GAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART X. THE VOLATILE OILS OF THE LEAVES OF SITKA AND ENGELMANN SPRUCE

1964 ◽  
Vol 42 (5) ◽  
pp. 1057-1062 ◽  
Author(s):  
E. VON RUDLOFF
Keyword(s):  
Liquid Chromatography ◽  
Sitka Spruce ◽  
Bornyl Acetate ◽  
Gas Liquid Chromatography ◽  
Volatile Oils ◽  
Percentage Composition ◽  
Average Percentage ◽  
Engelmann Spruce ◽  
Leaf Oil ◽  
Aliphatic Esters

The leaf oils from Sitka and Engelmann spruce were obtained in 0.36 and 0.094% yield respectively. The average percentage composition was determined by gas–liquid chromatography. Sitka spruce leaf oil was found to contain mainly d-myrcene (23.5%), l-piperitone (23.2%), and d-camphor (17.2%). Smaller amounts of 1,8-cineole, l-β-phellandrene, p-cymene, two aliphatic esters, d-bornyl acetate, d-borneol, and d-terpinen-4-ol were also isolated and several other esters appeared to be present in small amounts. Engelmann spruce leaf oil was found to contain mainly cis-hex-3-en-1-ol (18.5%), d-camphor (16.0%), d-bornyl acetate (8.6%), d-linalool (5.8%), and two unidentified compounds. Smaller amounts of myrcene, β-phellandrene, p-cymene, piperitone, and several sesquiterpenoids were also recorded. Tricyclene, α-pinene, camphene, β-pinene, 3-carene, limonene, γ-terpinene, and terpinolene were found in small amounts in both oils.Phylogenetic relationships between the different spruces and other conifers are discussed.

GAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART IV. THE ANALYSIS OF THE VOLATILE OIL OF THE LEAVES OF EASTERN WHITE CEDAR

1961 ◽  
Vol 39 (6) ◽  
pp. 1200-1206 ◽  
Author(s):  
E. von Rudloff
Keyword(s):  
Liquid Chromatography ◽  
Volatile Oil ◽  
Complete Analysis ◽  
Bornyl Acetate ◽  
Gas Liquid Chromatography ◽  
Commercial Sample ◽  
Percentage Composition ◽  
White Cedar ◽  
Positive Identification ◽  
Eastern White Cedar

The complete analysis of the neutral volatile oil of the leaves of Eastern white cedar (Thujaoccidentalis L.) by means of gas–liquid chromatography was attempted. The mixture of terpenes was resolved into 28 monoterpenoid components and the major ones were isolated in 5- to 20-mg amounts. Comparison of infrared spectra and retention times with those of authentic specimens led to the positive identification of d-α-pinene, camphene, sabinene, d-limonene, p-cymene, γ-terpinene, l-fenchone, l-α-thujone, d-isothujone, camphor, and bornyl acetate. α-Thujene, β-pinene, myrcene, 1,8-cineole, terpinolene, and terpinen-4-ol were tentatively identified. The percentage composition of a commercial sample of the oil and of one obtained from a tree grown in Saskatoon was determined. The latter oil contained 7.0 to 7.5% of sesquiterpenoid components, which were resolved into four peaks on polyester columns at 180 °C.

Gas-liquid chromatography of terpenes. Part XVI. The volatile oil of the leaves of Juniperus ashei Buchholz

1968 ◽  
Vol 46 (5) ◽  
pp. 679-683 ◽  
Author(s):  
E. Von Rudloff
Keyword(s):  
Liquid Chromatography ◽  
Volatile Oil ◽  
Bornyl Acetate ◽  
Gas Liquid Chromatography ◽  
Juniperus Ashei ◽  
Methylene Groups ◽  
Leaf Oil ◽  
Ashe Juniper ◽  
First Time ◽  
Unique Chemical

The major components of the leaf oil of the Ashe juniper were found to be d-camphor (42.1 %), d-bornyl acetate (22.5%), d-limonene (8.4%), tricyclene (4.8%), d-camphene (4.4%), d-borneol (2.9%), p-cymene (2.8%), d-α-myrcene (1.8%), d-α-pinene (1.7%), and d-camphene hydrate (1.5%). This appears to be the first time that the latter alcohol has been isolated from a natural source. Smaller amounts of linalool, carvone, elemol, and traces of trans-2-methyl-6-methylene-3,7-octadien-2-ol were also identified. Several alcohols having terminal methylene groups were isolated in trace amounts.The monoterpenes found in this oil are not typical for the genus Juniperus and this result offers a unique chemical approach to the study of introgression of the Ashe juniper with other juniper species.

