A new coumarin, pranferol, from the roots ofPrangos ferulacea

Summary A new coumarin, pranferol C₁₆H₁₆O₅, has been isolated from the roots ofPrangos ferulacea (L.) Lindl.The structure 5-(2-hydroxy-3-methylbutoxy)furo-2,3:7,6-coumarin has been proposed for pranferol.Khimiya Prirodnykh Soedinenii, Vol. 9, No. 5, pp. 310–315, 1966     

Floroselin, a new coumarin from the roots of Seseli sessiliflorum

Conclusions A new coumarin has been isolated from the roots ofSeseli sessiliflorum for which the structure of 3-angeloyloxy-2,2-dimethyl-4-(trans-3-methylthioacryloyloxy)-3, 4-dihydropyrano-5,6:8,7-coumarin has been proposed. This is the first time that esters of 3-methylthioacrylic acid have been found in the coumarin series.All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 517–521, September–October, 1970.     

Anomalin,a new natural pyranocoumarin

Summary A new coumarin C₂₄H₂₆O₇, which we have calledanomalin has been isolated from the roots ofAngelica anomala Avé-Lall. On the basis of its chemical properties, the results of a study of its saponification products and UV, IR, and NMR spectroscopy it has been established that anomalin is 2,2-dlmethyl-3,4-diangeloyl-3,4-dihydropyrano-5,6: 8, 7-cournarin.     

Coumarins of Smyrniopsis aucheri

Chemical transformations and spectral characteristics have enabled us to establish the structure and configurations of three coumarins: (+)-2,2-dimethyl-3-hydroxy-3,4-dihydropyrano(5,6:6,7)coumarin (I); (+)-4-hydroxy-5-(1-hydroxy-1-methylethyl)-4,5-dihydrofuro(2,3:6,7)coumarin (II); and (+)-4-hydroxy-5-(1-glucopyranosyloxy-1-methylethyl)-4,5-dihydrofuro(2,3:6,7)-coumarin (III) isolated from the roots ofSmyrnopsis aucheri Karjag. This is the first time that these compounds, which have been called smyrinol, smyrindiol, and smyrindioloside, have been detected in nature.Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Azerbaidzhan State University, Baku. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 36–40, January–February, 1992.     

Coumarins ofHaplophyllum ramosissimum

Summary 7-(3,3-Dimethylallyloxy)-6-methoxycoumarin and two new coumarins — ramosin and ramosinin — have been isolated from the epigeal part ofHaplophyllum ramosissimum.On the basis of IR, PMR, and mass spectroscopy and chemical reactions, the structure of 8-(3,3-dimethylallyl)-7-(3,3-dimethylallyloxy)coumarin (II) has been proposed for ramosin and that of 3-(1,1-dimethylallyl)-8-(3,3-dimethylallyl)-7-methoxycoumarin (III) for ramosinin.Leningrad Sanitary-Hygienic Medical Institute. Institute of Chemistry, Academy of Sciences of the Turkmen SSR, Ashkhabad. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 15–17, January–February, 1979.     

The structure of smyrnioridin

Conclusions A new coumarin, which has been called smyrniodidin, has been isolated from the roots ofSmyrniopsis aucheri acetoxy-1-methylethyl)-4-angeloyloxy-4,5dihydrofuro-2, 3: 7, 6-coumarin. Boiss. The NMR spectrum and a study of the saponification products of smyrnioridin have shown that it is 5-(1-     

Mass-spectrometric study of esters of marmesin and saturated acids

Summary From a methanolic extract of the roots ofPrangos biebersteinii Karjag., in addition to substances found previously, two other components — (I) and (II) — of the coumarin series have been isolated.The results of a study of their IR, NMR, and mass spectra, and also their chemical properties have enabled (I) to be identified as the known coumarin umbelliferone and the structure of 5-(1,2-dihydroxy-isopropyl)-4,5-dihydrofuro-2,3:7,6-coumarin to be proposed for (II), which has been named prandiol.Leningrad Sanitary-Hygenic Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 574–577, September–October, 1974.     

