Semi-micro chiral HPLC analysis of lignans

Journal of Wood Science

Volumn 50, Issue 1, 2004, Pages 93-96

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

^a KYOTO UNIVERSITY   (Japan)

^b NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

Author keywords

Enantiomer; Lignan; Semi micro chiral HPLC

Indexed keywords

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SEPARATION; STEREOCHEMISTRY;

ENANTIOMERIC SEPARATION;

AROMATIC COMPOUNDS;

LIGNANS; LIQUID CHROMATOGRAPHY; SEPARATION; STEREOCHEMISTRY;

EID: 4043117771     PISSN: 14350211     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10086-003-0520-3     Document Type: Article

References (38)

1. Umezawa T (2001) Biosynthesis of lignans and related phenylpropanoid compounds (in Japanese). Regul Plant Growth Dev 36:57-67
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. 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
6. 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
7. 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
8. Katayama T, Davin LB, Chu A, Lewis NG (1993) Novel benzylic ether reductions in lignan biogenesis in Forsythia intermedia. Phytochemistry 33:581-591
9. 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
10. Ozawa S, Davin LB, Lewis NG (1993) Formation of (-)-arctigenin in Forsythia intermedia. Phytochemistry 32:643-652
11. Umezawa T, Kuroda H, Isohata T, Higuchi T, Shimada M (1994) Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana. Biosci Biotechnol Biochem 58:230-234
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, Shimada M (1996) Formation of the lignan (+)- secoisolariciresinol by cell-free extracts of Arctium lappa. Biosci Biotechnol Biochem 60:736-737
15. Umezawa T, Shimada M (1996) Enantiomeric composition of (-)-pinoresinol, (+)-matairesinol and (+)-wikstromol isolated from Wikstroemia sikokiana. Mokuzai Gakkaishi 42:180-185
16. Katayama T, Masaoka T, Yamada H (1997) Biosynthesis and stereochemistry of lignans in Zanthoxylum ailanthoides. I. (+)-Lariciresinol formation by enzymic reduction of (±)-pinoresinols. Mokuzai Gakkaishi 43:580-588
17. 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 Biotechnol Biochem 62:1468-1470
18. Kawai S, Sugishita K, Ohashi H (1999) Identification of Thuja occidentalis lignans and its biosynthetic relationship. Phytochemistry 51:243-247
19. Okunishi T, Umezawa T, Shimada M (2000) Enantiomeric compositions and biosynthesis of Wikstroemia sikokiana lignans. J Wood Sci 46:234-242
20. Okunishi T, Umezawa T, Shimada M (2001) Isolation and enzymatic formation of lignans of Daphne genkwa and Daphne odora. J Wood Sci 47:383-388
21. Takaku N, Choi D-H, Mikame K, Okunishi T, Suzuki S, Ohashi H, Umezawa T, Shimada M (2001) Lignans of Chamaecyparis obtusa. J Wood Sci 47:476-482
22. 14C]sinapyl alcohol. J Wood Sci 47:41-47
23. Suzuki S, Umezawa T, Shimada M (2002) Stereochemical diversity in lignan biosynthesis of Arctium lappa L. Biosci Biotechnol Biochem 66:1262-1269
24. Mikame K, Sakakibara N, Umezawa T, Shimada M (2002) Lignans of Linum flavum var. compactum. J Wood Sci 48:440-445
25. Kim I-W, Okamoto Y, Carr PW, Ryu J-K, Park J-H (2002) Amylose tris(3,5-dimethylphenylcarbamate)-coated zirconia as a chiral stationary phase for micro HPLC. Bull Korean Chem Soc 23:1014-1016
26. Al-Dirbashi OY, Kuroda N, Wada M, Takahashi M, Nakashima K (2000) Quantification of methamphetamine, amphetamine and enantiomers by semi-micro column HPLC with fluorescence detection; applications on abusers' single hair analyses. Biomed Chromatogr 14:293-300
27. Al-Dirbashi OY, Wada M, Kuroda N, Takahashi M, Nakashima K (2000) Achiral and chiral quantification of methamphetamine and amphetamine in human urine by semi-micro column high-performance liquid chromatography and fluorescence detection. J Forensic Sci 45:708-714
28. Umezawa T, Shimada M (1994) Syntheses of (±)-lariciresinols. Mokuzai Gakkaishi 40:231-235
29. Jiao Y, Davin LB, Lewis NG (1998) Furanofuran lilgnan metabolism as a functin of seed maturation in Sesamun inducum: methylenedioxy bridge formation. Phytochemistry 49:387-394
30. Kato MJ, Chu A, Davin LB, Lewis NG (1998) Biosynthesis of antioxidant lignans in Sesamum indicum seeds. Phytochemistry 47:583-591
31. Miyauchi T, Ozawa S (1998) Formation of (+)-eudesmin in Magnolia kobus DC. var. borealis SARG. Phytochemistry 47:665-670
32. Tanahashi M, Karina M, Higuchi T (1987) Cleavage of lignin in wood by steam explosion. In: Proceedings of fourth international symposium on wood and pulping chemistry, vol 2, p 343
33. Katayama T, Sogo M (1989) An optically-active compound formed by the reduction of an β-ketonic lignin substructure model compound by Fusalium solani M-13-1. Mokuzai Gakkaishi 35:1116-1124
34. Katayama T, Kado Y (1998) Formation of optically active neolignans from achiral coniferyl alcohol by cell-free extracts of Eucommia ulmoides. J Wood Sci 44:244-246
35. Nabeta K, Nakahara K, Yonekubo J, Okuyama H, Sasaya T (1991) Lignan biosynthesis in Larix leptolepis callus. Phytochemistry 30:3591-3593
36. Okunishi T, Sakakibara N, Suzuki S, Umezawa T, Shimada M (2004) Stereochemistry of matairesinol formation by Daphne secoisolariciresinol dehydrogenase. J Wood Sci 50:77-81
37. Ohnishi A, Ichida A, Makino S (1996) Liquid chromatographic resolution of optical isomers: development and characteristics of chiral stationary phases consist of polysaccharide derivatives and application to large scale separation (in Japanese). J Synthetic Organic Chem 54:344-353
38. Okamoto Y (1992) Optical resolution (in Japanese). Chem Chem Ind 45:1224-1227