Metschnikowia pulcherrima 提取物抑制尿素酶的起源:与合成 Pulcherriminic Acid 和环-二亮氨酸的比较试验

IF 2.3 Q1 AGRICULTURE, MULTIDISCIPLINARY ACS agricultural science & technology Pub Date : 2024-03-22 DOI:10.1021/acsagscitech.3c00587
Rosa Aligué, Sergio Atarés, Vicente Dorado, Inés Jimeno, Ignasi Salaet, Tula Yance, Daniel Menao, Eugenio Vispe and José M. Fraile*, 
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摘要

这项工作的目的是确定 Pulcherriminic 酸是否是 Metschnikowia pulcherrima 酵母菌提取物抑制脲酶活性的原因。Pulcherriminic 酸是由 l-leucine 通过七步途径合成的,首先是 l-leucine 热环二聚化成相应的 2,5-二酮哌嗪,然后氧化成 2、5-二氯吡嗪,氧化成相应的二-N-氧化物,通过与苄氧基的亲核芳香取代进行脱氯,然后用三氟乙酸进行脱保护,中间产物没有分离出来。脲酶抑制试验表明,在 500 ppm 的 Pulcherriminic 酸浓度下,脲酶活性的抑制率为 57 ± 2.3%,远低于提取物的抑制率(提取物中未检测到 Pulcherriminic 酸)。提取物中含有环状二聚体 l-亮氨酸,对其抑制能力也进行了测试,结果表明,在 400 ppm 的浓度下,对脲酶活性的抑制率为 56.1 ± 6.11%,同样大大低于提取物的抑制率。这项工作表明,酵母 M. pulcherrima 提取物的抑制能力并不仅仅是由于 pulcherriminic acid 或其环状二肽前体。
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Origin of the Urease Inhibition of Metschnikowia pulcherrima Extracts: Comparative Assays with Synthetic Pulcherriminic Acid and Cyclo-dileucine

The objective of this work was to determine whether pulcherriminic acid was responsible for the urease inhibition activity of the extracts of the yeast Metschnikowia pulcherrima. Pulcherriminic acid was synthesized through a seven-step pathway from l-leucine, starting with the thermal cyclodimerization of l-leucine to the corresponding 2,5-diketopiperazine, followed by oxidation to the 2,5-dichloropyrazine through three consecutive steps without purification of the intermediates, oxidation to the corresponding di-N-oxide, dechlorination by nucleophilic aromatic substitution with benzyloxide, and deprotection with trifluoroacetic acid without isolation of an intermediate. The urease inhibition assay showed 57 ± 2.3% inhibition of the urease activity at 500 ppm of pulcherriminic acid, much lower than the percent inhibition obtain with the extract, in which pulcherriminic acid was not detected. The cyclic dimer of l-leucine was present in the extract, and its inhibitory capacity was also tested, showing a percent inhibition of 56.1 ± 6.11% of the urease activity at 400 ppm, again much lower than the percent inhibition of the extract. This work demonstrates that the inhibitory capacity of the extracts of the yeast M. pulcherrima is not due to either only pulcherriminic acid or only its cyclic dipeptide precursor.

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