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Oximidines I and II: Novel Antitumor Macrolides from Pseudomonas sp
Jin Woo Kim1, Kazuo Shin-Ya, Kazuo Furihata
1Institute of Molecular and Cellular Biosciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0032, Japan, and Department of Applied Biological Chemistry, Graduate School of Agriculture and Life Science, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan.
Abstract:
Our screening for cell-cycle inhibitors in transformed cells resulted in the isolation of novel active compounds, oximidines I (1) and II (2), from Pseudomonas sp. Q52002. The molecular formulas of 1 and 2 were established as C(23)H(24)N(2)O(7) and C(23)H(24)N(2)O(6), respectively, by high-resolution FABMS. The structures of the oximidines were elucidated by NMR spectral analysis, including a variety of two-dimensional techniques. The absolute stereochemistry of 1 was determined by using the modified Mosher method. The oximidines are novel 12-membered macrolides containing an O-methyloxime moiety. Oximidines I and II selectively inhibited the growth of rat 3Y1 cells transformed with E1A, ras, or src oncogenes.