Dihydrothiophene-condensed chromones from a marine-derived fungus Penicillium oxalicum and their structure-bioactivity relationship.
Four dihydrothiophene-condensed chromones including two new compounds oxalicumones D-E (1-2) and known oxalicumones A-B (3-4), along with five other known chromones were isolated from a culture broth of the marine gorgonian-associated fungus Penicillium oxalicum SCSGAF 0023. The structures of 1-2 were elucidated by spectroscopic analysis. Eleven derivatives 3a-3i and 4a-4b were obtained from the acylation of 3 and 4, respectively. Compounds 1-4, 3a-3e, 3g-3h, and 4b showed significant cytotoxicity against several carcinoma cell lines with IC50 ≤ 10 μM. And their structure-bioactivity relationship was discussed.
Key Laboratory of Tropical Marine Bio-resources and Ecology/RNAM Center for Marine Microbiology/Guangdong Key Laboratory of Marine Material Medical, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, PR China; Graduate School of the Chinese Academy of Sciences (University of Chinese Academy of Sciences), Beijing 100049, PR China.
Jie
J
Bao
Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Road, Guangzhou 510530, PR China.
Jin-Feng
JF
Luo
Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Road, Guangzhou 510530, PR China.
Xiao-Chu
XC
Qin
Key Laboratory of Tropical Marine Bio-resources and Ecology/RNAM Center for Marine Microbiology/Guangdong Key Laboratory of Marine Material Medical, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, PR China.
Xin-Ya
XY
Xu
Key Laboratory of Tropical Marine Bio-resources and Ecology/RNAM Center for Marine Microbiology/Guangdong Key Laboratory of Marine Material Medical, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, PR China.
Xiao-Yong
XY
Zhang
Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Road, Guangzhou 510530, PR China. Electronic address: tu_zhengchao@gibh.ac.cn.
Zheng-Chao
ZC
Tu
Key Laboratory of Tropical Marine Bio-resources and Ecology/RNAM Center for Marine Microbiology/Guangdong Key Laboratory of Marine Material Medical, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, PR China. Electronic address: shuhuaqi@scsio.ac.cn.
Shu-Hua
SH
Qi
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D020014:K562 Cells; D061986:MCF-7 Cells; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000737:chemistry*; D020298:U937 Cells
D000970:Antineoplastic Agents; D002867:Chromones; D013876:Thiophenes
Cytotoxicity; Dihydrothiophene-condensed chromones; Penicillium oxalicum; Structure–bioactivity relationship