Berberis alkaloids. XXXVII. Investigation of the alkaloids ofB. oblongata andB. integerrima. Crystal structure of 8-trichloromethyldihydroberberine

Two species of Berberis have yielded 10 isoquinoline alkaloids. In addition to known bases, two artifacts have been isolated — 8-trichloromethyldihydroberberine (I) and 8-trichloromethyldihydropalmatine. An x-ray structural analysis has been made of (1).Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 889–893, November–December, 1996. Original article submitted April 15, 1996.     

Epoxidation of alantolactone and isoalantolactone

Alantolactone and isoalantolactone have been epoxidized with peracetic, m-chloroperbenzoic, and trifluoroperacetic acids. The structure of 4(15)--epoxyisoalactone has been established by an x-ray structural investigation.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 879–884, November–December, 1996. Original article submitted May 20, 1996.     

Modifications based on coumarins I. Synthesis of monoesters of karatavikic and galbanic acids with sucrose

The synthesis has been achieved of water-soluble 6-O-monoesters of sucrose with natural coumarins — karatavikic and galvanic acids — by the transesterifacation of their methyl esters with sucrose. The structures of the compounds obtained have been confirmed by IR, UV, PMR, and¹³C NMR spectroscopies.A. B. Bekturov Institute of Chemical Sciences, National Academy of Sciences, Republic of Kazakhstan, Almaty, fax 61 57 65. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 541–544, July–August, 1996. Original article submitted January 30, 1996.     

Isolation and some properties of glucose isomerase from a hybrid strain ofStreptomyces atratus

A highly effective easily reproducible method of obtaining high purity preparations of glucose isomerase from initial and hybrid strains of Streptomyces atratus has been developed. Two enzymes have been characterized, with molecular masses of 160 and 120 kDa, isoelectric points of 5.2 and 5.0, pH optima of 8.0 and 9.0, and temperature optima of 80 and 90°C, respectively. The activity of glucose isomerase preparations obtained by purification from a hybrid strain of Streptomyces atratus was 60–70% greater than that of analogous preparations from the initial parental strain.Institute of Microbiology of the Academy of Sciences, Republic of Uzbekistan, Tashkent, fax (3712) 417129 Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 903–907, November–December, 1996. Original article submitte March 11, 1996.     

Chemical modification of britanin and of inuchenolide C

Analogs of helenalin possessing a broad spectrum of biological activity have been synthesized from the readily available sesquiterpene lactones britanin and inuchenolide C. Conditions for the hydrolysis, oxidative transformations, and skeletal rearrangements of the pseudoguaianolides that are characteristic for plants of the genus hula have been studied.Institute of Phytochemistry, Karaganda, fax (3212) 51 10 23. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 712–722, September–October, 1996. Original article submitted April 1, 1996.     

Succinates and maleates of some cardenolides,and their potassium salts

The succinates of corotoxigenin, digitoxigenin, and oleandrigenin, and the maleate of strophanthidin, and their potassium salts, have been synthesized. In contrast to the initial cardenolides (1, 4, 7, and 10), the succinates (2, S, and 8) and the maleate (11) and their potassium salts (3, 6, 9, and 12) possess no cardiotonic activity.Ukrainian Pharmaceutical Academy, Kharkov-2, ul. Pushkinskaya, 53. State Scientific Center for Drugs, Kharkov-85 ul. Astronomicheskaya 33. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 568–571, July–August, 1996 Original article submitted February 7, 1996     

Structural-functional characteristics of toxins from spiders of the araneidae family

With the aid of a series of chromatographic operations we have isolated 14 individual tow-molecular-mass compounds (M_T — 624-744 Da) blocking postsynaptic glutamate and acetylcholine receptors from the venoms of species of spiders of the family Araneidae. It has been shown that from their structural characteristics and the nature of their action they can be divided into two families differing by their chromophoric groups and the degree of reversibility of their interaction with various receptors.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 916–920, November–December, 1996. Original article submitted March 18, 1996.     

Berberis Alkaloids XXXVIII. Turcamine — A new isoquinoline alkaloid fromBerberis turcomanica

The new isoquinoline alkaloid turcamine (1) has been isolated from the leaves ofBerberis turcomanica, and its structure has been established as 8-hydroxy-7-methoxy-2-methyltetrahydroisoquinoline. A relationship has been found between a substituent at C-8 and the multiplicities of the signals from C-5 and C-6.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 894–896, November–December, 1996. Original article submitted April 15, 1996.     

Pheromones of insects and their analogs LIII. Synthesis of ferrulactone I —a pheromone ofCryptolestes ferrugineus

8-Acetoxy-3, 7-dimethyl-l-(phenylsulfonylacetoxy)octa-2E, 6E-diene has been synthesized, and its cyclization under the action of zerovalent palladium followed by desulfurization with the aid of sodium amalgam has led to ferrulactone I — one of the macrolide components of the aggregation pheromone of the rust-red grain beetle (Cryptolestes ferrugineus).Institute of Organic Chemistry, Urals Scientific Center of the Russian Academy of Sciences, 450054, Ufa pr. Oktyabrya, 71. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 932–935, November–December, 1996. Original article submitted May 27, 1996.     

