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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

Yu-Lin Sun
1   Key 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
3   Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China
,
Jie Bao
1   Key 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
3   Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China
,
Kai-Sheng Liu
2   Jinan University, Guangzhou, Guangdong, P. R. China
,
Xiao-Yong Zhang
1   Key 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
1   Key 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
2   Jinan University, Guangzhou, Guangdong, P. R. China
,
Xu-Hua Nong
1   Key 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
3   Graduate School of the Chinese Academy of Sciences, Beijing, P. R. China
,
Shu-Hua Qi
1   Key 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
› Author Affiliations
Further Information

Publication History

received 03 March 2013
revised 07 July 2013

accepted 07 August 2013

Publication Date:
13 September 2013 (online)

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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

Supporting Information

 

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