A sesquiterpene lactone-semopodin-from the seeds ofFerula oopoda

Conclusions From the seeds ofFerula oopoda (Boiss et Buhse) Boiss. a new sesquiterpene lactone with mp 177–178° C has been isolated which has been given the name semopodin. On the basis of the NMR, UV, and IR spectra semopodin has been ascribed the probable structure I or II.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 4, pp. 241–244, 1969     

Feropodin-a sesquiterpene lactone from the roots ofFerula oopoda

Conclusions From the resin of the roots ofFerula oopoda (Boiss. et Buhse) Boiss. a new sesquiterpene lactone, feropodin, with the composition C₁₅H₂₀O₂, mp 140–141° C, has been isolated. The alternative hypothetical structures I and II have been proposed for feropodin.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 4, pp. 245–247, 1969     

Structure of isobadkhysin. The stereochemistry of badkhysin and isobadkhysin

Conclusions 1. By chromatography of the total lactones obtained from the sodium carbonate treatment of the resin of the roots ofFerula oopoda (Boiss. et Buhse) Boiss. we isolated a previously unstudied sesquiterpene lactone C₂₀H₂₄O₅, mp 189–190° C, which we called isobadkhysin.2. It has been shown that isobadkhysin is a stereoisomer of badkhysin and is formed during the treatment of the resin with sodium carbonate.3. The stereochemical characteristics of badkhysin and isobadkhysin have been established on the basis of their NMR spectra.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 4, pp. 425–428, 1970     

Structure of ferulidin: A new sesquiterpene lactone

Conclusions 1. From the roots ofFerula oopoda (Boiss. et Buhse) Boiss. a new sesquiterpene lactone C₁₅H₁₈O₄ with mp 170–172° C has been isolated; it has been called ferulidin.2. We have shown that ferulidin has the structure I.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 4, pp. 428–431, 1970     

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     

Phenols of Ferula prangifolia

Summary From the roots ofFerula prangifolia (Boiss) Korov. two phenolic components have been isolated that are esters of p-hydroxybenzoic acid and sesquiterpene alcohols. On the basis of their physicochemical constants and hydrolysis products it has been shown that one of them isl-chimgin (borneol p-hydroxybenzoate) and the second, which has been called ferungin, is ferutinol p-hydroxybenzoate.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 718–721, November–December, 1972.     

A new guaianolide — Opoferzin from the roots of Ferula oopoda

A new guaianolide with the composition C₂₀H₂₂O₅, mp 150–152°C, has been isolated from the resin of the roots ofFerula oopoda, (Boiss. et Buhse) Boiss. It has been established that it corresponds to the structure of 11-angeloyloxy-2-oxo-5H, 6H-guaia-1(10), 3,7-trien-6,12-olide.V. L. Komarov Institute of Botany, Academy of Sciences of the Azerbaidzhan SSR, Baku. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 318–319, May–June, 1991.     

Triterpene glycosides of Astragalus and their genins XXXII. Cyclocarposide from Astragalus coluteocarpus

A new triterpene glycoside of the cycloartane series, which has been called cyclocarposide, has been isolated from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). The structure of cyclocarposide has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3β,6α,16β,25-tetraol 6-0-α-L-rhamnopyranoside 3-0-α-D-xylopyranoside. Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pamir Biological Institute, Academy of Sciences of the Tadzhik SSR, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–656, September–October, 1990.     

A polysaccharide from the pith of the stems ofAlthea flavovirens

It has been established that a polysaccharide from the pith of the stems ofAlthea flavovirens Boiss et Buhse growing in Azerbaidzhan (environs of the village of Dzhul'fy) has a branched molecule consisting of residues of ribose, rhamnose, glucose, and glucuronic and galacturonic acids (3:6:3:7:2). Among the products of the methylation of the polysaccharide reduced at the carboxy groups the following sugar derivatives have been identified: 2,3,4-tri-O-methyl-L-rhamnose, 3,4-di-O-methyl-L-rhamnose, 2,3,4,6-tetra-O-methyl-D-glucose, and 2,3,6-tri-O-methyl-D-glucose and 2,3,6-tri-O-methyl-D-galactose (unresolved mixture), and also 2,6-di-O-methyl-D-glucose (2:10:24:7:2).V. L. Komarov Botanical Institute, Academy of Sciences of the USSR, Leningrad. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 29–33, January–February, 1980.     

