Prodigiosin R3, a new multicyclic prodigiosin formed by prodigiosin cyclization genes in the roseophilin producer
Prodigiosin R3, a new multicyclic prodigiosin formed by prodigiosin cyclization genes in the roseophilin producer
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DOI：
10.1038/s41429-022-00572-0
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发表时间：
2022-10
期刊：
影响因子：
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通讯作者：
Shoko Kimata;T. Matsuda;Takashi Kawasaki;Y. Hayakawa
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文献类型：
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作者：
Shoko Kimata;T. Matsuda;Takashi Kawasaki;Y. Hayakawa
已经鉴定出了用于合成浪子红素的热基因簇inStreptomyces griseoviridis2464-S5，它能产生环状的浪子红素衍生物，包括嗜玫瑰素（roseophilin）(2)、浪子红素R1(3)和浪子红素R2(4)。利用colicololstreptomyces m511的红双干扰物，在胞簇中表达4个环化候选基因（rphG、rphG2、rphg3和rphg4），产生了一种新的环化巨噬菌素——巨噬菌素R3(1)。该化合物从稻谷病毒链霉菌2464- s5中分离得到。通过ESI和FAB质谱法确定了1的分子式为c27h33n30o。经核磁共振波谱分析，确定其结构为具有3个烷基键的多环芥子素。Prodigiosin R3(1)对HeLa人宫颈癌细胞和HT1080人纤维肉瘤细胞具有细胞毒性，ic50值分别为2.1µM和3.2µM。
Therphgene cluster for prodigiosin biosynthesis has been identified inStreptomyces griseoviridis2464-S5, which produces cyclic prodigiosin derivatives including roseophilin (2), prodigiosin R1 (3) and prodigiosin R2 (4). A new cyclic prodigiosin, prodigiosin R3 (1), was produced by theredG redPdouble disruptant ofStreptomyces coelicolorM511 expressing four cyclization gene candidates (rphG,rphG2,rphG3andrphG4) in therphcluster. The same compound was isolated fromStreptomyces griseoviridis2464-S5. The molecular formula of1was established as C27H33N3O by ESI and FAB mass spectrometry. The structure was determined to be a multicyclic prodigiosin with three alkyl linkages by NMR spectroscopic analysis. Prodigiosin R3 (1) showed cytotoxicity against HeLa human cervical carcinoma cells and HT1080 human fibrosarcoma cells with IC50s of 2.1 µM and 3.2 µM, respectively.