Lignans Matairesinol

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]. 

The plant systems adopted as biological partners were the Amazonian species, Virola surinamensis and the temperate plant, Forsythia intermedia, respectively. The latter accumulates the 8,8 -linked, optically pure lignans (-)-matairesinol 36b and (-)-arctigenin 74, whereas V. surinamensis affords surinamensin 50. Preliminary studies using either plants or cell-free extracts of V. surinamensis from ca one- to two-year-old plants and eugenol 40/ isoeugenol 41/[8-14C]coniferyl alcohol 13 as precursors did not result in formation of either surinamensin 50 or virolin 51 under the conditions employed. 

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. 

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. 

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,... 

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]. 

A number of biomimetic semi- or total syntheses using an oxidative coupling of a yatein or matairesinol-type intermediate to form stegane or isostegane lignans such as in Fig. (7) have been reported [35,87]. The major contributions will be reviewed in section 3.2.2. 

Umezawa T, Davin LB, Lewis NG (1991) Formation of the lignans (-) secoisolanciresinol and (-)-matairesinol with Forsythia intermedia cell-free extracts J Biol Chem 266(16) 10210-10217... 

The alcohols formed from some cinnamic acid derivatives, namely /7-coumaryl alcohol, coniferyl alcohol (LI), and sinapyl alcohol (L2), commonly known as monolignols, undergo dimerization reactions that yield lignans such as (-l-)-pinoresinol (L3), (-l-)-sesamin (L4), (-)-matairesinol (L5), and podophyllotoxin (L6) (Fig. 13). Several thousand lignans are found to occur in nature. Lignins, the structural components of plant cell walls, are polymers of monolignols and/or lignans. 

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