Chemosystematic studies in the genus Pinus: the leaf oil of Pinus contorta var. latifolia

1971 ◽  
Vol 49 (7) ◽  
pp. 1201-1210 ◽  
Author(s):  
G. Pauly ◽  
E. von Rudloff
Keyword(s):  
Rocky Mountains ◽  
Chromatographic Analysis ◽  
Pinus Contorta ◽  
Volatile Oil ◽  
Jack Pine ◽  
High Yield ◽  
Bornyl Acetate ◽  
Mean Values ◽  
Leaf Oil ◽  
Cis And Trans

Gas chromatographic analysis of the volatile oil of the leaf oil of lodgepole pine from the Rocky Mountains showed 1-β-phellandrene (34%) and 1-β-pinene (30.5%) as major components. Lesser amounts of α-pinene (6.5%), myrcene (3%), cis-ocimene (2.5%), 3-carene (1.5%), terpinolene (1%), γ-terpinene (0.3%), α-terpineol (4%), terpinen-4-ol (0.5%), estragole (0.5%), bornyl acetate (0.5%), linalool (0.3%), a mixture of cadinene isomers (5%), cadinol and muurolol isomers (1.5%), nerolidol (0.6%), and tentatively identified camphene, α-phellandrene, limonene, isopulegol, camphene hydrate, citronellol, bisabolol, and cis- and trans-farnesol were recorded. In addition, hex-2-en-1-al (1.5%) and cis-hex-3-en-1-ol (1%) were isolated, but these may be artefacts because the leaves had to be cut to obtain a high yield of oil. The variation in the relative amounts of terpenes in leaves at different heights on a tree was small. Quantitative analysis of 10 samples per population showed a relatively high tree-to-tree variation, but similar mean values for populations in the Bragg Creek – Kananaskis – Eisenhower Junction area of Alberta. Small, but possibly significant differences were recorded for the samples from the Cypress Hills. Populations north of Lake Louise Station to Jasper, Hinton, and Edson were found to contain a few individuals with terpenes characteristic of jack pine. This indicates that the effects of introgression of lodgepole and jack pine can be detected further southwest than previously reported.

Chemosystematic studies in the genus Abies. III. Leaf and twig oil analysis of amabilis fir

1977 ◽  
Vol 55 (24) ◽  
pp. 3087-3092 ◽  
Author(s):  
E. von Rudloff ◽  
R. S. Hunt
Keyword(s):  
Gas Chromatography ◽  
Volatile Oil ◽  
Quantitative Variation ◽  
Bornyl Acetate ◽  
Oil Analysis ◽  
Acetate Methyl ◽  
Leaf Oil ◽  
Cis And Trans

The volatile oil of the leaves, and also the twigs, of amabilis fir consists mainly of (−)-β-phellandrene, (+)-car-3-ene, (−)-β-pinene, (−)-α-pinene, myrcene, (−)-limonene, terpinolene, β-sesquiphellandrene, and β-bisabolene. Smaller relative amounts of santene, tricyclene, camphene, sabinene, α-phellandrene, cis- and trans-ocimene, γ-terpinene, linalool, terpinen-4-ol, α-terpineol, bornyl acetate, methyl thymol, thymol, α-cubebene, α-copaene, caryophyllene, humulene, and cadinene–muurolene isomers and their corresponding alcohols were also identified. The presence of three minor diterpene hydrocarbons and manool was indicated by gas chromatography – mass spectrometry.The quantitative variation within trees, between trees, and among northern, central, and southern populations was determined. The high tree-to-tree variability obscures any significant (P = 0.05) geographic trend that may exist. Several qualitative and many significant quantitative differences exist between the leaf oil compositions of amabilis, grand, alpine, and balsam firs andpossibly also noble, white, and California red firs, and these can serve well in chemosystematic studies.

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.

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.

scholarly journals Drying Induced Impact on Composition and Oil Quality of Rosemary Herb, Rosmarinus Officinalis Linn

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2830
Author(s):  
Hamdoon A. Mohammed ◽  
Mohsen S. Al-Omar ◽  
Salman A. A. Mohammed ◽  
Mohamed S. A. Aly ◽  
Abdulmalik N. A. Alsuqub ◽  
...  
Keyword(s):  
Gas Chromatography ◽  
Oil Quality ◽  
Radical Scavenging ◽  
Volatile Oil ◽  
Rosmarinus Officinalis ◽  
Major Constituent ◽  
Bornyl Acetate ◽  
Major Chemical ◽  
Gas Chromatography Mass Spectroscopy ◽  
The One

The natural drying of Rosmarinus officinalis Linn. herbs severely affects its volatile oil quality and yields, which is reported here for the first time. The oils obtained through hydrodistillation from fresh, one, two, and three-weeks dried herbs were analyzed by gas chromatography–mass spectroscopy (GC–MS) and gas chromatography–flame ionization detector (GC-FID), and the yields were 198 ± 3.45, 168.7 ± 5.11, and 97.8 ± 1.27 mg, respectively, as compared to the internal referral standard of 327 ± 5.91 mg yield of the one-week dried herbs’ oil. Camphor, the major constituent, significantly depleted from 20.96% to 13.84%, while bornyl acetate yields increased from 1.42% to 12.46% (p values < 0.0001) in three-weeks drying, reflecting the redox processes undergoing within the oil during drying. Several constituents (25) were found in one-week dried herbs’ oil as compared to the fresh, two-, and three-weeks oils, which consisted of 23, 19, and 14 constituents, respectively, leading to the recommendation of the one-week drying of the herb for maximum oil yield. The DPPH (2, 2-diphenyl-1-picryl-hydrazyl) reactivity was highest for the two- and three-weeks dried herb-based oils, followed by the one-week dried- and fresh-herb-based oils (p < 0.0001), again indicating major chemical changes during herbs’ dryings, affecting the free-radical scavenging capacity of these batches of oils obtained after different drying times.

