Neutral diterpenoids of oleoresins of five species of conifers of Transcarpathia

The compositions of the neutral diterpenoids of the oleoresins of five species of conifers growing in the Transcarpathia have been studied. It has been found that the oleoresins ofAbies alba M.,Larix decidua M., andPicea excelsa L. contain more than 50% of neutral diterpenoids. The group and qualitative compositions of the oxygen-containing diterpenoids have been determined. In the oleoresins ofAbies alba,Picea excelsa, andPicea abies tertiary alcohols — cis-abienol and isocembrol — predominate, while inLarix decidua the main component is the hydroxy ester larixyl acetate. Primary alcohols related to the resin acids have been found in all the oleoresins investigated. Features of the distribution of diterpenoids according to the species of conifers have been revealed. The results obtained are necessary for the chemotaxonomy of conifers of the family Pinceae.     

Gas-chromatographic determination of the composition of the volatile components of the oleoresins of some species of conifers

Using the method of analytical GLC in a glass capillary column, the compositions have been studied of the volatile fractions of the oleoresins of five species of conifers:Larix decidua,Pinus strobus,Pinus mugo,Picea excelsa, andPinus abies. In the oleoresins 21 monoterpene and 22 sesquiterpene compounds were identified from their relative retention times and with the aid of additives. The main components of the volatile fractions of the oleoresins were α- and β-pinenes and 3-carene among the monoterpenes, and longifolene caryophyllene, δ- and γ-cadinenes and α-murolene among the sesquiterpene compounds. The quantitative analysis of the fractions was carried out by the method of internal normalization from averaged correlation coefficients.     

Gas-chromatographic determination of the composition of the volatile components of the oleoresins of some species of conifers

Using the method of analytical GLC in a glass capillary column, the compositions have been studied of the volatile fractions of the oleoresins of five species of conifers:Larix decidua,Pinus strobus,Pinus mugo,Picea excelsa, andPinus abies. In the oleoresins 21 monoterpene and 22 sesquiterpene compounds were identified from their relative retention times and with the aid of additives. The main components of the volatile fractions of the oleoresins were - and -pinenes and 3-carene among the monoterpenes, and longifolene caryophyllene, - and -cadinenes and -murolene among the sesquiterpene compounds. The quantitative analysis of the fractions was carried out by the method of internal normalization from averaged correlation coefficients.Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 629–632, September–October, 1990.     

Mono- and sesquiterpenoids of the oleoresins ofAbies sachalinensis,A. mayriana,andA. gracilis

The compositions of the mono- and sesquiterpenoids of the oleoresins of the Sakhalin fir (Abies sachalinensis Fr. Schmidt), Mayr's fir (Abies mayriana Miyabe et Kudo), and the slender fir (Abies gracilis Kom.) have been studied. In the oleoresin ofA. gracilis 37 compounds were identified, of which 11 were monoterpene hydrocarbons, seven were oxygen-containing monoterpenoids, 16 were sesquiterpene hydrocarbons, and three were sesquiterpene alcohols. In each of the oleoresins ofA. sachalinensis andA. mayriana eight oxidized monoterpenoids, 18 sesquiterpene hydrocarbons, and a sesquiterpene alcohol — bisabolol — were identified.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 195–199, March–April, 1980.     

Terpenoids of the oleoresins ofPicea orientalis andAbies normanniana growing in the Caucasus

The terpenoid compositions of the oleoresins of the oriental spruce and of the Nordmann fir growing in the Caucasus have been studied. From the oleoresin ofPicea orientalis (L.) Link, which belongs to the sectionOmorica, 32 mono-, sesqui-, and diterpene compounds have been identified, and fromAbies nordmanniana Stev. 37 mono-, sesqui, and diterpene compounds. Together with other diterpenoids that are characteristic for the oleoresins of all species of fir, methyl dehydroabietate and methyl 15-hydroxy dehydroabietate have been found in the oleoresin of the Nordmann fir. Three new sesquiterpene hydrocarbons have been isolated.     

Terpenoids of the oleoresin of Pinus pumila

Summary 1. The composition of the acid fraction of the oleresin ofPinus pumila (Pall.) Regel. has been studied, and from it has been isolated, in addition to known compounds, the methyl ester of a new labdane acetoxy acid.2. In the hydrocarbon fraction of the oleoresin 11 monoterpenes and 26 sesquiterpenes have been found (and 17 of the latter have been identified).3. The composition of the fraction of neutral oxygen-containing diterpenoids fromP. pumila differs considerably in its diterpenoid components from the corresponding fractions of the oleoresins of botanically related species-P. sibirica andP. koraiensis. Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 299–302, May–June, 1976.     

Terpenoids of the needles of Picea abies

The composition of the terpenoids of the neutral petroleum-ether-soluble substances from an isopropanol extract of the needles of the Norway spruce has been studied. The main components of the extractive substances are polyprenol acetates, alcohols with the labdane type of structure, and epimanool and epitorulosol. It has been shown that the terpenoids from the needles differ in composition from the extractive substances of the trunk part of the tree and those from the oleoresins of the sprucesPicea abies, P. ajanensis, andP. obovata.S. M. Kirov Leningrad Academy of Wood Technology. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 168–176, March–April, 1986.     

