Wagner C, Eckardt K, Tresselt D, Ihn W, Schumann G, Fleck W F
J Basic Microbiol. 1985;25(10):687-93. doi: 10.1002/jobm.3620251021.
The isolation and identification of several anthracyclinones (designated as G44-K4/5, G44-G1, G44-G2) and anthracyclines (G44-A, B, C, D, E, F, G) produced by the mutant strain IMET JA 3933/G44 of the daunomycin-producing Streptomyces griseus strain IMET JA 3933 are described. G44-K4/5 was found to be identical with 7,11-dideoxy-13-dihydrodaunomycinone previously isolated from a mutant strain of Streptomyces coeruleorubidus. Compound G44-G1 was identified as 11-deoxydaunomycinone, the aglycone of the antibiotic 11-deoxydaunomycin. G44-G2 was found to be a stereoisomer of G44-G1. The NMR and CD spectral data suggest strongly that the compound is 7-epi-11-deoxydaunomycinone. Of the 7 isolated G44-glycosides only the major component G44-B could be identified. Comparison with an authentic sample revealed that this compound is 11-deoxydaunomycin which had previously been isolated from cultures of Streptomyces peucetius var. aureus and Micromonospora peucetica. As reported for S. coeruleorubidus, S. peucetius var. aureus, and Micromonospora peucetica the 11-deoxydaunomycinone derivatives described in this paper were isolated from the fermentation broth of a mutant of a daunomycin-producing wild type strain. This suggest that in general the accumulation of 11-deoxydaunomycinone derivatives may be the result of a block of C11-hydroxylation in the normal biosynthetic pathway of daunomycin and its analogues.
本文描述了由产柔红霉素的灰色链霉菌菌株IMET JA 3933的突变株IMET JA 3933/G44产生的几种蒽环醌（命名为G44-K4/5、G44-G1、G44-G2）和蒽环类抗生素（G44-A、B、C、D、E、F、G）的分离和鉴定。发现G44-K4/5与先前从天蓝淡红链霉菌突变株中分离出的7,11-二脱氧-13-二氢柔红霉素酮相同。化合物G44-G1被鉴定为11-脱氧柔红霉素酮，即抗生素11-脱氧柔红霉素的苷元。发现G44-G2是G44-G1的立体异构体。核磁共振和圆二色光谱数据强烈表明该化合物是7-表-11-脱氧柔红霉素酮。在分离出的7种G44-糖苷中，仅能鉴定出主要成分G44-B。与标准样品比较表明，该化合物是11-脱氧柔红霉素，先前已从产黄青霉变种和佩西链霉菌的培养物中分离得到。正如天蓝淡红链霉菌、产黄青霉变种和佩西链霉菌的报道一样，本文所述的11-脱氧柔红霉素酮衍生物是从产柔红霉素野生型菌株的突变体发酵液中分离得到的。这表明，一般来说，11-脱氧柔红霉素酮衍生物的积累可能是柔红霉素及其类似物正常生物合成途径中C11-羟基化受阻的结果。
