Alkaloids of Fumaria vaillantii structure of vaillantine

Summary The plantFumaria vaillantii Loisl. has yielded protopine, fumaridine, fumaramine, d--hydrastine,l-adlumine, d-bicuculline, andl-adlumidine (this being the first time thatl-adlumidine has been isolated from the genusFumaria), and the new base vaillantine. On the basis of UV, IR, NMR, and mass spectra, and also the identity of O,O-dimethylvaillantine with muramine, the structure of vaillantine has been established as 2,3-didemethylmuramine.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 476–478, July–August, 1974.     

Triterpene glycosides ofLeontice eversmannii

Summary The structures of the triterpene glycosides leontiside A and leontoside B fromLeontice eversmannii have been established. It has been shown that the leontoside A is hederagenin 3--L-arabopyranoside and leontoside B is hederagenin 3--L-arabopyranosido-4--D-glucopyranoside.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 101–105, 1967     

Rhodioloside fromRhodiola rosea andRh. quadrifida. I

Summary 1.Rh. quadrifida (Pall.) Fisch. et Mey has yielded a new glycoside which has been called rhodioloside and for which the structure of the -D-glucopyranoside of -(p-hydroxyphenyl)ethanol has been established.2. Rhodioloside is also present inRh. rosea L.3. -(p-Hydroxyphenyl)ethanol, which is the aglycone of the glucoside isolated, has been obtained from both plants.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 4, pp. 244–249, 1967     

Phytoecdysteroids ofSilene nutans. III. Nusilsterone

A new ecdysteroid — nusilsterone — has been insolated from the whole plantSilene nutans L. It has been shown that it is 1,2,3,14,20R,22R,24,25-octahydroxy-5--cholest-7-en-6-one.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii. No. 4, pp. 522–525, July–August, 1985.     

Flavonoids ofPhellodendron sachalinense andPh. amurense

Summary 1. About ten substances of a flavonoid nature have been found in the leaves ofPhellodendron sachalinense (F. Schm.) Sarg. andPh. amurense Rupr.2. The two species of cork tree each contain two new flavonoids, which have been called phelloside and dihydrophelloside. The results of chemical and spectroscopic studies have permitted phelloside to be characterized as the 7,-di-O--D-glucopyranoside of noricaritin and dihydrophelloside as the 7,-di-O--D-glucopyranoside of dihydronoricaritin, the base of which contains kaempferol and aromadendrin.3. Amurensin (the 7--D-glucopyranoside of noricaritin) and icariside-1 (the -O--D-glucopyranoside of noricaritin) have been isolated as intermediates in the stepwise hydrolysis of phelloside; the latter has not been previously found in the Amur and Japanese cork trees.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 2, pp. 77–82, 1968     

Withasteroids ofPhysalis. V. A study of the1H and13C NMR spectra of the withasteroids visconolide and 28-hydroxywithaperuvin C

The PMR and¹³C NMR spectra of new withasteroids — visconolide and 28-hydroxywithaperuvin C, isolated fromPhysalis viscosa L. — have been investigated. A detailed analysis of the spectral characteristics obtained is given. For visconolide is proposed the structure of 4,12,17,28-pentahydroxy-1-oxo-5, 6-epoxy-22R-witha-2,24-dienolide, and for 28-hydroxywithaperuvin C that of 6,14,17,20R, 28-pentahydroxy-l-oxo-22R-witha-2, 4, 24-trienolide.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 657–663, September–October, 1985.     

A new coumarin fromLibanotis schrenkiana

Conclusions A new coumarin C₁₉H₂₀O₅ with mp 78–79° C, [] _D ¹⁶ +213° (c 1.00; chloroform) has been isolated from the roots ofLibanotis schrenkiana, and we have called it libanorin. On the basis of chemical and spectral characteristics, the structure of the ,-dimethylacrylic ester of zosimol (columbianetin) has been proposed for libanorin.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 4, pp. 222–225, 1969     

Glycosides ofVaccaria segetalis

Summary The glucoflavonoid glycoside isosaponarin has been isolated from the seeds ofVaccaria segetalis. It has been shown that isosaponarin has the structure 5, 7, 4-trihydroxyflavone (6)-C--D-glucopyranosido-(4)-O--D-gluco-pyranoside.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 159–164, 1967     

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     

Glycosides ofVaccaria segetalis

Summary The enzymatic hydrolysis of vaccegoside, a triterpene glycoside fromVaccaria segetalis, has given D-glucose, D-xylose, D-glucuronic acid, an unknown disaccharide, and a 28-O-acyltetraoside of gypsogenin, esterified with sugars at the carboxyl group, containing D-glucose, D-rhamnose, L-arabinose, and D-xylose. It has been shown that the disaccharide has the structure 4-(D-xylopyranosido)-D-glucopyranose. The alkaline hydrolysis of vacsegoside yielded a gypsogenin tetraoside-vaccarotertraoside. The structure of vaccarotetraoside has been established as gypsogenin-(3)--D-glucopyranuronosido-(4 or 2)-D-glucopyranosido-(3)-D-glucopyranosido-(4) d-xylopyranose.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 6, pp. 372–379, 1965.     

Structure of coramine

Summary 1. It has been established that the base coramine isolated fromCorydalis pseudoadunca is a diisoquinoline alkaloid.2. It has been shown that the dimethyl ether of coramine is identical with xylopinine.3. The structure of coramine has been established by a study of the ozonolysis of the products of the Hofman degradation of its diethyl ether.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 5, pp. 340–344, 1966     

Triterpene glycosides ofSilphium perfoliatum. IV. Structure of siliphioside C

The epigeal part ofSilphium perfoliatum has a yielded a new triterpene glycoside, silphioside C — C₅₀H₈₀O₁₉, mp 207–210°C (from aqueous methanol), []_D ²⁵ +19.3 ± 2°C (c 0.88; methanol). On the basis of acid hydrolysis, mild alkaline saponification, and the results of GLC and of IR, mass, and¹H and¹³C spectroscopy the structure of silphioside C had been established as 28--D-glucopyranosyl 3-O-[O--D-glucopyranosyl-(12)-(6-O-acetyl--D-glucopyranosyl)oleanolate.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Pyatigorsk Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii. No. 4, pp. 519–522, July–August, 1985.     

