71 新規60員環マクロライド抗生物質quinolidomicin A_1の構造研究(ポスター発表の部)

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In the course of our screening for antitumor antibiotics, we isolated a novel macrolide, quinolidomicin A_1 (1), from the cultured mycelium of an actinomycete Micromonospora sp. 1 was highly cytotoxic against P388 murine leukemia cells (IC_<50> 8nM). The molecular formula of 1 was determined to be C_<83>H_<132>O_<23>S by HRFAB-MS. The ^<13>C NMR spectrum confirmed the presence of 83 carbons and the HSQC spectrum established all one-bond ^1H-^<13>C connectivities. Phase-sensitive DQF-COSY and HMBC experiments generated partial structures 2-6. The characteristic UV absorptions at λmax 257, 268 and 279 nm indicated the presence of a triene group formed by connection of C-40 and C-41. Partial structures representing C-47 to C-55 and C-21 to C-25 were elucidated by a phase-sensitive HSQC-HOHAHA experiment. A new technique phase-sensitive ^<13>C-decoupled HMBC revealed a correlation between 59-H and C-1 to generate a 60-membered lactone ring. The protons on C-4 to C-7 showed large vicinal-coupling constants and were required to be in a six-membered ring, thereby showing that C-3 was connected to C-7 with an ether linkage. The geometrical configurations of the olefinic bonds were established to be 11Z, 28E, 30E, 38E, 42E, 60E and 62E by their vicinal coupling constants. The stereochemistry of C-13 was determined to be E based on a high-field chemical shift for 14-CH_3 (δ_C 12.7) and an NOE observed between 12-H and 14-CH_3. The remaining olefinic bond (C-40) in the triene system was required to have an E configuration by the ^<13>C chemical shift similarity of C-38 to C-43 to those of the all-E triene moiety of pulvomycin. Thus, the planar structure of 1 was elucidated as shown in Fig. 1.
天然有機化合物討論会の論文
1992-09-10

71 新規60員環マクロライド抗生物質quinolidomicin A_1の構造研究(ポスター発表の部)

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