Phytoecdysteroids of plants of the genus Silene. XVIII. 2-Deoxyecdysterone 20,22-monoacetonide from Silene brahuica

In addition to the known 2-deoxy--ecdysone, 2-deoxyecdysterone, 2-deoxy--ecdysone-22-O-acetate, ecdysterone, integristerone A, and sileneoside A, B, and C, the new ecdysteroid 2-deoxyecdysterone 20,20-monoacetonide has been isolated from the roots of the plantSilene brahuica Boiss.Institute of Chemistry of Plant Substances Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 241–244, March–April, 1991.     

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     

Structure of ergolide

The epigeal part ofErigeron khorassanicus Boiss. has yielded a new sesquiterpene lactone of the pseudoguaiane type — ergolide C₁₇H₂₂O₅, mp 179–180°C (ethanol) [] _D ²⁰ +123° (c 4.88; ethanol). On the basis of chemical transformations and spectral characteristics, its structure and configuration have been established as 6-acetoxy-4-oxo-1,7H,6,8,10H-pseudoguai-11(13)-en-8,12-olide.Institute of the Chemistry of Plant Substances of the Uzbek Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 568–571, September–October, 1986.     

Triterpene glycosides of Astragalus and their genins XXXII. Cyclocarposide from Astragalus coluteocarpus

A new triterpene glycoside of the cycloartane series, which has been called cyclocarposide, has been isolated from the epigeal part of the plantAstragalus coluteocarpus Boiss. (Leguminosae). The structure of cyclocarposide has been established on the basis of chemical transformations and spectral characteristics as 20R,24S-epoxycycloartane-3,6,16,25-tetraol 6-0--L-rhamnopyranoside 3-0--D-xylopyranoside.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pamir Biological Institute, Academy of Sciences of the Tadzhik SSR, Khorog. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–656, September–October, 1990.     

Structure of ferulidin: A new sesquiterpene lactone

Chemistry of Natural Compounds - 1. From the roots ofFerula oopoda (Boiss. et Buhse) Boiss. a new sesquiterpene lactone C15H18O4 with mp 170–172° C has been isolated; it has been called...     

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-     

New synthesis of steroidal tetrahydrooxazin-2-ones

In the DMSO/NaHCO₃ system, 16α-aminomethyl-, 16α-benzylaminomethyl- and substituted benzylaminomethyl-3-methoxy-17β-tosyloxyestra-1,3, 5(10)-triene (3, 5a-k) do not undergo oxidation, but form a tetrahydrooxa-zin-2-one ring (7, 8a-k) via neighboring group participation. Under similar conditions, 16β-aminomethyl-3-methoxy-17β-tosylestra-1,3,5(10)-triene (4) decomposes into 16-methylene-3-methoxyestra-l,3,5(10)-trien-17-one (12).     

Determination of stereostructure of naturally occurring α, β-unsaturated δ-lactone derivatives through a stereoselective synthesis

The stereostructures of (Z)-tarchonanthuslactone (2) and the δ-lactone of (Z)-5, 7, 9, 11-tetrahydroxyhexacos-2-enoic acid (3) were established as9 and27 by the stereoselective syntheses of authentic9 and26 (triacetate of3), respectively.     

Synthesis of 3-methyl-coumarins, -thiacoumarins and -carbostyrils

Reaction of 3,6-dimethyl-4-phenyl-3,4-dihydrocoumarin5a with anhydrous aluminum chloride gave 3,6-dimethyl-coumarin (6a); likewise, 6-chloro-3-methyl-coumarin (6b) was obtained from5b. Substituted 3-methyl-thiacoumarins (8a,b and 3-methyl-carbostyrils (10a-e) were prepared from the reactions of the respectivea-methyl-cinnamoyl derivatives (7a,b and (9a-e), of thiophenols and anilines.