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解説
ブラスチシジンS，ブラスチシジンエス，ブラエスともいう．ヌクレオチド系抗かび性抗生物質の一つ．放線菌Streptomyces griseochromogenesの培養液から酸性で活性炭に吸着し，50％ メタノール-水で溶出される．分解点253～255 ℃．[α]D11"＋108.4°(水)．pK1 4.6，pK2 8.0．λmax 274 nm(0.1 mol L－1 塩酸)，267 nm(0.1 mol L－1 水酸化ナトリウム)．水に可溶，有機溶媒に不溶．抗かび作用をもち，とくにイネのイモチ病菌Piricularia oryzaeに有効で，農薬として用いられている．LD50 38 mg/kg(マウス，経口)．
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説明
Nucleoside antibiotic produced by Streptomyces griseochromogenes
(1). Biosynthesized from cytosine, glucose, arginine,
and methionine (2).
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使用
Blasticidin S is a nucleoside produced by several species of Streptomyces, first reported in the late 1950s. Blasticidin S is an antifungal agent with particularly potent activity against the rice pathogen, Piricularia oryzae, for which it was used commercially for some time in Japan. Blasticidin S inhibits protein synthesis and is active against bacteria, tumour cell lines and nematodes. More recently, blasticidin S has been used as a marker for strain manipulations. Blasticidin S provided by BioAustralis is presented as the free base to avoid problems associated with the use of the hydrochloride.
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定義
ChEBI: A blasticidin that is an antibiotic obtained from Streptomyces griseochromogene.
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調製方法
Blasticidin S is produced by Streptomyces griseochromogenes,
and has a wide range of antimicrobial activity (4).
This antibiotic was utilized in the Far East beginning in
1961 against the rice blast pathogen Pyricularia oryzae,
with effective control achieved at rates of 10–40 ppm (4).
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一般的な説明
Blasticidin S was found in the culture broth of Streptomyces griseochromogenes by Yonehara et al. of the University of Tokyo in 1958. It has a nucleoside-analogue structure and shows strong activity against phytopathogenic fungi, especially Pericularia oryzae, the pathogen causing rice blast. Blasticidin S has been used to protect rice plants.
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薬理学
Inhibits protein synthesis both in eukaryotes and in
prokaryotes (5,6). Interacts with ribosomal RNA in large
subunit, interfering with the transpeptidation step.
Inhibits cell-free protein synthesis in P. oryzae and
Escherichia coli.
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代謝経路
Several blasticidin S-resistant microorganisms are
found to produce blasticidin S deaminase which
catalyzes the hydrolytic deamination of the cytosine
moiety in blasticidin S to give a non-toxic
deaminohydroxy derivative.
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代謝
3H-blasticidin S administered to mice was excreted in
the urine and feces within 24 h. Cytomycin and cytosin
were identified as the main metabolites in and on rice
plants, respectively (7). In soil, DT50 < 5 d. Metabolized to
nontoxic deaminohydroxy blasticidin S by Aspergillus sp.
and resistant Bacillus cereus. Novel deaminase and coding
genes, BSD and bsr, were isolated as selectable marker
genes for genetic engineering (8).
