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...

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... 

Youn B, Moinuddin SGA, Davin LB et al (2005) Crystal structures of apo-form and binary/temary complexes of Podophyllum secoisolariciresinol dehydrogenase, an enzyme involved in formation of health-protecting and plant defense lignans. J Biol Chem 280 12917-12926... 

Moinuddin SGA, Youn B, Bedgar DL et al (2006) Secoisolariciresinol dehydrogenase mode of catalysis and stereospecificity of hydride transfer in Podophyllum peltatum. Org Biol Chem 4 808-816... 

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. 

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]. 

Figure 4.8 Biosynthetic pathway from coniferyl alcohol to (—)-matairesinol. Enzymes and proteins Involved are (1) pinoresinol synthase (laccase + dirigent protein), (2) pinoresinol/lariciresinol synthase, (3) secoisolariciresinol dehydrogenase.

Okunishi, T., Sakakibara, N., Suzuki, S., Umezawa, T. and Shimada, M. (2004) Stereochemistry of matairesinol formation by Daphne secoisolariciresinol dehydrogenase. /. Wood Sci, 50, 77-81. 

Xia, Z., Costa, M., Pelissier, H., Davin, L. and Lewis, N. (2001) Secoisolariciresinol dehydrogenase purification, cloning and functional expression. J. Biol. Chem., 276, 12614-23. 

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