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.     

Dzheiranbatanolide — A new guaianolide fromArtemisia fragrans

A new guaianolide which has been called dzheiranbatanolide (I), C₁₅H₂₀O₄, mp 186–188°C has been isolated from the epigeal part ofArtemisia fragrans Willd. The oxidation of (I) led to a keto derivative (II) with the composition C₁₅H₁₈O₄, mp 247–248°C. The structure of (I) has been established by the chemical and spectral (IR, UV, and¹³C NMR) analysis of (I) and (II).V. L. Komarov Institute of Botany, Academy of Sciences of the Azerbaijan SSR, Baku. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 595–598, September–October, 1984.     

Flavonoids of inflorescences of Calendula officinalis

By column chromatography on polyamide sorbent, the inflorescences of pot marigold calendula have yielded eight substances of flavonoid nature: two aglycons — quercetin (C₁₅H₁₀O₇, mp 309–311°C) and isorhamnetin (C₁₆H₁₂O₇, mp 314–316°C); six glycosides, of which three have been identified as isoquercetin (C₂₁H₂₀O₁₂, [] _D ²⁰ –36° in methanol, mp 218–220°C), isorhamnetin 3-O--D-glucoside (C₂₂H₂₂O₁₂, [] _D ²⁰ –59° in dimethylformamide, mp 193–195°C), narcissin (C₂₈H₃₂O₁₆, [] _D ²¹ –28° in dimethylformamide, mp 180–182°C), and three substances that have proved to be new and have been called calendoflaside (C₂₈H₃₂O₁₅, [] _D ²¹ –85° in methanol, mp 192–195°C; calendoflavoside (C₂₈H₃₂O₁₆, [] _D ²⁰ –106° in methanol, mp 189–192°C), and calendoflavobioside (c₂₇H₃₀O₁₆, [] _D ²⁰ –105° in methanol, mp 194–197°C).All-Union Scientific-Research Institute of Drug Chemistry, Khar'kov. Translated from Khimiya Prirodynkh Soedinenii, No. 6, pp. 795–801, November–December, 1988.     

The structure of feterin — A new terpenoid coumarin fromFerula teterrima

Summary From the roots ofFerula teterrima Kar. et Kir. a new terpenoid coumarin — feterin — has been isolated with the formula C₂₆H₃₂O₆, mp 155–158°C, [] _D ^2° -52.02° (chloroform), M⁺ 440, the structure and relative configuration of which have been established with the aid of the INDOR method and on the basis of a study of the PMR spectra in the presence of the paramagnetic shift reagent Eu(DMP)₃.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 318–322, May–June, 1978.     

Components ofHaplophyllum obtusifolium

Skimmianine, folimine, benzamide, and new alkaloid haplotusine (mp 118–119°C, C₁₁H₁₁NO₃, M⁺ 205) have been isolated from the epigeal part ofHaplophyllum obtusifolium Ledeb. growing in the environs of Kora-Koly, Turkmen SSR. By the analysis of spectral characteristics it has been established that haplotusine has the structure of 1,4-dimethoxy-2-quinolone.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 635–636, September–October, 1984.     

Structures of daurosides A and B — New acylated coumarin glycosides fromHaplophyllum dauricum

From the roots and epigeal parts ofHaplophyllum dauricum (L.) G. Don., new acylated courmarin glycosides have been isolated: dauroside A, C₂₃H₂₈O₁₃, mp 145–147°C (ethanol), [] _D ²² – 72.7° (methanol), and dauroside B, C₃₀H₃₂O₁₄, mp 145–150°C (methanol) [] _D ²² 0° (pyridine). Their structures have been established on the basis of chemical transformations and IR, UV, mass,¹H NMR and¹³C NMR spectra.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 142–147, March–April, 1983.     

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 and configuration of a new diterpenoid lactone fromLagochilus hirsutissimus

The epigeal part of the plantLagochilus hirsutissimus has yielded a new diterpenoid lactone — lagohirsidin, C₂₂H₃₄O₅, mp 144–145°C, [] _D ²² – 17.5° (c 1; ethanol). Reduction with LiAlH₄ has yielded a diol C₂₂H₃₈O₅, mp 165–166°C [] _D ²⁰ –1.2 (c 0.6; ethanol). Acid hydrolysis of the diol has led to the formation of lagochilin, C₂₀H₃₆O₅, mp 167–168°C, [] _D ²⁰ –3.9° (c 1; ethanol). The synthesis of lagohirsidin from lagochilin has been effected.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 788–792, November–December, 1979.     