Diterpen oids of the oleoresin of Picea koraiensis, P. glehnii, and P. excelsa

Summary 1. The composition of the neutral diterpenoids of the oleoreins of three species of spruce have been studied: Korean spruce, common spruce, and Sakhalin spruce.2. The distribution of diterpenoids over the species in the genusPicea has been shown. In the oleoresins of spruces of the section Morinda, tricyclic diterpenoids with the abietane skeleton predominate.3. It has been established that when abietinol is oxidized by atmospheric oxygen, aromatization of the ring takes place with the formation of dehydroabietinol.Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 653–657, September–October, 1977.     

Development of a method for determining bornyl acetate in the products of the processing of Abies sibirica

Summary The conditions for the reaction of esters—bornyl acetate—with an alkaline solution of hydroxylamine have been studied by the method of steepest ascent. A method has been developed for determining esters in a CO₂ extract ofAbies sibirica.Krasnodar Scientific-Research Institute of the Food Industry. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 303–306, May–June, 1976.     

Lipids of the fruit of Citrus unshiu

The compositions and the amounts of various groups of liposoluble compounds in the component elements of the fruits ofCitrus unshiu Marc. [satsuna variety of mandarin orange] — the flavedo, the albedo, the membrane, and the flesh — have been determined by chromatographic and chemical methods. About 30 groups of lipid compounds belonging to the classes of neutral lipids and glyco- and phospholipids have been identified and characterized. The fatty-acid compositions of the main classes of lipids have been studied. About 30 different carotenoids have been determined in the various elements of the satsuma orange.M. V. Lomonosov Odessa Technological Institute of the Food Industry. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 342–348, May–June, 1989.     

Phospholipids of the seeds of two species of Erysimum

Summary The phospholipid complexes of the seeds ofErysimum diffusum andE. sylvestris have been investigated. It has been found that the amount of phospholipids in the seeds ofE. diffusum is lower than in those ofE. sylvestris, but their qualitative compositions are similar. The fatty-acid compositions of the triglycerides and of the total phospholipids of the two plants investigated have been studied. It has been established that the total phospholipids of the species ofErysimum under consideration and individual fractions of them differ by the degree of saturation and the qualitative and quantitative composition of the acids that they contain and, consequently, the phospholipids present in greatest amount differ in their molecular compositions.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 623–627, September–October, 1977.     

Alkaloids of four species of Argemone

The alkaloid compositions of four species of plants of the genusArgemone (A. mexicana L.,A. alba L.,A. platyceras Link et Otto., andA. hybrida) collected in the flowering phase in the Tashkent Botanical Garden have been studied. They have yielded 16 alkaloids. Corydine and isocorydine have been detected in plants of this genus for the first time, and O-methyl-platycerine has been found in nature for the first time.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 204–206, March–April, 1986.     

Oils of the seeds of Ziziphora pedicellata and Eremostachys molluceloides

Summary The fatty oils of the seeds of the wild speciesZiziphora pedicellata andEremostachys molluceloides (Labiatae) have been investigated. The glyceride, pigment, and hydrocarbon compositions of these oils and the fatty-acid composition of the oil ofZ. pedicellata have been determined.The oil ofE. molluceloides contains laballenic acid.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 324–328, May–June, 1975.     

Mono- and sesquiterpenoids of the oleoresin ofPinus koraiensis andP. pumila. crystal structure of 1β,4αH,7αH,10βH-Guaiane-5α,14-diol

The composition of the mono- and sesquiterpenoids of the oleoresin of two species of conifers of thePinaceae family has been studied. In the oleoresin ofPinus koraiensis Sieb. et Zucc. 10 oxidized monoterpenoids, 18 sesquiterpene hydrocarbons, and six sesquiterpene alcohols have been identified. In theoleoresin ofPinus pumila (Pall.) Rg1. 10 monoterpene hydrocarbons, six oxidized monoterpenoids, 14 sesquiterpene hydrocarbons, and four sesquiterpene alcohols have been found. The structure of 1β,4αH,7αH,10βH-guaiane-5α,14-diol, one of the hydroboration-oxidation products of an unidentified sesquiterpene alcohol isolated from both oleoresins, has been determined by x-ray structural analysis.     

The seed oils of some species of the family Cruciferae

Summary The physicochemical properties of the oils of the seeds of seven plants of the family Cruciferae —Cakile maritima, Sisymbrium altissimum, Sisymbrium Loeselii, Descurainia Sophia, Erysimum cheiranthoides, Brassica amoracioides andCrambe pontica — have been studied and their fatty acid compositions have been determined. The results obtained showed no marked differences from those given in the literature.Zaporozhe Medical Institute. Ukrainian Scientific-Research Institute of the Oils and Fats Industry. Zaporozhe Oils and Fats Combine. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 15–18, January–February, 1973.     

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.     

A study of the oils of Ocimum basilicum and Cardaria repens

Summary The seed oils of the plantsOcimum basilicum andCardaria repens have been studied. Their physico-chemical properties and fatty acid and glyceride compositions have been determined. Both oils contain a hydroxy acid of undetermined structure. The oil ofOcimum basilicum contains an unusual trienic acid.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 7–11, January, 1971.