Cycloheptapeptides

  • 文章类型: Journal Article
    海洋天然产物在生物农药中发挥着重要作用。七种具有不同结构类型的新次级代谢产物,包括两个环七肽,sortideA(1)和sortideB(2),两种19-nor-二萜,滑石抗坏血酸烯H(3)和滑石抗坏血酸烯I(4),两种二萜酸,滑石抗坏血酸烯J(5)和滑石抗坏血酸烯K(6),和一种三萜类化合物,从海葵衍生的内生真菌TalaromycesscorteusAS-242中分离并鉴定了tal抗坏血酸L(7)。通过光谱数据分析对它们的结构进行了全面分配,单晶X射线衍射,串联质谱,和电子圆二色性(ECD)计算。抗菌试验结果表明,化合物1-6对几种人具有抑制活性,水生,和最低抑制浓度(MIC)值在1至64μg/mL范围内的植物病原体。特别是,化合物2和4对致病真菌弯孢菌均有显著的活性,MIC值为1μg/mL,提供2和4的实验基础,有可能作为先导化合物开发为生物农药。
    Marine natural products play an important role in biopesticides. Seven new secondary metabolites with different structural classes, including two cycloheptapeptides, scortide A (1) and scortide B (2), two 19-nor-diterpenoids, talascortene H (3) and talascortene I (4), two diterpenoid acids, talascortene J (5) and talascortene K (6), and one triterpenoid, talascortene L (7) were isolated and identified from the sea-anemone-derived endozoic fungus Talaromyces scorteus AS-242. Their structures were comprehensively assigned by spectroscopic data analysis, single-crystal X-ray diffraction, tandem mass spectrometry, and electronic circular dichroism (ECD) calculations. The result of the antimicrobial assay demonstrated that compounds 1 - 6 have inhibitory activity against several human, aquatic, and plant pathogens with minimum inhibitory concentration (MIC) values ranging from 1 to 64 μg/mL. Specially, compounds 2 and 4 showed significant activities against the pathogenic fungus Curvularia spicifera with the MIC value of 1 μg/mL, providing an experimental basis of 2 and 4 with the potential as lead compounds to be developed into biopesticides.
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  • 文章类型: Journal Article
    在基于MS/MS的分子网络的指导下,对软珊瑚衍生的真菌杂色曲霉的次级代谢产物的进一步见解导致了七个已知的环七肽的分离,即,五倍子酰胺A-C(1-3)和五倍子A-D(4-7)和一种不寻常的含吡咯并吲哚啉的新环七肽,五吡咯酮A(8)。通过全面的光谱数据分析阐明了8的结构,它的绝对配置是由先进的Marfey\的方法确定的。成功实现了1到8的半合成转化,并优化了反应条件。此外,半合成了一系列新的asperversiamideA(1)衍生物(10-19),并评估了它们对结核分枝杆菌H37Ra的抗结核活性。初步的结构-活性关系表明,丝氨酸羟基和色氨酸残基对活性很重要。
    UNASSIGNED:在线版本包含补充材料,可在10.1007/s42995-022-00157-8获得。
    Further insights on the secondary metabolites of a soft coral-derived fungus Aspergillus versicolor under the guidance of MS/MS-based molecular networking led to the isolation of seven known cycloheptapeptides, namely, asperversiamides A-C (1-3) and asperheptatides A-D (4-7) and an unusual pyrroloindoline-containing new cycloheptapeptide, asperpyrroindotide A (8). The structure of 8 was elucidated by comprehensive spectroscopic data analysis, and its absolute configuration was determined by advanced Marfey\'s method. The semisynthetic transformation of 1 into 8 was successfully achieved and the reaction conditions were optimized. Additionally, a series of new derivatives (10-19) of asperversiamide A (1) was semi-synthesized and their anti-tubercular activities were evaluated against Mycobacterium tuberculosis H37Ra. The preliminary structure-activity relationships revealed that the serine hydroxy groups and the tryptophan residue are important to the activity.
    UNASSIGNED: The online version contains supplementary material available at 10.1007/s42995-022-00157-8.
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