60(P-37) インドネシア産海綿Theonella swinhoeiから得られた環状ペプチド類(ポスター発表の部)

DOI

書誌事項

タイトル別名
  • 60(P-37) New Cyclic Peptides from the Indonesian Sponge Theonella swinhoei

抄録

In our continuing search for novel bioactive substances from marine organisms, we have isolated eight new compounds, theonellapeptolides Ile (5), IV (6), V (7), VI (8) and barangamides A (9)-D (12), along with known theonellapeptolides Ia (1), Id (2), Ie (3), IId (4) from the sponge Theonella swinhoei collected in Baranglompo Island, Indonesia. The structures and absolute configurations of the component amino acids were deduced from the ^1H NMR comparison of hydrolysates of each peptide with authentic samples and applications of Marfey' s method. Each of the new theonellapeptolides (5-8) existed as a mixture of several conformers in solution, thus showed broad and complex NMR signals. Therefore, the structure elucidation was mainly carried out by MS analysis of ring-opened products obtained by hydrolysis or methanolysis of 5-8. The structure of 5 was confirmed by conversion to 13 that also derived from the known compounds 2-4. Interpretation of the NMR spectra led to elucidation of the structures of barangamides (9-12). The positions of diastereomeric Me-Ile units in 9 and 11 were successfully assigned by detailed analysis of coupling constants and NOE data. Theonellapeptolides and barangamides are tridecapeptide lactones and cyclic undecapeptides, respectively, possessing a high proportion of D-amino acids and N-methylated amino acids. Known theonellapeptolides have been shown to be cytotoxic, whereas barangamide A (9) and new theonellapeptolide Ile (5) were inactive at the same concentration. Some of the theonellapeptolides (1,2,4) showed mild immunosuppressive activity, while barangamide A was inactive. It is interesting to note that small variation in the structures of these compounds significantly affect their biological activity. Further chemical and biological studies are under way.

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詳細情報 詳細情報について

  • CRID
    1390282681055081472
  • NII論文ID
    110006681962
  • DOI
    10.24496/tennenyuki.42.0_355
  • ISSN
    24331856
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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