6 沖縄産海綿より単離したnakijiquinone/metachromin類の構造と生物活性(口頭発表の部)

概要

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Sesquiterpenoid quinines and hydroquinones are representative marine natural products with unique structures and interesting biological activities. In our continuous search for bioactive compounds having unique structures from Okinawan marine sponges, we have isolated new sesquiterpenoid quinones, nakijiquinones E〜I (1〜5) and metachromins L-Q (6〜11), from three collections of Okinawan marine sponges. The structures of 1〜5 were elucidated on the basis of 2D NMR data, while those of 6〜11 were established by chemical correlations. Furthermore, biological activities for 1〜11 and synthetic metachromin analogs 15〜26 were examined. Nakijiquinones E (1) and F (2) were the first dimeric sesquiterpenoid quinones possessing a 3-aminobenzoate moiety, while nakijiquinones G〜I (3〜5) were new sesquiterpenoid quinones having a histamine unit, an agmatine unit, and 3-(methylsulfinyl) propan-1-amino group, respectively. Metachromins L〜Q (6〜11) were new sesquiterpenoid quinones containing a different amino group derived from amino acids. Most of nakijiquinones E〜I (1〜5), metachromins L〜Q (6〜11), and synthetic metachromin analogs (15〜26) showed modest cytotoxicity against murine leukaemia P388 and L1210 cells, and human epidermoid carcinoma KB cells (IC_<50>, 1〜10μg/mL). Inhibitory activity of 15〜26 against several tyrosine kinases are currently investigated.
天然有機化合物討論会の論文
2008-09-01