 mBq kg^–1 wet weight. The bivaive molluscsPatella vulgata andGibbula umbilicalis (the flesh ofP. vulgata andG. umbilicalis: 4 and 7 mBq kg^–1 wet weight respectively) also prove to be interesting biological indicatorsThe transfer modes of²³⁷Np to the various species as a function of their trophic levels are discussed as well as the distribution among the organs in the species consumed and the radiological impact of human consumption.     

Flavonoids of Bidens tripartita. III

Summary It has been established that substance 4, isolated previously fromBidens tripartita, is (R-2)isookanin 7-O--D-glucopyranoside [(R-2)flavanomarein]. The compound isolated is a new one for the genusBidens L.Khar'kov State Pharmaceutical Institute. Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 144–147, March–April, 1975.     

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.     

The structure of gummosin

Summary From the neutral fraction of an acetone extract of the roots of plants of the genusFerula,F. gummosa Boiss.,F. pseudoreoselinum Rgl. et Schmalh. (K-Pol.) andF. Samarkandica Eug. Kor., we have isolated a coumarin gummosin with the composition C₂₄H₃₀O₄, mp 176–177°C, [a]_D –54°C. The structure of gummosin corresponds to formula (III).With respect to structure, gummosin is a spatial isomer of farnesiferol A; it differs from the latter by the fact that the secondary OH group in gummosin is axial.Khimiya Prirodynkh Soedinenii, Vol. 2, No. 6, pp. 383–387, 1966     

A new flavone glycoside fromAntitoxicum funebrae

Summary A new flavonoid, antoside, which is the 3(7)-glucoside-7(3)-rhamnoside of quercetin has been isolated fromAntitoxicum funebrae.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 5, pp. 319–321, 1966     

The structure of arnifolin

Summary Structure (I) is proposed for arnifolin — a sesquiterpene lactone fromArnica foliosa Nutt. andArnica montana L.All-Union Scientific-Research Institute for Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 270–272, May–June, 1971.     

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.     

Esters of Ferula karakalensis. Structure and stereochemistry of karaferin and karaferinin

Two new guaiane esters — karaferin and karaferinin — have been isolated fromFerula karakalensis, and their structures and stereochemistry have been established. It has been shown that theFerula sesquiterpene alcohols angrendiol, ugamdiol, and karaferol are biogenetically interconnected and are products of a single chain of the biogenesis of terpenoids in plants.Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent; Botanical Garden of Moscow State University. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 227–231, March–April, 1993.     

Composition of the Neutral fraction of the oleoresin ofPinus sibirica

Summary It has been established that sibirene (isolated from the oleoresin ofPinus sibirica R. Mayr. has the structure 10-methyl-1-methylene-7-isopropyldecal-8-ene.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 4, pp. 239–244, 1966     

Alkaloids ofAndrachne rotundifolia

Summary 1. The content of total alkaloids in the hypogeal parts ofAndrachne rotundifolia C. A. Mey. (family Euphorbicease) is 0.2–0.3% and in the epigeal parts 0.06–0.08%.The total alkaloids in both the hypogeal and the epigeal parts ofAndrachne rotundifolia consist of five or six non-phenolic bases.2. Three individual substances have been isolated: andrachnine C₁₁H₁₇NO₂, which is a new alkaloid; base (II), giving a perchlorate with mp 139°–140° C; and base (III) with mp 135°–136° C.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 4, pp. 257–260, 1966     

Insect pheromones and their analogs. XLVII. Synthesis of 11-oxododeca-3,6-diynoic acid — The acyclic precursor of a macrolide component of pheromones of Oryzaephilus mercator and O. Surinamensis

A new approach is proposed to the synthesis of 11-oxododeca-3,6-diynoic acid — the acyclic precursor of a macrolide component of pheromones ofOryzaephilus mercator andO. surinamensis — from the readily available tetrahydropyran or allylacetone via the intermediate 5-bromo-2,2-ethylenedioxypentane.Institute of Organic Chemistry, Urals Division, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 288–292, March–April, 1993.     

Nontriterpenoid glycosides ofPatrinia intermedia

Conclusions The structure 7-hydroxy-3- (or -4-) -methyl-3,4-dihydrocoumarin has been proposed for the aglycone of a new glycoside-interoside B-isolated fromPatrinia intermedia Roem et Schult.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 4, pp. 213–216, 1968