Chemosystematic studies in the genus Picea (Pinaceae). IV. The introgression of white and Engelmann spruce as found along the Bow River

1968 ◽  
Vol 46 (7) ◽  
pp. 901-908 ◽  
Author(s):  
R. T. Ogilvie ◽  
E. von Rudloff
Keyword(s):  
Liquid Chromatography ◽  
Distribution Pattern ◽  
White Spruce ◽  
Distribution Patterns ◽  
Quantitative Variation ◽  
Morphological Data ◽  
Gas Liquid Chromatography ◽  
Engelmann Spruce ◽  
Leaf Oil

The leaf oil of the spruces found along the Bow River from the foothills to Bow Summit was analyzed by gas–liquid chromatography. The terpene distribution patterns obtained were compared with the morphological data derived from the cones and twigs of the same trees. The results obtained confirm that typical white spruce occurs at low elevation whereas active hybridization with Engelmann spruce occurs at levels above 5000 ft. Although the trees at the timberline (7200 ft) had predominantly Engelmann spruce characteristics, much variation from tree to tree was encountered. In the terpene composition the quantitative variation was too large to permit conclusions about a typical Engelmann spruce terpene distribution pattern.

CHEMOSYSTEMATIC STUDIES IN THE GENUS PICEA (PINACEAE): II. THE LEAF OIL OF PICEA GLAUCA AND P. MARIANA

1967 ◽  
Vol 45 (9) ◽  
pp. 1703-1714 ◽  
Author(s):  
E. Von Rudloff
Keyword(s):  
Liquid Chromatography ◽  
Distribution Pattern ◽  
Picea Glauca ◽  
Black Spruce ◽  
Gas Liquid Chromatography ◽  
Oil Composition ◽  
Eastern Canada ◽  
Leaf Oil ◽  
Different Populations ◽  
Ecological Differences

The leaf oils from white and black spruce obtained from different locations in Western and Eastern Canada, Michigan, and Minnesota, have been analyzed by gas liquid chromatography. Both species were found to have a remarkably consistent and distinctive distribution pattern of the leaf oil terpenes. The quantitative variations encountered in samples of the same species from different populations are relatively small and ecological differences are not found to affect the leaf oil composition. Hence, analysis of spruce leaf oils appears to be highly suitable for a study of introgression and hybridization.

scholarly journals Simplified Method of Volatile Leaf Oil Analysis for Identification of Citrus Cultivars

HortScience ◽  
1991 ◽  
Vol 26 (2) ◽  
pp. 186-188
Author(s):  
Jacob B. Bade ◽  
Frederick G. Gmitter ◽  
Kim D. Bowman
Keyword(s):  
Citrus Sinensis ◽  
Sweet Orange ◽  
Volatile Components ◽  
Gas Liquid Chromatography ◽  
Citrus Paradisi ◽  
Volatile Oils ◽  
Breeding Research ◽  
Simplified Method ◽  
Leaf Oil ◽  
Potential Use

Volatile oils were extracted from aqueous leaf suspensions of sweet orange [Citrus sinensis (L.) Osb.] cultivars Hamlin, Navel, and Valencia and grapefruit (Citrus paradisi Macf.) cultivars Marsh and Ray Ruby. Pressurized air was used as the sparging gas, and volatile oils were collected in a C-18 cartridge. Gas-liquid chromatography was used to separate and quantify 17 volatile components. Significant quantitative differences for individual components made it possible to distinguish sweet orange from grapefruit (four components), `Marsh' from `Ray Ruby' grapefruit (two components), `Hamlin' from `Valencia' or `Navel' orange (six components), and `Valencia' from `Navel' (three components). The simplicity and sensitivity of the procedure suggest potential use for Citrus taxonomic, genetic, and breeding research.

