1 葉たばこ中の新セスキテルペン配糖体の2次元NMRによる構造決定

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Three new sesquiterpene glycosides, 3-hydroxy-solanascone-β-sophoside (1), rishitin-β-sophoroside (5) and 3-hydroxy-solavetivone-β-glucoside (8) were isolated from flue-cured tobacco. The structure of (1) was elucidated by two dimensional NMR (2D NMR) spectra of its acetate (2). On the COSY 45N spectrum, the W type long range coupling was observed between H-10α and H-11α. In addition to the usual W type interactions, 1,3 diaxial coupling between H-3 and H-5 was resolved in the 2D J spectrum. Relative configuration was elucidated by the nuclear Overhauser effect (NOE) differential spectrum. The aglycone of (1) was 3-hydroxy derivative of solanascone which was characterized as stress compound. The structures of (5) and (8) were elucidated by the application of ^1H NMR and ^<13>C NMR. The aglycones of these glycosides, (5) and (8) were characterized as stress compounds. Antibacterial activities of these glycosides, (1), (5), (8), and sesquiterpene, solavetivone (10), solanascone (4), rishitin (7), 3-hydroxysolavetivone (9), were examined against a virulent strain of Pseudomonas solanacearum. The antibacterial activities of the glycosides were not detected, but the sesquiterpenes showed the activities at 2-5μg/spot.
天然有機化合物討論会の論文
1983-09-15