Pheromones of insects and their analogs. XXVIII. Practical synthesis of tetradeca-9Z,12E-dien-1-yl acetate — A component of the sex pheromones of insects of the order lepidoptera

Tetradeca-9Z,12E-dien-l-yl acetate, a sex pheromone of the Indian meal mothPlodia interpunctella has been synthesized from the readily available product of the hydrodimerization of butadiene — octa-1,7-diene.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 276–279, March–April, 1991.     

New sesquiterpenoids from the oleoresin of Abies alba

The structures of four new sesquiterpenoids from the oleoresin ofAbies alba have been studied. On the basis of various spectral characteristics, the structures of (10S, 11S)-himachala-2,4-diene, (10S, 11S)-himachala-3(12), 4-diene, humula-4,9-dien-8-ol, and (4S, 5S, 10S)-selina-6-en-4-ol have been proposed for the compounds isolated. The stereochemistry of the asymmetric centers was determined by the conversion of these compounds into known sesquiterpenes and also by analysis of PMR spectra with a shift reagent.Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 712–718, September–October, 1988.     

Terpenoids of the oleoresin of Pinus pumila

Summary 1. The composition of the acid fraction of the oleresin ofPinus pumila (Pall.) Regel. has been studied, and from it has been isolated, in addition to known compounds, the methyl ester of a new labdane acetoxy acid.2. In the hydrocarbon fraction of the oleoresin 11 monoterpenes and 26 sesquiterpenes have been found (and 17 of the latter have been identified).3. The composition of the fraction of neutral oxygen-containing diterpenoids fromP. pumila differs considerably in its diterpenoid components from the corresponding fractions of the oleoresins of botanically related species-P. sibirica andP. koraiensis. Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 299–302, May–June, 1976.     

Chemical composition of Ledum palustre

Summary Extraction of the herbLedum palustre with liquefied carbon dioxide and Khladon-11 has yielded 10 individual substances belonging to various classes and various groups of organic compounds: hydrocarbons, alcohols, ketones, monoterpenes, sesquiterpenes, and flavonoids.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 127–130, January–February, 1978.     

New terpenoids of the essential oil of Ledum palustre

The structures of two new natural compounds isolated from the essential oil ofLedum palustre L. have been established on the basis of their spectral characteristics as p-mentha-1,8(10)-diene 3,9-epoxide (lepaloks) and 3,10-epoxygermacr-4(14)-en-8-one (lepakson). The chemical structure of ledene as a sesquiterpene hydrocarbon has been determined by chemical correlation.Tomsk State Medical Institute. Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 24–29, January–February, 1991.     

Crystal and molecular structures of 4-acetamido-2,6-dibromo-4-hydroxy-1,2-dimethoxycyclohexa-2,5-diene

A complete x-ray investigation has been made of 4-acetamido-2,6-dibromo-4-hydroxy-1,1-dimethoxycyclohexa-2,5-diene, isolated from the marine spongeVerongia gigantea. It has been shown that the orientation of the acetamide group in the molecule is stabilized by an intramolecular O-H... O hydrogen bond with the hydroxy group.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 215–218, March–April, 1992.     

Structure of a new triterpenoid from the bark of the Siberian larch

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.     

Oxygenated acids of the reserve lipids of Rumex paulsenianus

The composition of the fatty mono- and dihydroxy acids of the fruit ofRumex paulsenianus Rech. fil. (familyPolygonaceae) has been determined by a combination of IRS, UVS, GLC, and mass-spectrometric methods. (22) Monohydroxy acids of the C₁₄–C₂₀ series, including isomers and isologues, and four dihydroxy acids from C₁₈ to C₂₀, including a new isomeric 9-OH-10, 12–17:2 acid have been detected.Institute of the Chemistry of Plant Substances, Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 762–765, November–December, 1991.     

Quantitative determination of triterpenoids of the dammarane series by the densitometry of thin-layer chromatograms

Summary Using the optical densitometry of thin-layer chromatograms, the amounts of triterpenoids of the dammarane series have been determined in the unsaponifiable fractions of ethereal extracts from the leaves of Far Eastern species of birch:Betula costata, B. mandshurica, B. dahurica, B. platyfolia, andB. kamtschatica. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, USSR, Vladivostok Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 349–353, May–June, 1977.     

Gas-chromatographic determination of the composition of the volatile components of the oleoresins of some species of conifers

Using the method of analytical GLC in a glass capillary column, the compositions have been studied of the volatile fractions of the oleoresins of five species of conifers:Larix decidua,Pinus strobus,Pinus mugo,Picea excelsa, andPinus abies. In the oleoresins 21 monoterpene and 22 sesquiterpene compounds were identified from their relative retention times and with the aid of additives. The main components of the volatile fractions of the oleoresins were - and -pinenes and 3-carene among the monoterpenes, and longifolene caryophyllene, - and -cadinenes and -murolene among the sesquiterpene compounds. The quantitative analysis of the fractions was carried out by the method of internal normalization from averaged correlation coefficients.Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 629–632, September–October, 1990.     

