matairesinol biosynthesis

Kim K, Smith CA, Daily MD, Cort JR, Davin LB, Lewis NG. Trimeric Structure of (+)-Pinoresinol-forming Dirigent Protein at 1.95 Å Resolution with Three Isolated Active Sites. Journal of Biological Chemistry. 2015 Jan;290(3):1308–18. doi: 10.1074/jbc.m114.611780.; Bayindir Ü, Alfermann AW, Fuss E. Hinokinin biosynthesis in Linum corymbulosum Reichenb. The Plant Journal. 2008 Aug 20;55(5):810–20. doi: 10.1111/j.1365-313x.2008.03558.x.; Hemmati S, Schmidt TJ, Fuss E. (+)-Pinoresinol/(-)-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B. FEBS Lett. 2007 Feb 20;581(4):603–10. doi: 10.1016/j.febslet.2007.01.018. PMID: 17257599.; Moinuddin SG, Youn B, Bedgar DL, Costa MA, Helms GL, Kang C, Davin LB, Lewis NG. Secoisolariciresinol dehydrogenase: mode of catalysis and stereospecificity of hydride transfer in Podophyllum peltatum. Org Biomol Chem. 2006 Mar 07;4(5):808–16. doi: 10.1039/b516563f. PMID: 16493463.; Saleem M, Kim HJ, Ali MS, Lee YS. An update on bioactive plant lignans. Nat Prod Rep. 2005 Dec;22(6):696–716. doi: 10.1039/b514045p. PMID: 16311631.; Davin LB, Lewis NG. Dirigent phenoxy radical coupling: advances and challenges. Curr Opin Biotechnol. 2005 Aug;16(4):398–406. doi: 10.1016/j.copbio.2005.06.010. PMID: 16023845.; von Heimendahl CB, Schäfer KM, Eklund P, Sjöholm R, Schmidt TJ, Fuss E. Pinoresinol-lariciresinol reductases with different stereospecificity from Linum album and Linum usitatissimum. Phytochemistry. 2005 Jun;66(11):1254–63. doi: 10.1016/j.phytochem.2005.04.026. PMID: 15949826.; Youn B, Moinuddin SGA, Davin LB, Lewis NG, Kang C. Crystal Structures of Apo-form and Binary/Ternary Complexes of Podophyllum Secoisolariciresinol Dehydrogenase, an Enzyme Involved in Formation of Health-protecting and Plant Defense Lignans. Journal of Biological Chemistry. 2005 Apr;280(13):12917–26. doi: 10.1074/jbc.m413266200.; Dixon RA. Phytoestrogens. Annu Rev Plant Biol. 2004;55():225–61. doi: 10.1146/annurev.arplant.55.031903.141729. PMID: 15377220.; Halls SC, Davin LB, Kramer DM, Lewis NG. Kinetic study of coniferyl alcohol radical binding to the (+)-pinoresinol forming dirigent protein. Biochemistry. 2004 Mar 09;43(9):2587–95. doi: 10.1021/bi035959o. PMID: 14992596.; Bloedon LT, Szapary PO. Flaxseed and cardiovascular risk. Nutr Rev. 2004 Jan;62(1):18–27. doi: 10.1111/j.1753-4887.2004.tb00002.x. PMID: 14995053.; Min T, Kasahara H, Bedgar DL, Youn B, Lawrence PK, Gang DR, Halls SC, Park H, Hilsenbeck JL, Davin LB, Lewis NG, Kang C. Crystal Structures of Pinoresinol-Lariciresinol and Phenylcoumaran Benzylic Ether Reductases and Their Relationship to Isoflavone Reductases. Journal of Biological Chemistry. 2003 Dec;278(50):50714–23. doi: 10.1074/jbc.m308493200.; Kim MK, Jeon JH, Davin LB, Lewis NG. Monolignol radical-radical coupling networks in western red cedar and Arabidopsis and their evolutionary implications. Phytochemistry. 2002 Oct;61(3):311–22. doi: 10.1016/s0031-9422(02)00261-3. PMID: 12359517.; Halls SC, Lewis NG. Secondary and quaternary structures of the (+)-pinoresinol-forming dirigent protein. Biochemistry. 2002 Jul 30;41(30):9455–61. doi: 10.1021/bi0259709. PMID: 12135368.; Burlat V, Kwon M, Davin LB, Lewis NG. Dirigent proteins and dirigent sites in lignifying tissues. Phytochemistry. 2001 Jul;57(6):883–97. doi: 10.1016/s0031-9422(01)00117-0. PMID: 11423139.; Xia ZQ, Costa MA, Pelissier HC, Davin LB, Lewis NG. Secoisolariciresinol dehydrogenase purification, cloning, and functional expression. Implications for human health protection. J Biol Chem. 2001 Apr 20;276(16):12614–23. doi: 10.1074/jbc.m008622200. PMID: 11278426.; Davin LB, Lewis NG. Dirigent proteins and dirigent sites explain the mystery of specificity of radical precursor coupling in lignan and lignin biosynthesis. Plant Physiol. 2000 Jun;123(2):453–62. PMID: 10859176; PMCID: PMC1539258.; Fujita M, Gang DR, Davin LB, Lewis NG. Recombinant Pinoresinol-Lariciresinol Reductases from Western Red Cedar (Thuja plicata) Catalyze Opposite Enantiospecific Conversions. Journal of Biological Chemistry. 1999 Jan;274(2):618–27. doi: 10.1074/jbc.274.2.618.; Ford JD, Davin LB, Lewis NG. Plant lignans and health: cancer chemoprevention and biotechnological opportunities. Basic Life Sci. 1999;66():675–94. doi: 10.1007/978-1-4615-4139-4_38. PMID: 10800470.; Davin LB, Wang HB, Crowell AL, Bedgar DL, Martin DM, Sarkanen S, Lewis NG. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science. 1997 Jan 17;275(5298):362–6. doi: 10.1126/science.275.5298.362. PMID: 8994027.; Dinkova-Kostova AT, Gang DR, Davin LB, Bedgar DL, Chu A, Lewis NG. (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. Protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase. J Biol Chem. 1996 Nov 15;271(46):29473–82. doi: 10.1074/jbc.271.46.29473. PMID: 8910615.; Chu A, Dinkova A, Davin LB, Bedgar DL, Lewis NG. Stereospecificity of (+)-pinoresinol and (+)-lariciresinol reductases from Forsythia intermedia. Journal of Biological Chemistry. 1993 Dec;268(36):27026–33. doi: 10.1016/s0021-9258(19)74213-6.; Umezawa T, Davin LB, Lewis NG. Formation of lignans (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia cell-free extracts. Journal of Biological Chemistry. 1991 Jun;266(16):10210–7. doi: 10.1016/s0021-9258(18)99211-2.

