114(P-44) 海洋生物由来新規サフラマイシン系天然物の構造と合成研究(ポスター発表の部)

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概要

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• Several naturally occurring isoquinolinequinones have been isolated from Actinomycetes and from marine sponges. These metabolites exhibit strong cytotoxicity toward cultured cells and show antitumor activity against several experimental tumors. Many of the most intriguing problems, however, marine natural compounds available in only truly minute quantities. During our bioactivity screening of Thai marine invertebrates collected from Sichang Island, we found the dichloromethane extract of a Thai blue sponge, Xestospongia sp., showed significant antimicrobial, ichthyotoxic, and cytotoxic activities. The antimicrobial assay-directed fractionation of this extract led to the isolation of three new saframycin type compounds. Their structure elucidations and conformation analyses were achieved by means of MS, UV, IR, 1D and 2D NMR, including ^1H-^1H COSY, HMQC, HMBC, ROESY, and NOESY. All of compounds whose structures had an acetone residue at C-7 position, were designated as 4, 5, and 6. In particularly, the major product 6 was the first example of the monoisoquinolinequinone type compound from the marine organism. On the other hand, recently two new saframycin type natural marine products were isolated from the MeOH extract of the bright blue sponge Haliclona cribricutis Densy by the India researchers. These compounds 2h and 2i have been purified on reverse phase HPLC and their structures finalized from their respective spectral data. Because 2h has an hydroxy group at bridge head C-6 position, we have focused our attention on the synthesis of the ABC model compound 7. The challenge address was the introduction of a hydroxy group into C-6 position of the lactam 8. Treatment of 8 with sec-BuLi in THF followed by nitrobenzene oxidation afforded 9 in 53% yield. The structure of 7 was supported by ^<13>C NMR spectrum, which shows two aliphatic methane carbons at δ 73.1 and 52.9 assigned to C-5 and C-15 carbon peaks and an aliphatic quaternary carbon at δ 85.6 (C-6). Comparison of ^1H NMR and ^<13>C NMR spectral data of 2h with those of the model compound 7, we wish to present here the revised structure of 2h, which has a same framework with ld and 6.

• 天然有機化合物討論会の論文
• 2000-10-01

著者

• 齋藤 直樹

  Meiji Pharmaceutical University

• 齋藤 直樹

  明治薬大薬

• 酒井 晴之

  明治薬大薬

• 関 隆一

  明治薬大薬

• 久保 陽徳

  明治薬大薬

• Suwanborirux Khanit

  チュラ大薬

• Pummangura Sunibhond

  チュラ大薬

• 久保 陽徳

  明治薬科大学

• Suwanborirux K

  Chulalongkorn Univ. Bangkok Tha

• Kubo Akinori

  Graduate School Of Pharmaceutical Sciences Meiji Pharmaceutical University

• Saito Norio

  Chemical Laboratory Meiji-gakuin University

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