Pinoresinol-lariciresinol reductases with opposite enantiospecificity determine the enantiomeric composition of lignans in the different organs of linum usitatissimum L.

Planta Medica

Volumn 76, Issue 9, 2010, Pages 928-934

  Hemmati, Shiva ^a,c   Heimendahl, Cosima B I Von ^a   Klaes, Michael ^b   Alfermann, A Wilhelm ^a   Schmidt, Thomas J ^b   Fuss, Elisabeth ^a,d  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c PURDUE UNIVERSITY   (United States)

^d UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

HPLC UV MS CD; lignin; Linaceae; Linum; pinoresinollariciresinol reductase; stereochemistry

Indexed keywords

LARICIRESINOL; LIGNAN; OXIDOREDUCTASE; PINORESINOL; SECOISOLARICIRESINOL; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; GENETIC CODE; GENETIC TRANSCRIPTION; LINSEED; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; PLANT LEAF; PLANT STEM;

DNA, COMPLEMENTARY; FLAX; FURANS; GENE EXPRESSION; GENES, PLANT; LIGNANS; OXIDOREDUCTASES; PLANT STRUCTURES; STEREOISOMERISM;

EMBRYOPHYTA; LINACEAE; LINUM; LINUM USITATISSIMUM;

EID: 77953837622     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0030-1250036     Document Type: Article

References (26)

1. Moss G P. Nomenclature of lignans and neolignans (IUPAC Recommendations 2000). Pure Appl Chem 2000 72 1493-1523
2. Westcott N D., Muir A D. Flax seed lignan in disease prevention and health promotion. Phytochem Rev 2003 2 401-417
3. Umezawa T. Diversity in lignan biosynthesis. Phytochem Rev 2003 2 371-390
4. Davin L B., Bedgar D L., Katayama T, Lewis N G. On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry 1990 31 3869-3874
5. Davin L B., Wang H-B, Crowell A L., Bedgar D L., Martin D M., Sarkanen S, Lewis N G. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 1997 275 362-366
6. Gang D R., Costa M A., Fujita M, Dinkova-Kostova A T., Wang H-B, Burlat V, Martin W, Sarkanen S, Davin L B., Lewis N G. Regiochemical control of monolignol radical coupling: a new paradigm for lignin and lignan biosynthesis. Chem Biol 1999 6 143-151
7. Xia Z-Q, Costa M A., Péllisier H, Davin L B., Lewis N G. Secoisolariciresinol dehydrogenase purification, cloning and functional expression. J Biol Chem 2001 276 12614-12623
8. Dinkova-Kostova A T., Gang D R., Davin L B., Bedgar D L., Chu A, Lewis N G. (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. J Biol Chem 1996 271 29473-29482
9. Fujita M, Gang D R., Davin L B., Lewis N G. Recombinant pinoresinol-lariciresinol reductases from Western Red Cedar (Thuja plicata) catalyze opposite enantiospecific conversions. J Biol Chem 1999 274 618-627
10. Suzuki S, Umezawa T, Shimada M. Stereochemical diversity in lignan biosynthesis of Arctium lappa L. Biosci Biotechnol Biochem 2002 66 1262-1269
11. Nakatsubo T, Mizutani M, Suzuki S, Hattori T, Umezawa T. Characterisation of Arabidopsis pinoresinol reductase, a new type of enzyme involved in lignin biosynthesis. J Biol Chem 2008 283 15550-15557
12. Hemmati S, Schmidt T J., Fuss E. (+)-pinoresinol/()-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B. FEBS Lett 2007 581 603-610
13. Ford J D., Huang K-S, Wang H B., Davin L B., Lewis N G. Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside- hydroxymethylglutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed. J Nat Prod 2001 64 1388-1397
14. Sicilia T, Niemeyer H B., Honig D M., Metzler M. Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. J Agric Food Chem 2003 51 1181-1188
15. von Heimendahl C B. I., Schäfer K M., Eklund P, Sjöholm R, Schmidt T J., Fuss E. Pinoresinol-lariciresinol reductases with different stereospecificity from Linum album and Linum usitatissimum. Phytochemistry 2005 66 1254-1263
16. Schmidt T J., Hemmati S, Fuss E, Alfermann A W. A combined HPLC-UV and HPLC-MS method for the identification of lignans and its application to the lignans of Linum usitatissimum L. and L. bienne Mill. Phytochem Anal 2006 17 299-311
17. Umezawa T, Davin L B., Lewis N G. Formation of the lignan, ()-secoisolariciresinol, by cell free extracts of Forsythia intermedia. Biochem Biophys Res Commun 1990 171 1008-1014
18. Umezawa T, Kuroda H, Isohata T, Higuchi T, Shimada M. Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana. Biosci Biotechnol Biochem 1994 58 230-234
19. Kumar S, Tamura K, Nei M. Integrated software for molecular evolutionary genetics analysis and sequence alignment. Brief Bioinform 2004 5 150-163
20. Bayindir Ü, Alfermann A W., Fuss E. Hinokinin biosynthesis in Linum corymbulosum Reichenb. Plant J 2008 55 810-820
21. Katayama T, Davin L B., Chu A, Lewis N G. Novel benzylic ether reductions in lignan biogenesis in Forsythia intermedia. Phytochemistry 1993 33 581-591
22. Schmidt T J., Alfermann A W., Fuss E. HPLC-MS identification of dibenzylbutyrolactone-type lignans: insights into ESI-MS/MS fragmentation of lign-7-eno-9,9-lactones and application to the lignans of Linum usitatissimum L. (common flax). Rapid Commun Mass Spectrom 2008 22 3642-3650
23. Eliasson C, Kamal-Eldin A, Andersson R, Åman P. High-performance liquid chromatographic analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction. J Chromatogr A 2003 1012 151-159
24. Davin L B., Lewis N G. An historical perspective on lignan biosynthesis: monolignol, allyphenol and hydroxycinnamic acid coupling and downstream metabolism. Phytochem Rev 2003 2 257-288
25. Davin L B., Lewis N G. Dirigent phenoxy radical coupling: advances and challenges. Curr Opin Biotechnol 2005 16 398-406
26. Min T, Kasahara H, Bedgar D L., Youn B, Lawrence P K., Gang D R., Halls S C., Park H, Hilsenbec J L., Davin L B., Lewis N G., Kang C. Crystal structures of pinoresinol-lariciresinol and phenylcoumaran benzylic ether reductases and their relationship to isoflavone reductases. J Biol Chem 2003 278 50714-50723