School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China.
Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China, Jinan University, Guangzhou 510632, China.
Org Biomol Chem. 2023 May 24;21(20):4309-4318. doi: 10.1039/d3ob00426k.
In fungi, there is a rare group of natural products harboring the 2,3,3a,9a-tetrahydro-4-furo[2,3-]chromene skeleton, represented by xyloketal B, which display a wide range of biological activities and have drawn significant attention. In this work, four new analogues simpliketals A-D (1-4), as well as two other new compounds simplilactones A and B (5 and 6), were isolated from sp. AHK071-01. Their structures were elucidated by extensive NMR spectroscopic methods, C NMR calculation, single-crystal X-ray diffraction, and ECD calculation. In addition, five known compounds (7-11) including alboatrin (7) were also obtained. Based on the structural similarity of the above compounds, we inferred that compounds 5, 6, and 8-11 might be biosynthetically related with 1-4 and 7, which allowed us to propose an alternative biosynthetic route to generate the furan-fused chromene skeleton of this class of compounds, instead of a previously presumed polyketide-terpenoid hybrid pathway. Finally, cytotoxicity assays showed that 1-4 exhibited weak inhibitory activity on PANC-1 cells and that 2 and 3 possessed moderate activity against SH-SY5Y cells.
在真菌中，存在一类罕见的天然产物，它们含有 2,3,3a,9a-四氢-4-呋喃并[2,3-]色烯骨架，以木脂素 B 为代表，具有广泛的生物活性，引起了广泛关注。在本工作中，从 sp. AHK071-01 中分离得到了四个新的类似物 simpliketals A-D（1-4）以及另外两个新化合物 simplilactones A 和 B（5 和 6）。通过广泛的 NMR 光谱方法、 13 C NMR 计算、单晶 X 射线衍射和 ECD 计算确定了它们的结构。此外，还获得了五个已知化合物（7-11），包括 alboatrin（7）。基于上述化合物的结构相似性，我们推断化合物 5、6 和 8-11 可能与 1-4 和 7 具有生物合成相关性，这使我们能够提出一种替代的生物合成途径来生成这类化合物的呋喃稠合色烯骨架，而不是之前假定的聚酮萜类杂合途径。最后，细胞毒性实验表明，化合物 1-4 对 PANC-1 细胞表现出较弱的抑制活性，而化合物 2 和 3 对 SH-SY5Y 细胞具有中等活性。
