Pinoresinol

Lundquist, K. Stomberg, R. On the occurrence of structural elements of the lignan type (P-P structures) in lignins. The crystal structures of (+ )-pinoresinol and ( )-trans-3,4-divanillyltetrahydrofuran. Holzforschung 1988, 42, 375-384. 

The structure of the 1 1 methanol solvate of olanzapine has been reported, where pairs of olanzapine molecules form a centrosymmetric dimer by means of C—H—-7t interactions [66]. The solvent molecule was linked to the drug substance through O—H-N, N—H O, and C—interactions. In a new polymorph of the 1 1 dioxane solvatomorph of (+)-pinoresinol, the structure was stabilized by O—H O hydrogen bonds between the compound and the solvent [67], Two new polymorphs of 2-cyano-3-[4-(/Y,jV-diethylamino)-phenyl]prop-2-enethioamide and its acetonitrile solvatomorph have been characterized [68], Although crystallization of the title compound was conducted out of a number of solvents, only the acetonitrile solvatomorph could be formed. 

Milder I E, Arts I C, van de Putte B, Venema D P and Hollman P C (2005), Lignan contents of Dutch plant foods a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol , Br J Nutr, 93, 393-402. 

Pinoresinol Kale Apricot Strawberry Peach Pear Brassica... 

However, the first four products identified 44), viz. dehydro-diconiferyl alcohol (II), DL-pinoresinol (IV), guaiacylglyccrol-p-coniferyl ether (VI) and conifcraldchydc (VII) ipOa) already revealed the nature of most of the secondary reactions taking place after formation of the free phenoxyl radicals by the enzymes, although this was not immediately... 

Biphcnylyl links between higher lignols, e.g. in the dehydrodipino-rcsinol obtained from pinoresinol (60), are easier to trace. Biphenylyl bonds may make up about 25 % of all the interunitary links in lignin (123) [cf. Units 9/10 and 12/13a in Fig. 9]. Again this is a strong, non-hydrolysable C—C bond. 

Fig. 12.4 Biosynthetic pathway for lignans with 9,9 -oxygen including yatein and fxsdophyUo-toxin. DP dirigent protein, PLR pinoresinol/laiiciresinol reductase, PrR pinoresinol reductase, and SIRD secoisolariciresinol dehydrogenase...

However, the enantiomeric control by DPs does not lead to the production of optically pure pinoresinol in plants, because the enantiomeric compositions of pinoresinol from various plant species vary widely and optically pure pinoresinol has not yet been isolated from plants [11,13, 53]. Downstream lignans in the lignan biosynthetic pathway, such as dibenzylbutyrolactone lignans including matairesinol, are optically pure [11, 13, 53]. These facts unequivocally indicate that not only was... 

Fig. 12.6 Enantioselective formation of pinoresinol. Forsythia intermedia dirigent protein mediates selective formation of (-l-)-pinoresinol...

Fig. 12.7 Reactions catalyzed by pinoresinol/lariciresinol reductases from Forsythia intermedia (PLR-Fil) [34], Thujaplicata (PLR-Tpl and PLR-Tp2) [37], Liram album (PLR-Lal) [41], Linum perenne (PLR-Lpl) [42], and Linum usitatissimum (PLR-Lul) [41] and pinoresinol reductases from Arabidopsis thaliana (AtPrRl and AtPrR2) [55]...

Katayama T, Davin LB, Lewis NG (1992) An extraordinary accumulation of (-)-pinoresinol in cell-free extracts of Forsythia intermedia evidence for enantiospecific reduction of (+)-pinoresinol. Phytochemistry 31 3875-3881... 

Chu A, Dinkova A, Davin LB et al (1993) Stereospecificity of (-l-)-pinoresinol and (-1-)-lariciresinol reductases from Forsythia intermedm. J Biol Chem 268 27026-27033... 

Dinkova-Kostova AT, Gang DR, Davin LB et al (1996) (-l-)-Pinoresinol/(-l-)-lariciresinol reductase from Forsythia intermedia. J Biol Chem 271 29473-29482... 

Katayama T, Masaoka T, Yamada H (1997) Biosynthesis and stereochemistry of lig-nans in Zanthoxylum ailanthoides 1. (-l-)-Lariciresinol formation by enzymatic reduction of ( )-pinoresinols. Mokuzai Gakkaishi 43 580-588... 

Fujita M, Gang DR, Davin LB et al (1999) Recombinant pinoresinol-lariciresinol reductases from western red cedar Thuja plicatd) catalyze opposite enantiospecific conversions. J Biol Chem 274 618-627... 

Min T, Kasahara H, Bedgar DL et al (2003) Crystal structures of pinoresinol-lariciresinol and phenylcoumaran benzylic ether reductases and their relationship to isoflavone reductases. J Biol Chem 278 50714-50723... 

Nakatsubo T, Mizutani M, Suzuki S et al (2008) Characterization of Arabidopsis thaliana pinoresinol reductase, a new type of enzyme involved in lignan biosynthesis. J Biol Chem 283 15550-15557... 

Other phenolic acids and derivatives 4- (Acetoxythyl) -1,2 -dihydroxybenzene Dopac (3,4-dihydroxyphenylacetic acid) 4-hydroxyphenylacetic acid COOH HO- HO Lignans (+)-l-Acetoxypino resinol (+)-Pinoresinol, / (+)-Hydroxypinoresinol "7 WR OCH3 HO OCH3... 

Pinoresinol, 1-acetoxy, (+) Bk°E092 Pinoresinol, 1-acetoxy, 4 - 3-D-glucoside (- -) ... 

Pinoresinol, 1-acetoxy, 4"-methyl ether-4 -O-P-D-glucoside (+) Bk 55°E02i Pinoresinol, l-acetoxy-4"-0-methyl ether (+) Bk 46.4° l ... 

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