Coumarins of theLibanotis buchtormensis

Conclusions From the roots ofLibanotis buchtormensis (Fisch.) D.C. have been isolated the furocoumarins bergapten, isoimperatorin, a pyranocoumarin, xanthogallol, and a new coumarin buchtormin C₁₉H₂₀O₅, for which the structure (+)-3-(,-dimethylacryloxy)-2,2-dimethyl-3, 4-dihydropyrano-5, 6:8, 7-coumarin has been proposed and confirmed by synthesis.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 3, pp. 145–149, 1968     

Thiazolobenzo-1, 2, 3-thiadiazoles and derived cyanine dyes

The following tricyclic heterocyclic compounds are synthesized: 2-methylthiazolov (5, 4-e) benzo-1, 2, 3thiadiazole, 2-methylthiazolo (4, 5-e) benzo-1, 2, 3-thiadiazole, 2-methylthiazolo (4, 5-g) benzo-1, 2, 3-thiadiazole, and 2-methylthiazolo (5, 4-g) benzo-1, 2, 3-thiadiazole. The quaternary salts of these bases are used to prepare symmetrical and unsymmetrical trimethinecyanines and dimethinemercocyanines containing N-ethylrhodanine residues. The absorption maxima of these dyes are shifted toward the long-wave region as compared with the corresponding thiacyanines.     

New terpenoid coumarins from Ferula tadshikorum

Summary Two new terpenoid coumarins — tadzhiferin (I) and tadzhikorin (II) — have been isolated from the fruit ofFerula tadshikorum M. Pimen.On the basis of physicochemical and spectral investigations, the structure of 7-(9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyloxy)coumarin is proposed for (I) and that of 7-(4-acetoxy-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyloxy)coumarin for (II).All-Union Scientific-Research Institute of Medicinal Plants, Moscow. M. V. Lomonosov State University. Botanical Garden, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 593–599, September–October, 1976.     

The structure of xanthalin

Conclusions From the roots ofXanthogalum purpurascens growing in the Transcaucasus, we have isolated a new coumarin, C₂₄H₂₆O₇ with mp 111–113°C, [] _D ²⁰ –164.2° (c 0.97; ethanol) which we have called xanthalin. On the basis of the NMR spectrum it has been established that xanthalin is 3, 4-diangeloyl-2, 2-dimethyl-3, 4-dihydropyrano-5, 6:6, 7-coumarin.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 5, pp. 280–283, 1968     

Structure of some components of the roots of Prangos ferulacea

Summary From a methanolic extract of the roots ofPrangos ferulacea (L) Lindl., growing in the Nakhichevan ASSR, in addition to the compounds found previously, another six substances (I–VI) have been isolated, of which (I) and (VI) have been identified as, respectively, meransin hydrate monoacetate, found for the first time in nature, and umbelliferone: and in the study of a crystalline mixture obtained from the resin of the roots of the plant under investigation collected in Armenia, two coumarins — (VII) and (VIII) — have been isolated.On the basis of a study of IR, NMR, and mass spectra and chemical properties, the structures of the six new cumarin derivatives (II–V, VII, and VIII) have been established. Compound (II) has the structure of 8-(3-methylbutenyloxy)furo-2,3:7,6-coumarin and has been called feruliden; (III) is 7-hydroxy-8-(3-hydroxy-2-senecioyloxyisopentyl) coumarin and has been called ferudiol; (IV) is 7-hydroxy-8-(3-methoxy-2-senecioyloxyisopentyl) coumarin; (V) is 5-[1-(2,3-dihydroxy-3-methylbutyroyloxy)-1-methylethyl]-4,5-dihydrofuro-2,3:7,6-coumarin and has been called lindiol; (VII) is 8-(2-hydroxy-3-methylbut-3-enyloxy)-7-methoxycoumarin and has been called ferudenol; (VIII) is 7-methoxy-8-(3-methyl-2-oxobut-3-enyl)coumarin and has been called prangone.Leningrad Sanitary-Hygenic Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 568–574, September–October, 1974.     

