Matairesinol

From bark, valuable chemicals, such as betulinol, can be obtained [5]. Betulinol is used as a health-promoting agent. Recently Holmbom et al. [27, 28] discovered that hydroxymatairesinol (HMR) is concentrated in the stems and knots of Norway spruce Picea abies). It can be extracted and transformed catalytically to matairesinol (MAT), which is an antioxidant and anticarcinogenic agent [29-31]. 

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. 

Matairesinol Pear Kale Strawberry Peach Apricot Brassica... 

For example, yatein and podophyllotoxin are biosynthesized from matairesinol (Fig. 12.4) [11, 13, 49]. This conversion involves 5-hydroxylation of one of the 3-methoxy-4-hydroxylphenyl (guaiacyl) moieties of matairesinol to give rise to 5-hydroxymatairesinol (thujaplicatin) followed by dual methylation at the 4- and 5-hydroxyls, giving rise to a 3,4,5-trialkoxyphenyl moiety (Fig. 12.4) [11, 13,49],... 

On the other hand, biosynthetic pathways that do not involve the conversion from coniferyl alcohol to matairesinol have been proposed for lignans composed of two syringyl (3,5-dimethoxy-4-hydroxyphenyl) groups (+)-syringaresinol formation in Liriodendron tulipifera [50] and (H-)-lyoniresinol biosynthesis in Lyonia ovalifolia var. elliptica [51]. Enantioselective coupling of two sinapyl alcohol units was proposed for the selective formation of (H-)-syringaresinol [50], On the other hand, a non-enantioselective dimerization of sinapyl alcohol was proposed for (+)-lyoniresinol biosynthesis and the enantioselectivity in the biosynthesis was ascribed... 

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... 

Umezawa T, Davin LB, Lewis NG (1991) Formation of lignans (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia ceU-free extracts. J Biol Chem 266 10210-10217 Okunishi T, Sakakibara N, Suzuki S et al (2004) Stereochemistry of matairesinol formation by Daphne secoisolariciresinol dehydrogenase. J Wood Sci 50 77-81 XiaZ-Q, Costa MA, Pelissier HC et al (2001) Secoisolariciresinol dehydrogenase purification, cloning, and functional expression. J Biol Chem 276 12614-12623... 

The lignans are a large group of plant phenolics, biosynthesized from the union of two phenylpropane molecules e.g., both matairesinol (Centaurea species, family Asteraceae) and podophyllotoxin Podophyllum peltatum, family Berberidaceae) are formed from the phenylpropane coniferyl alcohol. Lignans are essentially cinnamoyl alcohol dimers, though further cyclization and other structural modifications result in various structural types, e.g. dibenzylbutyrolactone and epoxy lignan. 

Xia et al (2000) proposed a biosynthetic route starting coniferyl alcohol (3.79) and subsequent formation of (+)-pinoresinol (3.82), as shown in Figure 3-12. The enzyme pinoresinol/lariciresionol reductase converts this compound to (+)-lariciresinol (3.87), and then to (-)-secoisolariciresionol (3.88). The enzyme secoisolariciresinol dehydrogenase converts (3.88) into (-)-matairesinol (3.83). The conversion from (-)-matairesinol (3.83) to podophyllotoxin (3.86) is likely to be similar to the route shown in Figure 3-11. 

Bannwart C, Adlercreutz H, Fotsis T, Wahala K, Hase T, Brunow G. 1984. Identification of o-desmethylangolensin, a metabolite of daidzein and of matairesinol, one likely plant precursor of the animal lignan enterolactone in human urine. Finn Chem Lett 4-5 120-125. 

The main lignan in flaxseed is SDG (Figure 2). Also present are a number of other lignans, that is, matairesinol (MAT), lariciresinol, hinokinin,... 

The palatability of safflower meal to poultry tends to be low (Ravindran and Blair, 1992) due to the presence of two phenolic glucosides matairesinol-p-glucoside, which imparts a bitter flavour, and 2-hydroxyarctiin-p-glucoside, which also has a bitter flavour and has cathartic properties (Darroch, 1990). Both glucosides are associated with the protein fraction of the meal, and they can be removed by extraction with water or methanol, or by the addition of P-glucosidase. 

Scheme 10 Four lignans oxidized with the MT0/H202 system lariciresinol (a), isolariciresinol (b), matairesinol (c), and 7-hydroxymatairesinol (d)...

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

The dibenzylbutyrolactone lignan matairesinol was also found to be an anti-HIV agent [110], although the sample used in this bioassay was not isolated from a Taxus species. Another dibenzylbutyrolactone lignan, arctigenin, as well as its unsubstituted benzyl derivative exhibited anti-HIV replication activity, with EC50 values of 0.16 and 22 ig/mL and therapeutic index values of 5 and 9.1, respectively [111]. 

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