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加利利链霉菌和佩西链霉菌蒽环类抗生素生产菌株的阻断突变体对阿克拉诺酸的生物转化。

Biotransformation of aklanonic acid by blocked mutants of anthracycline-producing strains of Streptomyces galilaeus and Streptomyces peucetius.

作者信息

Schumann G, Stengel C, Eckardt K, Ihn W

出版信息

J Basic Microbiol. 1986;26(4):249-55. doi: 10.1002/jobm.3620260416.

DOI:10.1002/jobm.3620260416
PMID:3464736
Abstract

Aklanonic acid is an anthracyclinone-related pigment that was found to be an intermediate at an early stage of the biosynthesis of daunomycinone glycosides by Streptomyces griseus. We now isolated anthracycline-negative mutants of other Streptomyces species and used them in feeding experiments with both natural and radioactive aklanonic acid. In cultures of the mutant Streptomyces galilaeus S 727 exogenous aklanonic acid was biotransformed to cinerubin A as the major product. The spectrum of the conversion products was qualitatively comparable to that of the parent strain. In cultures of mutant 21/8 derived from Streptomyces peucetius var. caesius the predominant conversion product was epsilon-rhodomycinone. Daunomycinone glycosides were isolated in small amounts. According to results obtained with the radioactively labelled precursor aklanonic acid was completely incorporated into the molecules of the conversion products. Our findings suggest that aklanonic acid is also a natural intermediate in the biosynthesis of anthracyclines by Streptomyces galilaeus and Streptomyces peucetius. Proposed biosynthetic pathways have been constructed.

摘要

阿克拉诺酸是一种与蒽环酮相关的色素,它被发现是灰色链霉菌生物合成柔红霉素酮糖苷早期阶段的一种中间体。我们现在分离出了其他链霉菌属物种的蒽环素阴性突变体,并将它们用于天然和放射性阿克拉诺酸的饲喂实验。在突变型加利利链霉菌S 727的培养物中,外源阿克拉诺酸被生物转化为主要产物灰黄霉素A。转化产物的谱图在质量上与亲本菌株的谱图相当。在源自尖孢链霉菌变种卡氏链霉菌的突变体21/8的培养物中,主要的转化产物是ε-红霉酮。少量分离出了柔红霉素酮糖苷。根据用放射性标记前体获得的结果,阿克拉诺酸完全掺入了转化产物的分子中。我们的发现表明,阿克拉诺酸也是加利利链霉菌和尖孢链霉菌生物合成蒽环素的天然中间体。已经构建了推测的生物合成途径。

相似文献

1
Biotransformation of aklanonic acid by blocked mutants of anthracycline-producing strains of Streptomyces galilaeus and Streptomyces peucetius.加利利链霉菌和佩西链霉菌蒽环类抗生素生产菌株的阻断突变体对阿克拉诺酸的生物转化。
J Basic Microbiol. 1986;26(4):249-55. doi: 10.1002/jobm.3620260416.
2
Aklanonic acid-producing mutants of Streptomyces galilaeus and Streptomyces peucetius var. caesius.加利利链霉菌和凯撒变株佩西链霉菌的产阿克洛宁酸突变体。
J Basic Microbiol. 1987;27(2):107-11. doi: 10.1002/jobm.3620270212.
3
Microbial transformation of aklanonic acid, a potential early intermediate in the biosynthesis of anthracyclines.阿克拉诺酸的微生物转化,阿克拉诺酸是蒽环类抗生素生物合成中一种潜在的早期中间体。
J Antibiot (Tokyo). 1984 Jun;37(6):691-2. doi: 10.7164/antibiotics.37.691.
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New anthracycline metabolites from mutant strains of Streptomyces galilaeus MA144-M1. I. Isolation and characterization of various blocked mutants.来自加利利链霉菌MA144-M1突变株的新型蒽环类代谢产物。I. 各种阻断突变体的分离与表征。
J Antibiot (Tokyo). 1981 Aug;34(8):951-8. doi: 10.7164/antibiotics.34.951.
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Biosynthesis of anthracycline antibiotics by Streptomyces galilaeus. I. Glycosidation of various anthracyclinones by an aclacinomycin-negative mutant and biosynthesis of aclacinomycins from aklavinone.加利利链霉菌合成蒽环类抗生素。I. 阿克拉霉素阴性突变体对各种蒽环酮的糖基化作用以及从阿克拉维酮合成阿克拉霉素。
J Antibiot (Tokyo). 1980 Nov;33(11):1331-40. doi: 10.7164/antibiotics.33.1331.
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Biosynthesis of daunorubicin glycosides: role of epsilon-rhodomycinone.柔红霉素糖苷的生物合成:ε-红霉酮的作用
Antimicrob Agents Chemother. 1980 Sep;18(3):454-64. doi: 10.1128/AAC.18.3.454.
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Intra- and interspecific cosynthetic activity of mutants of Streptomyces coeruleorubidus and Streptomyces galilaeus impaired in the biosynthesis of anthracyclines.在蒽环类生物合成中受损的天蓝链霉菌和加利利链霉菌突变体的种内和种间共合成活性。
Folia Microbiol (Praha). 1979;24(2):128-35. doi: 10.1007/BF02927296.
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New anthracyclinone metabolites from two blocked mutants of Streptomyces galilaeus MA144-M1.来自加利利链霉菌MA144-M1两个阻断突变体的新型蒽环酮代谢产物。
J Antibiot (Tokyo). 1982 Dec;35(12):1641-5. doi: 10.7164/antibiotics.35.1641.
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Hybrid anthracycline antibiotics: production of new anthracyclines by cloned genes from Streptomyces purpurascens in Streptomyces galilaeus.杂合蒽环类抗生素:通过来自紫色链霉菌的克隆基因在加利利链霉菌中生产新的蒽环类抗生素。
Microbiology (Reading). 1994 Jun;140 ( Pt 6):1351-8. doi: 10.1099/00221287-140-6-1351.
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Biotransformations of anthracyclinones in Streptomyces coeruleorubidus and Streptomyces galilaeus.天蓝淡红链霉菌和加利利链霉菌中蒽环酮的生物转化
Folia Microbiol (Praha). 1979;24(2):117-27. doi: 10.1007/BF02927295.

引用本文的文献

1
In vivo and in vitro bioconversion of epsilon-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA.ε-玫瑰霉素酮糖苷在体内和体外生物转化为阿霉素:DauP、DauK和DoxA的作用
J Bacteriol. 1997 Apr;179(8):2641-50. doi: 10.1128/jb.179.8.2641-2650.1997.
2
Nucleotide sequence analysis of five putative Streptomyces griseus genes, one of which complements an early function in daunorubicin biosynthesis that is linked to a putative gene cluster involved in TDP-daunosamine formation.对五个推测的灰色链霉菌基因进行核苷酸序列分析,其中一个基因补充了柔红霉素生物合成中的早期功能,该功能与一个涉及TDP-柔红糖胺形成的推测基因簇相关。
Mol Gen Genet. 1993 Oct;241(1-2):193-202. doi: 10.1007/BF00280217.
3
Streptomycetes producing daunomycin and related compounds: do we know enough about them after 25 years?
产生柔红霉素及相关化合物的链霉菌:25年后我们对它们了解得够多了吗?
Folia Microbiol (Praha). 1989;34(4):324-49. doi: 10.1007/BF02814475.