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

MacLean, Harold; Murakami, Koji

doi:10.1139/v66-229

Cited by 28 publications

(14 citation statements)

References 7 publications

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“…Depending on the species involved, its formation involves deposition of various metabolites (lignans, flavonoids, tannins, and other substances) into pre-lignified secondary xylem, and these can often account for Ͼ20% of the dry weight of the tissue (22)(23)(24)(25)(26)(27)(28)(29)(30). The composition and amounts of these metabolites can vary from plant to plant, and these determine, to a large extent, the properties of the different woods encountered in the plant kingdom.…”

Section: Resultsmentioning

confidence: 99%

Recombinant Pinoresinol-Lariciresinol Reductases from Western Red Cedar (Thuja plicata) Catalyze Opposite Enantiospecific Conversions

Fujita

Gang

Davin

et al. 1999

Journal of Biological Chemistry

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Although the heartwood of woody plants represents the main source of fiber and solid wood products, essentially nothing is known about how the biological processes leading to its formation are initiated and regulated. Accordingly, a reverse transcription-polymerase chain reaction-guided cloning strategy was employed to obtain genes encoding pinoresinol-lariciresinol reductases from western red cedar (Thuja plicata) as a means to initiate the study of its heartwood formation. (؉)-Pinoresinol-(؉)-lariciresinol reductase from Forsythia intermedia was used as a template for primer construction for reverse transcription-polymerase chain reaction amplifications, which, when followed by homologous hybridization cloning, resulted in the isolation of two distinct classes of putative pinoresinol-lariciresinol reductase cDNA clones from western red cedar. A representative of each class was expressed as a fusion protein with ␤-galactosidase and assayed for enzymatic activity. Using both deuterated and radiolabeled (؎)-pinoresinols as substrates, it was established that each class of cDNA encoded a pinoresinol-lariciresinol reductase of different (opposite) enantiospecificity. Significantly, the protein from one class converted (؉)-pinoresinol into (-)-secoisolariciresinol, whereas the other utilized the opposite (-)-enantiomer to give the corresponding (؉)-form. This differential substrate specificity raises important questions about the role of each of these individual reductases in heartwood formation, such as whether they are expressed in different cells/tissues or at different stages during heartwood development.

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Section: Resultsmentioning

confidence: 99%

Recombinant Pinoresinol-Lariciresinol Reductases from Western Red Cedar (Thuja plicata) Catalyze Opposite Enantiospecific Conversions

Fujita

Gang

Davin

et al. 1999

Journal of Biological Chemistry

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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 lignans of Western Red Cedar (Thuja plicata Donn)fallinto two classes, the five dibenzyl butyrolactones of the thujaplicatin series (1)(2)(3)(4) and plicatic acid and plicatin (I), the 4-aryltetrahydronaphthalene derivatives ( 5 , 6). These lignans are novel in that they all contain a guaiacyl ring in conjuilction with either a monomethylated pyrogallol or a syringyl group.…”

mentioning

confidence: 99%

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

MacLean¹,

MacDonald²

1969

Can. J. Chem.

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The isolation and structure of a new lignan, 1,6-dihydroxy-2-(hydroxymethyl)-7-methoxy-4-(3',4'-dihydroxy-5'-methoxypheny1)-3-naphthoic acid lactone (plicatinaphthol, 2), in which the 4-aryltetrahydronaphthalene structure of plicatin (1) has been arolnatized 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 (Thuja Plicata Donn): Iv. Thujaplicatin and Thujaplicatin Methyl Ether

Cited by 28 publications

References 7 publications

Recombinant Pinoresinol-Lariciresinol Reductases from Western Red Cedar (Thuja plicata) Catalyze Opposite Enantiospecific Conversions

Recombinant Pinoresinol-Lariciresinol Reductases from Western Red Cedar (Thuja plicata) Catalyze Opposite Enantiospecific Conversions

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

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

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