Skip to main content

Official Journal of the Japan Wood Research Society

  • Original Article
  • Published:

Four glucosides ofp-hydroxyphenyl derivatives from birch leaves

Abstract

The extractive of shirakamba (Betula platyphylla Sukatchev var.japonica Hara) leaves was investigated. Four glucosides ofp-hydroxyphenyl derivatives were isolated, and their structures were indentified as betuloside (I), 3,4′-dihydroxy-propiophenone-3-β-d-glucopyranoside (II), salidroside (III), and arbutin (IV). Arbutin was newly found in the leaves of shirakamba.

References

  1. Shen Y, Kojima Y, Terazawa M (1999) Two lignan rhamnosides from birch leaves. J Wood Sci 45:308–313

    Google Scholar 

  2. Higuchi R, Tokimitsu Y, Komori T (1988) An acylated triterpenoid saponin fromQuillaja saponaria. Phytochemistry 27:1165–1168

    Article  CAS  Google Scholar 

  3. Smite E, Lundgren LN, Andersson R (1993) Arylbutanoid and diarylheptanoid glycosides from inner bark ofBetula pendula. Phytochemistry 32:365–369

    Article  CAS  Google Scholar 

  4. Pan H, Lundgren LN (1994) Rhododendrol glycosides and phenyl glucoside esters from inner bark ofBetula pubescens. Phytochemistry 36:79–83

    Article  CAS  Google Scholar 

  5. Mori K, Qian ZH, Watanabe S (1992) Synthesis of 3,4′-dihyoxypropiophenone 3-β-d-glucopranoside, a constituent ofBetula platyphylla var.japonica, by enzymatic transglucosylation. Liebigs Ann Chem 485–487

  6. Pan H, Lundgren LN (1995) Phenolic extractives from root bark ofPicea abies. Phytochemistry 39:1423–1428

    Article  CAS  PubMed  Google Scholar 

  7. Terazawa M, Koga T, Okuyama H, Miyake M (1973) Isolation of platyphyllonol, a new diarylheptanoid from the green bark of shirakanba,Betula platyphylla Sukatch. var.japonica Hara. Mokuzai Gakaishi 19:47–48

    CAS  Google Scholar 

  8. Tscheshe R, Harz A, Wulff G (1974) 3,4-Dihydroxypropiophenon3-β-d-glucopranosid ausBetula alba. Phytochemistry 13:518–519

    Article  Google Scholar 

  9. Terazawa M, Koga T, Okuyama H, Miyake, M (1984) Phenolic compounds in living tissue of woods. III. Platyphylloside, a new diarylheptanoid glucoside from the green bark of shirakamba (Betula platyphylla Sukatchev var.japonica Hara). Mokuzai Gakkaishi 30:391–403

    CAS  Google Scholar 

  10. Friedrich VH (1960) Untersuchungen über die phenolichen inhaltsstoffe vonPyrus communis L. Pharmazie 15:650

    CAS  Google Scholar 

  11. Iida T, Noro Y, Ito K (1983) Magnostellin A and B, novel lignans fromMagnolia stellata. Phytochemistry 22:211–213

    Article  CAS  Google Scholar 

  12. Terazawa M, Kayama T (1989) Phenolic glycosides in the living tissues of woods. In: Proceedings of the international symposium of Wood and Pulping Chemistry (ISWPC), poster sessions. North Carolina State University Press, Raleigh, NC, pp 337–341

    Google Scholar 

  13. Hayashi E, Kojima Y, Terazawa M (1995) Extractives of asada,Ostrya japonica Sargent I: new glucosides ofp-hydroquinone dervatives from the inner bark. Mokuzai Gakaishi 41:925–931

    CAS  Google Scholar 

  14. Inoue T, Ishidate Y, Fujida M, Kubo M, Fukushima M, Nagai M (1978) Studies on the constituents of Aceraceae plants. I. Constituents in the leaves and the stem bark ofAcer nikoense Maxim. Chem Pharm Bull (Tokyo) 98:41–46

    CAS  Google Scholar 

  15. Klischies M, Zenk MH (1978) Stereochemistry of C-methylation in the biosynthesis of rhododendrin inAlnus andBetula. Phytochemistry 17:1281–1284

    Article  CAS  Google Scholar 

  16. Fuchino H, Konishi S, Satoh T, Yagi A, Saitsu K, Tatsumi T, Tanaka N (1996) Chemical evaluation ofBetula species in Japan. II. Constituents ofBetula platyphylla var.japonica. Chem Pharm Bull (Tokyo) 44:1033–1038

    Article  CAS  Google Scholar 

  17. Sunnerheim K, Palo T, Theander O, Knutsson PG (1988) Chemical defense in birch: platyphylloside: a phenol fromBetula pendula inhibiting digestibility. J Chem Ecol 14:549–559

    Article  CAS  PubMed  Google Scholar 

  18. Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H (1989) Ionone and lignan glycosides fromEpimedium diphyllum. Phytochemistry 28:3483–3485

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Minoru Terazawa.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shen, Y., Kojima, Y. & Terazawa, M. Four glucosides ofp-hydroxyphenyl derivatives from birch leaves. J Wood Sci 45, 332–336 (1999). https://doi.org/10.1007/BF00833499

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00833499

Key words