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Official Journal of the Japan Wood Research Society

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Lignans ofChamaecyparis obtusa

Abstract

Heartwood ofChamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan, hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans — xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and rnatairesinol (11) — were isolated from young shoots ofChamaecyparis obtusa cv. Breviramea. Eight lignans (1, 2, 4, 5, 7, 9,10, and11) were isolated from this plant for the first time. Chiral high-performance liquid Chromatographie analysis showed that8, 9, 10, and11, were found to be levorotatory and optically pure (>99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of8 are discussed.

References

  1. 1.

    Umezawa T (2000) Chemistry of extractives. In: Shiraishi N, Hon DN-S (eds) Wood and cellulosic chemistry, 2nd ed. Marcel Dekker, New York, pp 213–241

    Google Scholar 

  2. 2.

    Yoshiki Y, Ishiguro T (1933) Über die krystallisierten Bestandteile des Hinokiöls (in Japanese). Yakugaku Zasshi 53:73–151

    CAS  Article  Google Scholar 

  3. 3.

    Masumura M (1955) Studies on the component of young leaves ofChamaecyparis obtusa cv. Breviramea (first report); separation of crystallized component (in Japanese). Nippon Kagaku Zasshi 76:423–425

    CAS  Article  Google Scholar 

  4. 4.

    Masumura M (1955) Studies on the component of young leaves ofChamaecyparis obtusa cv. Breviramea (second report); structure of neutral component, hibalactone (in Japanese). Nippon Kagaku Zasshi 76:425–429

    CAS  Article  Google Scholar 

  5. 5.

    Masumura M (1955) Studies on the component of young leaves ofChamaecyparis obtusa cv. Breviramea (fourtn report); about hinoki acid andd-sesamin (in Japanese). Nippon Kagaku Zasshi 76:1318–1322

    CAS  Article  Google Scholar 

  6. 6.

    Umezawa T, Kuroda H, Isohata T, Higuchi T, Shimada M (1994) Enantioselective lignan synthesis by cell-free extracts ofForsythia koreana. Biosci Biotechnol Biochem 58:230–234

    CAS  Article  Google Scholar 

  7. 7.

    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 the pulp and paper industry. Uni, Tokyo, pp 507–512

    Google Scholar 

  8. 8.

    Ohashi H, Hayashi H, Yamada M, Yasue M (1987) Phenolic heartwood constituents and heartwood color of Japanese cypress (in Japanese). Res Bull Fac Agr Gifu Univ 52:131–139

    Google Scholar 

  9. 9.

    Gonzaléz MJTG, Pinto MMM, Kijjoa A, Anantachoke C, Herz W (1993) Stilbenes and other constituents ofKnema austrosiamensis. Phytochemistry 32:433–438

    Article  Google Scholar 

  10. 10.

    Rahman MMA, Dewick PM, Jackson DE, Lucas JA (1990) Lignans ofForsythia intermedia. Phytochemistry 29:1971–1980

    CAS  Article  Google Scholar 

  11. 11.

    Fang JM, Liu MY, Cheng YS (1990) Lignans from wood ofCalcocedms formosana. Phytochemistry 29:3048–3049

    CAS  Article  Google Scholar 

  12. 12.

    Shieh HL, Cordell GA, Lankin DC, Lotter H (1990) The liquid, solid, and molecular force field calculated conformations of savinin. J Org Chem 55:5139–5145

    CAS  Article  Google Scholar 

  13. 13.

    Banerji J, Das B, Chatterjee A, Shoolery JN (1984) Gadain, a lignan fromJatropha gossypifolia. Phytochemistry 23:2323–2327

    CAS  Article  Google Scholar 

  14. 14.

    Zhuang L-G, Seligmann O, Lotter H, Wagner H (1983) (−)-Dihydrosesamin, a lignan fromDaphne tangutica. Phytochemistry 22:265–267

    Article  Google Scholar 

  15. 15.

    Stevens DR, Whiting DA (1992) Stereospecific synthesis of the 2,3-trans-34-cis trisubstituted tetrahydrofuran lignan (±)-dihydrosesamin. J Chem Soc Perkin Trans I:633–637

    Article  Google Scholar 

  16. 16.

    Hull HM, Jones RG, Knight DW (1998) An alternative diastereospecific approach to (±)-samin and 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane [furanofuran] lignans based on the Ireland-Claisen rearrangement of unsaturated oxa-macrolides. J Chem Soc Perkin Trans I:1779–1787

    Article  Google Scholar 

  17. 17.

