从产生放线菌素 D 的红树林根瘤土壤源链霉菌 A-30 中分离出一种新的酪氨酸衍生物。

IF 1.9 3区 化学 Q3 CHEMISTRY, APPLIED Natural Product Research Pub Date : 2024-11-18 DOI:10.1080/14786419.2024.2429114
Jingjing Ye, Juren Cen, Jingwan Wu, Zhenchang Wen, Hongjun Chen, Jing Xu
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引用次数: 0

摘要

通过对从红树植物根瘤菌土壤中分离出的链霉菌 A-30 进行化学研究,分离出了一种新的光学代谢物 (R)-N-(5-氨基-2-羟基-1-氧代戊基)-酪氨酸 (2)、以及七种已知代谢物,包括放线菌素 D (1)、(S)-2-甲基六氢吡咯并[1,2-a]吡嗪-1,4-二酮 (3)、尿嘧啶 (4)、N-乙酰基酪胺 (5)、邻苯二甲酸二(2-乙基己基)酯 (6)、二间苯二酚 (7) 和 4-羟基苯乙醇 (8)。其中,放线菌素 D(1)是主要成分(1 克,5.13%),化合物 3 则是首次作为天然产物分离出来。根据大量光谱数据以及与文献数据的比较,这些化合物的结构得到了明确的阐释。对所有分离出的化合物进行了免疫抑制和细胞毒性活性评估。化合物 1 对 HepG-2 和 Hela 具有显著的细胞毒性,其 IC50 值分别为 2.62 ± 0.22 和 0.37 ± 0.88 µM,表明它是 S. parvulus A-30 产生显著总细胞毒性效应的主要原因。
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A new tyrosine derivative isolated from an actinomycin D producing mangrove rhizosphere soil-derived Streptomyces parvulus A-30.

Chemical investigation of Streptomyces parvulus A-30, isolated from the mangrove plant Rhizophora apiculata rhizosphere soil resulted in the isolation of an optically new metabolite (R)-N-(5-amino-2-hydroxy-1-oxopentyl)-tyrosine (2), and seven known metabolites, including actinomycin D (1), (S)-2-methylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione (3), uracil (4), N-acetyltyramine (5), bis (2-ethylhexyl) phthalate (6), diorcinol (7), and 4-hydroxyphenethyl alcohol (8). Amongst, actinomycin D (1) was found to be a major component (1 g, 5.13%) and compound 3 was isolated as a natural product for the first time. Their structures were unambiguously elucidated on the basis of extensive spectroscopic data and comparison with the data of literature. All compounds isolated were subjected to immunosuppressive and cytotoxic activities evaluation. Compound 1 exhibited significant cytotoxicity against HepG-2 and Hela with IC50 values of 2.62 ± 0.22 and 0.37 ± 0.88 µM, respectively, indicating it is principally responsible for the significant total cytotoxic effect of S. parvulus A-30.

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来源期刊
Natural Product Research
Natural Product Research 化学-医药化学
CiteScore
5.10
自引率
9.10%
发文量
605
审稿时长
2.1 months
期刊介绍: The aim of Natural Product Research is to publish important contributions in the field of natural product chemistry. The journal covers all aspects of research in the chemistry and biochemistry of naturally occurring compounds. The communications include coverage of work on natural substances of land and sea and of plants, microbes and animals. Discussions of structure elucidation, synthesis and experimental biosynthesis of natural products as well as developments of methods in these areas are welcomed in the journal. Finally, research papers in fields on the chemistry-biology boundary, eg. fermentation chemistry, plant tissue culture investigations etc., are accepted into the journal. Natural Product Research issues will be subtitled either ""Part A - Synthesis and Structure"" or ""Part B - Bioactive Natural Products"". for details on this , see the forthcoming articles section. All manuscript submissions are subject to initial appraisal by the Editor, and, if found suitable for further consideration, to peer review by independent, anonymous expert referees. All peer review is single blind and submission is online via ScholarOne Manuscripts.
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