Survey and enzymatic formation of lignans of Anthriscus sylvestris

Journal of Wood Science

Volumn 48, Issue 6, 2002, Pages 536-541

  Suzuki, Shiro ^a   Sakakibara, Norikazu ^a   Umezawa, Toshiaki ^a   Shimada, Mikio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Anthriscus sylvestris; Biosynthesis; Lignan

Indexed keywords

ALCOHOLS; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY;

STEREOCHEMICAL PROPERTIES;

ENZYMES;

ALCOHOLS; ENZYMES; GAS CHROMATOGRAPHY; LIGNANS;

ANTHRISCUS; ANTHRISCUS SYLVESTRIS; ARCTIUM; ARCTIUM LAPPA; FORSYTHIA;

EID: 0141465298     PISSN: 14350211     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00766653     Document Type: Article

References (41)

1. Umezawa T, Okunishi T, Shimada M (1997) Stereochemical diversity in lignan biosynthesis. Wood Res 84:62-75
2. Umezawa T (2001) Biosynthesis of lignans and related phenylpropanoid compounds (in Japanese). Regul Plant Growth Dev 36:57-67
3. Umezawa T (1997) Lignans. In: Higuchi T (ed) Biochemistry and molecular biology of wood. Springer-Verlag, Berlin, pp 181-194
4. MacRae WD, Towers GHN (1984) Biological activities of lignans. Phytochemistry 23:1207-1220
5. Umezawa T (1996) Biological activity and biosynthesis of lignans (in Japanese). Mokuzai Gakkaishi 42:911-920
6. Ayres DC, Loike JD (1990) Lignans: chemical, biological and clinical properties. Cambridge University Press, Cambridge
7. Sackett D (1993) Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchicine site of tubulin. Pharmacol Ther 59:163-223
8. Canel C, Moraes RM, Dayan FE, Ferreira D (2000) Molecules of interest: podophyllotoxin. Phytochemistry 54:115-120
9. 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
10. Cragg G, Boyd M, Khanna R, Newman D, Sausville E (1999) Natural product drug discovery and development: the United States National Cancer Institute role. In: Romeo J (ed) Recent advances in phytochemistry. Kluwer Academic/Plenum, New York, pp 1-29
11. Konuklugil B (1996) Aryltetralin lignans from genus Linum. Fitoterapia 67:379-381
12. Broomhead AJ, Dewick PM (1990) Aryltetralin lignans from Linum flavum and Linum capitatum. Phytochemistry 29:3839-3844
13. Noguchi T, Kawanami M (1940) The active components of the Umbelliferae. X. Components of Anthriscus sylvestris (in Japanese). Yakugaku Zasshi 60:629-636
14. Kozawa M, Morita N, Hata K (1978) Chemical components of the roots of Anthriscus sylvestris Hoffm. I. Structures of an acyloxycarboxylic acid and a new phenylpropanoidester, anthriscusin (in Japanese). Yakugaku Zasshi 98:1486-1490
15. Kurihata T, Kikuchi M, Suzuki S, Hisamichi S (1978) Studies of the constituents of Anthriscus sylvestris HOFFM. I. On the components of the radix (in Japanese). Yakugaku Zasshi 98:1586-1591
16. Turabelidze DG, Mikaya GA, Kemertelidze P, Vul'son NS (1982) Lignan lactones from the roots of wild chervil Anthriscus nemerosa (Bieb.) Spreng. Sov J Bioorg Chem 8:374-379
17. Ikeda R, Nagao T, Okabe H, Nakano Y, Matsunaga H, Katano M, Mori M (1998) Antiproliferative constituents in Umbelliferae plants. IV. Constituents in the fruits of Anthriscus sylvestris HOFFM. Chem Pharm Bull (Tokyo) 46:875-878
18. Ikeda R, Nagao T, Okabe H, Nakano Y, Matsunaga H, Katano M, Mori M (1998) Antiproliferative constituents in Umbelliferae plants. III. Constituents in the root and the ground part of Anthriscus sylvestris HOFFM. Chem Pharm Bull (Tokyo) 46:871-874
19. Koh D, Lim Y (1999) Anti-allergic activities of anthricin and its structure elucidation. Agric Chem Biotechnol 42:208-209
20. Xia ZQ, Costa MA, Proctor J, Davin LB, Lewis NG (2000) Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum. Phytochemistry 55:537-549
21. Weiss SG, Tin-Wa M, Perdue RE Jr, Farnsworth NR (1975) Potential anticancer agents. II. Antitumor and cytotoxic lignans from Linum album (Linaceae). J Pharm Sci 64:95-98
22. Lim YH, Leem MJ, Shin DH, Chang HB, Hong SW, Moon EY, Lee DK, Yoon SJ, Woo WS (1999) Cytotoxic constituents from the roots of Anthriscus Sylvestris. Arch Pharm Res 22:208-212
23. Jackson DE, Dewick PM (1984) Biosynthesis of Podophyllum lignans. II. Interconversions of aryltetralin lignans in Podophyllum hexandrum. Phytochemistry 23:1037-1042
24. Kamil WM, Dewick PM (1986) Biosynthetic relationship of aryltetralinlactone lignans to dibenzylbutyrolactone lignans. Phytochemistry 25:2093-2102
25. Erdtman H, Harmatha J (1979) Phenolic and terpenoid heartwood constituents of Libocedrus yateensis. Phytochemistry 18:1495-1500
26. 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
27. 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
28. Okunishi T, Umezawa T, Shimada M (2000) Enantiomeric compositions and biosynthesis of Wikstroemia sikokiana lignans. J Wood Sci 46:234-242
29. Umezawa T, Shimada M (1994) Syntheses of (±)-lariciresinols. Mokuzai Gakkaishi 40:231-235
30. Umezawa T, Isohata T, Kuroda H, Higuchi T, Shimada M (1992) Biosynthesis of lignans. In: Kuwahara M, Shimada M (eds) Biotechnology in pulp and paper industry. Uni Publishing, Tokyo, pp 507-512
31. 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
32. Bradford M (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
33. Pelter A (1968) The mass spectra of some lignans of the 1-phenyl-1,2,3,4,-tetrahydronaphthalene series. J Chem Soc (c):74-79
34. Umezawa T, Shimada M (1996) Formation of the lignan (+)- secoisolariciresinol by cell-free extracts of Arctium lappa. Biosci Biotechnol Biochem 60:736-737
35. 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
36. Katayama T, Davin LB, Chu A, Lewis NG (1993) Novel benzylic ether reductions in lignan biogenesis in Forsythia intermedia. Phytochemistry 33:581-591
37. 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
38. 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
39. 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
40. Lewis NG, Davin LB (1999) Lignans: biosynthesis and function. In: Sankawa U (ed) Comprehensive natural products chemistry, vol 1. Elsevier Science, Oxford, pp 639-712
41. Broomhead AJ, Rahman MMA, Dewick PM, Jackson DE, Lucas JA (1991) Matairesinol as precursor of Podophyllum lignans. Phytochemistry 30:1489-1492