Pheromones of insects and their analogs LIV. Synthesis of dodec-9E-en-1-ol and its acetate —components of the sex pheromone ofSparganothis pilleriana

Using the Claisen rearrangement in the construction of a double bond with the E configuration, we have synthesized dodec-9E-en-l-ol and its acetate, which are components of the sex pheromone ofSparganothis pilleriana.Scientific Research Institute of Fine Organic Synthesis of the Academy of Sciences, Republic of Belarus. Ufa State Petroleum Technical University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 936–939, November–December, 1996. Original article submitted May 11, 1996.     

Lipids of the vegetative and generative organs ofHibiscus sp.

The lipids of the leaves, stems, and roots ofHibiscus sp. have been studied. Their fatty acid compositions have been determined. The greatest amount of unsaturated fatty acids was present in the glycolipids of the leaves and the stems. More than 25% of low-molecular-mass C₁₀-C₁₂ fatty acids have been found in the neutral lipids of the roots.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 705–708, September–October, 1996. Original article submitted March 11, 1996.     

Berberis alkaloids XXXVI. Turcomanidine — A new alkaloid fromBerberis turcomanica

The alkaloid composition of the leaves ofBerberis turcomanica has been studied. Together with known 1-benzylisoquinoline alkaloids, we isolated a new one — turcomanidine, the structure of which has been established by chemical transformations and a study of spectral characteristics. Of the known alkaloids, N-methylcorydaldine has been detected in plants of the Berberis genus for the first time.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 885–888, November–December, 1996. Original article submitted March 4, 1996.     

Preparation of new amino derivatives of the lactone tanachin and their antimicrobial activity

Several amino derivatives have been obtained from the sesquiterpene lactone tanachin by means of the Michael reaction, and their structures have been confirmed by spectral methods. The antimicrobial activities of the compounds synthesized relative to some strains of microorganisms are considered.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 24–28, January–February, 1996. Original article submitted October 21, 1994.     

Detection of diol lipids in plants of the Elaeagnaceae family and the properties of their synthetic analogs

The compositions of the alcohols of the triacylglycerol fraction of the fruit ofHippophae rhamnoides and of the seeds ofElaeagnus angustifolia have been determined. The behavior under the action of pancreatic lipase of synthetic analogs of the diol compounds detected has been studied.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 697–700, September–October, 1996. Original article submitted February 12, 1996.     

Study of structure-activity relationships in a series of alkaloids ofAconitum zeravschanicum and their analogs

The toxic and antiarrhythmic activities of diterpene alkaloids fromAconitum zeravschanicum and their synthetic analogs have been investigated. It has been established that, in the series of compounds studied, activity and toxicity depend on the type of skeleton, the nature and positions of substituents, and the basicity of the nitrogen atom.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 384–387, May–June, 1996. Original article submitted February 26, 1996.     

Modification of microcrystalline cellulose by a binary mixture of pyromellitic dianhydride and phosphoric acid

The reactions involved in the esteriification of microcrystalline cellulose with a binary mixture of pyromellitic dianhydride and phosphoric acid have been studied. By changing the molar ratio of dianhydride to acid it is possible to regulate the course of the reaction and to obtain products with required contents of phosphoric acid and carboxy groups.Tashkent Institute of Chemical Technology, 700034, Tashkent, ul. Shevchenko, 1. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 583–586, July–August, 1996. Original article submitted January 22, 1996.     

Labdanoids ofMarrubium anisodon

The first chemical investigation has been made of Marrubium anisodon (fam. Lamiaceae). Two diterpenoids of the labdane type — vulgarol and manubiin — have been isolated. An x-ray analysis has been performed for the latter and its crystal amd molecular structures have been determined.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 54–58, January–February, 1996. Original article submitted December 11, 1995.     

Unsaponifiable substances of the lipids of the leaves ofHibiscus sp

The unsaponifiable substances of the lipids of the leaves ofHibiscus sp. have been studied. The compositions have been found of seven classes of compounds: hydrocarbons, carotenoids, tocopherols, isoprenols, triterpenols, and phytosterols and their esters.The materials of the paper were presented at the IInd International Symposium on the Chemistry of Natural Compounds (SCNC, Turkey, Eskiehir, October 22–24, 1996).Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 40 64 75. Translated from Khimiya Prirodnykh Soedinenii, Vol. 33, No. 1, pp. 49–51, January–February, 1997.     

Synthesis and alkylation of 6-methyl-5-phenylcarbamoyl-3-cyano-4-ethylpyridine-2(1H)thione

By condensation of the anilide of acetoacetic acid, propionaldehyde, and cyanothioacetamide, 6-methyl-5-phenylcarbamoyl-3-cyano-4-ethylpyridine-2(IH)thione has been obtained. In an alkaline medium, this compound is alkylated, forming the corresponding substituted 2-pyridyl sulfides. From these pyridines, substituted thienoj2,3-blpyridines have been synthesized through the Thorpe-Ziegler reaction.T. G. Shevchenko Lugansk Pedagogical Institute, Lugansk 348011. N. D. Zelinskii Institute of Organic Chemistry, Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1232–1234, September, 1996. Original article submitted May 13, 1996.     

Alkaloids ofDelphinium retropilosum

Elasine, methyllycaconitine, lycoctonine, and the new alkaloid delretine have been isolated from the plantDelphinium retropilosum, and the structure of delretine has been determined.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 739–742, September–October, 1996. Original article submitted March 4, 1996.