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Phytotoxic Metabolites Produced by Diaporthella cryptica, the Causal Agent of Hazelnut Branch Canker
Journal of Agricultural and Food Chemistry ( IF 6.1 ) Pub Date : 2018-03-14 00:00:00 , DOI: 10.1021/acs.jafc.8b00256
Alessio Cimmino 1 , Paola Nocera 1 , Benedetto Teodoro Linaldeddu 2 , Marco Masi 1 , Marcin Gorecki 3 , Gennaro Pescitelli 3 , Lucio Montecchio 2 , Lucia Maddau 4 , Antonio Evidente 1
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From the culture filtrates of Diaporthella cryptica, an emerging hazelnut pathogen, 2-hydroxy-3-phenylpropanoate methyl ester and its 3-(4-hydroxyphenyl) and 3-(1H-indol-3-yl) analogues, named crypticins A–C, were isolated together with the well-known tyrosol. Crypticins A–C were identified by spectroscopic (essentially nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry) methods. The R absolute configuration (AC) of crypticin A was determined by comparing its optical rotation and electronic circular dichroism (ECD) spectrum with those of papuline, the methyl ester of (−)(S)-phenyllactic acid isolated as the main phytotoxin of Pseudomonas syringae pv. papulans, responsible for apple blister spot. The ACs of crypticins B and C were determined by time-dependent density functional theory calculations of their ECD spectra. Papuline and the new metabolites herein isolated, except tyrosol, were tested at 1 mg/mL on cork oak, grapevine, hazelnut, and holm oak leaves using the leaf puncture assay. They were also tested on tomato cuttings at 0.5 and 0.05 mg/mL. In the leaf puncture assay, none of the compounds was found to be active. Crypticin C and papuline were active in the tomato cutting assay. Additionally, crypticin C displayed moderate inhibitory effect against Phytophthora cambivora.

中文翻译:

榛子分支溃疡病的致病因子隐藻产生的植物毒性代谢物。

从一种新出现的榛子病原体-隐孢子虫的培养滤液中,提取2-羟基-3-苯基丙酸酯甲酯及其3-(4-羟基苯基)和3-(1 H-吲哚-3-基)类似物,命名为crypticins A– C与已知的酪醇一起分离。通过光谱分析法(本质上是核磁共振和高分辨率电喷雾电离质谱法)鉴定了Crypticins A–C。隐霉素A的R绝对构型(AC)通过将其旋光度和电子圆二色性(ECD)光谱与木瓜碱(分离为假单胞菌主要植物毒素的(-)(S)-苯乳酸的甲酯)的木瓜碱进行比较来确定丁香科植物 丘疹,负责苹果水疱点。隐菌素B和C的AC通过其ECD谱的时变密度泛函理论计算确定。使用叶穿刺试验在软木栎树,葡萄树,榛子树和圣栎树的叶子上以1 mg / mL的浓度检测出除酪醇外的Papuline及其分离的新代谢产物。他们还以0.5和0.05 mg / mL的番茄切块进行了测试。在叶穿刺试验中,没有发现任何化合物具有活性。Crypticin C和papuline在番茄切块测定中具有活性。另外,隐霉素C显示出对冈比亚疫霉的中等抑制作用。
更新日期:2018-03-14
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