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Characterization of diketopiperazine heterodimers as potential chemical markers for discrimination of two dominant black aspergilli, Aspergillus niger and Aspergillus tubingensis
Phytochemistry ( IF 3.8 ) Pub Date : 2020-08-01 , DOI: 10.1016/j.phytochem.2020.112399
Ce Xu 1 , Kuo Xu 2 , Xiao-Long Yuan 2 , Guang-Wei Ren 2 , Xiao-Qiang Wang 2 , Wei Li 3 , Ning Deng 2 , Xiu-Fang Wang 2 , Peng Zhang 2
Affiliation  

Black aspergilli are distributed worldwide and represent one of the most prolific sources of metabolites with biomedical and agrochemical interests. However, due to their similar morphological characteristics and insufficient molecular identification, the taxonomic classification of black aspergilli remains ill-defined. The production of specialised metabolites is often unique for species among black aspergilli and could be used as diagnostic chemical markers for species identification. In this study, chemical investigation of Aspergillus tubingensis OUCMBIII 143291 led to the discovery of the diagnostic chemical marker asperazine, a complex diketopiperazine heterodimer, as well as two previously undescribed analogues, asperazine B and C. In addition, an undescribed 2-benzylpyridin-4(1H)-one-containing amide, pestalamide D, along with four known related metabolites were isolated. Their chemical structures, including their absolute configurations, were established on the basis of comprehensive spectral analysis and chiral HPLC analysis of the acidic hydrolysates. Asperazines B and C can serve as potential chemical markers for distinguishing A. tubingensis from A. niger, two representative species of black aspergilli that are usually incorrectly identified. Moreover, the isolated compounds were evaluated for their antifungal activity against eight phytopathogenic fungi including Alternaria alternata, A. brassicae, Botrytis cinerea, Colletotrichum lagenarium, Fusarium oxysporum, Gaeumannomyces graminis, Penicillium digitatum, and Valsa mali. Pestalamide D exhibited significant activities against B. cinerea, C. lagenarium, and V. mali, with MIC values of 4, 8, and 8 μg/mL, respectively, compared with the positive controls carbendazim (MICs = 8, 4, and 4 μg/mL) and prochloraz (MICs = 8, 8, and 4 μg/mL). The results of this study reveal two additional chemical markers and provide a powerful tool for the rapid identification of black aspergilli.

中文翻译:

二酮哌嗪异二聚体作为区分两种优势黑曲霉、黑曲霉和塔宾曲霉的潜在化学标记物的表征

黑曲霉分布于世界各地,是具有生物医学和农业化学兴趣的代谢物的最多产来源之一。然而,由于它们相似的形态特征和分子鉴定不足,黑曲霉的分类学分类仍然不明确。特殊代谢物的产生对于黑曲霉中的物种而言通常是独一无二的,可用作物种鉴定的诊断化学标记。在这项研究中,对塔宾曲霉 OUCMBIII 143291 的化学研究发现了诊断化学标记物 asperazine,一种复杂的二酮哌嗪异二聚体,以及两种以前未描述的类似物,asperazine B 和 C。此外,一种未描述的 2-benzylpyridin-4 (1H)-含一酰胺,pestalamide D,连同四种已知的相关代谢物被分离出来。它们的化学结构,包括它们的绝对构型,是在酸性水解物的综合光谱分析和手性 HPLC 分析的基础上建立的。Asperazines B 和 C 可以作为区分塔宾曲霉和黑曲霉的潜在化学标记物,黑曲霉的两种代表性物种通常被错误地识别。此外,还评估了分离的化合物对八种植物病原真菌的抗真菌活性,包括链格孢、芸苔、灰葡萄孢、炭疽菌、尖孢镰刀菌、禾本科青霉、指状青霉和马里青霉。Pestalamide D 对 B. cinerea、C. lagenarium 和 V. mali 表现出显着的活性,MIC 值为 4、8、和 8 μg/mL,分别与阳性对照多菌灵(MIC = 8、4 和 4 μg/mL)和丙氯灵(MIC = 8、8 和 4 μg/mL)进行比较。这项研究的结果揭示了另外两个化学标记,并为快速识别黑曲霉提供了强大的工具。
更新日期:2020-08-01
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