Antibiotic Substances from the Heart Wood of Thuja plicata D. Don. III. The Constitution of alpha-Thujaplicin.

Gripenberg, Jarl; Laaksonen, Terttu

doi:10.3891/acta.chem.scand.02-0639

Cited by 20 publications

(6 citation statements)

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“…a-Thujaplicin, which is known for its fungicidal properties, has been found in various Cupressaceae together with P-and y-thujaplicin (16), particularly in Thuja plicata (17). It was identified in T. occidentnlis by early workers (18).…”

Section: Resultsmentioning

confidence: 99%

Essential Oil of the Wood ofThuja occidentalisL.

Andersen¹,

Gagnon

Collin

et al. 1995

Journal of Essential Oil Research

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Publication details, including instructions for authors and subscription information: ABSTRACT: Composition of the heartwood oil of Thuja occidentalis L. was investigated by a combination of capillary GC (retention indices) and GUMS. The oil was obtained by steam &stillation ofvarious lots ofwaste residues from cedar shingle industries. Twelve out of 20 observed compounds were identified. Monooxygenated sesquiterpene compounds are the most important components (80% of the total). Occidentalol is the main component: its relative concentration varies between 20% and 50%, dependng on the isolation parameters. This concentration decreased as the isolation proceeded, typically from 40-50% to 10-20% between 1 and 5 hours of &stillation. Three occidol isomers, occidenol, and a-, p-, and y-eudesmols were also observed in relative concentrations of 4% to 12%. The monoterpene family is represented by terpinen-4-01, and carvacrol. a-Thujaplicin, a tropolone derivative, is also among the products. The relative concentration of thujaplicin decreased from 5% to 0% between 1 and 5 hours of distillation.

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Section: Resultsmentioning

confidence: 99%

Essential Oil of the Wood ofThuja occidentalisL.

Andersen¹,

Gagnon

Collin

et al. 1995

Journal of Essential Oil Research

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“…The three isomeric isopropylpimelic acids obtained by catalytic reduction followed by permanganate oxidation were fully identified in each case by synthesis either of the acids themselves (4,125) or of the derived cyclohexanone (109). This provided direct proof of the positions of the isopropyl group as illustrated for the case of 7-thujaplicin (5-isopropyltropolone):…”

Section: • Oxidationmentioning

confidence: 87%

“…In a few cases these have been obtained crystalline and compared with synthetic specimens of known structure, thus providing, perhaps, the most direct proof of the orientation of substituents in the tropolone nucleus (96,98). As the hydrogenation may produce a mixture of cis and trans diols (and thus with additional substituents a complex mixture of stereoisomers may result), it has more frequently been found preferable to oxidize the crude hydrogenation product (including ketols) to the corresponding substituted pimelic acid, whose identification likewise provides satisfactory evidence for the orientation of substituents in the original tropolone (4,109,125,131).…”

Section: Reductionmentioning

confidence: 99%

“…More extensive oxidations with permanganate or chromic acid, although largely or wholly destroying the tropolone ring, have nevertheless contributed important evidence for the structures of purpurogallin (18) and of colchicine (455), and for the presence of isopropyl groups in -, ß-, and 7-thujaplicin and nootkatin (4,109,111,125, 401) and the 3-methyl-2-butenyl side chain in the latter compound (101,111).…”

Section: • Oxidationmentioning

confidence: 99%

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Tropones and Tropolones

Pauson¹

1955

Chem. Rev.

184

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“…The heartwood of T. plicata has been shown to be a source of tropone monoterpenoids [27][28][29][30][31] and lignans [32][33][34][35][36][37][38][39][40], and the dilactone thujin [41], while the bark and aerial parts have yielded diterpenoid derivatives [42,43]. There have been several investigations on the foliar essential oil compositions of T. plicata growing wild in western North America [44,45], cultivated in Poland [46,47], cultivated in Serbia [48], and growing wild in Idaho, USA [49].…”

Section: Introductionmentioning

confidence: 99%

Chemical Compositions and Enantiomeric Distributions of Foliar Essential Oils of Chamaecyparis lawsoniana (A. Murray bis) Parl, Thuja plicata Donn ex D. Don, and Tsuga heterophylla Sarg.

Ankney,

Swor,

Poudel

et al. 2024

Plants

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As part of our continuing interest in the essential oil compositions of gymnosperms, particularly the distribution of chiral terpenoids, we have obtained the foliar essential oils of Chamaecyparis lawsoniana (two samples), Thuja plicata (three samples), and Tsuga heterophylla (six samples) from locations in the state of Oregon, USA. The essential oils were obtained via hydrodistillation and analyzed by gas chromatographic techniques, including chiral gas chromatography—mass spectrometry. The major components in C. lawsoniana foliar essential oil were limonene (27.4% and 22.0%; >99% (+)-limonene), oplopanonyl acetate (13.8% and 11.3%), beyerene (14.3% and 9.0%), sabinene (7.0% and 6.5%; >99% (+)-sabinene), terpinen-4-ol (5.0% and 5.3%; predominantly (+)-terpinen-4-ol), and methyl myrtenate (2.0% and 5.4%). The major components in T. plicata essential oil were (−)-α-thujone (67.1–74.6%), (+)-β-thujone (7.8–9.3%), terpinen-4-ol (2.7–4.4%; predominantly (+)-terpinen-4-ol), and (+)-sabinene (1.1–3.5%). The major components in T. heterophylla essential oil were myrcene (7.0–27.6%), α-pinene (14.4–27.2%), β-phellandrene (6.6–19.3%), β-pinene (6.4–14.9%; >90% (−)-β-pinene), and (Z)-β-ocimene (0.7–11.3%). There are significant differences between the C. lawsoniana essential oils from wild trees in Oregon and those of trees cultivated in other geographical locations. The essential oil compositions of T. plicata are very similar, regardless of the collection site. There are no significant differences between T. heterophylla essential oils from the Oregon Coastal Range or those from the Oregon Cascade Range. Comparing essential oils of the Cupressaceae with the Pinaceae, there are some developing trends. The (+)-enantiomers seem to dominate for α-pinene, camphene, sabinene, β-pinene, limonene, terpinen-4-ol, and α-terpineol in the Cuppressaceae. On the other hand, the (−)-enantiomers seem to predominate for α-pinene, camphene, β-pinene, limonene, β-phellandrene, terpinen-4-ol, and α-terpineol in the Pinaceae.

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Antibiotic Substances from the Heart Wood of Thuja plicata D. Don. III. The Constitution of alpha-Thujaplicin.

Cited by 20 publications

References 0 publications

Essential Oil of the Wood ofThuja occidentalisL.

Essential Oil of the Wood ofThuja occidentalisL.

Tropones and Tropolones

Chemical Compositions and Enantiomeric Distributions of Foliar Essential Oils of Chamaecyparis lawsoniana (A. Murray bis) Parl, Thuja plicata Donn ex D. Don, and Tsuga heterophylla Sarg.

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