Molecular and crystal structure of the sequiterpene lactone austricin

An x-ray structural study has been made of the sesquiterpene lactone austricin: diffractometer, MoK radiation, 1147 reflections, direct method, R=0.045. The spatial structure of the molecule has been determined. The conformation of the pentane carbocycle is 1-envelope, of the heptane ring 1,10, 7-chair, and of the lactone ring 7-envelope. The lactone ring is trans-linked with the guaiane skeleton.Institute of Organic Synthesis and Coal Chemistry, Kazakh SSR Academy of Sciences, Karaganda. A. N. Nesmeyanov Institute of Heteroorganic Compounds, USSR Academy of Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 788–791, November–December, 1989.     

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.     

Cerebrosides of the Far Eastern sponge Hymeniacidon assimilis

Cerebrosides have been isolated from chloroform-ethanol extract of the spongeHymeniacidon assimilis. Their structures have been established with the aid of¹H NMR spectroscopy, acid hydrolysis, and ozonolysis as the -galactosides of the C₁₆-, C₁₇-, and C₁₈-erythro-⁴-sphingenines of normal, iso, and anteiso structures acylated in the amino groups with C₂₁-, C₂₂-, and C₂₃--hydroxy acids. The cerebrosides fromH. assimilis differ in structure from the corresponding compounds isolated previously from sponges.Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Institute of Marine Biology, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 634–639, September–October, 1989.     

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.     

Steroids of the spirostan and furostan series from plants of the genus Allium. XXV. Structure of anzurogenin B from Allium suvorovii and Allium Stipitatum

A new genin of the spirostan series — anzurogenin B having the structure of 2,5-epoxy-(25R)-spirostan-3,6-diol — has been isolated form the collective fruit of the cocultivatedAllium suvorovii Rgl. andAllium stipitatum Rgl. (family Liliaceae).Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 218–221, March–April, 1988.     

Triterpene glycosides of Gleditschia triacanthos IV. The structure of triacanthosides A1 and G

Summary The pericarps ofGleditschia triacanthos L. have yielded a new triterpene glycoside — triacanthoside A₁ — and it has been shown that it has the structure of echynocystic acid 3-O-[-D-xylopyranosyl-(14)--L-arabopyranosyl-(13)--D-glucopyranoside].It has been shown that the O-glycosidic moiety of triacanthoside G coincides in structure with triacanthoside A₁. The O-acyloside moiety of triacanthoside G contains the trisaccharide D-glucopyranosyl-(13)-O-L-arabopyranosyl-(14)-O-L-rhamnopyranose.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 314–316, May–June, 1973.     

New glycosides from plants of the genus Phlojodicarpus

From plants of the genusPhlojodicarpus have been isolated the new coumarins umbelliferone -D-apiosyl (1 6)--D-glucopyranoside (I) and 8-(2,3-dihydroxy-3-methylbutyl)umbelliferone 7-O--D-glucopyranoside (II) and also the flavone glycoside diosmetin 7-O--D-glucopyranoside (III). The result of IR, UV, PMR, and¹³C NMR spectroscopy are given.Institute of Chemistry, Academy of Sciences of the Mongolian Peoples' Republic, Ulan-Bator; Irkutsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 36–39, January–February, 1986.     

Isoflavones and stilbenes of the heartwood ofMaackia amurensis

The isoflavin retusin, squalene, 3,4,5-trihydroxystilbene (resveratrol), 3,3,4,5-tetrahydroxystilbene, and a new compound constructed of fragments of retusin and 3,3,4,5-tetrahydroxystilbene have been isolated for the first time from an ethanolic extract of the heartwood ofMaackia amurensis Rupr. et Maxim (Fabaceae) growing in Maritime Territory. The high-molecular-weight polyphenols that impart the characteristic coloration to macckia wood are present in an amount of 7%. The majority of the phenolic compounds isolated showed a high antiradical and antioxidant activity.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. 775–781, November–December, 1985.     

The structure of calendulosides C and D from the roots of Calendula officinalis

Summary The structure of new triterpene glycosides from the roots of potmarigold calendula (C. officinalis) has been established: oleanolic acid 3-{[galactopyranosido-(13)] [glucopyranosido-(12)]--D-glucopy-ranoside} (calenduloside C) and the 28-acyl--D-glucopyranoside of calenduloside C (calenduloside D).All-Union Scientific-Research Institute of Medicinal Plants. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 366–373, May–June, 1975.     

