Lignans of Western Red Cedar (<i>Thuja</i><i>plicata</i> Donn). VIII. Plicatinaphthol

MacLean, Harold; MacDonald, B. F.

doi:10.1139/v69-066

Cited by 12 publications

(5 citation statements)

References 4 publications

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“…The phenylhydrazones were obtained in good yield by reaction of 5-nitro-2-furaldehyde with substituted phenylhydrazines ( Table I). The phenylhydrazines were prepared as described by Hunsberger et al (4).…”

Section: Oh I Och3 I1mentioning

confidence: 99%

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Isolation and Characterization of Cytotoxic Principles from Hyptis verticillata Jacq

German

1971

Journal of Pharmaceutical Sciences

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Section: Oh I Och3 I1mentioning

confidence: 99%

“…The distribution coefficients of normally distributed polyoxyethylated octylphenols (3,4), where each surfactant has a range o f p values, are also plotted against the HLB in Fig. 1.…”

mentioning

confidence: 99%

Isolation and Characterization of Cytotoxic Principles from Hyptis verticillata Jacq

German

1971

Journal of Pharmaceutical Sciences

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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%

“…There are two separate ranges of T. plicata, a Coast-Cascade portion from southeastern Alaska (56°30′ N) to northwestern California (40°30′ N), and a Rocky Mountain section from British Columbia (54°30′ N) to Idaho and Montana (45°50′ N) (Figure 4) [26]. 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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“…The volatile fraction consists partly of compounds that are tropolone derivatives, the thujaplicins. The nonvolatile WRC heartwood extractives are mainly lignans (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). WRC is recognized as one of the world's most durable woods.…”

Section: Introductionmentioning

confidence: 99%

Thujin, a novel lactone isolated from the discolored heartwood of Thuja plicata Donn.

Jin¹,

Wilson²,

Swan³

1988

Can. J. Chem.

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. 66, 51 (1988).The chemical structure of a novel lactone isolated from the discolored heartwood of living western red cedar (WRC) (Thuja plicara Donn.) trees has been determined as 3,3,4,7,7,8-hexamethyl-2,6-dioxa-I,5-anthracene-dione, and given the trivial name thujin (1). The isolation, purification, and determination of the structure were carried out by a combination of chemical, chromatographic, and spectroscopic methods.LEHONG JIN, JACK W. WILSON et ERIC P. SWAN. Can. J. Chem. 66, 51 (1988) On a dttermink que la structure chimique d'une nouvelle lactone, qui a CtC isolke du bois dur dtcolort de ckdres rouges de I'ouest (cro) (Thuja plicata Donn.), est l'hexamtthyl-3,3,4,7,7,8 dioxa-2,6 anthracknedione-l,5 et que son nom trivial est thujine (I). On a isolk et purifit le produit et on a dttermint sa structure en faisant appel i une combinaison de mtthodes --chihiques, chromatographiques et spectroscopiques.[Traduit par la revue] Introduction During the past three decades, the large-scale chemical investigation of western red cedar (WRC) (Thuja plicata Donn.) heartwood extractives has led to identification of more than a dozen biologically active phenolic compounds (1). These heartwood extractives can be separated readily into volatile and nonvolatile fractions by steam distillation. The volatile fraction consists partly of compounds that are tropolone derivatives, the thujaplicins. The nonvolatile WRC heartwood extractives are mainly lignans (2-12). WRC is recognized as one of the world's most durable woods. It has long been understood from chemical and biological studies that the above two major groups of compounds in WRC heartwood extractives give the wood its durability. It is observed, however, that in certain areas of British Columbia (B.C.) there is a serious WRC heartwood decay problem, especially in living mature and over-mature trees. Questions arise on the biological roles of WRC heartwood extractives in response to microorganism attacks in living trees. In this study, a comparison of differences in extractive composition between healthy and discolored heartwood within the same growth zones in the tree was made. The discoloration of healthy wood was due to infection by microorganism attacks. We now report a novel lactone compound isolated from discolored heartwood extractives that was not present in healthy WRC heartwood extractives. Associated biological tests (13) in this study positively demonstrated that this lactone compound was a biodegradation product of the thujaplicins during infection by a fungus, Sporothrix sp., in the heartwood of a once living WRC tree.

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Lignans of Western Red Cedar (Thujaplicata Donn). VIII. Plicatinaphthol

Cited by 12 publications

References 4 publications

Isolation and Characterization of Cytotoxic Principles from Hyptis verticillata Jacq

Isolation and Characterization of Cytotoxic Principles from Hyptis verticillata Jacq

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.

Thujin, a novel lactone isolated from the discolored heartwood of Thuja plicata Donn.

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