Structures of fertenidin and fertenicin

Two new esters have been isolated from the roots ofFerula tenuisecta by column chromatography: fertenidin, C₂₂H₃₂O₅, mp 236–238°C, []_D + 145° (c 0.5; ethanol) and fertenicin, C₂₂H₃₀O₄ (amorphous), and the following most probable structures have been suggested for them: 6,10-dihydroxy-8-(p-hydroxybenzoyl)germacr-4(14)-ene and 10-hydroxy-8-(p-hydroxybenzoyl)germacra-4,6-diene, respectively.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 42–46, January–February, 1980.     

Steroids of the spirostan and furostan series from plants of the genus Allium. Structure of anzurogenin A from Allium suvorovii and A. stipitatum

The collective fruit of the cocultivatedAllium suvorovii Rgl. andA. stipitatum Rgl. (familyLiliaceae) has yielded a new genin of the spirostan series — anzurogenin A, which is 2,3,5-trihydroxy-(25R)-spirostan-6-one.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 68–73, January–February, 1988.     

Synthesis of polypeptides with the sequences-Gly-Gly-Ala-, -Gly-Gly-Lys(Tos)-, and-Gly-Gly-Glu(OCH3)- and the influence of triethylamine on the degree of their polycondensation

Summary From the herbGlaucium flavum have been isolated O-methylatheroline, sinoacutine, and a new alkaloid of the aporphine series, C₂₀H₁₇NO₅, which has been called glauvine.A structural formula has been proposed for glauvine on the basis of chemical reactions and spectral information.All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 214–218, March–April, 1972.     

Use of the paramagnetic shift agent Eu(DPM)3 for studying the structure and stereochemistry of conferol and conferone

Summary A spectrophotometric method is proposed for determining the content of aspidin in a crystalline powder and in the rhizomes of the fernsDryopteris spinulosa (M),D. phegopteris (L.), andD. fragrans (L.) Schott.All-Union Scientific-Research Institute for Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 684–687, November–December, 1970.     

Polyketide exometabolites of the causative agent of rice blast and their role in pathogenesis

A polyketide exometabolite — 3,4,8-trihydroxy-3,4-dihydronaphthalen-1(2H)-one (3,4,8-TDH) — has been isolated from the culture liquids of four isolates of the phytopathogenic fungusPiricularia oryzae Cavara. It has been shown that all the natural isolates investigated, and also nonpathogenic rose mutants and a series of dwarf mutants synthesize 3,4,8-TDH. This substance was not detected in filtrates of cultures of albino mutants. One of the natural isolates produces, together with 3,4,8-TDH, another polyketide — piriculol. The role in pathogenesis of the exometabolites isolated is discussed.All-Union Scientific-Research Institute of Phytopathology of Gosagroprom SSR. Golitsyno. V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 572–577, July–August, 1988.     

Investigation of the protein component of the lipopolysaccharide-protein complex ofYersinia pseudotuberculosis

It has been established by electrophoresis in polyacrylamide gel that the protein component of the lipopolysaccharide-protein complex ofYersinia pseudotuberculosis consists of two poly-peptides with molecular weights of 42,000–45,000 and 18,000–20,000. These polypeptides have been detected in the cell wall ofY. pseudotuberculosis as the main components. Protein fractions B-2 and B-3, differing with respect to solubility in phenol, were isolated from the LPPC ofY. pseudotuberculosis by extraction with hot 45% phenol. These protein fractions had the same polypeptide composition, which is characteristic for membrane proteins. B-3 included the LPS component and B-2 contained lipid A or fragments of it as impurity. Fractions B-3 and B-2 precipitated with antiserum to the LPPC.Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 92–97, January–February, 1980.     

The structure of the sesquiterpene lactone saupirin

Conclusions A new sesquiterpene lactone, saupirin, has been isolated from the epigeal green part ofSaussurea neopulchella Lipsch. andSaussurea pulchella Fisch., and structure (I) has been proposed for it.All-Union Scientific-Research Institute for Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 727–736, November–December, 1971.     

The seed oils of some species of the family Cruciferae

Summary The physicochemical properties of the oils of the seeds of seven plants of the family Cruciferae —Cakile maritima, Sisymbrium altissimum, Sisymbrium Loeselii, Descurainia Sophia, Erysimum cheiranthoides, Brassica amoracioides andCrambe pontica — have been studied and their fatty acid compositions have been determined. The results obtained showed no marked differences from those given in the literature.Zaporozhe Medical Institute. Ukrainian Scientific-Research Institute of the Oils and Fats Industry. Zaporozhe Oils and Fats Combine. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 15–18, January–February, 1973.