Lv Huawei, Su Haibo, Xue Yaxin, Jia Jia, Bi Hongkai, Wang Shoubao, Zhang Jinkun, Zhu Mengdi, Emam Mahmoud, Wang Hong, Hong Kui, Li Xing-Nuo
College of Pharmaceutical Science & Key Laboratory of Marine Fishery Resources Exploitment & Utilization of Zhejiang Province, Zhejiang University of Technology, Hangzhou, 310014 China.
School of Pharmaceutical Sciences, Wuhan University, Wuhan, 430072 China.
Mar Life Sci Technol. 2023 Mar 31;5(2):232-241. doi: 10.1007/s42995-023-00170-5. eCollection 2023 May.
Metabolites of microorganisms have long been considered as potential sources for drug discovery. In this study, five new depsidone derivatives, talaronins A-E () and three new xanthone derivatives, talaronins F-H (), together with 16 known compounds (), were isolated from the ethyl acetate extract of the mangrove-derived fungus species WHUF0362. The structures were elucidated by analysis of spectroscopic data and chemical methods including alkaline hydrolysis and Mosher's method. Compounds and each attached a dimethyl acetal group at the aromatic ring. A putative biogenetic relationship of the isolated metabolites was presented and suggested that the depsidones and the xanthones probably had the same biosynthetic precursors such as chrysophanol or rheochrysidin. The antimicrobial activity assay indicated that compounds , , , and showed potent activity against with minimum inhibitory concentration (MIC) values in the range of 2.42-36.04 μmol/L. While secalonic acid D () demonstrated significant antimicrobial activity against four strains of with MIC values in the range of 0.20 to 1.57 μmol/L. Furthermore, secalonic acid D () exhibited cytotoxicity against cancer cell lines Bel-7402 and HCT-116 with IC values of 0.15 and 0.19 μmol/L, respectively. The structure-activity relationship of depsidone derivatives revealed that the presence of the lactone ring and the hydroxyl at C-10 was crucial to the antimicrobial activity against . The depsidone derivatives are promising leads to inhibit and provide an avenue for further development of novel antibiotics.
The online version contains supplementary material available at 10.1007/s42995-023-00170-5.
微生物代谢产物长期以来一直被视为药物发现的潜在来源。在本研究中,从红树林来源的真菌WHUF0362的乙酸乙酯提取物中分离出5种新的缩酚酸酮衍生物,塔拉罗宁A - E()和3种新的呫吨酮衍生物,塔拉罗宁F - H(),以及16种已知化合物()。通过光谱数据分析和化学方法(包括碱性水解和莫舍尔法)阐明了结构。化合物和在芳环上各连接有一个二甲基缩醛基团。提出了分离代谢产物的推定生源关系,并表明缩酚酸酮和呫吨酮可能具有相同的生物合成前体,如大黄酚或大黄根素。抗菌活性测定表明,化合物、、和对具有强效活性,最低抑菌浓度(MIC)值在2.42 - 36.04 μmol/L范围内。而secalonic酸D()对4株表现出显著的抗菌活性,MIC值在0.20至1.57 μmol/L范围内。此外,secalonic酸D()对癌细胞系Bel - 7402和HCT - 116表现出细胞毒性,IC值分别为0.15和0.19 μmol/L。缩酚酸酮衍生物的构效关系表明,内酯环和C - 10位羟基的存在对针对的抗菌活性至关重要。缩酚酸酮衍生物是抑制的有前景的先导化合物,并为新型抗生素的进一步开发提供了途径。
在线版本包含可在10.1007/s42995 - 023 - 00170 - 5获取的补充材料。