Publication: Asperidines A–C, pyrrolidine and piperidine derivatives from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178
Issued Date
2018-08-15
Resource Type
ISSN
14643391
09680896
09680896
Other identifier(s)
2-s2.0-85050890135
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Mahidol University
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SCOPUS
Bibliographic Citation
Bioorganic and Medicinal Chemistry. Vol.26, No.15 (2018), 4502-4508
Suggested Citation
Patima Phainuphong, Vatcharin Rukachaisirikul, Saowanit Saithong, Souwalak Phongpaichit, Jariya Sakayaroj, Chutima Srimaroeng, Atcharaporn Ontawong, Acharaporn Duangjai, Paradorn Muangnil, Chatchai Muanprasat Asperidines A–C, pyrrolidine and piperidine derivatives from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178. Bioorganic and Medicinal Chemistry. Vol.26, No.15 (2018), 4502-4508. doi:10.1016/j.bmc.2018.07.036 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45081
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Title
Asperidines A–C, pyrrolidine and piperidine derivatives from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178
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.