Asperversins A and B, Two Novel Meroterpenoids with an Unusual 5/6/6/6 Ring from the Marine-Derived Fungus Aspergillus versicolor

Asperversins A (1) and B (2), two novel meroterpenoids featuring an uncommon 5/6/6/6 ring system, along with five new analogues (3–7) and a known compound asperdemin (8), were obtained from the marine-derived fungus Aspergillus versicolor. Their structures and absolute configurations were confirmed by extensive spectroscopic analyses, single-crystal X-ray diffraction studies, and electronic circular dichroism (ECD) calculation. All new compounds were tested for their acetylcholinesterase enzyme (AChE) inhibitory activities and cytotoxic activities, of which compound 7 displayed moderate inhibitory activity against the AChE with an IC50 value of 13.6 μM.

[1]  I. Abe,et al.  Unique chemistry of non-heme iron enzymes in fungal biosynthetic pathways. , 2018, Natural product reports.

[2]  Qian-qian Xu,et al.  Aspermerodione, a novel fungal metabolite with an unusual 2,6-dioxabicyclo[2.2.1]heptane skeleton, as an inhibitor of penicillin-binding protein 2a , 2018, Scientific Reports.

[3]  Yonghui Zhang,et al.  Atrichodermones A-C, three new secondary metabolites from the solid culture of an endophytic fungal strain, Trichoderma atroviride. , 2017, Fitoterapia.

[4]  Junjun Liu,et al.  Bioassay-Guided Isolation of Antibacterial Metabolites from Emericella sp. TJ29. , 2017, Journal of natural products.

[5]  Junjun Liu,et al.  Spiroaspertrione A, a Bridged Spirocyclic Meroterpenoid, as a Potent Potentiator of Oxacillin against Methicillin-Resistant Staphylococcus aureus from Aspergillus sp. TJ23. , 2017, The Journal of organic chemistry.

[6]  Junjun Liu,et al.  Amaryllidaceae alkaloids with new framework types from Zephyranthes candida as potent acetylcholinesterase inhibitors. , 2017, European journal of medicinal chemistry.

[7]  P. Barth,et al.  Computational design of ligand binding membrane receptors with high selectivity , 2017, Nature chemical biology.

[8]  Yongjun Lu,et al.  Cytotoxic and Antibacterial Preussomerins from the Mangrove Endophytic Fungus Lasiodiplodia theobromae ZJ-HQ1. , 2016, Journal of natural products.

[9]  A. Kaur,et al.  Talarolutins A-D: Meroterpenoids from an endophytic fungal isolate of Talaromyces minioluteus. , 2016, Phytochemistry.

[10]  Xiaoyi Wei,et al.  Antiviral Merosesquiterpenoids Produced by the Antarctic Fungus Aspergillus ochraceopetaliformis SCSIO 05702. , 2016, Journal of natural products.

[11]  I. Abe,et al.  A methyltransferase initiates terpene cyclization in teleocidin B biosynthesis. , 2014, Journal of the American Chemical Society.

[12]  M. Rudolph,et al.  Structures of human acetylcholinesterase in complex with pharmacologically important ligands. , 2012, Journal of medicinal chemistry.

[13]  B. Oakley,et al.  Molecular genetic characterization of a cluster in A. terreus for biosynthesis of the meroterpenoid terretonin. , 2012, Organic letters.

[14]  A. Kalinovsky,et al.  A new meroterpenoid from the marine fungus Aspergillus versicolor (Vuill.) Tirab. , 2010 .

[15]  Takayuki Itoh,et al.  Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases. , 2010, Nature chemistry.

[16]  T. J. Simpson,et al.  Meroterpenoids Produced by Fungi , 2009 .

[17]  M. Fischbach,et al.  Assembly-line enzymology for polyketide and nonribosomal Peptide antibiotics: logic, machinery, and mechanisms. , 2006, Chemical reviews.

[18]  Yichao Zhang,et al.  Novel antiinsectan oxalicine alkaloids from two undescribed fungicolous Penicillium spp. , 2003, Organic letters.

[19]  S. Cutler,et al.  Novel bioactive breviane spiroditerpenoids from Penicillium brevicompactum Dierckx. , 2000, The Journal of organic chemistry.

[20]  Moncrief Jw,et al.  Structures of leurocristine (vincristine) and vincaleukoblastine. X-ray analysis of leurocristine methiodide. , 1965 .

[21]  K. Courtney,et al.  A new and rapid colorimetric determination of acetylcholinesterase activity. , 1961, Biochemical pharmacology.

[22]  E. Fernholz On the Constitution of α-Tocopherol , 1938 .

[23]  I. Abe,et al.  Biosynthesis of fungal meroterpenoids. , 2016, Natural product reports.

[24]  Weiguang Sun,et al.  and B , two unprecedented meroterpenoids from Aspergillus terreus with BACE 1 inhibitory activities † , 2016 .

[25]  B. Moore,et al.  Merochlorins A-D, cyclic meroterpenoid antibiotics biosynthesized in divergent pathways with vanadium-dependent chloroperoxidases. , 2012, Journal of the American Chemical Society.

[26]  W. Lipscomb,et al.  Structures of leurocristine (vincristine) and vincaleukoblastine. X-ray analysis of leurocristine methiodide. , 1965, Journal of the American Chemical Society.