Antiviral Cyclopropane Acids from Deep-Sea-Derived Fungus <i>Aspergillus sydowii</i>
Siwen Niu,
Shuhuan Huang,
Bihong Hong,
Qixi Huang,
Xiupian Liu,
Zongze Shao,
Gaiyun Zhang
Affiliations
Siwen Niu
Technology Innovation Center for Exploitation of Marine Biological Resources, Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
Shuhuan Huang
Technology Innovation Center for Exploitation of Marine Biological Resources, Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
Bihong Hong
Technology Innovation Center for Exploitation of Marine Biological Resources, Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
Qixi Huang
Fangchenggang Center of Inspection and Testing, Fangchenggang 538000, China
Xiupian Liu
Technology Innovation Center for Exploitation of Marine Biological Resources, Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
Zongze Shao
Technology Innovation Center for Exploitation of Marine Biological Resources, Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
Gaiyun Zhang
Technology Innovation Center for Exploitation of Marine Biological Resources, Key Laboratory of Marine Genetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, Xiamen 361005, China
Four novel monocyclic cyclopropane acids, namely, sydocyclopropanes A–D (1–4), along with one known congener hamavellone B (5), were isolated from the Aspergillus sydowii MCCC 3A00324 fungus, which was isolated from the deep-sea sediment. The gross structures of novel compounds were established by detailed analyses of the spectroscopic data (HRESIMS and NMR spectra), and their absolute configurations were resolved on the basis of the quantum chemical calculations of ECD and NMR data, in association with DP4+ probability analyses. Sydocyclopropanes A–D, featuring the 1,1,2,3-tetrasubstituted cyclopropane nucleus with different lengthy alkyl side chains, were discovered in nature for the first time. All compounds exhibited antiviral activities against A/WSN/33 (H1N1), with IC50 values ranging from 26.7 to 77.2 μM, of which compound 1 exhibited a moderate inhibitory effect (IC50 = 26.7 μM).
