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.     

Structure of karatavicin

Summary From the neutral fraction of the resin of the roots ofFerula karatavica Rgl. et Schmalh. an optically inactive coumarin, karatavicin, C₂₄H₃₀O₅, has been isolated; it is an ether of umbelliferone and a sesquiterpene aliphatic ketodiol. Two possible structural formulae (I) and (II) have been proposed for karatavicin.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 4, pp. 223–226, 1967     

Investigation of Aconite alkaloids

Summary The composition of the alkaloids in plants of the genus Aconitum —A. kirinense,A. altaicum, A. coreanum, andA. nemorosum — has been studied. Four new alkaloids of composition C₂₆H₄₁O₈N·HNO₃, C₃₅H₄₁O₁₀N·HBr, C₂₀H₂₅O₃N, and C₂₃H₂₉O₆N have been isolated.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 2, pp. 113–116, 1965.     

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     

Diterpenoids fromMarrubium peregrinum. I

Summary Two new diterpenoids have been isolated fromMarrubium peregrinum L.: a bicyclic diol C₂₀H₃₆O₂, peregrinol — and a hydroxyketolactone C₂₀H₂₅O₅, peregrinin. A substance C₁₉H₁₈O₆ has been obtained as a by-product.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 4, pp. 249–251, 1966     

The structure of karatavic acid

Conclusions Karatavic acid has been isolated from the resin of the roots ofFerula karatavica Rgl. et Schmalh; this is an ether of umbelliferone and a hydroxy acid C₁₅H₂₄O₃ probably having the humulane type of hydrocarbon skeleton. Two possible structural formulas—(I) and (II)—have been proposed for karatavic acid.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 5, pp. 283–287, 1968     

An isomer of coronopilin

Conclusions From the racemes ofC. xanthifolia Fresen. have been isolated a sesquiterpene lactone C₁₆H₂₀O₄, the structural (+)-isomer of (–)-coronopilin, which has not been studied previously; structure I has been proposed for it.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 5, pp. 375–377, 1969     

Structure of the sesquiterpene hydroxyacid fromArtemisia vachanica Krasch

Summary From the leaves and flower heads ofArtemisia vachanica Krasch. we have isolated a new sesquiterpene hydroxyacid of the composition C₁₅H₂₄O₃ which has been called vachanic acid and for which structural formula I is proposed as the most probable.Khimiya Prirodnykh Soedinenii, Vol. 1, No. 5, pp. 306–311, 1965     

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.     

Sesquiterpene lactones from Artemisia caucasica

Conclusions 1. Two sesquiterpene lactones have been isolated from the epigeal green part ofArtemisia caucasica Willd.: one with the composition C₁₅H₁₈O₅·H₂O, which has been called grossmisin, and one with the composition C₁₅H₁₈O₅, identified as rutifolin. Structure (I) has been proposed for grossmisin.2. The structure of anhydroaustricin has been reviewed. Structure (II) is proposed for it.Pyatigorsk Pharmaceutical Institute. All-Union Scientific-Research Institute for Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 741–744, November–December, 1971.     

Lucidin primeveroside fromRubia iberica. II

Conclusions A new anthraglycoside with the composition C₂₆H₂₈O₁₄ and mp 210–212°C, lucidin primeveroside, has been isolated from the roots ofRubia iberica C. Koch.Khimiya Prirodnykh Soedinenii, Vol. 4, No. 5, pp. 273–277, 1968     

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     

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.     

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 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     

Alkaloids of Stephania delovayi III. Stephodeline

Summary From the epigeal part ofStephania delovayi Diels (Menispermaceae) have been isolated cycleanine and a new amorphous alkaloid, stephodeline, with the composition C₂₁H₂₇O₅N, a structure for which is proposed.All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 650–653, September–October, 1973.     

Natural quinones

Summary A new anthraquinone of composition C₁₇H₁₄O₅, mp 182–183° (decomp., from benzene) has been isolated from the roots ofRubia iberica (Fisch. ex D.C.); it has been called ibericin and has the structure of 1, 3-dihydroxy-4-ethoxy-methylanthraquinone.Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 12–15, 1966     

Pranferol from the roots ofPrangos ferulacea

Conclusions From the roots ofPrangos ferulacea (L.) Lindl. growing in Armenia an optically inactive furocoumarin C₁₆H₁₆O₅, an isomer of pranferol, has been isolated.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 1, pp. 3–5, 1969