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Non-geminal Aliphatic Dihalogenation Pattern in Dichlorinated Diaporthins from Hamigera fusca NRRL 35721
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-05-24 00:00:00 , DOI: 10.1021/acs.jnatprod.8b00041 Celso Almeida 1 , Ignacio Pérez-Victoria 1 , Víctor González-Menéndez 1 , Nuria de Pedro 1 , Jesús Martín 1 , Gloria Crespo 1 , Thomas Mackenzie 1 , Bastien Cautain 1 , Fernando Reyes 1 , Francisca Vicente 1 , Olga Genilloud 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-05-24 00:00:00 , DOI: 10.1021/acs.jnatprod.8b00041 Celso Almeida 1 , Ignacio Pérez-Victoria 1 , Víctor González-Menéndez 1 , Nuria de Pedro 1 , Jesús Martín 1 , Gloria Crespo 1 , Thomas Mackenzie 1 , Bastien Cautain 1 , Fernando Reyes 1 , Francisca Vicente 1 , Olga Genilloud 1
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Two new epimeric dihalogenated diaporthins, (9R*)-8-methyl-9,11-dichlorodiaporthin (2) and (9S*)-8-methyl-9,11-dichlorodiaporthin (3), have been isolated from the soil fungus Hamigera fusca NRRL 35721 alongside the known regioisomeric isocoumarin 8-methyl-11,11-dichlorodiaporthin (1). Their structures were elucidated by high-resolution mass spectrometry and NMR spectroscopy combined with molecular modeling. Compounds 1–3 are the first isocoumarins and the first halogenated metabolites ever reported from the Hamigera genus. The new compounds 2 and 3 display a non-geminal aliphatic dichlorination pattern unprecedented among known fungal dihalogenated aromatic polyketides. A bifunctional methyltransferase/aliphatic halogenase flavoenzyme is proposed to be involved in the biosynthesis of dichlorinated diaporthins 1–3. These metabolites are weakly cytotoxic.
中文翻译：
Hamigera fusca NRRL 35721的二氯二甲双胍中的非基因型脂族二卤化模式
从土壤中分离出了两种新的差向性二卤代双氮萘啶（9 R *）- 8-甲基-9,11-二氯二氮杂吩啶（2）和（9 S *）- 8-甲基-9,11-二氯二氮杂吩啶（3）。真菌Hamigera fusca NRRL 35721以及已知的区域异构异香豆素8-甲基-11,11-二氯二氮杂hin啶（1）。通过高分辨率质谱和NMR光谱结合分子建模阐明了它们的结构。化合物1 - 3是第一异香豆素和第一卤化代谢物不断从所报告的半内果菌属的属。新化合物2和图3显示了在已知的真菌二卤代芳族聚酮化合物中前所未有的非二元脂肪族二氯化模式。提出了一种双官能甲基/脂肪族halogenase黄素酶参与二氯化diaporthins的生物合成1 - 3。这些代谢物具有弱细胞毒性。
更新日期：2018-05-24
中文翻译：
Hamigera fusca NRRL 35721的二氯二甲双胍中的非基因型脂族二卤化模式
从土壤中分离出了两种新的差向性二卤代双氮萘啶（9 R *）- 8-甲基-9,11-二氯二氮杂吩啶（2）和（9 S *）- 8-甲基-9,11-二氯二氮杂吩啶（3）。真菌Hamigera fusca NRRL 35721以及已知的区域异构异香豆素8-甲基-11,11-二氯二氮杂hin啶（1）。通过高分辨率质谱和NMR光谱结合分子建模阐明了它们的结构。化合物1 - 3是第一异香豆素和第一卤化代谢物不断从所报告的半内果菌属的属。新化合物2和图3显示了在已知的真菌二卤代芳族聚酮化合物中前所未有的非二元脂肪族二氯化模式。提出了一种双官能甲基/脂肪族halogenase黄素酶参与二氯化diaporthins的生物合成1 - 3。这些代谢物具有弱细胞毒性。
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