Lignans of western red cedar (Thuja plicata Donn). VII. Dihydroxythujaplicatin

1967 ◽  
Vol 45 (7) ◽  
pp. 739-740 ◽  
Author(s):  
Harold MacLean ◽  
B. F. MacDonald
Keyword(s):  
Hot Water ◽  
Thuja Plicata ◽  
Red Cedar ◽  
Degradation Studies ◽  
Western Red Cedar ◽  
Thuja Plicata Donn

The structure of a seventh lignan from the hot-water extractive of western red cedar, which was partially separated in a previous paper, has been determined as 2,3-dihydroxy-2-(3″,4″-dihydroxy-5″-methoxybenzyl)-3-(4′-hydroxy-3′-methoxybenzyl)-butyrolactone (I). This lignan is the fifth member of the thujaplicatin series and is trivially named dihydroxythujaplicatin. Methylation, ethylation, and degradation studies provide proof of structure by comparison with known compounds.

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

1966 ◽  
Vol 44 (15) ◽  
pp. 1827-1830 ◽  
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.

THE POLYOXYPHENOLS OF WESTERN RED CEDAR (THUJA PLICATA DONN). II. DEGRADATION STUDIES ON PLICATIC ACID, A POSSIBLE LIGNAN ACID

1960 ◽  
Vol 38 (12) ◽  
pp. 2387-2394 ◽  
Author(s):  
J. A. F. Gardner ◽  
B. F. MacDonald ◽  
Harold MacLean
Keyword(s):  
Thuja Plicata ◽  
Benzoic Acids ◽  
Red Cedar ◽  
Alkaline Permanganate ◽  
Benzene Rings ◽  
Trimethyl Ether ◽  
Degradation Studies ◽  
Western Red Cedar ◽  
Thuja Plicata Donn

Plicatic acid, C20H22O10, a polyoxyphenol from western red cedar heartwood, described in a previous paper, has been further characterized by preparation and analysis of additional crystalline derivatives. Crystalline trimethyl and triethyl ethers have been oxidized by alkaline permanganate. The trimethyl ether yielded 3,4,5-trimethoxybenzioc acid, 4,5-di-methoxyphthalic acid (m-hemipinic acid), a pentamethoxy anthraquinone, and a pentamethoxy o-benzoylbenzoic acid which decarboxylated to 3,4,5,3′,4′-pentamethoxy benzophenone. Correspondingly, the triethyl ether gave 3,4-diethoxy-5-methoxybenzoic and 4-ethoxy-5-methoxyphthalic acids, a mixture of pentaalkoxy anthraquinones and a pentaalkoxy o-benzoylbenzoic acid which decarboxylated to 3,3′,4-triethoxy-4′,5-dimethoxy benzophenone identified by cleavage to 3-ethoxy-4-methoxybenzoic and 3,4-diethoxy-5-methoxy-benzoic acids. These results fix the positions of the two methoxyl, three phenolic hydroxyls, and mode of linkage of the two benzene rings. Further evidence is provided indicating plicatic acid is probably a lignan of the 4-aryltetrahydronaphthalene series.

LIGNANS OF WESTERN RED CEDAR (THUJA PLICATA DONN): IV. THUJAPLICATIN AND THUJAPLICATIN METHYL ETHER

1966 ◽  
Vol 44 (13) ◽  
pp. 1541-1545 ◽  
Author(s):  
Harold MacLean ◽  
Koji Murakami
Keyword(s):  
Thin Layer ◽  
Methyl Ether ◽  
Hot Water ◽  
The Other ◽  
Thuja Plicata ◽  
Chemical Structures ◽  
Red Cedar ◽  
Degradation Analysis ◽  
Western Red Cedar ◽  
Thuja Plicata Donn