Withanolides of Datura stramonium II. Withastramonolide

Summary A new withanolide called withastramonolide has been isolated from the leaves ofDatura stramonium f. violaceae. It has the structure of 5,12,27-trihydroxy-1-oxo-6,7-epoxy-22R-witha-2,24-dienolide.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 91–95, January–February, 1978.     

Alkaloids of the Monolian flora. IV. Turcosine — A new alkaloid from Aconitum turczaninowi

As the result of a further study of the total alkaloids from the epigeal part ofAconitum turczaninowi we have isolated beiwutine and delcaroline and also a new alkaloid, which has been called turcosine. The structure of turcosine as 6,16-dimethoxy-4-methoxymethyl-1,7,8,10,14-pentahydroxy-N-ethylaconitane has been shown from a study of the IR, mass, PMR, and¹³C NMR spectra of the alkaloid and of the triacetate obtained from it.Institute of Chemistry, Mongolian People's Republic Academy of Sciences. Institute of the Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedeninii, No. 1, pp. 60–62, January–February, 1993.     

Triterpene glucosides of Dipsacus azureus. III. Structure of dipsacobioside

A new triterpene glycoside — dipsacobioside — has been isolated from the root of theDipsacus azureus Schrenk. By chemical transformation and spectral methods its structure has been established as hederagenin 3-O-[O--L-rhamnopyranosyl-(14)--L-arabinopyranoside].Institute of Organic Chemistry, Kirgiz SSR Academy of Sciences, Frunze. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 204–207, March–April, 1989.     

Triterpene glycosides of Astragalus and their genins. XXXI. Cycloorbigenin B from Astragalus orbiculatus

A new methylsteroid of the cycloartane series has been isolated from the epigeal part ofAstragalus orbiculatus Ledeb. (Leguminosae); it has the structure of a (23R,24S)-16,23; 16,24-diepoxycycloartane-3,6,25-tetraol.Institute of the Chemistry of Plant Substances, Uzbek SSR. Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, Vol. 6, pp. 809–812, November–December, 1989.     

Triterpene glycosides of Astragalus and their genins. XXIV. Cycloorbicoside G from Astragalus orbiculatus

A bisdesmosidic glycoside — cycloorbicoside G — has been isolated from the epigeal parts of the plantAstragalus orbiculatus Ledeb. (Leguminosae), and on the basis of chemical transformations and spectral characteristics its structure has been established as (23R,24S)-16,23;16,24-diepoxycycloartane-3,7,25-triol 25-O--D-glucopyranoside 3-O--D-xylopyranoside.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 837–842, November–December, 1987.     

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.     

Igalan, a new sesquiterpene lactone from Inula grandis

Conclusions A new sesquiterpene lactone C₁₅H₂₀O₂ with mp 79–79.5°C, [] _D ²⁰ +105° (chloroform) has been isolated from the roots ofInula grandis Schrenk., and we have called it igalan. On the basis of chemical and spectral characteristics, it has been established that its most probable structure is eleman-8,11-olide.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 508–512, September–October, 1970.     

Structure of sevedamine

From the combined chloroform-extracted material of the epigeal part ofKorolkowia sewerzowii Regel the new alkaloid sevedamine has been isolated, with mp 256–258°C (acetone) []_D +3.6° (c 1.25; ethanol), C₂₇H₄₅NO₃. On the basis of the results of a study of the UV, IR, PMR, and mass spectra of sevedamine and also performance of a transition to the known alkaloid korseverilinedione it has been established that sevedamine has the structure and configuration of 3,6,14-trihydroxycevanine.Institute of the Chemistry of Plant Substances of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 622–624, September–October, 1986.     

Triterpene glycosides of Gypsophila trichotoma III. Structure of trichoside B

Summary The structure of trichoside B — a gypsogenin tetraoside fromGypsophila trichotoma Wend. — has been established. The glycosidic carbohydrate chain is O--D-glucopyranosyl-(1 3)-O--D-glucuronopyranosyl and the acyloside chain is O--D-glucopyranosyl-(1 4)-O--D-galactopyranosyl.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 431–434, July–August, 1971.