College of Pharmaceutical Sciences, Key Laboratory of Pharmaceutical Quality Control of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnostics of Education Ministry of China , Hebei University , Baoding 071002 , People's Republic of China.
College of Life Sciences , Hebei University , Baoding 071002 , People's Republic of China.
J Nat Prod. 2019 Feb 22;82(2):386-392. doi: 10.1021/acs.jnatprod.8b01030. Epub 2019 Feb 6.
Investigation of the marine-derived fungus Pleosporales sp. CF09-1 cultured in modified PDB medium led to the isolation of six new azaphilone derivatives, pleosporalones B and C (1 and 2) and pleosporalones E-H (4-7), and one known analogue (3). The absolute configurations of C-2' and C-3' in 3 were assigned by a vibrational circular dichroism method. The C-11 relative configurations for the pair of C-11 epimers (4 and 5) were established by comparing the magnitude of the computed C NMR chemical shifts (Δδ) with the experimental C NMR values (Δδ) for the epimers. Antiphytopathogenic and anti- Vibrio activities were evaluated for 1-7. Pleosporalone B (1) exhibited potent antifungal activities against the fungi Alternaria brassicicola and Fusarium oxysporum with the same MIC value of 1.6 μg/mL, which were stronger than the positive control ketoconazole among these compounds. Additionally, pleosporalone C (2) displayed significant activity against the fungus Botryosphaeria dothidea (MIC, 3.1 μg/mL). Compounds 6 and 7 displayed moderate anti- Vibrio activities against Vibrio anguillarum and Vibrio parahemolyticus, with MIC values of 13 and 6.3 μg/mL for 6 and 6.3 and 25 μg/mL for 7, respectively.
从改良 PDB 培养基中培养的海洋来源真菌 Pleosporales sp. CF09-1 的研究中，分离得到了六个新的氮杂菲酮衍生物，pleosporalones B 和 C（1 和 2）以及 pleosporalones E-H（4-7），以及一个已知的类似物（3）。通过振动圆二色性方法确定了 3 中 C-2'和 C-3'的绝对构型。通过比较计算的 C NMR 化学位移（Δδ）与差向异构体的实验 C NMR 值（Δδ），确定了一对 C-11 差向异构体（4 和 5）的 C-11 相对构型。对 1-7 进行了抗植物病原和抗弧菌活性评价。pleosporalone B（1）对真菌芸薹链格孢和尖孢镰刀菌表现出强烈的抗真菌活性，MIC 值相同，均为 1.6 μg/mL，比这些化合物中的阳性对照酮康唑更强。此外，pleosporalone C（2）对真菌葡萄座腔菌显示出显著的活性（MIC，3.1 μg/mL）。化合物 6 和 7 对鳗弧菌和副溶血性弧菌表现出中等的抗弧菌活性，MIC 值分别为 13 和 6.3 μg/mL 用于 6 和 6.3 和 25 μg/mL 用于 7。
