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.     

Alkaloids ofAndrachne rotundifolia

Summary 1. The content of total alkaloids in the hypogeal parts ofAndrachne rotundifolia C. A. Mey. (family Euphorbicease) is 0.2–0.3% and in the epigeal parts 0.06–0.08%.The total alkaloids in both the hypogeal and the epigeal parts ofAndrachne rotundifolia consist of five or six non-phenolic bases.2. Three individual substances have been isolated: andrachnine C₁₁H₁₇NO₂, which is a new alkaloid; base (II), giving a perchlorate with mp 139°–140° C; and base (III) with mp 135°–136° C.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 4, pp. 257–260, 1966     

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.     

Sesquiterpenes of the roots of Inula grandis

Summary The roots ofInula grandis Schrenk has yielded a sesquiterpene lactone C₁₅H₂₀O₃, mp 134–135°C and 270°C, which has been called igalin, and two diols — C₁₅H₂₆O₂ with mp 102–102.5°C and C₁₅H₂₈O₅ with mp 320°C — which have been called igalol and grandol, respectively.Igalol is identical with the diol obtained by the reduction of igalan with sodium borohydride, and has the structure elemane-8,12-diol.The sesquiterpene hydroxy lactone lactone No. 8 has been isolated in the form of an oil and it is now being studied.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 17–20, January, 1971.     

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.     

Structure and stereochemistry of pallinin

The roots ofFerula pallida Korov. have yielded pallinin, C₂₅H₃₈O₅, mp 79–80°C, []D²⁰ –148.5° (c 0.1; CHCl₃) — an ester of the new carotane alcohol pallinol and angelic acid. A structure and absolute configuration have been proposed for it on the basis of chemical transformations and spectral characteristics.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 53–56, January–February, 1986.     

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.     

Alkaloids of Vinca major

Summary 1. From the epigeal part ofVinca major have been isolated the known bases akuammicine, vincamajine, vincamajoridine, and ervine, and the new alkaloid majorinine with the composition C₂₂H₂₄N₂O₄, mp 195–196°C.2. On the basis of chemical transformations and IR, UV, mass, and PMR spectra using the methods of double resonance collapse and INDOR the structure of 21-hydroxy-10-methoxyvinorine and the stereochemistry (I) have been established for majorinine.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 382–387, May–June, 1977.     

A sesquiterpene lactone badkhysinin from the roots ofFerula oopoda

Summary A sesquiterpene lactone with the composition C₂₀H₂₄O₅, mp 104°–105° C, []_D –212.4° C (alcohol) has been isolated from the roots ofFerula oopoda Boiss. and has been called badkhysinin. Badkhysinin is an ester of angelic acid and an epoxyhydroxylactone C₁₅H₁₈O₄ with mp 185°–186° C apparently related to guaianolide with a hydrocarbon skeleton of irregular structure. A number of possible structural formulas for badkhysinin are given.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 2, pp. 93–99, 1966     

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.     

Phytoecdysteroids of plants of the genus Silene. XVI. Viticosterone E 22-O-benzoate from Silene wallichiana

A new phytoecdysteroid, viticosterone E 22-O-benzoate (I), C₃₆H₅₀O₀, mp 147–149°C (methanol-water), [] _D ²⁰ +63.2° (methanol), has been isolated from the epigeal organs ofSilene wallichiana Klotzsch. The alkaline hydrolysis of (I) led to viticosterone E and benzoic acid. The acetylation of (I) gave the 2,3-diacetate (II), C₄₀H₅₄O₁₁, mp 152–153°C (methanol-water), [] _D ²⁰ +65.5° (methanol). Details of the IR, PMR, and mass spectra of (I) and (II) are given.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 546–549, July–August, 1988.     

Alkaloids ofPetilium raddeana. V. Structure of petisidinone

From the epigeal part ofPetilium raddeana have been isolated the known alkaloids edpetiline and edpetine and the new base petisidinone with mp 217–219°C, []_D 0° (c 0.169; chloroform), C₂₇H₃₉NO₃ (I). When the known alkaloid petisidine was oxidized, a product identical with petisidinone (I) was obtained. Thus, the structure of (I) has been established as 26,23-nitrilocholestane-3,6,22-trione. Details of the IR, PMR, and mass spectra of (I) are given.Institute of the Chemistry of Plant Substances of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh soedinenii, NO. 5, pp. 620–622, September–October, 1986.     

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     

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.     

Lactones ofFerula gigantea

The following substances have been isolated from an acetone extract ofFerula gigantea B. Fedtsch.: a coumarin — umbelliferone, C₉H₆O₂, mp 230–233°C; and sesquiterpene lactones — talassin A, C₂₅H₃₀O₇, mp 188–191°C; malaphyllinin, C₂₄H₂₄O₇, mp 231–235°C; malaphyll, C₂₉H₃₂O₉, mp 212–213°C; and malaphyllin, C₂₆H₂₈O₉, mp 216–218°C. Structures have been proposed for three new sesquiterpene lactones on the basis of an analysis of their spectral characteristics.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. M. V. Lomonosov Moscow State University, Botanical Garden, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 490–495, July–August, 1979.     

Structure of korselimine

The new base korselidine with mp 272–274°C (methanol), []_D-75°, C₂₇H₄₃NO₂ (I), (ethanol), composition C₂₇H₄₃NO₂, has been isolated from the total alkaloids of the epigeal part ofKorolkowia sewerzowii Regel. As a result of the study of the chemical properties of the alkaloid itself and of its products of its transformation, the structure and partial configuration of korselamine have been established as (1,3,-dihydroxy-^8,14)-cevanene.Institute of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–46, January–February, 1989.