In addition to the already known plicatic acid and plicatin, five new lignans have been separated by thin-layer and column chromatography from the hot-water extractive of western red cedar (Thujaplicata Donn) heartwood, and two chemical structures have been identified. These are 2-(4″-hydroxy-3″,5″-dimethoxybenzyl)-3-(4′-hydroxy-3′-methoxybenzyl)-butyrolactone (thujaplicatin methyl ether) (I) and 2-(3″,4″-dihydroxy-5″-methoxybenzyl)-3-(4′-hydroxy-3′-methoxybenzyl)-butyrolactone (thujaplicatin) (II). The former is the first known example of a lignan containing a guaiacyl and a syringyl nucleus and the first example of a syringyl-group lignan isolated from a conifer. Proof of structure by synthesis, degradation, analysis, and various spectra is presented. The other components which apparently belong to this lignan series are still being investigated.

Selfing and correlated paternity in relation to pollen management in western red cedar seed orchards

Botany ◽  
2020 ◽  
Vol 98 (7) ◽  
pp. 353-359
Author(s):  
Kermit Ritland ◽  
Allyson Miscampbell ◽  
Annette Van Niejenhuis ◽  
Patti Brown ◽  
John Russell
Keyword(s):  
Mating System ◽  
Seed Orchard ◽  
Paternity Analysis ◽  
Thuja Plicata ◽  
Red Cedar ◽  
Management Schemes ◽  
Unbiased Estimates ◽  
Western Red Cedar ◽  
New Feature ◽  
Thuja Plicata Donn

We used microsatellite genetic markers to evaluate the mating system of western red cedar (Thuja plicata Donn ex D. Don) under various seed orchard pollen management schemes. We primarily examined whether supplemental mass pollination (SMP) can reduce the observed selfing rates. Pollen blowing and “hooding” were also examined in smaller tests. Only SMP was consistently effective in reducing the selfing rate, from 30% to 20%. The correlation of paternity was quite high (60%–90%) in two of three orchards, and in these two orchards the application of SMP reduced this correlation by about 10% as well. The correlation of paternity is the fraction of full-sibling vs. half-sibling progeny, and unbiased estimates can be obtained with few loci, even single loci, in contrast to other types of paternity analysis. We also find the microsatellite amplicon sizes should be pooled into “bins” of 2–4 nucleotides, owing to unintended errors of assay; otherwise the estimates are biased. This new feature of mating system estimation was incorporated into the computer program MLTR.

OCCURRENCE OF β-DOLABRIN (4-ISOPROPENYLTROPOLONE) IN WESTERN RED CEDAR (THUJA PLICATA DONN.)

1958 ◽  
Vol 36 (12) ◽  
pp. 1612-1615 ◽  
Author(s):  
J. A. F. Gardner ◽  
G. M. Barton
Keyword(s):  
Fractional Crystallization ◽  
Paper Chromatography ◽  
Sodium Salt ◽  
Volatile Oil ◽  
Thuja Plicata ◽  
Salt Precipitation ◽  
Red Cedar ◽  
Approximate Composition ◽  
Western Red Cedar ◽  
Thuja Plicata Donn

The steam-volatile oil of western red cedar contains traces of a fifth tropolone, β-dolabrin (4-isopropenyltropolone), in addition to α-, β-, and γ-thujaplicin and 7-hydroxy-4-isopropyltropolone. The presence of β-dolabrin, previously obtained from Japanese "Hiba" wood by Nozoe, was detected by paper chromatography and proved by isolation of a sample from the steam-volatile oil by a combination of sodium salt precipitation, fractional crystallization, and preparative paper chromatography. The approximate composition of the steam-volatile oil from butt heartwood is given.

