Pheromones of insects and their analogs. XXIX. Methyl-branched pheromones from 4-methyltetrahydropyran 4: Synthesis of (±)-15,19,23-trimethylheptatriacontane — A pheromone of Glossina morsitans morsitans

Racemic 15,19,23-trimethylheptatriacontane (the sex pheromone of the tsetse flyGlossina morsitans morsitans) has been synthesized from 1,5-dibromo-3-methylpentane, a product of the acid hydrolysis of 4-methyltetrahydropyran.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 417–419, May–June, 1991.     

Polyphenols of the herb Hypericum perforatum and the preparation novoimanin

Summary 1. The herbHypericum perforatum L. has been shown by paper chromatography to contain 14 substances with a polyphenolic nature, five from the flavonoid group (identified as hyperoside, isoquercitrin, quercitrin, rutin, and quercetin), four from the dianthrone group, and five from the group of low-polarity phenolic glycosides of undetermined structure.2. The composition of the polyphenols of novoimanin has been studied. This preparation has been found to contain five substances from the group of low-polarity phenolic glycosides, which are present in considerable amounts, and nine substances from the group of flavonoids and dianthrones which are present in small amounts.3. It has been established that theH. perforatum raw material after the extraction of the novoimanin still contains a considerable amount of flavonoid compounds, and the raw material can be used for the preparation of quercetin and hyperoside.4. A spectrophotometric method for the quantitative determination of hyperoside in the herbage, stems, and flowers ofH. perforatum and in the wastes from the production of novoimanin has been developed.Kiev Institute for the Further Training of Doctors. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 363–367, May–June, 1971.     

A new synthesis 2-acyl-1,2,3,6,7,11b-hexahydropyrazino[2,1-a]isoquinolin-4-ones based on N-cyanomethyl derivatives of 2-phenyl-ethylamides of acylglycines

A new route for the synthesis of 2-acyl-1,2,3,6,7,11b-hexahydropyrazino[2,1-a]isoquinolin-4-ones has been studied which includes a stage in which substituted piperazinones are obtained by reductive cyclization of N-cyanomethyl derivatives of 2-phenylethylamides of acylglycines under influence of Raney alloy in formic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 197–201, February, 1993.     

Phospholipase A2 from the venom of the spider Eresus niger

A phospholipase A₂ with a molecular mass of 12–14 kDa has been isolated from the venom of the spiderEresus niger by three-stage column chromatography. Asparagine has been identified as the N-terminal amino acid.Institute of Physiology, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 557–560, July–August, 1991.     

Steroid saponins II. Glycosides of Tribulus terrestris

Summary 1. It has been established that the epigeal part ofTribulus terrestris L. contains five steroid saponins. Diosgenin was identified as the aglycone of all these compounds.2. The carbohydrate compositions of the saponins have been determined.For Communication I, see Izv. Akad. Nauk MSSR Ser. Khim. i Biol. Nauk,1971, No. 4, 76.Institute of Chemistry, Academy of Sciences of the Moldavian SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 475–477, July–August, 1972.     

Alkaloids of Stephania hernandifolia VIII. Methylhernandine

Summary A new hasubanan alkaloid with the composition C₂₀H₂₇O₆N, mp 152–153°C (ether-methanol) has been isolated from the herbStephania hernandifolia and has been called methylhernandine. The alkaloid has been shown to be identical with the methylamino alcohol obtained in the hydrolysis of hernandifoline.All-Union Scientific Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 455–457, July–August.     

The structure of nutanoside

Summary The complete structure of nutanoside — a triterpene glycoside isolated from the roots ofSilene nutans L. — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 412–416, July–August, 1971.     

Investigation of a CO2 extract of the fruit of Capsicum annuum

Summary The composition of a CO₂ extract of the fruit of the pepperCapsicum annuum L. with respect to the main classes of compounds has been studied. A method has been developed for the extraction and quantitative determination of capsaicine.Krasnodar Scientific-Research Institute of the Food Industry. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 481–485, July–August, 1974.     

Triterpene glycosides of Dianthus deltoides II. Structure of dianthoside C

Summary The structure of dianthoside C — a triterpene glycoside fromDianthus deltoides L. — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 420–425, July–August, 1971.     

Investigation of the coumarins and furocoumarins ofHippomarathrum caspium (DC.) Grossh.

