The Polyoxyphenols of Western Red Cedar (Thuja Plicata Donn). Ii. Degradation Studies on Plicatic Acid, a Possible Lignan Acid

Gardner, John A.; MacDonald, B. F.; MacLean, Harold

doi:10.1139/v60-324

Cited by 27 publications

(13 citation statements)

References 9 publications

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“…Eleven of these lignans have been identified and described (Gardner et al 1960(Gardner et al , 1966MacDonald and Swan 1970;MacDonald and Barton 1973;Kirbach and Chow 1976): thujaplicatin, di hydroxy t hujapl icat i n, t hujapl icat i n methyl ether, hydroxy thujaplicatin methyl ether, di hydroxy t hujaplicatin methyl ether, y-thujaplicatene, plicatic acid, plicatin, plicatinapht halene, plicat inapht hol, and paplopl icat itoxin.…”

Section: Forest Products Laboratory 1955)mentioning

confidence: 99%

Western redcedara literature review.

Minore¹

1983

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Section: Forest Products Laboratory 1955)mentioning

confidence: 99%

Western redcedara literature review.

Minore¹

1983

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“…Spectrum: v , , , , no hydroxyl band, 1 756 (lactone) c~n -~. .4ll;aline permanganate oxidation was carried out a s in previous \vork ('2) to yield 3,4-diet11oxy-5-methoxybenzoic and 4-ethoxy-3-methoxybenzoic acids, identified by mixed melting point and infrared spectral comparison with authentic samples (2). hCICNO\VLEDGMENT \\ie thank Dr. L. D. I-Iall, University of British Columbia, for helpful discussions concerning the nuclear mag~letic resonance spectra.…”

Section: Th~ljaplicatin (11)mentioning

confidence: 99%

“…In previous papers (1)(2)(3) the structures of the lignans plicatic acid and plicatin, the main components of the hot-water extractive of western red cedar heartwood, were presented. Development of adequate thin-layer and preparative chromatographic systems has permitted the detection and separation of five new components of much lower concentration (Scheme I ) , all of which appear to be related lignans.…”

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confidence: 99%

Lignans of Western Red Cedar (Thuja Plicata Donn): Iv. Thujaplicatin and Thujaplicatin Methyl Ether

MacLean¹,

Murakami²

1966

Can. J. Chem.

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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 wester11 red cedar (Tltz~ja plicata 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"-methoxybenzy1)-3-(4'-hydr0xy-3~-methoxybenzyl)-butyrolactone (thujaplicatin) (11). The former is the first linoxv~i 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.In previous papers (1-3) the structures of the lignans plicatic acid and plicatin, the main components of the hot-water extractive of western red cedar heartwood, were presented. Development of adequate thin-layer and preparative chromatographic systems has permitted the detection and separation of five new components of much lower concentration (Scheme I ) , all of which appear to be related lignans. The structure of two of these components is reported in this paper. Investigation of the chemistry of the remaining co~npounds is continuing.Because the first lignan of this series to be identified was the methyl ether of the second, and there are iildicatioils that the other lignans will also be derivatives of the second, the coinmon names assigned are thujaplicatin methyl ether for I and thujaplicatin for 11. The numbering and chemical naming systems follow the review of I-Iearon and NIacGregor (4). The chemical names proposed by Freudenberg and Weinges (6) are given a t the end of the discussion of each lignan. Thujaplicutin iklethyl Ether ( I )This compound gave approxiinately equal yields of vanillin and syringaldehyde on nitrobenzene oxidation (6). Analytical data obtained for this lignan and its di-0-methyl ether (111) were satisfactory ; infrared spectra were as expected, showing 110 hydroxyl band after methylation. The ultraviolet spectrum of I had a maxiinu~n a t 281 mp shifting to 293 mp in alkaline solvent. Nuclear magnetic resonance (n.m.r.) spectra with integrals accounted for all proton species in the diinethyl ether (111) and the diacetate (IV), the spectrum of the parent lignan being unsatisfactory because of low solubility in deuteriochloroform. Synthesis of the diinethyl derivative (111) uras accoinplished by condensing ( k ) -3 -(3',4'-dimethoxybenzy1)-butyrolactone (V) (7) in sodium methoxide with 3,4,5-trimethoxybenzaldehyde (8, 9) to yield (k)-2-(3",4",5"-trimethoxybenzylidene)-3-(3',4'-di~nethoxy-benzy1)-butyrolactonc (VI) (lo), the double bond of which \vas reduced by hydrogen over 'Prwiozls papers in this series were entitled "Polyorypltenols of T

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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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The Polyoxyphenols of Western Red Cedar (Thuja Plicata Donn). Ii. Degradation Studies on Plicatic Acid, a Possible Lignan Acid

Cited by 27 publications

References 9 publications

Western redcedara literature review.

Western redcedara literature review.

Lignans of Western Red Cedar (Thuja Plicata Donn): Iv. Thujaplicatin and Thujaplicatin Methyl Ether

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

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The Polyoxyphenols of Western Red Cedar (Thuja Plicata Donn). Ii. Degradation Studies on Plicatic Acid, a Possible Lignan Acid

Cited by 27 publications

References 9 publications

Western redcedar&#151;a literature review.

Western redcedar&#151;a literature review.

Lignans of Western Red Cedar (Thuja Plicata Donn): Iv. Thujaplicatin and Thujaplicatin Methyl Ether

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

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Western redcedara literature review.

Western redcedara literature review.