    Brieskorn CH, Huber H (1976) Vier neue Lignane ausAptosimum spinescens. Tetrahedron Lett 26:2221–2224

    Article  Google Scholar 

  18. 18.

    Fukuda Y, Osawa T, Namiki M, Ozaki T (1985) Studies on anti-oxidative substances in sesame seed. Agric Biol Chem 49:301–306

    CAS  Google Scholar 

  19. 19.

    Takaku N, Mikame K, Okunishi T, Suzuki S, Umezawa T, Shimada M (2001) New lignan, isoactifolin, fromChamaecyparis obtusa cv. Breviramea. J Wood Sci 47:493–496

    CAS  Article  Google Scholar 

  20. 20.

    Umezawa T, Okunishi T, Shimada M (1997) Stereochemical diversity in lignan biosynthesis. Wood Res 84:62–75

    CAS  Google Scholar 

  21. 21.

    Keimatsu S, Ishiguro T (1936) Üntersuchung der Bestandteile der Harze. (VII. Mitteilung) Über die Konstitution des Hinokinins (in Japanese). Yakugaku Zasshi 56:103–118

    Article  Google Scholar 

  22. 22.

    Kariyone T, Isoi K (1954) Studies on plant waxes. VI. Lignans from the leaves of coniferae (1) (in Japanese). Yakugaku Zasshi 74:1312–1314

    CAS  Article  Google Scholar 

  23. 23.

    Umezawa T (1997) Lignans. In: Higuchi T (ed) Biochemistry and molecular biology of wood. Springer, Berlin, pp 181–194

    Google Scholar 

  24. 24.

    Lewis NG, Davin LB (1999) Lignans: biosynthesis and function. In: Comprehensive natural products chemistry. Vol 1. Polyketides and other secondary metabolites including fatty acids and their derivatives Sankawa U (ed). Elsevier Science, Oxford, pp 639–712

    Google Scholar 

  25. 25.

    Umezawa T (1996) Biological activity and biosynthesis of lignans. Mokuzai Gakkaishi 42:911–920

    CAS  Google Scholar 

  26. 26.

    Mikame K, Umezawa T, Shimada M (1997) Lignan synthesis by cell-free extracts fromLinum flavum (in Japanese). In: Proceedings of the 42nd Lignin Symposium, Sapporo, Japan, pp 65–68

  27. 27.

    Suzuki S, Umezawa T, Shimada M (1998) Lignan biosynthesis inAnthriscus sylvestris Hoffm. (in Japanese). In: Proceedings of the 42nd Lignin Symposium, Tokyo, pp 131–132

  28. 28.

    Katayama T, Masaoka T, Yamada H (1997) Biosynthesis and stereochemistry of lignans inZanthoxylum ailanthoides. I. (+)-Lariciresinol formation by enzymatic reduction of (±)-pinoresinols. Mokuzai Gakkaishi 43:580–588

    CAS  Google Scholar 

  29. 29.

    Umezawa T, Shimada M (1996) Formation of the lignan (+)-secoisolariciresinol by cell-free extracts ofArctium lappa. Biosci Biotechnol Biochem 60:736–737

    CAS  Article  Google Scholar 

  30. 30.

    Suzuki S, Umezawa T, Shimada M (1998) Stereochemical difference in secoisolariciresinol formation between cell-free extracts from petioles and from ripening seeds ofArctium lappa L. Biosci Biotechnol Biochem 62:1468–1470

    CAS  Article  PubMed  Google Scholar 

  31. 31.

    Kato MJ, Chu A, Davin LB, Lewis NG (1998) Biosynthesis of antioxidant lignans inSesamum indicum seeds. Phytochemistry 47:583–591

    CAS  Article  Google Scholar 

  32. 32.

    Bauer W, Zenk MH (1991) Two methylenedioxy bridge forming cytochrome P-450 dependent enzymes are involved in (S)-stylopine biosynthesis. Phytochemistry 30:2953–2961

    CAS  Article  Google Scholar 

  33. 33.

    Lin TC, Fang JM, Cheng YS (1999) Terpenes and lignans from leaves ofChamaecyparis formosensis. Phytochemistry 51:793–801

    CAS  Article  Google Scholar 

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Correspondence to Toshiaki Umezawa.

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Takaku, N., Choi, D., Mikame, K. et al. Lignans ofChamaecyparis obtusa . J Wood Sci 47, 476–482 (2001). https://doi.org/10.1007/BF00767901

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Key words

  • Lignan
  • Stereochemistry
  • Chamaecyparis obtusa
  • Chamaecyparis obtusa cv. Breviramea
  • Heartwood