Citation: Hai-Ying Yu, Yu-Wei Huang, Li-Ping Lin, Ren-Xiang Tan. Unprecedented diphenyl ether hybrids and spiro-diphenyl ether with antioxidant activity from Aspergillus sp. F1-8A associated with toad venom[J]. Chinese Chemical Letters, ;2026, 37(2): 111121. doi: 10.1016/j.cclet.2025.111121 shu

Unprecedented diphenyl ether hybrids and spiro-diphenyl ether with antioxidant activity from Aspergillus sp. F1-8A associated with toad venom

Hai-Ying Yu ^a ,
Yu-Wei Huang ^a ,
Li-Ping Lin ^{a, *,} ,
Ren-Xiang Tan ^{a, b}

a.
State Key Laboratory of Technologies for Chinese Medicine Pharmaceutical Process Control and Intelligent Manufacture, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
b.
State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, School of Life Sciences, Nanjing University, Nanjing 210033, China

Lplin@njucm.edu.cn

Received Date: 27 December 2024
Revised Date: 14 March 2025
Accepted Date: 19 March 2025
Available Online: 25 March 2025

Figures(7)

Asplactones A–E (1–5), five unique diphenyl ether hybrids, along with two rare spiro-diphenyl ethers, aspviolaceols A (6) and B (7), were isolated and characterized from Aspergillus sp. F1–8A, an endophytic fungus associated with the parotoid glands of Bufo gargarizans Cantor. Compounds 1–5 represent the first examples of diphenyl ether hybrids fused with unusual moieties, including conjugated γ-butyrolactone and cyclopentenone. Compounds 6 and 7 are the first known natural spiro-diphenyl ethers, with 6 featuring an uncommon 6/6/6/6-membered carbon skeleton, and 7 possessing a distinct 6/6/6/6/6/6-membered diphenyl ether spiro-heterodimer carbon framework. Structural elucidation was performed using a combination of spectroscopic techniques, X-ray crystallography, and quantum-chemical calculations, and plausible biosynthetic pathways were proposed. Biologically, compounds 1, 2, 4, 6, and 7 exhibited antioxidant activity comparable to or surpassing that of vitamin C in 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS), and ferric reducing power assays. They also significantly improved cell viability in H₂O₂-induced oxidative injury assays using A549 cells.
- Diphenyl ether hybrids,
- Spiro-diphenyl ethers,
- γ-Butyrolactone,
- Cyclopentenone,
- Aspergillus,
- Bufo gargarizans Cantor,
- Antioxidant activity
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