Triterpenoids from Abies species

Three new triterpenoid acids have been isolated from an ethereal extract of Siberian fir needles, and the structures of their methyl esters have been established on the basis of spectral characteristics.Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 212–219, March–April, 1989.     

Triterpenoids from Abies sp. IX. Triterpene lactones from Abies sibirica bark

Four lanostane lactones have been isolated from an ethereal extract of Siberian fir bark — abieslactone and its hydroxy and keto analogs, and also (25R)-24,25-dihydroabieslactone, the structure of which was established on the basis of a chemical and spectral correlation with known compounds.Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 220–225, March–April, 1989.     

Triterpenoids from Abies species VII. New lanostane lactones from Siberian fir needles

Two new lanostane lactones have been isolated from the neutral fraction of an ethereal extract of Siberian fir needles by chromatography, and their structures have been established on the basis of their spectral characteristics and chemical transformations.Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. S. M. Kirov Leningrad Academy of Wood Technology. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 207–212, March–April, 1989.     

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.     

Triterpenoids from Abies species

From an acid fraction of an ethereal extract of Siberian fir needles two new stereoisomeric acids, the molecules of which have a modified lanostane carbon skeleton, have been isolated in the form of methyl esters. The structures of the molecules of these substances have been established by the use of¹³C and¹H NMR,¹H-¹H and¹³C-¹H two-dimensional NMR spectra, circular dichroism, and chemical transformations as (24Z)- and (24E)-8(14 13)-abeo-17,13-friedo-lanosta-8,14(30),24-triene-3,23-dion-26-oic acids.Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 511–517, July–August, 1991.     

New sesquiterpenoids from the oleoresin of Abies alba

The structures of four new sesquiterpenoids from the oleoresin ofAbies alba have been studied. On the basis of various spectral characteristics, the structures of (10S, 11S)-himachala-2,4-diene, (10S, 11S)-himachala-3(12), 4-diene, humula-4,9-dien-8-ol, and (4S, 5S, 10S)-selina-6-en-4-ol have been proposed for the compounds isolated. The stereochemistry of the asymmetric centers was determined by the conversion of these compounds into known sesquiterpenes and also by analysis of PMR spectra with a shift reagent.Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 712–718, September–October, 1988.     

Triterpenoids from Abies species. IV. New triterpene acids from the needles of Abies sibirica

Four new triterpene acids of the mariesiic acid series have been isolated from an extract of the needles of the Siberian fir in the form of their methyl esters, and their structures have been established on the basis of chemical transformations, spectral characteristics, and x-ray structural analysis.     

Triterpenoids from Abies species X. Two new 3,4-secotriterpene acids from the oleoresin of the silver fir

Two new 3,4-secotriterpene acids have been isolated in the form of dimethyl esters from the acid fraction of the oleoresin of the silver firAbies alba Mill. On the basis of spectral characteristics and the results of a chemical correlation with the known triterpenoids methyl abiesolidate, dimethyl abiesonate and methyl firmanoate it has been established that they are (25R)-3,4-seco-9-lanosta-4(28),7-dien-23-one-3,26-dioic acid and (25R)-3,4-seco-abiesa-4(28),7,14(30)-trien-23-one-3,26-dioic acid.Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 765–770, November–December, 1990.     

Triterpenoids of plants of the genus Abies Hill

A review is given for the first time of the results of investigations of Soviet and foreign authors on the isolation of triterpenoids from the bark, needles, oleoresin, and seeds of various species ofAbies (fir) and the determination of their structures and properties. Features of the PMR, mass, UV, and CD spectra of the compounds under consideration are discussed specially and information is given on their classification, distribution in firs, and biological activities.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 443–455, July–August, 1990.     

Chemical investigation ofHippopha? rhamnoides. II. Main components of the neutral reaction of the saponification products of an extract of the leaves of the sea buckthorn

The qualitative and quantitative compositions of the neutral fraction of the products of the saponification of a diethyl ether extract of a sea buckthorn leaves have been investigated. Fourteen triterpene compounds and eight aliphatic alcohols have been identified from the results of GLC, CMS, and PMR and also from their melting points.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Institute of Catalysis, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 514–519, July–August, 1985.     

Composition of the resinous substances of conifer needles. III. Waxy substances from the woody verdure ofPinus sylvestris

The individual compositions of the wax isolated from an isopropyl extract of the woody verdure and of an industrial sample of needle wax have been investigated with the aid of GLC. The acids isolated from the wax have been identified, and the alcoholic fraction has been separated without identification. It has been shown that the wax obtained from the isopropyl alcohol extracts is suitable for industrial use.Siberian Technological Institute, Krasnoyarsk. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 264–266, March–April, 1985.     