Metabolites

(-)-Lariciresinol

Formula: C20H24O6 (360.1572804)

CAS ID: 83327-19-9

(+)-Pinoresinol

Formula: C20H22O6 (358.1416312)

CAS ID: 487-36-5

Coniferyl alcohol

Formula: C10H12O3 (180.0786402)

CAS ID: 32811-40-8

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Hydrogen peroxide

Formula: H2O2 (34.0054792)

CAS ID: 7722-84-1

Lariciresinol

Formula: C20H24O6 (360.1572804)

CAS ID: 27003-73-2

Matairesinol

Formula: C20H22O6 (358.1416312)

CAS ID: 580-72-3

Oxygen

Formula: O2 (31.98983)

CAS ID: 7782-44-7

Secoisolariciresinol

Formula: C20H26O6 (362.17292960000003)

CAS ID: 29388-59-8

NADPH(4-)

Formula: C21H26N7O17P3 (741.0598016)

CAS ID: 53-57-6

NAD(1-)

Formula: C21H26N7O14P2 (662.1012936000001)

CAS ID: 53-84-9

NADP(3-)

Formula: C21H25N7O17P3 (740.051977)

CAS ID: 53-59-8

Ammonium Persulfate

Formula: H8N2O8S2 (227.9722088)

CAS ID: 7727-54-0



Enzyme

EC Number name full name note


Proteins

Protein ID name full name