Labdane and cembrane diterpenoids from the oleoresin of thePicea ajanensis

From the oleoresin of the Yeddo spruce (Picea ajanensis Fisch.) have been isolated cis-abienol, isocembrol, geranyllinalool, epimanool, and labd-13E-ene-8,15-diol. It has been established that the biosynthesis of isocembrol and epimanool in the Yeddo spruce is not accompanied by the formation of epimers of these compounds — 4-epiisocembrol and manool — and that cis-abienol is the main neutral oxygen-containing compound of the oleoresin investigated in terms of content.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 178–181, March–April, 1981.     

Neutral substances of the oleoresin ofAbies sibirca

Conclusions From the oleoresin ofAbies sibirica Ledeb. have been isolated manoyl oxide and a new diterpene alcohol with the composition C₂₀ H₃₄ O (I) which we have called neoabienol. It has been established that it is labd-11,13-dien-8-ol.Khimiya Prirodnykh Soedinenii, Vol. 5, No. 4, pp. 247–251, 1969     

Volatile components of the oleoresin of Abies alba

The composition of the volatile compoents of the oleoresin ofAbies alba Mill, has been studied. In this oleoresin 19 monoterpene compounds have been identified, the main ones of which are - and -pinenes and limonene. Among the 24 sesquitepene compounds identified in the oleoresin, 4 new terpenoids have been found: 10S,11S-himachala-2,3-diene, 10S,11S-himachala-3(12),4-diene, humula-4,9-dien-8-ol, and 4S,5S,10S-selin-6-en-4-ol. For the first time, , , and -himachalenes, 9-epicaryophyllene, intermedeol, and longiborneol have been found in the oleoresins of conifers of the genus Albies. A distinguishing feature of firs of the Albae series is the low content of oxygen-containing monoterpenoids and of sesquiterpenoids of the bisabolane series.Novosibirsk Institute of Organic Chemistry, Siberian Branch, USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 193–197, March–April, 1988.     

Composition of the neutral fraction of the oleoresin ofPinus sibirica

Summary Three sesquiterpene hydrocarbons, muurolene-1, muurolene-2, and muurolene-3, have been isolated from the oleoresin ofPinus sibirica R. Mayr.Muurolene-3 is D--muurolene and has the structure (VIII).Khimiya Prirodnykh Soedinenii, Vol. 2, No. 3, pp. 173–176, 1966     

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.     

Terpenoids ofPinus funebris

The complete chemical composition of the oleoresin of the Chinese pine growing in the Far East has been studied. It has been shown that the main components of the monoterpenes are -pinene, -phellandrene, and -terpineol. The sesquiterpenes contain longifolene and compounds related to it. The oleoresin of the Chinese pine is distinguished by a high content of diterpene cembrane compounds. Among the resin acids, dehydroabietic acid predominates (42.4%).Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 444–448, July–August, 1984.     

Terpenoids of the oleoresin of the larch growing in Kamchatka

The complete chemical composition of the oleoresin of the larchLarix cajanderi M. growing in Kamchatka has been studied. Fifty-four terpene compounds have been isolated and identified. It has been shown that among the monoterpenes the main constituents are - and -pinenes, their amounts being 66.3% and 18.3%, respectively. Among the sesquiterpene hydrocarbons the main components are -cadiene and -elemene (15 and 17%). Diterpenoids are represented mainly by bicyclic labdane compounds — epimanool (15%), larixylacetate (28%), and larixol (40%). In the acidic fraction of the oleoresin, isopimaric acid (40%) predominates.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 340–343, May–June, 1980.     

The sesquiterpene lactones ofStizolophus balsamita

Summary From the epigeal part ofStizolophus balsamita (Lam.) Cass. ex Takht. a new sesquiterpene lactone balsamin has been isolated with the composition C₂₀H₂₆O₆, mp 242–244°C (from ethanol), [] _D ¹⁷ –45.70° (c 1.9; chloroform). Do the basis of the basis of the IR, UV, and PMR spectra of balsamin and its acetate, a stereochemical structure has been proposed for balsamin, and the structures of stizolin and stizolicin isolated previously from the same plant have also been supplemented by stereochemistry.All-Union Scientific-Research Institute of Medicinal Plants, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 467–472, July–August, 1976.     

Labdane acids and other components of the needles ofPinus pumila

The terpenoid and aliphatic components of an ethereal extract of the olerosein of the Japanese stone pine have been investigated. Among them, 33 compounds have been identified, ten of which were isolated in the individual state. The labdane acids of the oleoresin investigated were represented by 19-0-succinylagatholic and 3-hydroxy-, 3-acetoxy, and 3-ketoanticopalic acids.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 206–211, March–April, 1985.     

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.     