Steroid glycosides from the seeds ofPetunia hybrida. Structures of petuniosides B,D, and F

Oplodiol, 3-hydroxyepimanool, and epitorulosol have been isolated for the first time from the oleoresin ofPicea ajanensis. On the basis of the results obtained, it may be assumed that the species studied is possibly a hybrid of Yeddo spruce and Siberian spruce.Novosibirsk Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 359–363, May–June, 1994.     

Polyprenols and dolichols from the needles, needle-free shoots, and bark ofPinus sibirica

The presence of bioregulators of animal organisms — dolichols — has been established in the needles, needle-free shoots, and bark of the Siberian stone pine. The qualitative and quantitative compositions of the mixtures of the isoprenologues and polyprenols have been established by the HPLC method. In addition, known diterpene alcohols ((E,E,E)-geranylgeraniol and labd-8(17),13E-dien-15-ol) esterified with higher fatty acids have been identified in the bark.Novosibirsk Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 729–733, November–December, 1994.     

Seasonal dynamics of the essential oil ofAbies sibirica

The qualitative and quantitative compositions of the essential oils of the woody verdure and bark of the Siberian fir have been studied. It has been shown that the oils investigated differ both in their amount and in the ratio of their individual components. The annual dynamics of the main substances are also different.Deceased.V. N. Sukachev Forest and Timber Institute, Siberian Branch, Academy of Sciences of the USSR, Krasnoyarsk. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 718–721, November–December, 1983.     

Identification of prostaglandins E (series 1 and 2) isolated from the living tissues ofLarix sibirica andPopulus balzamifera

Prostaglandins E₁ and E₂ have been isolated for the first time from living tissues of the Siberian larch and the southern pine. The crude extract was purified by column and preparative thin-layer chromatography. The PGEs were identified by TLC and GLC, by UV and IR spectroscopy, and by chromato-mass spectrometry.Siberian Technological Institute, Krasnoyarsk, Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 567–571, September–October, 1984.     

Triterpenoids from Abies species

From an acid fraction of an ethereal extract of Siberian fir needles two new stereoisomeric acids, the molecules of which have a modified lanostane carbon skeleton, have been isolated in the form of methyl esters. The structures of the molecules of these substances have been established by the use of¹³C and¹H NMR,¹H-¹H and¹³C-¹H two-dimensional NMR spectra, circular dichroism, and chemical transformations as (24Z)- and (24E)-8(14 → 13)-abeo-17,13-friedo-lanosta-8,14(30),24-triene-3,23-dion-26-oic acids.     

Triterpenoids from Abies spp. VI. “Isofirmanic” and (24E)-lanosta-8,24-diene-3,23-dion-26-oic acids from Siberian fir needles

Two triterpene acids have been isolated in the form of methyl esters from an extract of Siberian fir needles, and their structures have been established as 9β-lanosta-7,25-diene-3,23-dion-26-oic and (24E)-lanosta-8,24-dien-3,23-dion-26-oic acids, respectively.     

Ultraviolet absorption of flavonoids VI. Protonation constants of some dihydroxyflavones

Summary The protonation (basicity) constants of six disubstituted flavones have been determined by the spectrophotometric method.Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 587–590, September–October, 1975.     

IR spectroscopy of wood and its main components. XVIII. IR spectra of preparations of lignosulfonic acids from the wood of coniferous and broad-leaved species

General features characterizing the IR spectra of lignosulfonic acids obtained from the wood of coniferous and broad-leaved species have been established the use of which together with quantitative spectral and chemical characteristics of preparations of lignosulfonic acids from spruce- and birchwoods will permit, in spectro-chemical investigations, the characteristics of analogous preparations obtained from the wood of coniferous and broad-leaved species to be given.Siberian Scientific-Research Institute of Pulp and Board, Bratsk. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 774–779, November–December, 1981.     

The monoterpenes of the essential oils of coniferous trees of Siberia

Summary 1. The essential oils of some coniferous Siberian trees isolated under industrial conditions have been investigated.2. The physicochemical characteristics and group compositions of the essential oils have been determined.3. The substance compositions of the monoterpene hydrocarbons have been determined by the GLC method.Siberian Technological Institute, Krasnoyarsk. Translated from Khimiya Prirodnykh Soedinenii, N. 6, pp. 784–786, November–December, 1977.