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Phaseocyclopentenones A and B, Phytotoxic Penta- and Tetrasubstituted Cyclopentenones Produced by Macrophomina phaseolina, the Causal Agent of Charcoal Rot of Soybean in Argentina
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-01-25 , DOI: 10.1021/acs.jnatprod.0c01287 Marco Masi 1 , Francisco Sautua 2 , Roukia Zatout 1, 3 , Stefany Castaldi 4 , Lorenzo Arrico 5 , Rachele Isticato 4 , Gennaro Pescitelli 5 , Marcelo Anibal Carmona 2 , Antonio Evidente 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-01-25 , DOI: 10.1021/acs.jnatprod.0c01287 Marco Masi 1 , Francisco Sautua 2 , Roukia Zatout 1, 3 , Stefany Castaldi 4 , Lorenzo Arrico 5 , Rachele Isticato 4 , Gennaro Pescitelli 5 , Marcelo Anibal Carmona 2 , Antonio Evidente 1
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Two new penta- and tetrasubstituted cyclopentenones, named phaseocyclopentenones A and B (1 and 2), together with guignardone A (3), were isolated from Macrophomina phaseolina cultures. The phytopathogenic fungus was isolated from infected soybean tissues showing charcoal rot symptoms in Argentina. Charcoal rot is a devastating disease considering that soybean is one of the main legumes cultivated in the world. Phaseocyclopentenones A and B were characterized by 1D and 2D 1H and 13C NMR spectroscopic and HRESIMS spectrometric data and chemical methods as 4-benzoyl-3,4,5-trihydroxy-2-phenylcyclopent-2-enone and 3,5-dihydroxy-2,4-diphenylcyclopent-2-enone, respectively. The relative configuration of phaseocyclopentenones A and B was assigned by 1H and NOESY NMR methods, while their absolute configurations were assigned by electronic circular dichroism methods. When assayed on a nonhost plant (Solanum lycopersicum L.) by the leaf puncture assay, phaseocyclopentenones A and B and guignardone A showed phytotoxic activity, while only 1 and 2 were toxic when tested on cuttings of the same plant. No phytotoxicity or antifungal activity was detected for the three compounds on the host plant soybean (Glycine max L.) and against some of its fungal pathogens, namely, Cercospora nicotianae and Colletotrichum truncatum, also isolated from infected soybean plants in Argentina.
中文翻译：
菜豆环戊烯酮 A 和 B，植物毒性五取代和四取代环戊烯酮，由Macrophhomina Phaseolina 产生，是阿根廷大豆炭腐病的病原体
从Macrophhomina Phaseolina培养物中分离出两种新的五取代和四取代环戊烯酮，分别命名为phaseocyclopentenoneone A 和B ( 1和2 )，以及guignardone A ( 3 )。这种植物病原真菌是从阿根廷表现出木炭腐烂症状的受感染大豆组织中分离出来的。考虑到大豆是世界上种植的主要豆类之一，木炭腐病是一种毁灭性的疾病。相环戊烯酮 A 和 B 通过 1D 和 2D 1 H 和13 C NMR 光谱和 HRESIMS 光谱数据以及化学方法表征为 4-苯甲酰基-3,4,5-三羟基-2-苯基环戊-2-烯酮和 3,5-二羟基分别为-2,4-二苯基环戊-2-烯酮。相环戊烯酮A和B的相对构型通过1 H和NOESY NMR方法确定，而它们的绝对构型通过电子圆二色性方法确定。当通过叶穿刺试验对非寄主植物（ Solanum lycopersicum L.）进行测定时，相环戊烯酮 A 和 B 以及吉尼亚酮 A 显示出植物毒性活性，而当对同一植物的插条进行测试时，只有1和2具有毒性。未检测到这三种化合物对宿主植物大豆 ( Glycine max L.) 及其某些真菌病原体（即烟草尾孢和元宝炭疽病菌）具有植物毒性或抗真菌活性，这些病原体也是从阿根廷受感染的大豆植物中分离出来的。
更新日期：2021-02-26
中文翻译：
菜豆环戊烯酮 A 和 B，植物毒性五取代和四取代环戊烯酮，由Macrophhomina Phaseolina 产生，是阿根廷大豆炭腐病的病原体
从Macrophhomina Phaseolina培养物中分离出两种新的五取代和四取代环戊烯酮，分别命名为phaseocyclopentenoneone A 和B ( 1和2 )，以及guignardone A ( 3 )。这种植物病原真菌是从阿根廷表现出木炭腐烂症状的受感染大豆组织中分离出来的。考虑到大豆是世界上种植的主要豆类之一，木炭腐病是一种毁灭性的疾病。相环戊烯酮 A 和 B 通过 1D 和 2D 1 H 和13 C NMR 光谱和 HRESIMS 光谱数据以及化学方法表征为 4-苯甲酰基-3,4,5-三羟基-2-苯基环戊-2-烯酮和 3,5-二羟基分别为-2,4-二苯基环戊-2-烯酮。相环戊烯酮A和B的相对构型通过1 H和NOESY NMR方法确定，而它们的绝对构型通过电子圆二色性方法确定。当通过叶穿刺试验对非寄主植物（ Solanum lycopersicum L.）进行测定时，相环戊烯酮 A 和 B 以及吉尼亚酮 A 显示出植物毒性活性，而当对同一植物的插条进行测试时，只有1和2具有毒性。未检测到这三种化合物对宿主植物大豆 ( Glycine max L.) 及其某些真菌病原体（即烟草尾孢和元宝炭疽病菌）具有植物毒性或抗真菌活性，这些病原体也是从阿根廷受感染的大豆植物中分离出来的。
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