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

The isolation and structure of a new lignan, 1,6-dihydroxy-2-(hydroxymethyl)-7-methoxy-4-(3′,4′-dihydroxy-5′-methoxyphenyl)-3-naphthoic acid lactone (plicatinaphthol, 2), in which the 4-aryltetrahydronaphthalene structure of plicatin (1) has been aromatized to a 4-arylnaphthol nucleus are described. Proof of structure of the parent compound and its tetramethyl, tetraacetyl, and tetraethyl derivatives is presented both by analytical and spectral techniques, in addition to the synthesis of the tetramethyl derivative starting from podophyllotoxin.

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Lignans of western red cedar (Thujaplicata Donn). IX. Plicatinaphthalene

Canadian Journal of Chemistry ◽

10.1139/v69-743 ◽

1969 ◽

Vol 47 (23) ◽

pp. 4495-4498 ◽

Cited By ~ 7

Author(s):

Harold MacLean ◽

B. F. MacDonald

Keyword(s):

Thin Layer ◽

Water Soluble ◽

Hot Water ◽

Methylenedioxy Group ◽

Red Cedar ◽

Naphthoic Acid ◽

Trimethyl Ether ◽

Acid Lactone ◽

Western Red Cedar ◽

Layer Chromatography

The last of nine lignans detectable by thin-layer chromatography in the hot-water soluble extractives of western red cedar (Thujaplicata Donn) heartwood has been determined as 6-hydroxy-2(hydroxy-methyl)-7-methoxy-4-(3′,4′-dihydroxy-5′-methoxyphenyl)-3-naphthoic acid lactone (plicatinaphthalene 2) by spectrometric methods, by degradation studies of derivatives, and by preparation of its trimethyl ether derivative 3 from dehydroanhydropicropodophyllin by opening of the methylenedioxy group with boron trichloride.

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LIGNANS OF WESTERN RED CEDAR (THUJA PLICATA DONN): V. HYDROXYTHUJAPLICATIN METHYL ETHER

Canadian Journal of Chemistry ◽

10.1139/v66-274 ◽

1966 ◽

Vol 44 (15) ◽

pp. 1827-1830 ◽

Cited By ~ 7

Author(s):

Harold MacLean ◽

Koji Murakami

Keyword(s):

Methyl Ether ◽

Parent Compound ◽

Analytical Data ◽

Hot Water ◽

Spectral Studies ◽

Thuja Plicata ◽

The Third ◽

Red Cedar ◽

Western Red Cedar ◽

Thuja Plicata Donn

The structure of another guaiacyl–syringyl type lignan, which was previously separated from the hot-water extractive of western red cedar (Thujaplicata Donn), has now been determined as 2-hydroxy-2-(4″-hydroxy-3″,5″-dimethoxybenzyl)-3-(4′-hydroxy-3′-methoxybenzyl)-butyrolactone (III). This lignan is the third member of the thujaplicatin series and has been given the name of hydroxythujaplicatin methyl ether. Analytical data and degradational and spectral studies of the parent compound and its methylated derivatives are presented as proof of structure.

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Lignans of Western Red Cedar (Thuja plicata Donn). XI. β-Apoplicatitoxin

Canadian Journal of Chemistry ◽

10.1139/v73-074 ◽

1973 ◽

Vol 51 (4) ◽

pp. 482-485 ◽

Cited By ~ 5

Author(s):

Bruce F. MacDonald ◽

G. M. Barton

Keyword(s):

Carboxylic Acid ◽

Stereoselective Synthesis ◽

Thuja Plicata ◽

Red Cedar ◽

Acid Lactone ◽

Western Red Cedar ◽

Thuja Plicata Donn

The structure of the eleventh in the series of novel lignans from the heartwood of western red cedar (Thuja plicata Donn) has been determined as 1,4-dihydronaphthalene-6-hydroxyl-2-(hydroxymethyl)-7-methoxy-4(3′,4′-dihydroxy-5′-methoxyphenyl)-3-carboxylic acid lactone (β-apoplicatitoxin) (1) by spectrometric methods and by aromatization to the known compound trimethylplicatinaphthalene. This lignan provides an intermediate to the possible stereoselective synthesis of derivatives related to the picropodophyllin series.

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Mass and nutrient content of woody debris and forest floor in western red cedar and western hemlock forests on northern Vancouver Island

Canadian Journal of Forest Research ◽

10.1139/x93-134 ◽

1993 ◽

Vol 23 (6) ◽

pp. 1052-1059 ◽

Cited By ~ 58

Author(s):

Rodney J. Keenan ◽

Cindy E. Prescott ◽

J.P. Hamish Kimmins

Keyword(s):

