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.     

Structure of dictysine

The results are given of an investigation of the structure of the new diterpene alkaloid dictysine C₂₁H₃₃NO₃ isolated from the epigeal part ofDelphinium dictyocarpum DC. On the basis of the results of a study of chemical and spectral characteristics, dictysine has been shown to have the sengorine skeleton, with hydroxy groups at C₁₅, C₁₆, and C₂₀.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 812–817, November–December, 1979.     

Investigation of Aconite alkaloids

Summary The composition of the alkaloids in plants of the genus Aconitum —A. kirinense,A. altaicum, A. coreanum, andA. nemorosum — has been studied. Four new alkaloids of composition C₂₆H₄₁O₈N·HNO₃, C₃₅H₄₁O₁₀N·HBr, C₂₀H₂₅O₃N, and C₂₃H₂₉O₆N have been isolated.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 2, pp. 113–116, 1965.     

The structure of karakoline

Summary We have isolated from the tubers ofAconitum karakolicum collected in the Kirghiz SSR, Kungei Alatau range, songorine, napelline, a base with mp 159–160°C, and the new alkaloids karakoline and a base with mp 222–224°C.The results of a study of the chemical reactions and spectral characteristics of karakoline have shown that it consists of a lycoctonine skeleton with N-ethyl and C₄-methyl groups, hydroxyls at C₁, C₈, and C₁₀ and a methoxy group at C₁₅.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 199–205, March–April, 1973.     

A chemical study ofPlectranthus glaucocalyx Maxim.

Summary A previously unknown crystalline substance C₂₀H₂₈O₄, calledplectrin, has been isolated from the leaves ofPlectranthus glaucocalyx Maxim., family Labiatae.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 6, pp. 427–428, 1965     

Natural quinones

Summary A new anthraquinone of composition C₁₇H₁₄O₅, mp 182–183° (decomp., from benzene) has been isolated from the roots ofRubia iberica (Fisch. ex D.C.); it has been called ibericin and has the structure of 1, 3-dihydroxy-4-ethoxy-methylanthraquinone.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 12–15, 1966     

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     

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.     

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.     

Structure of fegolide

A chloroform extract of the seeds ofFerula penninervis Rgl et Schmahl has yielded a new sesquiterpene lactone of the guaiane type — fegolide: C₂₀H₂₈O₅, mp 165–166°C []_D –150°C (c 0.17; chloroform).Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 335–337, May–June, 1985.     

Pranferol from the roots ofPrangos ferulacea

Conclusions From the roots ofPrangos ferulacea (L.) Lindl. growing in Armenia an optically inactive furocoumarin C₁₆H₁₆O₅, an isomer of pranferol, has been isolated.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 1, pp. 3–5, 1969     

Structure of the new monoterpenoid liganolide

The structure of the new ester liganolide C₂₇H₃₈O₈, isolated from the roots ofLigularia thomsonii has been established by x-ray structural analysis. Liganolide is a monoterpenoid including a six-membered ring with substitutents at C(2), C(3), and C(4), and an epoxy group at C(1) and C(6).Deceased.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Science, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 799–803, November–December, 1987.     

The structures of chimganin and chimgin

Summary The roots ofFerula tschimganica Lipsky have yielded two new compounds with the compositions C₁₈H₂₄O₄ (mp 85°C) and C₁₇H₂₂O₃ (mp 155°C), which have been calledchimganin andchimgin. On the basis of their UV, IR, and NMR spectra and the products of alkaline hydrolysis, it has been shown that chimganin is the ester of 4-hydroxy-3-methoxybenzoic acid and chimgin that of 4-hydroxybenzoic acid with (+)-borneol.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 59–63, January–February, 1972.     

Insect pheromones and their analogs III. Synthesis of the sex attractants of some Lepidoptera

A new route to the synthesis of a number of attractants of Lepidoptera(Argyrotaenia velutinana, Mamestra configurata, andLycorea ceres ceres) have been developed. These substances are acetates of enols with the cis configuration: tetradec-11-en-1-ol, hexadec-11-en-1-ol, and octadec-11-en-1-ol, respectively. The constants of the substances obtained agree completely with those given in the literature. The method is based on the coupling of the C₃, C₅, and C₇ aldehydes with methyl 11-bromoundecanoate (I) by the Wittig reaction. To obtain compound (I) from methyl undeca-2E,5E,10-trienoate or methyl undeca-10-enoate we used hydroboration according to Brown followed by hydrogenation and bromination of the alcohol obtained. The advantage of this method is the use as starting materials of esters of unsaturated acids readily obtained by the homogeneous catalytic co-oligomerization of 1,3-dienes with acrylates.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 97–102, January–February, 1980.     

Solid-state structure of (+)-phendimetrazine bitartarate,an anorexic drug

The anorexic drug (+)-(2S, 3S, 4S)-phendimetrazine-2R, 3R)-bitartarate crystallized in the orthorhombic space groupP2₁2₁2₁ and at 293 Ka=7.7710(4),b=13.1379(7),c=15.9913(9) Å,V=1632.6(2) ų,Z=4,R(F)=0.062, andR _w (F)=0.026. A chair conformation 2,3-trans-1,4-oxazine ring with equatorially oriented 2-phenyl,3-methyl, andN-methyl substituents was found as predicted by an earlier reported solid-state CP-MAS¹³C-NMR investigation of crystalline (±)-phendimetrazine bitartarate. The O-CH₂-CH₂-N torsion angle of –58.4(6)° in the solid-state agrees nicely with the 56.0(7)° dihedral angle value estimated by¹H NMR spectroscopy for the major (equatorialN-methyl) phendimetrazine mesylate species in CD₂Cl₂ solution. A common solid-state conformational arrangement was found for (+)-phendimetrazine and a series of six other anorexic drugs structurally analogous to (+)-(2S, 3S)-pseudoephedrine. In this arrangement, NCH(Me)CPh has (S)-configuration, there is a (–)-gaucheMe-CH-C-Ph torsion angle, an antiperiplanarN-CH-C-Ph torsion angle, and the phenyl ring approximately eclipses the C-H bond of the attached carbon (e.g., H-C-C_ipso-C_ortho ca. 4° for 2,3-transphendimetrazine). Nonbonded interactions involving the 3-methyl and the 2-phenyl groups open up the H-C-C_ipso-C_ortho angle in a series of solid-state structures containing the epimeric (–)-(2R, 3S)-ephedrine moiety (e.g., ca. 45° for molecular mechanics calculated 2,3-cis-phendimetrazine model).     

Alkaloids of Aconitum monticola structure of acomonine

Summary The roots ofAconitum monticola have yielded songorine, songaramine, norsongorine, an amorphous base with the composition C₂₂H₃₅NO₆, a base C₂₂H₃₃NO₆ with mp 166–167°C, a base C₂₂H₃₃NO₅ with mp 161–164°C, and the new alkaloid acomonine. The structure of acomonine has been established on the basis of chemical transformations and spectral properties: It consists of a lycoctonine nucleus with an -hydroxy group at C₃, an -methoxy group at C₁₀,-methoxy groups at C₆ and C₁₅, an -glycol system at C₇ and C₈, and a methoxy group at C₁₉.Institute of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 389–395, May–June, 1975.     

Diterpenoids fromMarrubium peregrinum. I

Summary Two new diterpenoids have been isolated fromMarrubium peregrinum L.: a bicyclic diol C₂₀H₃₆O₂, peregrinol — and a hydroxyketolactone C₂₀H₂₅O₅, peregrinin. A substance C₁₉H₁₈O₆ has been obtained as a by-product.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 4, pp. 249–251, 1966