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Further secondary metabolites produced by the fungus Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris).
Chirality ( IF 2.8 ) Pub Date : 2020-07-20 , DOI: 10.1002/chir.23270 Marco Masi 1 , Ernesto Santoro 2 , Suzette Clement 3 , Susan Meyer 3 , Patrizia Scafato 2 , Stefano Superchi 2 , Antonio Evidente 1
Chirality ( IF 2.8 ) Pub Date : 2020-07-20 , DOI: 10.1002/chir.23270 Marco Masi 1 , Ernesto Santoro 2 , Suzette Clement 3 , Susan Meyer 3 , Patrizia Scafato 2 , Stefano Superchi 2 , Antonio Evidente 1
Affiliation
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The fungal pathogen Pyricularia grisea has been studied to evaluate its production of phytotoxins for the biocontrol of the buffelgrass (Cenchrus ciliaris L.) weed. A first investigation allowed to isolate several new and known phytotoxic metabolites. However, the further investigation on the organic extract obtained from the fungus liquid culture showed the presence of other metabolites possibly contributing to its phytotoxicity. Thus, four known metabolites were isolated and identified by spectroscopic (nuclear magnetic resonance [NMR] and high‐resolution electrospray ionization mass spectrometry [HRESIMS]) methods as dihydropyriculol (1), epi‐dihydropyriculol (2), 3‐methoxy‐6,8‐dihydroxy‐3‐methyl‐3,4‐dihydroisocoumarin (3), and (R)‐mevalonolactone (4). The absolute configuration of 1–3 was determined for the first time by a computational analysis of their electronic circular dichroism (ECD) spectra. When the isolated compounds were bioassayed at a concentration of 5 × 10–3 M in a buffelgrass coleoptile and radicle elongation test no toxicity was detected. On the contrary, compounds 1 and 3 showed a significant stimulating effect of radical elongation. Furthermore, the difference in growth stimulation between 1 and its epimer 2 highlights the tight relationship between absolute configuration and biological activity of these fungal metabolites.
中文翻译：
从水牛（Cenchrus ciliaris）中分离出的由稻瘟病菌真菌Pyricularia grisea产生的其他次级代谢产物。
已经研究了真菌病原性稻瘟病菌，以评估其产生的植物毒素，以用于水牛（Cenchrus ciliaris L.）杂草的生物防治。首次研究允许分离出几种新的和已知的植物毒性代谢产物。但是，对从真菌液体培养物中获得的有机提取物的进一步研究表明，可能存在其他代谢产物的植物毒性。因此，四个已知代谢物分离并通过光谱（核磁共振[NMR]和高分辨率电喷雾电离质谱[HRESIMS]）方法作为dihydropyriculol（标识1），外延-dihydropyriculol（2），3-甲氧基-6,8-二羟基-3-甲基-3,4-二氢异香豆素（3）和（R）-甲戊内酯（4）。的绝对构型1 - 3通过它们的电子圆二色性（ECD）光谱的计算分析确定的第一次。当在水牛草胚芽鞘和胚根伸长试验中以5×10 –3 M的浓度对分离的化合物进行生物测定时，未检测到毒性。相反，化合物1和3显示出显着的自由基伸长刺激作用。此外，1和它的差向异构体2在生长刺激上的差异 强调了这些真菌代谢物的绝对构型与生物学活性之间的紧密关系。
更新日期：2020-07-20
中文翻译：
从水牛（Cenchrus ciliaris）中分离出的由稻瘟病菌真菌Pyricularia grisea产生的其他次级代谢产物。
已经研究了真菌病原性稻瘟病菌，以评估其产生的植物毒素，以用于水牛（Cenchrus ciliaris L.）杂草的生物防治。首次研究允许分离出几种新的和已知的植物毒性代谢产物。但是，对从真菌液体培养物中获得的有机提取物的进一步研究表明，可能存在其他代谢产物的植物毒性。因此，四个已知代谢物分离并通过光谱（核磁共振[NMR]和高分辨率电喷雾电离质谱[HRESIMS]）方法作为dihydropyriculol（标识1），外延-dihydropyriculol（2），3-甲氧基-6,8-二羟基-3-甲基-3,4-二氢异香豆素（3）和（R）-甲戊内酯（4）。的绝对构型1 - 3通过它们的电子圆二色性（ECD）光谱的计算分析确定的第一次。当在水牛草胚芽鞘和胚根伸长试验中以5×10 –3 M的浓度对分离的化合物进行生物测定时，未检测到毒性。相反，化合物1和3显示出显着的自由基伸长刺激作用。此外，1和它的差向异构体2在生长刺激上的差异 强调了这些真菌代谢物的绝对构型与生物学活性之间的紧密关系。
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