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.     

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.     

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 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.     

Triterpene glycosides of Thalictrum squarrosum. II. Molecular and crystal structure of squarrofuric acid

The structure of squarrofuric acid (an artifactual genin fromThalictrum squarrosum) has been confirmed by x-ray structural analysis and the configurations of the C13, C14, C17, C20, and C22 asymmetric centers have been established, which has enabled this compound to be assigned to the lanostane series with the following structure: 3,30-dihydroxy-20(S),22(S)-22,25-epoxylanost-9(11)-en-21-oic acid.Novosibirsk Institute of Organic Chemistry, Siberian Branch of the USSR Academy of Science. Irkutsk Institute of Organic Chemistry, Siberian Branch of the USSR Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 533–537, July–August, 1987.     

Structure of a new triterpenoid from the bark of the Siberian larch

A petroleum ether extract of the bark of the Siberian larch has yielded a new triterpenoid — the methyl ester of 3-hydroxy-24S,25R-epoxylanost-9(11)-en-27-oic acid, the structure of which has been established on the basis of spectral characteristics, chemical transformations, and x-ray structural analysis.Institute of Organic Chemistry, Siberian Branch Academy of Sciences of the USSR, Novosibirsk. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 641–645, September–October, 1990.     

Abietic and dehydroabietic acid derivatives from needle-free shoots of shoots ofPinus sylvestris

Methyl ethers of hydroxy and keto derivatives of abietic and dehydroabietic acids — 12-hydroxy- and 12-ketoabietic and 12-hydroxy-, 15-hydroxy-, and 17-ketodehydroabietic acids — have been isolated from an extract of needle-free shoots of the Scotch pine and have been identified in the form of methyl esters.S. M. Kirov Leningrad Academy of Wood Technology. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 345–351, May–June, 1985.     

Resin acids of the oleoresins of conifers growing in Transcarpathia

The chemical composition of the resin acids of the oleoresins of five species of the conifers of Transcarpathia has been studied. The oleoresins contain eight resin acids. ^8,9-Isopimaric and anticopalic acids have been found in the acid part of the oleoresin of the Weymouth pine.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 212–214, March–April, 1987.     

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.