scholarly journals Leaf Essential Oil Composition of Five Species of Beilschmiedia from Monteverde, Costa Rica

2007 ◽  
Vol 2 (1) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
William N. Setzer ◽  
William A. Haber
Keyword(s):  
Costa Rica ◽  
Essential Oil ◽  
Carbonyl Compounds ◽  
Essential Oil Composition ◽  
Chemical Compositions ◽  
Oil Composition ◽  
Germacrene D ◽  
Leaf Oil ◽  
Leaf Essential Oil ◽  
Cis And Trans

The leaf essential oils of five species of Beilschmiedia from Monteverde, Costa Rica (Beilschmiedia alloiophylla, B. brenesii, B. costaricensis, B. tilaranensis, and an undescribed Beilschmiedia species “chancho blanco”) have been obtained by hydrodistillation and analyzed by GC-MS in order to discern the differences and similarities between the volatile chemical compositions of these species. The principal constituents of B. alloiophylla leaf oil were germacrene D (18.9%), cis- and trans-β-ocimene (18.8% and 9.3%, respectively), α-pinene (11.8%), and bicyclogermacrene (9.1%). The leaf oil of B. brenesii was composed largely of the sesquiterpenes germacrene D (19.3%), β-caryophyllene (13.4%), α-copaene (9.0%), α-humulene (8.1%), and δ-cadinene (5.8%), and the carbonyl compounds 2-undecanone (12.8%), trans-2-hexenal (8.8%), and 2-tridecanone (3.8%). α-Bisabolol (72.1%) dominated the leaf oil of B. costaricensis, while B. tilaranensis had germacrene D (54.9%), β-caryophyllene (14.8%), and δ-cadinene (5.1%) as major components. Beilschmiedia “chancho blanco” leaf oil was composed largely of β-caryophyllene (16.6%), bicyclogermacrene (14.1%), and α-pinene (12.1%).

Chemosystematic studies in the genus Abies. II. Leaf oil analysis of grand fir

1976 ◽  
Vol 54 (16) ◽  
pp. 1926-1931 ◽  
Author(s):  
E. von Rudloff
Keyword(s):  
Mass Spectrometer ◽  
Geographical Variation ◽  
Geranyl Acetate ◽  
Bornyl Acetate ◽  
Oil Analysis ◽  
Gas Chromatograph ◽  
South Central ◽  
White Fir ◽  
Leaf Oil

The volatile leaf oil of the grand fir consists mainly of (−)-α-pinene, (−)-camphene, (−)-β-pinene, (−)-β-phellandrene, (−)-bornyl acetate, cadinene and muurolene isomers, and two cubebol isomers. Santene, tricyclene, myrcene, car-3-ene, limonene, terpinolene, p-cymene, camphenolene aldehyde, camphor, borneol, terpinen-4-ol, α-terpineol, citronellyl and geranyl acetate, α-cubebene, α-copaene, calamenene, and two farnesol isomers were also isolated. Attempts to identify these terpenes with a combined gas chromatograph – mass spectrometer failed to give unequivocal data and identities had to be confirmed by isolation and recording of other spectra. Except for β-pinene and β-phellandrene, within-tree and tree-to-tree variation of terpene percentages was relatively small. The leaf oil terpene composition appears to be well suited to determine geographical variation. Only minor differences were recorded between some northern coastal and interior populations, but samples from south-central Oregon showed major differences that are indicative of introgression with white fir.

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.

The Distribution and Composition of Extractives in Jack Pine Trees

1973 ◽  
Vol 3 (4) ◽  
pp. 516-521 ◽  
Author(s):  
G. D. Sinclair ◽  
D. K. Dymond
Keyword(s):  
Chromatographic Analysis ◽  
Jack Pine ◽  
Resin Acids ◽  
Extractive Content ◽  
Single Tree ◽  
Pine Trees ◽  
Liquid Chromatographic Analysis ◽  
Different Diameters ◽  
Liquid Chromatographic

The distribution of acetone-soluble extractives in jack pine trees of different diameters, and at different locations within a single tree was studied. The amount of extractives varied from 3% in a 10 cm diameter tree to 9.6% in a 50 cm diameter tree. Within a single tree the top had the least amount of extract, 2.7%, while the needle bearing twigs had the greatest amount, 4.6%. Gas–liquid chromatographic analysis of the extracts showed that the composition was relatively similar for all sizes of trees and within one tree except in the top and the branches. The heartwood of the tree had a much higher extractive content than the sapwood and contained a higher concentration of resin acids, pinocembrin, and pinobanksin.

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.

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