Secondary metabolites from Aspergillus terreus F6-3, a marine fungus associated with Johnius belengerii

Youmin Ying; Shubao Tu; Jiayue Ni; Xuejun Lu; Xiaoyan Hu; Panyi Lei; Xingnuo Li; Ying Wang; Guoqian Jin; Hong Wang

doi:10.1016/j.fitote.2023.105662

Secondary metabolites from Aspergillus terreus F6-3, a marine fungus associated with Johnius belengerii

Fitoterapia. 2023 Oct:170:105662. doi: 10.1016/j.fitote.2023.105662. Epub 2023 Aug 28.

Authors

Youmin Ying¹, Shubao Tu², Jiayue Ni², Xuejun Lu², Xiaoyan Hu², Panyi Lei², Xingnuo Li², Ying Wang³, Guoqian Jin⁴, Hong Wang⁵

Affiliations

¹ College of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China. Electronic address: ymying@zjut.edu.cn.
² College of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China.
³ School of Life Science and Technology, China Pharmaceutical University, 211198 Nanjing, China.
⁴ School of Traditional Chinese Pharmacy, China Pharmaceutical University, Nanjing 211198, China.
⁵ College of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, China; Key Laboratory of Marine Fishery Resources Exploitment and Utilization of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, China. Electronic address: hongw@zjut.edu.cn.

PMID: 37648028
DOI: 10.1016/j.fitote.2023.105662

Abstract

Two new terrein derivatives asperterreinones A-B (1-2), one new octahydrocoumarin derivative (±)-asperterreinin A (6), along with seventeen known compounds, were isolated from Aspergillus terreus F6-3, a marine fungus associated with Johnius belengerii. The structures of 1, 2, and 6 were established on the basis of 1D and 2D NMR, mass spectroscopy, comparative electronic circular dichroism (ECD) spectra analysis, density functional theory calculation of ¹³C NMR, and DP4+ probability analysis. Among all the isolates, eurylene (7), a constituent of the Malaysian medicinal plant Eurycoma longifolia, was obtained from a microbial source for first time. In the in vitro bioassay, 11 and 13 showed potent inhibitory activity against the Escherichia coli β-glucuronidase (EcGUS) with IC₅₀ values of 27.75 ± 0.73 and 17.73 ± 0.81 μM, respectively. It was the first time that questinol (11) and (±)-aspertertone B (13) were reported as potent EcGUS inhibitors.

Keywords: Aspergillus terreus; Octahydrocoumarin; Secondary metabolite; Terrein; β-Glucuronidase.

MeSH terms

Aspergillus* / chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure

Supplementary concepts

Aspergillus terreus