Esters of Ferula karakalensis. Structure and stereochemistry of karaferin and karaferinin

Two new guaiane esters — karaferin and karaferinin — have been isolated fromFerula karakalensis, and their structures and stereochemistry have been established. It has been shown that theFerula sesquiterpene alcohols angrendiol, ugamdiol, and karaferol are biogenetically interconnected and are products of a single chain of the biogenesis of terpenoids in plants.Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent; Botanical Garden of Moscow State University. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 227–231, March–April, 1993.     

Crystal and molecular structure of 20S,24S-dihydroxydammar-25-en-3-one

The complete spatial structure of 20S,24S-dihydroxydammar-25-en-3-one — a triterpenoid isolated from the leaves of a Far-Eastern species of birch,Betula mandschurica — has been established. Intermolecular cooperative hydrogen bonds that are unusual for a triterpenoid system have been detected in crystals of 20S,24S-dihydroxydammar-25-en-3-one, with the participation of both hydroxy groups in one chain of bonds and an orientation of the associated molecules that is characteristic for a bimolecular layer.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Branch, Russian Academy of Sciences, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 667–672, September–October, 1991.     

Triterpene glycosides of Dianthus deltoides II. Structure of dianthoside C

Summary The structure of dianthoside C — a triterpene glycoside fromDianthus deltoides L. — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 420–425, July–August, 1971.     

The structure of nutanoside

Summary The complete structure of nutanoside — a triterpene glycoside isolated from the roots ofSilene nutans L. — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 412–416, July–August, 1971.     

Triterpenoid saponins Communication 16. Structure of araloside C

Summary The complete structure of araloside C — a triterpenoid saponin from the roots ofAralia manshurica (Rupr. et Mey) — was established.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimisheskaya, No. 7, pp. 1214–1222, July, 1965     

Triterpene glycosides of Gypsophila patrinii III. The structure of philoside B

Summary The structure of philoside B — a gypsogenin nonaoside isolated from the roots ofGypsophila patrinii — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan'Branch, Academy of Sciences of the USSR. Correspondence Institute of Soviet Commerce. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 603–607, September–October, 1974.     

Triterpenoid saponins Communication 18. Structure of kalopanax saponin B

Conclusions The complete structure of kalopanax saponin B — a pentaoside of hederagenin isolated from the roots ofKalopanax septemlobum (Aralia family) — was established.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1588–1594, September, 1966.     

The structure of teucrin A

Summary The structure of a new 18-norditerpenoid — teucrin A, isolated from the plantTeucrium chamaedrys L. — has been demonstrated. It has been shown that it belongs to the furolactones with a rearranged labdane skeleton.Institute of Chemistry, Academy of Sciences of the Moldavian SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 31–35, January–February, 1973.     

Isolation of hemigossypol quinone from a cotton plant infected with wilt

Summary From the stems of the cotton plant infected with the fungusVerticillium dahliae Kleb. has been isolated a quinone derivative of hemigossypol — hemigossypolone — for which the structure 8-formyl-6,7-dihydroxy-5-isopropyl-3-methyl-1,4-naphthoquinone is proposed, and its fungitoxicity has been determined.Division of Bioorganic Chemistry of the Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 341–344, May–June, 1977.     

Alkaloids ofColchicum luteum

The paper gives a review of the alkaloids ofColchium luteum Baker from various growth sites. The structure of luteidine — one of the main alkaloids of the plant — has been established. In addition, two new alkaloids have been isolated from the plant and the structure of one of them has been established as collutine N-oxide.M. I Kalinin Turkmen Agricultural Institute, Ashkhabad, and V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 810–815, November–December, 1985.     

Insect pheromones and their analogs. XLVII. Synthesis of 11-oxododeca-3,6-diynoic acid — The acyclic precursor of a macrolide component of pheromones of Oryzaephilus mercator and O. Surinamensis

A new approach is proposed to the synthesis of 11-oxododeca-3,6-diynoic acid — the acyclic precursor of a macrolide component of pheromones ofOryzaephilus mercator andO. surinamensis — from the readily available tetrahydropyran or allylacetone via the intermediate 5-bromo-2,2-ethylenedioxypentane.Institute of Organic Chemistry, Urals Division, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 288–292, March–April, 1993.     

A new plant growth regulator of microbial origin

A new plant growth regulator — an inhibitor of the germination of mustard seeds — has been isolated from a culture filtrate of a phytopathogenic fungus of the genusPhoma. The methyl and trimethylsilyl derivatives of this compound have been obtained. Its empirical formula — C₁₆H₂₂O₅ — has been determined. On the basis of the results of IR and NMR spectroscopy and mass spectrometry, the compound isolated has been assigned the structure of 3,5-dihydroxy-2-octanoylphenylacetic acid.All-Union Scientific-Research Institute of Applied Molecular Biology and Genetics. V. I. Lenin Academy of Agricultural Sciences, Moscow. Translated from Khimiya Prirodnykh Soedinenii No. 3, pp. 387–391, May–June, 1985.     

O-acylated lignans from the wood of Abies species

Summary From the wood of the Siberian firAbies sibirica Ledeb. and the Khingan firA. nephrolepis Maxim., five new compounds have been isolated which are ester derivatives of the lignans lariciresinol, olivil, and hydroxymatairesinol.It has been established that olivil is esterified at the primary alcoholic hydroxyl by hydroxycinnamic acids — p-coumaric or ferulic — and lariciresinol is esterified by vanillic acid. A representative of the guaialignanolides — hydroxymatairesinol — is esterified at the secondary aliphatic hydroxy group with p-hydroxybenzoic or vanillic acid.Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 337–341, May–June, 1977.     

Phytoecdysteroids of plants of the genus Melandrium I. Polypodin B 22-acetate from Melandrium turkestanicum

Known ecdysteroids — ecdysterone, ecdysterone 22-acetate, polypodin B, integristerone A, and sileneosides A and D — and a new phytoecdysteroid — polypodin B 22-acetate — have been found in the epigeal parts of the plantMelandrium turkestanicum (Rg1.) Vved. (family Caryophyllaceae).Institute of Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 480–483, July–August, 1990.     

Structure of artabin

Summary FromArtemisia absinthium L. a new sesquiterpene lactone of the germacrane type — artabin — has been isolated. Structure I is proposed for it.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedineii, No. 6, pp. 691–694, November–December, 1970.     

Alkaloid specioseine from Colchicum speciosum

The fraction of weak bases fromColchicum speciosum Stev. (family Liliaceae) has yielded a new compound — specioseine. The structure of 10-demethylspeciosine has been established for this base by chemical and spectral methods.V. I. Lenin Tashkent State University. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 253–258, March–April, 1991.     

Synthesis of (E)-dodec-3-en-1-yl acetate — The main component of sex pheromones of Scrobipalpa ocellatella and Scrobipalpopsis solanivora

(E)-Dodec-3-en-l-yl acetate — the main component of the sex pheromones ofScrobipalpa ocellatella andScrobipalpopsis solanivora — has been obtained by a three-stage synthesis from decanal and malonic acid. The overall yield of pheromone was 33% calculated on the initial aldehyde.A. S. Sadykov Institute of Bioorganic Chemistry, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 682–683, September–October, 1988.