Cytotoxic Dihydrothiophene-Condensed Chromones from the
                    Marine-Derived Fungus Penicillium oxalicum

Yu-Lin Sun; Jie Bao; Kai-Sheng Liu; Xiao-Yong Zhang; Fei He; Yi-Fei Wang; Xu-Hua Nong; Shu-Hua Qi

doi:10.1055/s-0033-1350805

Planta Medica, Table of Contents

Planta Med 2013; 79(15): 1474-1479
DOI: 10.1055/s-0033-1350805

Natural Product Chemistry

Letters

Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Dihydrothiophene-Condensed Chromones from the Marine-Derived Fungus Penicillium oxalicum

Authors

Yu-Lin Sun

¹Key Laboratory of Marine Bio-resources Sustainable Utilization/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, The Chinese Academy of Sciences, Guangzhou, Guangdong, P. R. China

³Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China
Jie Bao

¹Key Laboratory of Marine Bio-resources Sustainable Utilization/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, The Chinese Academy of Sciences, Guangzhou, Guangdong, P. R. China

³Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China
Kai-Sheng Liu

²Jinan University, Guangzhou, Guangdong, P. R. China
Xiao-Yong Zhang

¹Key Laboratory of Marine Bio-resources Sustainable Utilization/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, The Chinese Academy of Sciences, Guangzhou, Guangdong, P. R. China
Fei He

¹Key Laboratory of Marine Bio-resources Sustainable Utilization/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, The Chinese Academy of Sciences, Guangzhou, Guangdong, P. R. China
Yi-Fei Wang

²Jinan University, Guangzhou, Guangdong, P. R. China
Xu-Hua Nong

¹Key Laboratory of Marine Bio-resources Sustainable Utilization/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, The Chinese Academy of Sciences, Guangzhou, Guangdong, P. R. China

³Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China
Shu-Hua Qi

¹Key Laboratory of Marine Bio-resources Sustainable Utilization/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, The Chinese Academy of Sciences, Guangzhou, Guangdong, P. R. China

Abstract

Two new dihydrothiophene-condensed chromones and a new natural chromone, namely oxalicumones A–C (1–3), respectively, were isolated from a culture broth of a marine-derived fungus, Penicillium oxalicum. The structures of 1–3 and acetylated derivatives of 1 (4–7) were elucidated on the basis of spectroscopic methods and chemical reactions. The absolute configuration of 1 and 2 were established by using the modified Mosher ester method and circular dichroism data of an in situ formed [Rh₂(OCOCF₃)₄] and [Mo₂(OAc)₄] complex. (R)-MTPA ester of 1 showed cytotoxicity against A375, SW-620, and HeLa carcinoma cell lines with IC₅₀ values of 8.9, 7.8, and 18.4 µM, respectively. Compound 1 displayed cytotoxicity against A375 and SW-620 cell lines with IC₅₀ values of 11.7 and 22.6 µM, respectively. The structure–biological activity relationship of 1 was discussed.

Key words

Penicillium oxalicum - Trichocomaceae - dihydrothiophene-condensed chromone - cytotoxicity

Full Text

References

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