Novel Lanostane and Rearranged Lanostane-Type Triterpenoids from Abies sachalinensis : II

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Abstract

In the previous work we reported five A-<i>seco</i>-rearranged lanostane triterpenoids as antibacterial constituents from the ethyl acetate soluble fraction of <i>Abies sachalinensei</i> leaves. In further study on the isolation of constituents from the ethyl acetate soluble fraction, two new rearranged lanostane and lanostane-type triterpenoids (3, 4) and three reported compound (1, 2, 5) were isolated. The structures of new compound 3 and 4 were determined to be 3,4-<i>seco</i>-4(28),6,8(14),24-mariesatetraen-26,23-olide-23-hydroxy-3-oic acid and 3,4-<i>seco</i>-4(28),7,24-lanostatrien-26,23-olide-23-hydroxy-3-oic acid, respectively, by spectral studies on HR-MS, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, and 2D-NMR spectra. Compound 1 was identified with pindrolactone and its structure was revised as 7,14,22<i>Z</i>,24-mariesatetraen-26,23-olide-3α-ol. Structures of 2 and 5 were determined as 7,14,24-mariesatrien-26,23-olide-3α,23-diol and 3α-hydroxy-7,14,24<i>E</i>-mariesatrien-23-oxo-26-oic acid. Of these compounds, 2, 3 and 4 were obtained as lactol tautomer mixtures at γ-lactone structures of side chains.

Journal

  • Chemical and Pharmaceutical Bulletin

    Chemical and Pharmaceutical Bulletin 56(4), 554-558, 2008-04-01

    The Pharmaceutical Society of Japan

References:  12

Cited by:  1

Codes

  • NII Article ID (NAID)
    110006649362
  • NII NACSIS-CAT ID (NCID)
    AA00602100
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    00092363
  • NDL Article ID
    9433031
  • NDL Source Classification
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-D167
  • Data Source
    CJP  CJPref  NDL  NII-ELS  J-STAGE 
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