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Lignans Pinoresinol

The lignans (+)-pinoresinol 20a and (-)-matairesinol 36b, isolated from Forsythia species inhibit cAMP phosphodiesterase which catalyses the breakdown of the second messenger, cAMP, inside the cells (99). Cis-hinokiresinol 102 and oxy-c/.y-hinokiresinol 103 from Anemarrhena asphodeloides (100), and (+)-syringaresinol-di-0-P-D-glucopyranoside 104 and (+)-hydroxypinoresinol 4, 4"-di-0-p-D-glucopyranoside 105 from Eucommia ulmoides (Eucommiaceae) bark (101) are also inhibitors of this phosphodiesterase. [Pg.150]

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. [Pg.413]

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. [Pg.327]

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... 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... [Pg.186]

Hemmati S, Schmidt TJ, Fuss E (2007) (-l-)-Pinoresinol/(-)-lariciresinol reductase from Liman perenne himmelszelt involved in the biosynthesis of justicidin B. FEBS Lett 581 603-610 Umezawa T, Davin LB, Yamamoto E et al (1990) Lignan biosynthesis in Forsythia species. J Chem Soc Chem Commun 1405-1408... [Pg.196]

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... [Pg.196]

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... [Pg.599]

The plant precursors of mammalian lignans include secoisolaricinol, laricresinol, matair-esinol, 7-hydroxymatairesinol, pinoresinol, and lignin. ° ° Flaxseed and whole cereal grains are considered the most important dietary sources, but many others are known, for example, strawberry achenes, berries, coffee beans, tea leaves, etc. ... [Pg.330]

The morama bean is an excellent source of lignans (Holse et al., 2010). The content of secoisolariciresinol in morama beans (305-406 gg/100 g) is higher than that of soybean (13-273 gg/100 g) and peanut (333 pg/100 g) (Mazur et al., 1998). Likewise, the level of lariciresinol in morama beans (614-825 [tg/100 g) is higher than that of soybeans (287 gg/lOO g), while the level of pinoresinol in morama beans (21-23 gg/lOO g) is lower than the level in soybeans (446 gg/lOO g) (Penalvo et ah, 2004). These lignans can be converted by intestinal bacteria into enterolignans, which possess biological activities such as (anti) estrogenic and antioxidant action. Therefore, they may reduce the risk of certain types of cancers as well as cardiovascular diseases (Adlercreutz, 2007). [Pg.204]

The term lignan typically refers to dimers of monolignols that are linked via an 8-8 (P-P ) bond, whereas the term neolignan refers to dimers and oligomers that contain bonds other than the 8-8 bond. Most lignans are optically active, and typically only one enantiomer is found in a given species. Examples of lignans include (+)-pinoresinol (1.72), (+)-sesamin (1.73), and (-)-plicatic acid (1.74). [Pg.19]

Investigations of gymnosperms and angiosperms showed the existence of a common lignan biosynthetic pathway where it acts as enzymes, particularly pinoresinol/lariciresinol reductase [30] and secoisolariciresinol dehydrogenase [31]. [Pg.112]

Although structural elucidation of lignans is not a difficult task, the similarities between the structures can create problems. In particular, the determination of stereochemistry at the chiral center requires NOE/ NOESY NMR experiments and/or X-ray analyses. The enantiomeric excesses of the known lignans (+)-lariciresinol, (-)-secoisolariciresinol and (+)-taxiresinol, isolated from Japanese yew T. cuspidata roots, were determined by chiral high-performance liquid chromatographic analyses [78] except for (+)-pinoresinol (77% enantiomeric excess), they were found to be optically pure by Kawamura et al. In an earlier study, the presence of taxiresinol in Taxus species was reported by Mujumdar et al. [69] after they had isolated it from the heartwood of T. baccata, although they did not study its stereochemistry. [Pg.124]

Butyrolactone and bistetrahydrofuran lignans such as matairesinol, nor-trachelogenin and pinoresinol are also known to possess antileukemia and cAMP-inhibitory activities [108]. [Pg.136]

Lignans 1 Podophyllotoxin 2 Arctnn, phillyrin cpipinorcsinol-4 -/i-D-glucoside matairesomde, and pinoresinol 4 ft D glucoside Buchardt et al 1986 Nishibe et al 1988... [Pg.550]

The non-phenolic furofuran lignan, (-l-)-eudesmin, from Magnolia kobus var. borealis is formed from pinoresinol by two SAM-dependent methylation steps (Miyauchi and Ozawa, 1998). Cell-free extracts catalysed the successive non-stereospecific methylation both of (-1-)- and (—)-pinoresinol. Thus, the stereospecificity has to be established in an earlier step. [Pg.219]


See other pages where Lignans Pinoresinol is mentioned: [Pg.125]    [Pg.107]    [Pg.120]    [Pg.602]    [Pg.647]    [Pg.267]    [Pg.268]    [Pg.856]    [Pg.247]    [Pg.13]    [Pg.147]    [Pg.125]    [Pg.107]    [Pg.120]    [Pg.602]    [Pg.647]    [Pg.267]    [Pg.268]    [Pg.856]    [Pg.247]    [Pg.13]    [Pg.147]    [Pg.80]    [Pg.180]    [Pg.184]    [Pg.194]    [Pg.598]    [Pg.135]    [Pg.135]    [Pg.542]    [Pg.18]    [Pg.22]    [Pg.88]    [Pg.112]    [Pg.112]    [Pg.139]    [Pg.152]    [Pg.94]    [Pg.565]    [Pg.286]    [Pg.287]    [Pg.215]    [Pg.216]    [Pg.216]    [Pg.220]   
See also in sourсe #XX -- [ Pg.65 ]




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