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Official Journal of the Japan Wood Research Society

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Phenolic constituents ofTaxus cuspidata I: lignans from the roots

Abstract

The phenolic constituents of the roots ofTaxus cuspidata (Japanese yew) were investigated. Four lignans, [(+)-taxiresinol (1), (+)-lariciresinol (2), (−)-secoisolariciresinol (3), and (+)-pinoresinol (4)] were isolated and identified. The assignment of proton and carbon atoms for the lignans were finally solved by one- and twodimensional-nuclear magnetic resonance spectra. The enantiomeric excess of these lignans were determined by chiral high-performance liquid Chromatographic analyses. (+)-Lariciresinol and (−)-secoisolariciresinol were optically pure; (+)-taxiresinol was also suggested to be optically pure, although (+)-pinoresinol was not (77% enantiomeric excess).

References

  1. Wall ME, Wani MC (1994) Taxol: discovery to clinic: In: Wagner H, Farnsworth NR (eds) Economic medical plant reseach (vol. 6). Academic, London, pp 299–320

    Google Scholar 

  2. Kingston DGI (1994) Taxol: the chemistry and structure-activity relationships of a novel anticancer agent. Trends Biotechnol 12:222–227

    Article  CAS  PubMed  Google Scholar 

  3. Kobayashi J, Ogiwara A, Hosoyama H, Shigemori H, Yoshida N, Sasaki T, Li Y, Iwasaki S, Naito M, Tsuruo T (1994) Taxuspines A-C, new taxoids from Japanese yewTaxus cuspidata: inhibiting drug transport activity of P-glycoprotein in multidrug-resistant cells. Tetrahedron 50:7401–7416

    Article  CAS  Google Scholar 

  4. Maki Y, Sako M (1993) The chemistry of taxane diterpenoids: the present status of development of taxol as a new type of antitumor agent. J Synth Org Chem Jpn 51:298–307

    Article  CAS  Google Scholar 

  5. Parmer VS, Vardhan A, Taneja P, Sinha R, Patnaik GK, Tripathi SC, Boll PM, Larsen S (1991) Absolute configuration ofepirhododendrin and (−)-rhododendrol [= (−)-betuligenol] and X-ray crystal and molecular structure of rhododendrin [=betuloside], a hepatoprotective constituent ofTaxus baccata. J Chem Perkin Trans 1:697–699

    Google Scholar 

  6. Vohora SB, Kumar I (1971) Studies onTaxus baccata. Planta Med 20:100–107

    Article  CAS  PubMed  Google Scholar 

  7. Mujumdar RB, Srinivasan R, Venkataraman K (1972) Taxiresinol, a new lignan in the heartwood ofTaxus baccata. Indian J Chem 10:677–680

    CAS  Google Scholar 

  8. Umezawa T, Davin LB, Lewis NG (1991) Formation of lignans (−)-secoisolariciresinol and (−)-matairesinol withForsythia intermedia cell-free extracts. J Biol Chem 266:10210–10217

    CAS  PubMed  Google Scholar 

  9. Kawamura F, Ohashi H, Kawai S, Teratani F, Kai Y (1996) Photodiscoloration of Western hemlock (Tsuga heterophylla) sapwood. II. Structures of constituents causing photodiscoloration. Mokuzai Gakkaishi 42:301–307

    CAS  Google Scholar 

  10. Erdtman H, Tsuno K (1969) Taxus heartwood constituents. Phytochemistry 8:931–932

    Article  CAS  Google Scholar 

  11. Erdtman H, Tsuno K (1969) The chemistry of the order cupressales. 56. Heartwood constituents ofFitzroya cupressoides. Acta Chem Scand 23:2021–2024

    Article  CAS  Google Scholar 

  12. Ayres DC, Loike JD (1990) Lignans: chemical, biological and clinical properties. Cambridge University Press, Cambridge, pp 1–11

    Book  Google Scholar 

  13. Katayama T, Davin LB, Chu A, Lewis NG (1993) Novel benzylic ether reductions in lignan biogenesis inForsythia intermedia. Phytochemistry 33:581–591

    Article  CAS  Google Scholar 

  14. Tazaki H, Hayashiba T, Ishikawa F, Taguchi D, Takasawa T, Nabeta K (1999) Lignan biosynthesis in liverwortsJamesoniella autumnalis andLophocolea heterophylla. Tetrahedron Lett 40:101–104

    Article  CAS  Google Scholar 

  15. Davin LB, Wang H-B, Crowell AL, Bedgar DL, Martin DM, Sarkanen S, Lewis NG (1997) Stereoselective bimolecular phenoxy radical coupling by an auxiliary (diligent) protein without an active center. Science 275:362–366

    Article  CAS  PubMed  Google Scholar 

  16. 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 

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

    Article  CAS  Google Scholar 

  18. Aoyama T, Terasawa S, Sudo K, Shioiri T (1984) New methods and reagents in organic synthesis. 46. A convenient reagent for the O-methylation of phenols and enols. Chem Pharm Bull 32:3759–3760

    Article  CAS  Google Scholar 

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Correspondence to Fumio Kawamura.

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Kawamura, F., Kikuchi, Y., Ohira, T. et al. Phenolic constituents ofTaxus cuspidata I: lignans from the roots. J Wood Sci 46, 167–171 (2000). https://doi.org/10.1007/BF00777366

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  • DOI: https://doi.org/10.1007/BF00777366

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