72(P53) 海洋バクテリアの生産する新規アルカロイドUlbactin類(ポスター発表の部)

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As marine microorganisms live in different environment and are seemed to have different metabolic systems from those of terrestrial ones, they are likely to produce new chemical substances. In the course of our screening for novel compounds by using an HPLC/MS with a photo diode array detector, we found novel alkaloids, Ulbactins Al (3), A2 (4), B (5) and enantiomer of Aerugine (1) which were produced by Vibrio sp. B-93, as well as Ulbactins C1 (7) and C2 (8) which were produced by Alteromonas sp. D-12. Vibrio sp. B-93 and Alteromonas sp. D-12 were also found to produce known compounds, Yersiniabactin (2) and Aerugine (6), respectively. The structure of 1-8 were elucidated on the basis of MS, UV, IR, 1^H- and ^<13>C-NMR spectroscopic studies. 1 and 6 were identified to he (-)-(S)-Aerugine and (+)-(R)-Aerugine, respectively, based on the comparison of those specific rotations with synthetic ones. 2 was found to be one of the diastereomers of Yersiniabactin (isomer II). All of the UV spectra of 3-5, 7 and 8 showed the similar pattern, which attributed to 2-(o-hydroxyphenyl)-2-thiazoline moiety. 3 and 4 were suggested to have additional one thiazolidin ring with hydroxymethyl by 1^H-1^H COSY and HSQC, allowing us to establish the structures shown in Fig. 1. 5 was found to have 2-(2-(o-hydroxyphenyl)-2-thiazoline-4-yl)thiazolidine, which was the same partial structure as 3 and 4. An extra C_5H_8O_2 unit was considered to build bicyclo-ring system with thiazolidin through amide bond, which was supported by IR and 2D-NMR. 7 and 8 had two thiazolidin rings, 4''' position of which was attached by 2-amino-1,3-propanediol residue through amide bond. 3, 4, 7 and 8 tended to racemize in CDCl_3", solutions.
天然有機化合物討論会の論文
1996-09-02

72(P53) 海洋バクテリアの生産する新規アルカロイドUlbactin類(ポスター発表の部)

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