Isolation and enzymatic formation of lignans of Daphne genkwa and Daphne odora

Journal of Wood Science

Volumn 47, Issue 5, 2001, Pages 383-388

  Okunishi, Tomoya ^a,b   Umezawa, Toshiaki ^a   Shimada, Mikio ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

Author keywords

Daphne genkwa; Daphne odora; Lignan; Pinoresinol reductase; Thymelaeaceae

Indexed keywords

CATALYSIS; ENZYMES; PLANTS (BOTANY); STEREOCHEMISTRY;

ENZYMATIC REACTIONS;

WOOD;

CATALYSTS; LIGNANS; STEREOCHEMISTRY;

DAPHNE; DAPHNE ODORA; THYMELAEACEAE;

EID: 0009292826     PISSN: 14350211     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00766790     Document Type: Article

References (29)

1. Umezawa T (1997) Lignans. In: Higuchi T (ed) Springer series in wood science, Biochemistry and molecular biology of wood. Springer-Verlag, Berlin, pp 181-194
2. Umezawa T, Davin LB, Lewis NG (1990) Formation of the lignan, (-)-secoisolariciresinol, by cell free extracts of Forsythia intermedia. Biochem Biophys Res Commun 171:1008-1014
3. Umezawa T, Davin LB, Yamamoto E, Kingston DGI, Lewis NG (1990) Lignan biosynthesis in Forsythia species. J Chem Soc Chem Commun 1405-1408
4. Umezawa T, Davin LB, Lewis NG (1991) Formation of lignans (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia cell-free extracts. J Biol Chem 266:10210-10217
5. Davin LB, Bedgar DL, Katayama T, Lewis NG (1992) On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry 31:3869-3874
6. Katayama T, Davin LB, Lewis NG (1992) An extraordinary accumulation of (-)-pinoresinol in cell-free extracts of Forsythia intermedia: evidence for enantiospecific reduction of (+)-pinoresinol. Phytochemistry 31:3875-3881
7. Katayama T, Davin LB, Chu A, Lewis NG (1993) Novel benzylic ether reductions in lignan biogenesis in Forsythia intermedia. Phytochemistry 33:581-591
8. Chu A, Dinkova A, Davin LB, Bedgar DL, Lewis NG (1993) Stereospecificity of (+)-pinoresinol and (+)-lariciresinol reductases from Forsythia intermedia. J Biol Chem 268:27026-27033
9. Ozawa S, Davin LB, Lewis NG (1993) Formation of (-)-arctigenin in Forsythia intermedia. Phytochemistry 32:643-652
10. Umezawa T, Kuroda H, Isohata T, Higuchi T, Shimada M (1994) Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana. Biosci Biotech Biochem 58:230-234
11. Paré PW, Wang H-B, Davin LB, Lewis NG (1994) (+)-Pinoresinol synthesis: a stereoselective oxidase catalysing 8,8′-lignan formation in Forsythia intermedia. Tetrahedron Lett 35:4731-4734
12. Dinkova-Kostova AT, Gang DR, Davin LB, Bedgar DL, Chu A, Lewis NG (1996) (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. J Biol Chem 271:29473-29482
13. Davin LB, Wang H-B, Crowell AL, Bedgar DL, Martin DM, Sarkanen S, Lewis NG (1997) Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275:362-366
14. Umezawa T (1996) Biological activity and biosynthesis of lignans. Mokuzai Gakkaishi 42:911-920
15. Umezawa T, Shimada M (1996) Formation of the lignan (+)- secoisolariciresinol by cell-free extracts of Arctium lappa. Biosci Biotech Biochem 60:736-737
16. Suzuki S, Umezawa T, Shimada M (1998) Stereochemical difference in secoisolariciresinol formation between cell-free extracts from petioles and from ripening seeds of Arctium lappa L. Biosci Biotech Biochem 62:1468-1470
17. Mikame K, Umezawa T, Shimada M (1997) Lignan synthesis by cell-free extracts from Linum flavum. Proceedings of the 42nd Lignin Symposium, Sapporo, pp 65-68
18. Suzuki S, Umezawa T, Shimada M (1998) Lignan biosynthesis in Anthriscus sylvestris Hoffm. Proceedings of the 43rd Lignin Symposium, Tokyo, pp 131-132
19. Katayama T, Masaoka T, Yamada H (1997) Biosynthesis and stereochemistry of lignans in Zanthoxylum ailanthoides. I. (+)-Lariciresinol formation by enzymatic reduction of (±)-pinoresinols. Mokuzai Gakkaishi 43:580-588
20. Umezawa T, Okunishi T, Shimada M (1997) Stereochemical diversity in lignan biosynthesis. Wood Res 84:62-75
21. Tatematsu H, Kurokawa M, Niwa M, Hirata Y (1984) Piscicidal constituents of Stellera chamaejasme L. II. Chem Pharm Bull 32:1612-1613
22. Umezawa T, Shimada M (1996) Enantiomeric composition of (-)-pinoresinol, (+)-matairesinol and (+)-wikstromol isolated from Wikstroemia sikokiana. Mokuzai Gakkaishi 42:180-185
23. Okunishi T, Umezawa T, Shimada M (2000) Enantiomeric compositions and biosynthesis of Wikstroemia sikokiana lignans. J Wood Sci 46:234-242
24. Kogiso S, Wada K, Munakata K (1977) Nematicidal substances from Daphne odora. Report of the 26th international congress of pure and applied chemistry, Tokyo, p 291
25. Wang W, Zhou B, Wang C (1995) Chemical constituents of Maoruixiang (Daphne odora). Zhongcaoyao 26:566-567
26. Umezawa T, Shimada M (1994) Syntheses of (±)-lariciresinols. Mokuzai Gakkaishi 40:231-235
27. Umezawa T, Isohata T, Kuroda H, Higuchi T, Shimada M (1992) Chiral HPLC and LC-MS analysis of several lignans. In: Kuwahara M, Shimada M (eds) Biotechnology in pulp and paper industry, Uni, Tokyo, pp 507-512
28. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
29. Fujita M, Gang DR, Davin LB, Lewis NG (1999) Recombinant pinoresinol-lariciresinol reductases from western red cedar (Thuja plicata) catalyze opposite enantiospecific conversions. J Biol Chem 274:618-627