Two new glycosylated alkylresorcinols, resorcinosides A (1) and B (2), were isolated from a strain of the fungus Penicillium janthinellum derived from a marine sediment sample collected from Cu Lao Cham Island, Vietnam. The structures of 1 and 2 were established by interpretation of 1D and 2D NMR and high-resolution ESIMS data, and their absolute configurations were confirmed by the coupling constant of the anomeric proton, acid hydrolysis, subsequent HPLC analysis, Mosher's method, and quantum-mechanics-based computational analysis of NMR chemical shifts. The structure elucidation indicated that 1 and 2 are new alkylresorcinols with D-glucose, and 2 has an α-pyrone moiety attached to the aromatic ring. Compound 1 exhibited cytotoxic activity against the NUGC-3 cancer cell line with a GI50 value of 9.3 μM.
cytotoxicity, resorcinosides, Penicillium janthinellum
NCBI PubMed ID: 31668073Publication DOI: 10.1021/acs.jnatprod.9b00776Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Shin HJ
Institutions: Department of Marine Biotechnology, University of Science and Technology (UST), Daejeon, South Korea, Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology (KIOST), Busan, South Korea, Nha Trang Institute of Technology Research and Application, Vietnam Academy of Science and Technology, Nha Trang, Vietnam, Graduate University of Science and Technology, Vietnam Academy of Science and Technology, Ha Noi, Vietnam, Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul, South Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju, South Korea
Methods: 13C NMR, 1H NMR, NMR-2D, IR, DNA sequencing, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, CC, RP-HPLC, cell growth, HR-ESI-MS, cytotoxicity assay, derivatization, BLAST
Found