Structures of grixazone A and B, A-factor-dependent yellow pigments produced under phosphate depletion by Streptomyces griseus
Structures of grixazone A and B, A-factor-dependent yellow pigments produced under phosphate depletion by Streptomyces griseus
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DOI：
10.7164/antibiotics.57.218
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发表时间：
2004-03-01
影响因子：
3.3
通讯作者：
Horinouchi, S
中科院分区：
文献类型：
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作者：
Ohnishi, Y;Furusho, Y;Horinouchi, S
A因子（2-异辛酰-3R-羟甲基-γ-丁内酯）作为一种微生物激素，在灰色链霉菌中诱导形态发育和次生代谢。一种可扩散的黄色色素由S.在磷酸盐耗竭下，以A因子依赖的方式抑制灰核菌。详细分析了S.在含有不同浓度磷酸盐的最低液体培养基中培养的griseus表明，在低浓度磷酸盐的存在下，色素的产生是活跃的，而在2.5 mm KH 2 PO 4的存在下，色素的产生被完全抑制。培养上清液的HPLC分析表明，该色素由两种主要的结构相关的化合物组成，它们根据培养基中磷酸盐的浓度以不同的比例产生。通过光谱分析确定了两个主要化合物的结构，命名为grixazone A和B，分别为1-[[2-（乙酰氨基）-2-羧乙基]硫基]-2-氨基-3-氧代-S-甲酰基-3H-吩恶嗪和1-[[2-（乙酰氨基）-2-羧乙基]硫基]-2-氨基-3-氧代-8-羧基-3H-吩恶嗪。Grixazone A是一种新化合物，尽管grixazone B在专利中被报道为由链霉菌DSM 3813产生的杀寄生虫剂。
A-factor (2-isocapryloyl-3R-hydroxymethyl-gamma-butyrolactone) acts as a microbial hormone that induces morphological development and secondary metabolism in Streptomyces griseus. A diffusible yellow pigment is produced by S. griseus in an A-factor-dependent manner under phosphate depletion. Detailed analysis of the pigment production by S. griseus cultivated in minimal liquid medium containing different concentrations of phosphate showed that the pigment was actively produced in the presence of low concentrations of phosphate and the production of the pigment was completely repressed in the presence of 2.5 mm KH2PO4. HPLC analysis of the culture supernatant showed that the pigment consisted of two major, structurally related compounds and they were produced at different ratios depending on the concentration of phosphate in the medium. The structures of the two major compounds, designated as grixazone A and B, were determined by spectroscopic analyses as 1-[[2-(acetylamino)2-carboxyethyl]thio]-2-amino-3-oxo-S-formyl-3H-phenoxiazine and 1-[[2-(acetylamino)-2-carboxyethyl]thio]-2-amino-3-oxo-8-carboxyl-3H-phenoxiazine, respectively. Grixazone A was a novel compound, although grixazone B was reported in a patent as a parasiticide produced by Streptomyces sp. DSM3813.