Triterpene glycosides of Astragalus and their genins. XXXVIII. Cycloalpigenin D and cycloalpioside D from Astragalus alopecurus

Eight compounds of triterpenoid nature have been isolated from the epigeal parts of the plantAstragalus alopecurus Pall. (Leguminosae) and have been designated in order of increasing polarity as substance 1–8. On the basis of chemical transformations and spectral characteristics, we have established the structures of 4 and 8, which have been called cycloalpigenin D and cycloalpioside D, respectively. Cycloalpigenin D is 20R,24S-epoxycycloartane-3,7,16,25-tetraol. Cycloalpioside D is cycloalpigenin D 3-O--D-xylopyranoside.Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 377–384, May–June, 1991.     

A study of the substances present in essential oils

Conclusions The essential oil ofJuniperus pseudosabina Fisch. et Mey, obtained from small flowers by steam distillation has been investigated. It has been established that it contains not less than 43 components, of wich the following have been identified:l--pinene (67%), camphene (0.5%),l--pinene (3.5%), sabinene (0.5%), ³-carene (0.3%), -myrcene (1.2%), -phellandrene (0.1%),l-limonene (0.7%),l--phellandrene (0.2%), -terpinene (0.3%), p-cymene (0.2%), terpinolene (0.1%), methyl n-nonyl ketone (2.4%), d-thujone (0.3%),l-camphor (0.2%), d-terpinen-4-ol (0.3%),l-linalool (0.7%),l-borneol (0.3%),l-terpineol (0.4%), nerol (0.2%), geraniol (0.25%), d-cedrol (12%), elemol (0.3%), eudesmol (0.35%), and sesquiterpene hydrocarbons (5.6%):l--cedrene,l--elemene,l--cedrene, d--cadinene, d-ar-curcumene,l-calamenene, and d-calacorene.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 6, pp. 482–487, 1969     

Structure of a glucuronoxylan of the stems ofSymphytum asperum

The results are given of an investigation of the structure of a glucuronoxylan of the stems ofSymphytum asperum Ler. The xylan was isolated by alkaline extraction and was purified by reprecipitation via the copper complex. The polysaccharide was homogeneous according to the results of gel filtration and electrophoresis. It was shown by hydrolysis, periodate oxidation, methylation, oxidation with chromium trioxide and IR and¹³C NMR spectroscopy that the macromolecules were based on a -(14)-polyxyloside chain having side chains at the second carbon atoms in the form of 4-O-Me-D-glucuronic acid. To each side chain there were not less than 12 xylose residues.M. V. Lomonosov Technological Institute of the Food Industry, Odessa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 478–481, July–August, 1985.     

Culcitoside C1 from the starfishCulcita novaeguineae andLinckia guildingi

By repeated chromatography on Polikhrom-1, silica gel, and Florisil, ethanolic extracts of two species of starfish,Culcita novaeguineae andLinckia guildingi, have yielded the new steroid glycoside culcitoside C₁ (I): 5-cholestan-3,4,6,8,15,24-hexaol 24-O-[2,4-di-O-methyl--D-xylopyranosyl-(12)--L-arabinofuranoside], C₃₉H₆₈O₁₄, mp 245–248°C, []_D -35.8°, c 0.6; methanol). Its structure was shown by the results of acid hydrolysis, acetylation and methylation, and¹H and¹³C NMR spectroscopy.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 801–804, November–December, 1985.     

Culcitosides C2 and C3 from the starfishCulcita novaeguineae

Two steroid glycosides not previously described have been isolated from the digestive system of the starfishCulcite novaeguiniae, and these have been called culcitosides C₂ and C₃. With the aid of chemical and spectral methods, the chemical structure of C₂ has been established as 24-methyl-5-cholestane-3,4,6,8,15,16,28-heptaol 28-O-[O-(2,4-di-O-methyl--D-xylopyranosyl)-(1 2)--L-arabinofuranoside, and that of C₃ as its 4-deoxy analogue.Pacific Ocean Institute of Bioorganic Chemistry of the Far Eastern Scientific Center of the USSR Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 592–596, September–October, 1986.     

Saponins ofDioscorea polystachya

Summary A new water-soluble saponin, dioscinin, consisting of a glucoside-dirhamnoside-glucoside of 25D-22-spirost-5-en-3-ol has been isolated from the rhizomes ofDioscorea polystachya. In addition to dioscin and dioscinin, the rhizomes ofDioscorea polystachya contain a small amount of gracillin and the kikuba-saponin corresponding to it.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 155–158, 1967     

Flavonoids ofThalictrum foetidum

Conclusions Two fluavonoid glucosides have been isolated from the herbThalictrum foetidum L.: rutin and a new flavonoid glucorhamnin with an aglycone rarely found in nature. Glucorhamnin has been characterized as rhamentin 3--D-glucopyranoside.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 5, pp. 369–371, 1969     

Triterpene glycosides fromSaponaria officinalis

Conclusions The roots ofSaponaria officinalis L. have yielded the known triterpene glycoside gypsoside and the first glycoside of gypsogenic acid, which has been named saponaroside. Saponaroside is the 3--D-xylopyranoside of gypsogenic acid.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 5, pp. 389–394, 1969