Alkaloids ofOxytropis. III. Trichophydine

A new alkaloid, which has been named trichophydine, has been isolated from the epigeal part ofOxytropis trichophysa growing in Mongolia. On the basis of the spectral characteristics of the hydrochloride, the structure of 2-O-benzoyl-2()-phenylethylamine, which has been synthesized previously, has been established for trichophydine.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, FAX (3712) 62 73 48. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 414–416, May–June, 1994.     

Pinusolide, a new diterpenoid from Pinus sibirica and P. korsensis

Conclusions From the neutral fraction of the oleoresin ofPinus sibirica R. Mayr andP. koraensis Sieb. et Zucc. a new diterpenoid has been isolated which we have called pinusolide, whose structure has been shown to be that of methyl labd-8(20)-1,3-dien-16,15-olid-19-oate.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 541–545, September–October, 1970.     

Flavonoids of Bidens tripartita. III

Summary It has been established that substance 4, isolated previously fromBidens tripartita, is (R-2)isookanin 7-O--D-glucopyranoside [(R-2)flavanomarein]. The compound isolated is a new one for the genusBidens L.Khar'kov State Pharmaceutical Institute. Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 144–147, March–April, 1975.     

Chrysin and its derivatives in plants of the genusScutellaria

Summary 1. A glycoside (II) identified by chrysin 7--glucopyranosiduronic acid has been isolated from the epigeal part ofScutellaria scordiifolia in a yield of 2.0–2.2%.2. A glycoside (IV), characterized as 2-methoxychrysin 7--D-glucopyranosiduronic acid has been isolated from the roots ofS. granulosa.3. This is the first time that chrysin and 2-methoxychrysin and their 7-glucuronides have been isolated from theScutellaria species mentioned.Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Ukrainian Zonal Research Station for Medicinal Plants, Poltava. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 730–735, November–December, 1976.     

Berberis alkaloids XXXV. The structure of nummularine

The new N-benzyltetrahydroisoquinoline alkaloid nummularine has been isolated from the leaves ofBerberis nummularia. On the basis of a study of its spectral characteristics (PMR, IR, and mass spectra), the structure of nummularine has been established as 6-hydroxy-N-(3-hydroxy-4-methoxybenzyl)-7-methoxy-1-methyltetrahydroisoquinoline.Translated from Khimiya Prirodnykh Soedinenii, Vol. 33, No. 1, pp. 91–93, January–February, 1997.     

Sorption of hafnium on hydrous titanium oxide using radiotracer technique

The sorption of hafnium on hydrous titanium oxide (TiO₂·1.94 H₂O) has been studied in detail. Maximum sorption of hafnium can be achieved from a pH 7 buffer solution containing boric acid and sodium hydroxide using 50 mg of the oxide after 30 minutes shaking. The value ofk _d, the rate constant of intraparticle transport for hafnium sorption, from 0.01M hydrochloric and perchloric acid and pH 7 buffer solutions has been found to be 17 mmole·g^–1·min^–2. The kinetics of hafnium sorption follows Lagergren equation in 0.01M HCl solution only. The values of the overall rate constantK=6.33·10^–2 min^–1 and of the rate constant for sorptionk ₁=6.32·10^–2 min^–1 and desorptionk ₂=2.28·10^–5 min^–1 have been evaluated using linear regression analysis. The value of correlation factor() is 0.9824. The influence of hafnium concentration on its sorption has been examined from 4.55·10^–5 to 9.01·10^–4 M from pH 7 buffer solution. The sorption data followed only the Langmuir sorption isotherm. The saturation capacity of 9.52 mmole·g^–1 and of a constant related to sorption energy have been estimated to be 2917 dm³·mole^–1. Among all the additional anions and cations tested only citrate ions reduce the sorption significantly. Under optimal experimental conditions selected for hafnium sorption, As(III), Sn(V), Co(II), Se(IV) and Eu(III) have shown higher sorption whereas Mn(II), Ag(I) and Sc(III) are sorbed to a lesser extent. It can be concluded that a titanium oxide bed can be used for the preconcentration and removal of hafnium and other metal ions showing higher sorption from their very dilute solutions. The oxide can also be employed for the decontamination of radioactive liquid waste and for pollution abatement studies.     

Diterpenoids ofPulicaria salviifolia. III. The structure of salvicinin

The new diterpene acid salvicinin has been isolated from the epigeal part ofPulicaria salviifolia and its structure has been established as 15-acetoxy-6-hydroxy-trans-cleroda-3,13-dien-19-oic acid. A capacity of salvicinin for undergoing lactonization in the presence of acetic anhydride has been revealed, and the lactone formed has been isolated and chracterized.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, Fax (3712) 62 73 48. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 246–249, March–April, 1994.     

Triterpenoids from the leaves ofBetula costata

Summary From the unsaponifiable part of an ethereal extract of the leaves ofBetula costata four triterpenoids of the dammarane series have been isolated. For the previously unknown triterpenoids A and C the structures of dammar-24-ene-3,17,20-triol and of betulafoliene-tetraol oxide, respectively, have been proposed.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center of the Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 757–762, November–December, 1976.