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从植物内生真菌层出镰刀菌中提取的 3-羟基丙酸作为一种抗菌剂。

3-hydroxypropionic acid as an antibacterial agent from endophytic fungi Diaporthe phaseolorum.

机构信息

Department of Genetics, Escola Superior de Agricultura Luiz de Queiroz, University of São Paulo, Av. Pádua Dias 11, Piracicaba, Brazil.

出版信息

Curr Microbiol. 2012 Nov;65(5):622-32. doi: 10.1007/s00284-012-0206-4. Epub 2012 Aug 12.

DOI:10.1007/s00284-012-0206-4
PMID:22886401
Abstract

Endophytic fungi are considered a rich source of active compounds resulting from their secondary metabolism. Fungi from marine environment grow in a habitat with unique conditions that can contribute to the activation of metabolic pathways of synthesis of different unknown molecules. The production of these compounds may support the adaptation and survival of the fungi in the marine ecosystem. Mangroves are ecosystems situated between land and sea. They are frequently found in tropical and subtropical areas and enclose approximately 18.1 million hectares of the planet. The great biodiversity found in these ecosystems shows the importance of researching them, including studies regarding new compounds derived from the endophytic fungi that inhabit these ecosystems. 3-hydroxypropionic acid (3-HPA) has been isolated from the mangrove endophytic fungus Diaporthe phaseolorum, which was obtained from branches of Laguncularia racemosa. The structure of this compound was elucidated by spectroscopic methods, mainly 1D and 2D NMR. In bioassays, 3-HPA showed antimicrobial activities against both Staphylococcus aureus and Salmonella typhi. The structure of this antibiotic was modified by the chemical reaction of Fischer-Speier esterification to evaluate the biologic activity of its chemical analog. The esterified product, 3-hydroxypropanoic ethyl ester, did not exhibit antibiotic activity, suggesting that the free carboxylic acid group is important to the pharmacological activity. The antibiotic-producing strain was identified with internal transcribed spacer sequence data. To the best of our knowledge, this is the first report of antibacterial activity by 3-HPA against the growth of medically important pathogens.

摘要

内生真菌被认为是具有生物活性化合物的丰富来源,这些化合物是由其次生代谢产生的。来自海洋环境的真菌在具有独特条件的生境中生长,这些条件可能有助于激活不同未知分子的合成代谢途径。这些化合物的产生可能有助于真菌在海洋生态系统中的适应和生存。红树林是位于陆地和海洋之间的生态系统。它们常见于热带和亚热带地区,约占地球面积的 1810 万公顷。这些生态系统中存在的巨大生物多样性表明对它们进行研究的重要性,包括对栖息在这些生态系统中的内生真菌衍生的新化合物的研究。3-羟基丙酸(3-HPA)已从红树林内生真菌 Diaporthe phaseolorum 中分离出来,该真菌是从 Laguncularia racemosa 的树枝中获得的。通过光谱方法,主要是 1D 和 2D NMR,阐明了该化合物的结构。在生物测定中,3-HPA 对金黄色葡萄球菌和伤寒沙门氏菌均表现出抗菌活性。通过 Fischer-Speier 酯化反应的化学反应对该抗生素的结构进行修饰,以评估其化学类似物的生物学活性。酯化产物 3-羟基丙酸乙酯没有表现出抗生素活性,这表明游离羧酸基团对药理学活性很重要。通过内部转录间隔区序列数据鉴定了产生抗生素的菌株。据我们所知,这是 3-HPA 对抗医学上重要病原体生长的抗菌活性的首次报道。

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