Summary 1. Osthole, oxypeucedanin, heraclenin, and oxypeucedanin hydrate have been isolated from the roots ofHippomarathrum caspium (DC) Grossh. and identified; the presence of traces of isoimperatorin, imperatorin, and umbelliferone has been established chromatographically. A substance with mp 149–150° apparently belonging to the sitosterol group has been obtained.2. Xanthotoxin has been isolated from the leaves and stems; the presence of a small amount of bergaptene and umbelliferone has been detected chromatographically.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 5, pp. 356–359, 1965     

Metabolites of the pathogenic fungus Verticillium dahliae VII. The phytotoxic pigment PKZh-1 from the culture liquid

Summary The phytotoxic pigment PKZh-1 that causes the characteristic symptoms of wilt in tests on cotton-plant shoots in a concentration of 100–150 µg/ml, has been isolated from the culture liquid of the fungusVerticillium dahliae Kleb.On the basis of qualitative reaction, spectral characteristics, and a study of hydrolysis products, PKZh-1 has been assigned to the peptide group. A red substance identified as 3,6,8-trihydroxy-1,4-naphthaquinone has been isolated from an acid hydrolyzate of PKZh-1.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 690–693, September–October, 1977.     

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.     

Alkaloids of Sophora alopecuroides tricrotonyltetramine

Summary From the fraction of strong bases ofSophora alopecuroides (flowering stage) a base C₁₂H₂₄N₄, mp 101–103°C, has been isolated which has been identified as tricrotonyltetramine. Its stereoconfiguration has been established.All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 752–754, November–December, 1974.     

Structure of the alkaloid kalidine

The spatial structure of the alkaloid kalidine obtained from the epigeal part ofKalidium gracile Fenzl. has been determined by IR and NMR spectroscopy and x-ray structural analysis. It has been established that it is the chloride of the trimethyl derivative of glycinamide.Institute of the Chemistry of Plant Substances of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 558–561, July–August, 1987.     

Neutral diterpenoids of oleoresins of five species of conifers of Transcarpathia

The compositions of the neutral diterpenoids of the oleoresins of five species of conifers growing in the Transcarpathia have been studied. It has been found that the oleoresins ofAbies alba M.,Larix decidua M., andPicea excelsa L. contain more than 50% of neutral diterpenoids. The group and qualitative compositions of the oxygen-containing diterpenoids have been determined. In the oleoresins ofAbies alba,Picea excelsa, andPicea abies tertiary alcohols — cis-abienol and isocembrol — predominate, while inLarix decidua the main component is the hydroxy ester larixyl acetate. Primary alcohols related to the resin acids have been found in all the oleoresins investigated. Features of the distribution of diterpenoids according to the species of conifers have been revealed. The results obtained are necessary for the chemotaxonomy of conifers of the family Pinceae.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodynkh Soedinenii, No. 6, pp. 812–816, November–December, 1988.     

O-acylated lignans from the wood of Abies species

Summary From the wood of the Siberian firAbies sibirica Ledeb. and the Khingan firA. nephrolepis Maxim., five new compounds have been isolated which are ester derivatives of the lignans lariciresinol, olivil, and hydroxymatairesinol.It has been established that olivil is esterified at the primary alcoholic hydroxyl by hydroxycinnamic acids — p-coumaric or ferulic — and lariciresinol is esterified by vanillic acid. A representative of the guaialignanolides — hydroxymatairesinol — is esterified at the secondary aliphatic hydroxy group with p-hydroxybenzoic or vanillic acid.Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 337–341, May–June, 1977.     

Insect pheromones and their analogues

The synthesis has been effected of octa-2E,6E-diene-1,8-diol diisovalerate — the sex pheromone of the Crimean click beetleAgriotes tauricus — by the carboxymethylenation of the readily available 6-methylhept-5-en-2-one, the allyl oxidation of a terminal methyl group, reduction of the ester fraction, and interaction of the diol so obtained with isovaleryl chloride. The required pheromone can also be obtained from available cyclic oligomers of isoprene.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 565–568, July–August, 1991.     

Histones of the cotton plant. Molecular characteristics of histone H1

A characterization of the histones of two varieties of the cotton plant,Gossypium hirsutum andG. barbadense, has been given with the aid of various electrophoretic systems. Their molecular weights have been determined. An analysis has been made of the cleavage of histone H1 at tyrosine residues. The positive charge and the molecular length of histone H1 have been determined by the method of incomplete succinylation.V. I. Nikitin Institute of Chemistry, Academy of Sciences of the Tadzhik SSR, Dushanbe. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 491–497, July–August, 1986.     

Alkaloids of Papaver fugax

Papaver fugax growing on the shore of Lake Kazenoi Am in the Checheno-Ingushskii ASSR at the boundary with the Dagestan ASSR has yielded 0.39% of alkaloids. Seven alkaloids have been isolated, of which cheilanthifoline, scoulerine, and reticuline have been detected in this species for the first time, while it is the first time that d-remeroline has been found in a plant of thePapaver genus.Pyatigorsk Pharmaceutical Institute. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 559–562, July–August, 1988.