67(P43) Pseudomonas sp. Q38009から単離された抗腫瘍性活性を有するYM-75518A-Dの構造(ポスター発表の部)

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In the course of our screening program for new cytotoxicl substances, we isolated YM-75518A-D from the fermentation broth of Pseudomonas sp. Q38009. The extensive spectroscopic analysis, including the Pulsed Field Gradient ^<15>N-^1H HMQC and ^<15>N-^1H HMBC NMR techniques at natural abundance, revealed the unique skeleton. Q38009 was isolated from a soil sample collected in Indonesia. The molecular formula of YM-75518A was determined to be C_<27>H_<32>N_2O_8 on the basis of negative-ion high resolution FAB-MS. The IR spectral data had two strong carbonyl absorptions at 1745 and 1730cm^<-1> and an amide carbonyl absorption at 1647cm^<-1>. The 2D NMR analysis including COSY, HMQC and HMQC, revealed the unique 15-membered ring. In order to elucidate unique structure, ^<15>N-^1H HMQC and ^<15>N-^1H HMBC were applied at natural abundance. The D_2O exchangeable proton (δ_H 10.24, J=9.8Hz), coupled to H5, showed the correlation to the nitrogen signal at δ_N 141 in the PFG ^<15>N-^1H HMQC spectrum. Therefore, it was revealed that the D_2O exchangeable proton (δ_H 10.24) was a NH proton. The ^<15>N chemical shift was consistent with amide nitrogen chemical shift. Furthermore, we obtained the direct information on the Cl carbon bonded to the imino nitrogen. In the ^<15>N-^1H HMBC spectrum, the cross peaks from H1 (δ_H, 8.98, d, J=10.4Hz), H2 ( δ_H 6.52, t, J=10.4Hz) and H27 (δ_H 3.86, s) to δ_N 408 ^<15>N signal were observed and δ_N 408 was consistent with a imino nitrogen chemical shift. In conclusion, the structure of YM-75518A was determined by ^<15>N-^1H HMQC and ^<15>N-^1H HMBC at natural abundance. The structure of YM-75518A consisted of a unique 15-membered macrolactone ring and a methoxy imino structure.
天然有機化合物討論会の論文
1999-09-01

67(P43) Pseudomonas sp. Q38009から単離された抗腫瘍性活性を有するYM-75518A-Dの構造(ポスター発表の部)

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