Strobiloscyphones A–F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscypha sp. AZ0266, a Leaf-Associated Fungus of Douglas Fir,Journal of Natural Products

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Strobiloscyphones A–F, 6-Isopentylsphaeropsidones and Other Metabolites from Strobiloscypha sp. AZ0266, a Leaf-Associated Fungus of Douglas Fir
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-09-08 , DOI: 10.1021/acs.jnatprod.1c00662
Wei Qu _{1,

2} , E M Kithsiri Wijeratne ₁ , Bharat P Bashyal ₁ , Jian Xu ₂ , Ya-Ming Xu ₁ , Manping X Liu ₁ , Marielle C Inácio ₁ , A Elizabeth Arnold ₃ , Jana M U'Ren ₄ , A A Leslie Gunatilaka ₁

Affiliation

Six new 6-isopentylsphaeropsidones, strobiloscyphones A–F (1–6), and a new hexadecanoic acid, (2Z,4E,6E)-8,9-dihydroxy-10-oxohexadeca-2,4,6-trienoic acid (7), together with sphaeropsidone (8) and its known synthetic analogue 5-dehydrosphaeropsidone (9) were isolated from Strobiloscypha sp. AZ0266, a fungus inhabiting the leaf litter of Douglas fir (Pseudotsuga menziesii). The structures of 1–7 were established on the basis of their high-resolution mass and 1D and 2D NMR spectroscopic data, and their relative and/or absolute configurations were determined by NOE, comparison of experimental and calculated ECD spectra, and application of the modified Mosher’s ester method. Of these, strobiloscyphone F (6) contains a novel highly oxygenated tetracyclic oxireno-octahydrodibenzofuran ring system. Natural products 1, 6, and 9 and the semisynthetic analogue 12 derived from 8 exhibited cytotoxic activity, whereas 9 and 12 showed antimicrobial activity. Possible biosynthetic pathways to 1–6, 8, and 9 are proposed.

中文翻译：

Strobiloscyphones A–F、6-Isopentylsphaeropsidones 和来自 Strobiloscypha sp. 的其他代谢物。AZ0266，花旗松的叶相关真菌

六种新的 6-isopentylsphaeropsidone、strobiloscyphones A–F ( 1 – 6 ) 和一种新的十六烷酸 (2 Z ,4 E ,6 E )-8,9-dihydroxy-10-oxohexadeca-2,4,6-trienoic从Strobiloscypha sp.中分离出酸 ( 7 ) ，以及球孢菌素( 8 ) 及其已知的合成类似物 5-脱氢球芹酮( 9 ) 。AZ0266，一种寄生在花旗松 ( Pseudotsuga menziesii )落叶中的真菌。1 – 7的结构建立在其高分辨率质量和 1D 和 2D NMR 光谱数据的基础上，它们的相对和/或绝对构型由 NOE、实验和计算 ECD 光谱的比较以及改进的 Mosher 酯方法的应用确定。其中， strobiloscyphone F ( 6 ) 包含新的高度氧化的四环环氧-八氢二苯并呋喃环系统。天然产物1，6，和9和半合成类似物12衍生自8显示出细胞毒活性，而9和12显示出抗微生物活性。可能的生物合成途径1 – 6、8和9被提出。

更新日期：2021-09-24

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