College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, China; CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; College of Pharmacy, Jinan University, Guangzhou 510632, China.
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458, China.
Bioorg Chem. 2021 Feb;107:104600. doi: 10.1016/j.bioorg.2020.104600. Epub 2020 Dec 31.
Two new hybrid sorbicillinoids (1 and 5), three new bisorbicillinoids (2-4), and three monomeric sorbicillinoids (6-8), along with eighteen known sorbicillinoids (9-26) were isolated from cultures of the deep-sea sediment derived fungus Penicillium sp. SCSIO06871. Their structures and absolute configurations were elucidated based upon the extensive spectroscopic analysis, X-ray crystallography analysis and the comparison of the experimental and calculated ECD data. Bisorbicillpyrone A (4) is the first example of bisorbicillinoid containing an α-pyrone derivative unit. All of the isolated compounds were evaluated for their antibacterial, antifungal and enzyme inhibitory activities against α-glycosidase and acetylcholinesterase (AChE) in vitro. Compound 6 displayed more potent inhibitory activity against α-glycosidase than acarbose with IC value of 36.0 μM and compounds 4, 12, 18, 22, 23 exhibited moderate inhibitory activity with IC values ranging from 115.8 to 208.5 μM. Compounds 10 and 22 showed weak enzyme inhibitory activities against AChE with 55.1% and 51.1% inhibitions at concentration of 50 μg/mL, respectively. Besides, compounds 11 and 12 exhibited significant antibacterial activities against Staphylococcus aureus with MIC values of 10.0 and 5.0 μg/mL, respectively. The hypothetical biosynthetic pathway of the isolated sorbicillinoids with three different structural types was discussed.
从深海沉积物来源的真菌 Penicillium sp. SCSIO06871 的培养物中分离得到两个新的混合索比尔菌素（1 和 5）、三个新的双索比尔菌素（2-4）和三个单体索比尔菌素（6-8）以及十八个已知的索比尔菌素（9-26）。基于广泛的光谱分析、X 射线晶体学分析以及实验和计算 ECD 数据的比较，确定了它们的结构和绝对构型。双索比啶酮 A（4）是第一个含有α-吡喃酮衍生物单元的双索比尔菌素。对所有分离得到的化合物进行了体外抗菌、抗真菌和对α-糖苷酶和乙酰胆碱酯酶（AChE）的酶抑制活性评价。化合物 6 对α-糖苷酶的抑制活性比阿卡波糖更强，IC 值为 36.0 μM，化合物 4、12、18、22、23 具有中等抑制活性，IC 值范围为 115.8 至 208.5 μM。化合物 10 和 22 对 AChE 表现出较弱的酶抑制活性，在 50 μg/mL 浓度下抑制率分别为 55.1%和 51.1%。此外，化合物 11 和 12 对金黄色葡萄球菌表现出显著的抗菌活性，MIC 值分别为 10.0 和 5.0 μg/mL。讨论了三种不同结构类型的分离得到的索比尔菌素的假设生物合成途径。