Structure of ursinoic acid and ursinin

Conclusions On the basis of UV, IR, and NMR spectroscopy, and the preparation of derivatives, the most probable structures of ursinoic acid and ursinin, aromatic oxo acids isolated previously from the roots ofAngelica ursina Rupr. et Schmalh., have been established. It has been shown that the former has the structure 2,2-dimethylpyrano-5, 6:5, 6-(2, 4-dimethoxy)benzoylacetic acid while the second is 2,2-dimethylpyrano-5,6:5, 6-(2-methoxy)benzoylacetic acid.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 4, pp. 421–424, 1970     

1,2-bis(2',6'-dimethyl-i',3'-dioxa-6'-aza-2'-silacyclooctyl-2')ethane and the corresponding ethylene and acetylene derivatives

Conclusions The reaction of 1,2-bis(methyldimethoxysilyl)ethane and the corresponding ethylene and acetylene derivatives with bis(2-hydroxyethyl)methylamine gives 1,2-bis(2,6-dimethyl-1,3-dioxa-6-aza-2-silacyclooctyl-2)ethane and the corresponding ethylene and acetylene derivatives. Analogously, 1,2-bis(vinyldimethoxysilyl)acetylene gave 1,2-bis(2-vinyl-6-methyl-1,3-dioxa-6-aza-2-silacyclooctyl-2)acetylene.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1420–1421, June, 1988.     

Nitration,amination, and halogenation of Di-O-methylphloracetophenone

Chlorination of the title compound gave 5- and 3-chloro-2-hydroxy-4,6-dimethoxyacetophenone. The nitration of its acetate, followed successively by reduction, diazotization, and reaction with cuprous chloride, gave the 3-substituted series, 2-acetoxy-4,6-dimethoxy-3-nitroacetophenone, 3-amino-2-hydroxy-4,6-dimethoxyacetophenone, and 3-chloro-2-hydroxy-4,6-methoxyacetophenone, respectively. The orientation of substituents in the products was proved. The amino and chloro members of the isomeric 5-substituted series were availablevia 2-hydroxy-4,6-dimethoxy-5-phenylazoacetophenone, the product of the reaction of the title compound with benzenediazonium chloride.

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Nitrierung, Aminierung und Halogenierung von Di-O-methylphloracetophenon

Zusammenfassung Chlorierung der Titelverbindung gab 5- und 3-Chlor-2-hydroxy-4,6-dimethoxyacetophenon. Die Nitrierung des Acetats, gefolgt von Reduktion, Diazotierung und Reaktion mit CuCl ergab die 3-substituierte Reihe: 2-Acetoxy-4,6-dimethoxy-3-nitroacetophenon, 3-Amino-2-hydroxy-4,6-dimethoxyacetophenon und 3-Chlor-2-hydroxy-4,6-dimethoxyacetophenon. Die Orientierung der Substituenten wird diskutiert. Die Amino- und Chlorderivate der isomeren 5-substituierten Reihe sind über 2-Hydroxy-4,6-dimethoxy-5-phenylacetophenon zugängig, dem Produkt der Reaktion der Titelverbindung mit Phenyldiazoniumchlorid.

     

Determination of the absolute configuration of carbohydrate components of flavonol glycosides of the chestnut

Conclusions On the basis of the rates of their acid hydrolysis, their optical activities, and their IR spectra, it has been established that the glycosides ofAesculus hippocastanum L. are (SK-1) 3--L-arabofuranosyloxy-5,7,4-trihydroxyflavone, (SK-2) 3--L-rhamnofuranosyloxy-5,7,4-trihydroxyflavone, (SK-3) 3--L-arabofuranosyloxy-5,7,3,4-tetrahydroxyflavone, and (SK-4) 3--L-rhamnofuranosyloxy-5,7,3,4-tetrahydroxyflavone.The glycoside SK-3 is identical with avicularin isolated from the leaves ofPsidium quajava [5]. The complete structures of the other three glycosides have been established for the first time.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 1, pp. 5–7, 1969