Protosappanin C from Sappan Lignum and Absolute Configuration of Protosappanins(Organic,Chemical)

1 Citations
  • NAGAI M.
    Institute of Medicinal Chemistry, Hoshi University
  • NAGUMO SEIJI
    Faculty of Pharmaceutical Sciences, Hoshi University

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Description

A new dibenz[b,d]oxocin derivative, named protosappanin C (3), C_<16>H_<14>O_6, amorphous powder, [α]^<23>_D 〜39.8° (MeOH), was isolated from Sappan Lignum(the dried heart-wood of Cacsalplnia sappan L. (Leguminosae)). It yielded sappanin (4) on alkaline fusion, an oxime (5), a dimethyl acetal (6) on treatment with jrj-toluenesulfonic acid in methanol, and protosappanin B (2) on reduction with sodium borohydride. The circular dichroism spectra of 3 and 6 indicated that their biphenyl system preferentially takes 5 configuration, from which R configuration was assigned to C-7 of 3. On the basis of the above chemical and spectroscopic evidence, the chemical structure of 3 was established as (7R)-7,8-dihydro-3,7,10,11-tetrahydroxy-7(6H)-dibenz[b,d]oxoctncarbal-dehyde. A possible route of biosynthesis of protosappanins from sappanchalcone is discussed.

Journal

  • Chem. Pharm. Bull.

    Chem. Pharm. Bull. 35 3002-3005, 1987

    The Pharmaceutical Society of Japan

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Details 詳細情報について

  • CRID
    1570291227372036992
  • NII Article ID
    110006281352
  • NII Book ID
    AA00602100
  • ISSN
    00092363
  • Text Lang
    en
  • Data Source
    • CiNii Articles

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