Forest Floor ◽

Forest Type ◽

Woody Debris ◽

Nutrient Content ◽

Vancouver Island ◽

Western Hemlock ◽

N Availability ◽

Red Cedar ◽

The Mean ◽

Western Red Cedar

Biomass and C, N, P, and K contents of woody debris and the forest floor were surveyed in adjacent stands of old-growth western red cedar (Thujaplicata Donn)–western hemlock (Tsugaheterophylla (Raf.) Sarg.) (CH type), and 85-year-old, windstorm-derived, second-growth western hemlock–amabilis fir (Abiesamabilis (Dougl.) Forbes) (HA type) at three sites on northern Vancouver Island. Carbon concentrations were relatively constant across all detrital categories (mean = 556.8 mg/g); concentrations of N and P generally increased, and K generally decreased, with increasing degree of decomposition. The mean mass of woody debris was 363 Mg/ha in the CH and 226 Mg/ha in the HA type. The mean forest floor mass was 280 Mg/ha in the CH and 211 Mg/ha in the HA stands. Approximately 60% of the forest floor mass in each forest type was decaying wood. Dead woody material above and within the forest floor represented a significant store of biomass and nutrients in both forest types, containing 82% of the aboveground detrital biomass, 51–59% of the N, and 58–61% of the detrital P. Forest floors in the CH and HA types contained similar total quantities of N, suggesting that the lower N availability in CH forests is not caused by greater immobilization in detritus. The large accumulation of forest floor and woody debris in this region is attributed to slow decomposition in the cool, wet climate, high rates of detrital input following windstorms, and the large size and decay resistance of western red cedar boles.

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Influence of nursery culture on western red cedar

New Forests ◽

10.1007/bf00025370 ◽

1994 ◽

Vol 8 (3) ◽

pp. 231-247 ◽

Cited By ~ 5

Author(s):

Raymund S. Folk ◽

Steven C. Grossnickle ◽

John E. Major ◽

James T. Arnott

Keyword(s):

Nursery Culture ◽

Red Cedar ◽

Western Red Cedar

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Characterization of the complete plastome of western red cedar, Thuja plicata (Cupressaceae)

Conservation Genetics Resources ◽

10.1007/s12686-017-0948-1 ◽

2017 ◽

Vol 11 (1) ◽

pp. 79-81

Author(s):

Kole F. Adelalu ◽

Xiao-Jian Qu ◽

Yan-Xia Sun ◽

Tao Deng ◽

Hang Sun ◽

...

Keyword(s):

Thuja Plicata ◽

Red Cedar ◽

Western Red Cedar

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THE BEHAVIOUR OF FIVE WOOD SPECIES IN COMPRESSION

IAWA Journal ◽

10.1163/22941932-90000298 ◽

2002 ◽

Vol 23 (2) ◽

pp. 201-211 ◽

Cited By ~ 11

Author(s):

Simon Ellis ◽

Paul Steiner

Keyword(s):

Young’S Modulus ◽

Populus Tremuloides ◽

Wood Species ◽

Young's Modulus ◽

Douglas Fir ◽

Thuja Plicata ◽

Trembling Aspen ◽

Moisture Contents ◽

Red Cedar ◽

Western Red Cedar

Five wood species, Oregon ash (Fraxinus latifolia Benth.), Balau (Shorea spp.), Douglas-fir (Pseudotsuga menziesii (Mirb.) Franco), Western red cedar (Thuja plicata Donn ex D. Don), and Trembling aspen (Populus tremuloides Michx.) were loaded in compression longitudinally, radially and tangentially. The wood cubes were conditioned to one of four moisture contents prior to loading. Small cubes were loaded until no void space remained after which samples were released and soaked in water. Stress /strain curves were recorded over the whole range of strain and cube thicknesses were recorded at the end of the compression, after release from the testing apparatus, and after soaking in water. Denser woods resulted in a greater Young’s modulus, higher levels of stress and shorter time to densification than did less dense woods. Higher initial moisture contents apparently increased the plasticity of the wood leading to a lower Young’s modulus and lower levels of stress during compression, greater springback after release of stress and greater recovery after swelling in water. Differences observed in the radial and tangential behaviours were believed to be due to the supporting action of the rays when the wood was compressed in the radial direction in balau and trembling aspen and to the relative difference between the lower density earlywood and higher density latewood regions in ash, Douglas-fir and western red cedar.

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Lignans of western red cedar (Thuja plicata Donn). VI. Dihydroxythujaplicatin methyl ether

Canadian Journal of Chemistry ◽

10.1139/v67-054 ◽

1967 ◽

Vol 45 (3) ◽

pp. 305-309 ◽

Cited By ~ 5

Author(s):

Harold MacLean ◽

Koji Murakami

Keyword(s):

Nuclear Magnetic Resonance ◽

Magnetic Resonance ◽

Methyl Ether ◽

Degradation Products ◽

Parent Compound ◽

Thuja Plicata ◽

Red Cedar ◽

Magnetic Resonance Data ◽

Resonance Data ◽

Thuja Plicata Donn

Proof of structure is presented for another lignan of the thujaplicatin series, 2,3-dihydroxy-2-(4″-hydroxy-3″,5″-dimethoxybenzyl)-3-(4′-hydroxy-3′-methoxybenzyl)-butyrolactone (I) (dihydroxythujaplicatin methyl ether). Analytical and spectral (ultraviolet, infrared, and nuclear magnetic resonance) data on derivatives and degradation products, in addition to the parent compound, are presented.

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