Antibacterial polyketides and ascochlorins from deep-sea cold-seep-derived fungus Furcasterigmium furcatum (syn. Acremonium furcatum)
Antibacterial polyketides and ascochlorins from deep-sea cold-seep-derived fungus Furcasterigmium furcatum (syn. Acremonium furcatum)
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DOI：
10.1016/j.dsr.2023.104114
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发表时间：
2023-07-25
影响因子：
2.4
通讯作者：
Li, Xin
中科院分区：
文献类型：
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作者：
Chen, Xiao-Dan;Yang, Sui-Qun;Li, Xin
从Furcasterigmium furcatum CS-280（syn.叉枝顶孢Acremonium furcatum CS-280），是从南海深海冷泉沉积物中分离到的一种真菌。通过核磁共振波谱和质谱数据的详细解释确定了它们的结构。通过NOESY关联、GIAO NMR位移计算和DP 4+概率分析对化合物1-3的相对构型进行了归属，通过含时密度泛函ECD计算和比旋光度计算对化合物1-3的绝对构型进行了归属.化合物1对人致病性细菌铜绿假单胞菌表现出有效的活性，最小抑制浓度（MIC）值为8 μ g/mL。分离的子囊二氢菌素还显示出对水生细菌的有效活性，特别是对哈氏弧菌和溶藻弧菌，MIC值与氯霉素相当。构效关系分析表明，肉桂酸酯衍生物如化合物1，或子囊二氢卟酚衍生物中氯原子的存在如化合物4、6和7，均显著增强了其抗菌活性。这是首次报道子囊二氢酚衍生物的抗弧菌活性。
Three new secondary metabolites, including a new polyketide, acrefurcatone A (1), a new ascochlorin analogue, acremochlorin N (2), and 3-phenylcyclopentane-1,2-diol (& PLUSMN;-3), a pair of new naturally occurring enantiomers, along with nine known ascochlorins (4-12), were identified from Furcasterigmium furcatum CS-280 (syn. Acremonium furcatum CS-280), a fungus isolated from the deep-sea cold-seep sediment samples collected in the South China Sea. Their structures were determined by detailed interpretation of NMR spectroscopic and mass spectrometric data. The relative configurations of compounds 1-3 were assigned by NOESY correlations combined with gauge-independent atomic orbital (GIAO) NMR shift calculations and DP4+ probability analysis, while their absolute configurations were assigned by time-dependent density functional (TDDFT) ECD calculations and specific rotation calculations. Compound 1 exhibited potent activity against the human pathogenic bacterium Pseudomonas aeruginosa, with a minimum inhibitory concentration (MIC) value of 8 & mu;g/mL. The isolated ascochlorins also showed potent activities against aquatic bacteria, especially for Vibrio harveyi and V. alginolyticus, with MIC values comparable to chloramphenicol. Analysis of the structure-activity relationship indicated that the cinnamate derivative, such as compound 1, or the presence of chlorine atom in ascochlorin derivatives, such as compounds 4, 6, and 7, significantly enhanced the antibacterial activities. This is the first report of anti-Vibrio activities for ascochlorin derivatives.