Gas–liquid chromatography of terpenes. Part XVIII. The volatile oil of the leaves of Juniperus communis L.

1969 ◽  
Vol 47 (11) ◽  
pp. 2081-2086 ◽  
Author(s):  
E. von Rudloff ◽  
V. K. Sood
Keyword(s):  
Volatile Oil ◽  
Bornyl Acetate ◽  
Quantitative Composition ◽  
Hydroxy Ketone ◽  
Gas Liquid Chromatography ◽  
Citronellyl Acetate ◽  
Leaf Oil ◽  
The Many ◽  
Trace Constituents ◽  
Common Juniper

The volatile leaf oil of the local common juniper was found to consist mainly of α-pinene (73 to 83%) and smaller amounts (0.5 to 5%) of β-pinene, 3-carene, myrcene, limonene, methyl citronellate, bornyl acetate, myrtenal, myrtenol, myrtenyl acetate, α-terpineol, citronellol, citronellyl acetate, nerolidol, farnesol, and an unusual hydroxy ketone. Of the many trace constituents, β-phellandrene, citronellal, "iso-" citronellal, linalool, geraniol, isopulegol, 4-terpinenol, and ε-cadinene were isolated, whereas camphene, sabinene, α-phellandrene, γ-terpinene, terpinolene, p-cymene, fenchone, thujone, isothujone and δ-cadinene could only be tentatively identified.There was little variation in the quantitative composition of the leaf oil from one plant to another. Since the composition of this oil differs significantly from that of other juniper leaf oils, chemotaxonomic studies by means of leaf oil analysis are feasible.

Chemosystematic studies in the genus Pinus. IV. Leaf oil composition and geographic variation in jack pine of eastern North America

1982 ◽  
Vol 60 (12) ◽  
pp. 2762-2769 ◽  
Author(s):  
Martin S. Lapp ◽  
E. von Rudloff
Keyword(s):  
North America ◽  
Jack Pine ◽  
Bornyl Acetate ◽  
Eastern North America ◽  
Gas Liquid Chromatography ◽  
Oil Composition ◽  
Leaf Oil ◽  
Euclidean Distances ◽  
The Mean ◽  
Individual Trees

Leaf terpenes of 420 jack pines from 43 sites (Petawawa provenances) in eastern North America were analyzed by gas–liquid chromatography (GLC). In most trees the major components were α-pinene, β-pinene, myrcene, car-3-ene, limonene, β-phellandrene, and bornyl acetate. Eighteen other monoterpenes were identified and 13 sesquiterpenes were characterized by their spectral properties and GLC retention times. These data were analyzed by centroid cluster analysis of the mean-squared Euclidean distances, which showed that jack pine is a diverse species of two major terpene types with eight minor types and a few outlying individual trees. With the exception that the minor clusters and outliers tend to occur at the fringes of the jack pine range, there is no obvious geographic pattern to these clusters.

Chemosystematic studies in the genus Tsuga. Leaf and twig oil analysis of western hemlock

1975 ◽  
Vol 53 (9) ◽  
pp. 933-939 ◽  
Author(s):  
E. von Rudloff
Keyword(s):  
Chemical Composition ◽  
Eastern Hemlock ◽  
Western Hemlock ◽  
Bornyl Acetate ◽  
Oil Analysis ◽  
Volatile Oils ◽  
The Family ◽  
Leaf Oil ◽  
Different Populations ◽  
And Storage