Triterpene glycosides of Astragalus and their genins. XX. Cycloorbigenin from Astragalus orbiculatus

A new genin — cycloorbigenin (I), C₃₀H₄₈O₅, mp 217–219°C, [] _D ²⁰ +28.3° (c 1.19; ethanol) has been obtained from a glycoside isolated from the epigeal parts of the plantAstragalus orbiculatus (Leguminosae), and on the basis of chemical transformation and spectral characteristics its structure has been established as 16,23:16,24-diepoxy-23(R),24(S)cycloartane-3,7,25-triol. The acetylation of (I) with acetic anhydride in pyridine yielded its diacetate (II), C₃₄H₅₂O₇, mp 148–150°C, [] _D ²⁰ +32.6° (c 0.92; methanol) and its triacetate (III), C₃₆H₅₄O₈, mp 137–139°C, [] _D ²⁰ +75° (c 0.4; methanol). The Jones oxidation of (I) led to a diketone (IV), C₃₀H₄₄O₅, mp 155–158°C, [] _D ²⁰ -73° (c 0.63; methanol). Details of the PMR, IR, and mass spectra are given for all the compounds.Institute of The Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 455–460, July–August, 1986.     

Coumarins fromPhlojodicarpus sibiricus

Phlojodicarpin [8-(2,3-epoxy-1-hydroxy-3-methylbutyl)-7-methoxycoumarin, C₁₅H₁₆O₅, mp 143–145°C, [] _D ²⁵ -37.5°], and isophlojodicarpin [8-(1,2-epoxy-3-hydroxy-3-methylbutyl)-7-methoxycoumarin, C₁₅H₁₆O₅, mp 132–134°C, [] _D ²⁵ -102.5°] have been isolated from the epigeal part ofPhlojodicarpus sibiricus. The results of the IR, UV, PMR, and mass spectrometry of these compounds 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. 47–49, January–February, 1981.     

Structure of ferulide

The structure of a new sesquiterpene lactone — ferulide fromFerula penninervis Regel et Schmalh — has been established on the basis of its spectral characteristics. This compound has the composition C₂₀H₂₄O₅, mp 135–137°C.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 240–242, March–April, 1987.     

Structure of isoregecoline

The structure of the alkaloid isoregecoline (I) with the composition C₁₉H₂₃O₄N⁺, mp. 284–286°C, isolated previously fromColchicum kesselringii Regel growing in the flood plains of the R. Chirchik has been established. It has been shown by IR, PMR and mass spectroscopy and chemical transformations that (I) is an epimer of regecoline isolated from a plant of the same species.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 808–810, November–December, 1985.     

Natural product chemistry,part 100: The structure of carissone,C15H24O2

Summary C₁₅H₂₄O₂,M=236.2, monoclinic, P 2₁,a=7.229(7),b=14.925 (9),c=6.235 (9) Å, =92.40 (9)°,V=672.1 ų,T=–133 °C,Z=2,D _x=1.17 g cm^–3. The X-ray diffraction analysis of this sesquiterpenoid fromCarissa opaca confirmed the previously proposed constitution of the isolate and, furthermore, allowed precise NMR assignment.

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Naturstoffchemie, 100. Mitt.: Die Struktur des Carissons, C₁₅H₂₄O₂

Zusammenfassung C₁₅H₂₄O₂,M=236.2, monoklin, P 2₁,a=7.229 (7),b=14.925 (9),c=6.235 (9) Å, =92.40 (9)°,V=672.1 ų,T=–133 °C,Z=2,D _x=1.17 g cm^–3. Die Röntgenstrukturanalyse dieses Sesquiterpenoids ausCarissa opaca bestätigte die bereits vorgeschlagene Struktur und erlaubte ferner eine genaue NMR-Zuordnung.

     

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.     

A chemical investigation ofAchillea nobilis

From the flower heads and leaves ofAchillea nobilis collected in the flowering phase close to Balytkykol, Egindybulak region, Karaganda Province, Kazakh SSR, by extraction with chloroform and chromatography of the combined substances on a column of silica gel we have isolated a new sesquiterpene lactone anobin C₁₅H₂₀O₅, mp 175.5–177.5°C and have identified for the first time estafiatin, C₁₅H₁₈O₃, mp 102–104°C []²⁰ –10.3° (chloroform); hanphyllin, C₁₅H₂₀O₃, mp 189°C (decomp), [] _D ²⁰ + 58.6° (c 0.39; chloroform), and 3,5-dihydroxy-6,7,8-trimethoxyflavone, C₁₈H₁₆O₇, mp 148–150°C. On the basis of chemical and spectral characteristics it has been established that anobin has the structure of 4,10-dihydroxy-2,3-epoxy-5,7(H),6(H)-guai-11(13)-en-6,12-olide. It has been established that estafiatin possesses a pronounced growth regulating activity.Deceased.Chemical and Metallurgical Institute, Academy of Sciences of the Kazakh SSR, Karaganda. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 603–607, September–October, 1984.     

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.