Herbicidal and Antifungal Xanthone Derivatives from the Alga-Derived Fungus Aspergillus versicolor D5
Herbicidal and Antifungal Xanthone Derivatives from the Alga-Derived Fungus Aspergillus versicolor D5
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来自藻类真菌 Aspergillus versicolor D5 的除草和抗真菌呫吨酮衍生物
DOI：
10.1021/acs.jafc.0c04265
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发表时间：
2020-10-07
影响因子：
6.1
通讯作者：
Zhang, Cheng-Sheng
中科院分区：
文献类型：
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作者：
Zhao, Dong-Lin;Han, Xiao-Bin;Zhang, Cheng-Sheng
真菌已被证明是功能性次生代谢物的有前途和多产的来源，具有强大的农业应用价值。本研究从藻源真菌versicolor Aspergillus versicolor D5中分离得到14个口山酮衍生物（1-14），包括6个新衍生物versicones I-N（1- 4,7,11）和一个生物遗传学相关衍生物（15）。用综合光谱方法对它们的结构进行了分析。Versicone L(4)具有较宽的抑菌谱和较强的抑菌效果，最小抑菌浓度（MIC）为152 μ M，比阳性对照多菌灵（MIC = 1.05 × 10(3) μ M）强7倍。Dihydrosterigmatocystin（13）在MIC = 38.3 mu M时对灰绿杆菌表现出较强的抑菌活性，比多菌灵强近30倍。与此同时，其中13种对红苋菜具有较强的除草活性，其MIC为24.5 μ M，比阳性对照草甘膦（MIC = 94.7 μ M）强约4倍。此外，13对苋菜属其他杂草也表现出显著的除草活性。结构-除草活性关系分析表明，双铀环对山酮的植物毒性起重要作用，呋喃环上存在双键可降低山酮的植物毒性。本研究表明，山酮类化合物可作为农用化学品的先导化合物。
Fungi have been proved as promising and prolific sources of functional secondary metabolites with potent agricultural applications. In this study, 14 xanthone derivatives (1-14), including six new ones, versicones I-N (1-4, 7, 11), and a biogenetically related derivative (15), were isolated from the alga-derived fungus Aspergillus versicolor D5. Their structures were elucidated by comprehensive spectroscopic methods. Versicone L ( 4) exhibited a broad antifungal spectrum and prominent inhibitory effects on Botrytis cinerea at a minimum inhibitory concentration (MIC) of 152 mu M, 7-fold stronger than that of the positive control, carbendazim (MIC = 1.05 x 10(3) mu M). Dihydrosterigmatocystin (13) showed strong antifungal activity toward B. cinerea at MIC = 38.3 mu M, almost 30-fold stronger than that of carbendazim. Meanwhile, 13 exhibited potent herbicidal activity toward Amaranthus retroflexus L. with an MIC of 24.5 mu M, approximately 4-fold stronger than that of the positive control, glyphosate (MIC = 94.7 mu M). Additionally, 13 also displayed remarkable activity against other weeds belonging to Amaranth sp. Analysis of the structure-herbicidal activity relationship indicated that the bifuranic ring played an important role in xanthone phytotoxicity and the presence of a double bond in the furan ring could decrease phytotoxicity. This study indicated that xanthones can be served as promising candidates for lead compounds of agrochemicals.