The chemical composition of the volatile oils of the leaves and twigs of western hemlock and the variations caused by transportation and storage, and those found within trees and within populations, were determined. Whereas the leaf oil was found to be well suited for chemosystematic studies, that of the twigs is unsatisfactory. The major components (3–25%) of the leaf oil were β-phellandrene, myrcene, α-pinene, β-pinene, cis-ocimene, limonene, and α-phellandrene and smaller amounts of α-terpineol, methyl thymol, terpinolene, cadinene and muurolene isomers and their corresponding alcohols, terpinene-4-ol, trans-ocimene, camphene, γ-terpinene, bornyl acetate, thymol, and nerolidol were identified. cis-Ocimene (8–14%) appears to be highly characteristic of the species and it, as well as other quantitative differences, may serve as a distinguishing feature with regard to mountain hemlock, eastern hemlock, and other species of the family Pinaceae. Leaf samples from 10 trees give terpene patterns that are representative of a population; no significant differences at different elevations (10–700 m) were recorded. Although the means of the major terpenes from different populations may vary by several percent, consistent differences between coastal and interior populations of British Columbia were not found.

sGAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART XI. THE VOLATILE OIL OF THE LEAVES OF JUNIPERUS SCOPULORUM SARG

1964 ◽  
Vol 42 (8) ◽  
pp. 1890-1895 ◽  
Author(s):  
E. von Rudloff ◽  
F. M. Couchman
Keyword(s):  
Liquid Chromatography ◽  
Ornamental Plants ◽  
Rocky Mountain ◽  
Volatile Oil ◽  
Major Constituent ◽  
Gas Liquid Chromatography ◽  
Leaf Oil ◽  
Juniperus Scopulorum

The neutral leaf oil of Rocky Mountain juniper was analyzed by gas–liquid chromatography. d-Sabinene was found to be the major constituent (45.7%) and smaller amounts of d-limonene (11.4%), d-α-pinene (4.2%), γ-terpinene (1.15%), p-cymene (1.4%), l-linalool (1.2%), d-terpinen-4-ol (2.9%), citronellol (0.2%),l-β-elemene (0.2–0.3%), three isomeric cadinenes (2.7%), l-elemol (6.0%), and safrole (1.85%) were isolated. α-Thujene, camphene, car-3-ene, myrcene, α-terpinene, terpinolene, thujone, isothujone, methyl citronellate, sabinyl acetate, sabinol, geraniol, α- and δ-cadinol, and trans-isoeugenol were tentatively identified. An unidentified acetate (II) (4.7%) was isolated from the oxygenated sesquiterpene fraction and another appears to be present in trace amounts.The composition of the oils from the leaves of four local ornamental plants was found to differ significantly from that of the wild juniper.

GAS–LIQUID CHROMATOGRAPHY OF TERPENES: PART XIII. THE VOLATILE OIL OF THE LEAVES OF JUNIPERUS HORIZONTALS MOENCH

1965 ◽  
Vol 43 (5) ◽  
pp. 1017-1021 ◽  
Author(s):  
F. M. Couchman ◽  
E. Von Rudloff
Keyword(s):  
Liquid Chromatography ◽  
Rocky Mountain ◽  
Volatile Oil ◽  
Major Constituent ◽  
Gas Liquid Chromatography ◽  
Leaf Oil

The neutral leaf oil of the creeping juniper from the Prairies was analyzed by gas–liquid chromatography. d-Sabinene (36.5%) was found to be the major constituent, and smaller amounts of d-limonene (17.5%), p-cymene (3.0%), d-α-pinene (1.6%), γ-terpinene (0.4%), d-terpinen-4-ol (4.6%), linalool (0.8%), citronellol (0.8%), γ-cadinene (1.3%), l-elemol (3.8%), α-cadinol or γ-eudesmol (1.6%), and impure α-cyperone (3.9%) were isolated. α-Thujene (3.0%), camphene (0.2%), β-pinene (0.3%), myrcene (3.0%),β-phellandrene (0.2%,), terpinolene (0.1%), 2,4-(8)-p-menthadiene (0.1%), methyl citronellate (0.4%), and geraniol (0.2%) were tentatively identified. The composition of this oil closely resembles that of Rocky Mountain juniper leaves. A small amount of the oil from a hybrid of these two species was analyzed and the possibility of detecting hybridization by analysis of the leaf oil is discussed.

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