EXPERIMENTS ON THE PRECOCIOUS FLOWERING OF WESTERN RED CEDAR AND FOUR SPECIES OF CUPRESSUS WITH GIBBERELLINS A3 AND A4/A7 MIXTURE

1967 ◽  
Vol 45 (9) ◽  
pp. 1519-1524 ◽  
Author(s):  
Richard P. Pharis ◽  
William Morf
Keyword(s):  
Foliar Application ◽  
Thuja Plicata ◽  
Cupressus Lusitanica ◽  
Precocious Flowering ◽  
Red Cedar ◽  
Long Day ◽  
Western Red Cedar ◽  
Cupressus Arizonica ◽  
Further Development ◽  
Thuja Plicata Donn

Induction of staminate and ovulate strobili was obtained on western red cedar (Thuja plicata Donn) by foliar application of gibberellin A3. Staminate strobili could be induced as early as age 4 months after 3.5 months of treatment under long-day conditions, but further development of the strobilus required a photoperiodic sequence of long-day — short-day — long-day. Induction of the ovulate strobilus may also have occurred under long-day conditions at an early age, but development did not become apparent until the above photoperiodic sequence had been given. Age at this time was 12 months. It is concluded that induction and development of the strobilus is under photoperiodic as well as hormonal control.Foliar application of gibberellin A3 and a gibberellin A4/A7 mixture to pygmy cypress (Cupressus pygmaea Sarg.), Portuguese cypress (Cupressus lusitanica Mill.), and Arizona cypress (Cupressus arizonica Greene) at age 7–9 months resulted in induction of staminate strobili on all plants. Length of time to flowering varied both with species of plant and gibberellin. Application of gibberellin A3 to Arizona and Portuguese cypress seedlings resulted in production of ovulate as well as staminate strobili at ages 21 and 10 months respectively. Mourning cypress (Cupressus funebris Endl.) still in a juvenile needle stage at age 9 months has proved unresponsive to foliar application of gibberellin A3 for at least 100 days.

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

1988 ◽  
Vol 66 (1) ◽  
pp. 51-53 ◽  
Author(s):  
Lehong Jin ◽  
Jack W. Wilson ◽  
Eric P. Swan
Keyword(s):  
Chemical Structure ◽  
Thuja Plicata ◽  
Spectroscopic Methods ◽  
Red Cedar ◽  
Western Red Cedar ◽  
Thuja Plicata Donn

The chemical structure of a novel lactone isolated from the discolored heartwood of living western red cedar (WRC) (Thuja plicata Donn.) trees has been determined as 3,3,4,7,7,8-hexamethyl-2,6-dioxa-1,5-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.

OCCURRENCE OF 2,7-DIHYDROXY-4-ISOPROPYL-2,4,6-CYCLOHEPTATRIEN-1-ONE (7-HYDROXY-4-ISOPROPYLTROPOLONE) IN WESTERN RED CEDAR (THUJA PLICATA DONN.)

1957 ◽  
Vol 35 (9) ◽  
pp. 1039-1048 ◽  
Author(s):  
J. A. F. Gardner ◽  
G. M. Barton ◽  
H. MacLean
Keyword(s):  
Paper Chromatography ◽  
Diazonium Salt ◽  
Thuja Plicata ◽  
Oxidation Reactions ◽  
Red Cedar ◽  
Western Red Cedar ◽  
Color Reactions ◽  
Copper Chelates ◽  
Thuja Plicata Donn ◽  
Persulphate Oxidation

The tropolones of western red cedar were collected as the green copper chelates deposited on copper–bronze screen exposed to the vapor from the heated wood in commercial kilns. Decomposition of the chelates with hydrogen sulphide yielded a new tropolone as well as the expected thujaplicins. Its infrared and ultraviolet absorption together with hydrogenation and oxidation reactions established it to be 2,7-dihydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one. Synthesis was achieved by persulphate oxidation of γ-thujaplicin. The natural substance is identical with the 7-hydroxyhinokitiol obtained by Nozoe from the diazonium salt of 7-amino-hinokitiol and on the basis of color reactions and Rf appears to be the unknown "enol" previously noted by Zavarin and Anderson in paper chromatography of tropolone fractions of western red cedar and incense cedar. The concentration in the wood, determined by quantitative paper chromatography, ranged from 0.01 to 0.08%.

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