Key Laboratory of Functional Molecules Analysis and Biotransformation of Universities in Yunnan Province, Yunnan Characteristic Plant Extraction Laboratory, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China; Institute of International Rivers and Eco-Security, Yunnan University, Kunming 650500, China.
Key Laboratory of Functional Molecules Analysis and Biotransformation of Universities in Yunnan Province, Yunnan Characteristic Plant Extraction Laboratory, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
Fitoterapia. 2023 Dec;171:105690. doi: 10.1016/j.fitote.2023.105690. Epub 2023 Sep 25.
Two new pyranonaphthoquinones, phialoyxinones A (1) and B (2), a new eighteen-membered ring lactone, phialoyxtone (3), and five known pyranonaphthoquinone derivatives were identified from the fungus Phialocephala sp. YUD18001, which was isolated from the rhizospheric soil associated with Gastrodia elata. Their structures were unequivocally established by a comprehensive interpretation of the spectroscopic data, with the stereochemistry for 1-3 was defined by a combination of TDDFT calculations, and the DP4+ probability analysis based on NMR chemical shift calculations. All of the new compounds 1-3 were evaluated for cytotoxicity and acetylcholinesterase inhibitory, compound 2 exhibited in vitro cytotoxic activities against five human cancer cell lines (HL-60, SMMC-7721, A549, MCF-7 and SW480) with IC values ranging from 11.80 to 19.32 μM. Compounds 2 and 3 exhibited moderate AChE inhibitory activities. A putative biosynthetic pathway for the pyranonaphthoquinones was proposed.
从与天麻相关的根际土壤中分离到的真菌 Phialocephala sp. YUD18001 中鉴定出两个新的吡喃并萘醌，即 phialoyxinones A（1）和 B（2），一个新的十八元环内酯 phialoyxtone（3），以及五个已知的吡喃并萘醌衍生物。通过对光谱数据的综合解释，明确了它们的结构，1-3 的立体化学通过 TDDFT 计算和基于 NMR 化学位移计算的 DP4+ 概率分析相结合来确定。对所有新化合物 1-3 进行了细胞毒性和乙酰胆碱酯酶抑制活性评估，化合物 2 对五种人癌细胞系（HL-60、SMMC-7721、A549、MCF-7 和 SW480）表现出体外细胞毒性活性，IC 值范围为 11.80-19.32 μM。化合物 2 和 3 表现出中等的 AChE 抑制活性。提出了吡喃并萘醌的可能生物合成途径。
