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Title: Asperidines A–C, pyrrolidine and piperidine derivatives from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178
Authors: Patima Phainuphong
Vatcharin Rukachaisirikul
Saowanit Saithong
Souwalak Phongpaichit
Jariya Sakayaroj
Chutima Srimaroeng
Atcharaporn Ontawong
Acharaporn Duangjai
Paradorn Muangnil
Chatchai Muanprasat
University of Phayao
Walailak University
Mahidol University
Prince of Songkla University
Chiang Mai University
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry;Pharmacology, Toxicology and Pharmaceutics
Issue Date: 15-Aug-2018
Citation: Bioorganic and Medicinal Chemistry. Vol.26, No.15 (2018), 4502-4508
Abstract: © 2018 Elsevier Ltd One new pyrrolidine derivative, asperidine A (1), and two new piperidine derivatives, asperidines B (2) and C (3), were isolated from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178 together with two known alkaloids. Compound 3 possessed an unprecedented 7-oxa-1-azabicyclo[3.2.1]octane skeleton with four chiral centers. Their structures were determined by spectroscopic evidence. The absolute configurations of compounds 2 and 3 were established using Mosher's method and further confirmed for compound 3 by X-ray crystallographic data. Compound 2 dose-dependently inhibited the CFTR-mediated chloride secretion in T84 cells with an IC50 value of 0.96 μM whereas 3 displayed the same activity with the IC50 value of 58.62 μM. Compounds 2 and 3 also significantly reduced intracellular ROS under both normal and H2O2-treated conditions compared with their respective controls in a dose-dependent manner without cytotoxic effect on Caco-2 cells. In addition, compound 3 was inactive against noncancerous Vero cells whereas compound 2 was considered to be inactive with the IC50 value of >10 μM.
ISSN: 14643391
Appears in Collections:Scopus 2018

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