Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 3, Pages 1534-1541Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02830
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Funding
- Program for Changjiang Scholars of the Ministry of Education of the People's Republic of China [T2016088]
- National Natural Science Foundation for Distinguished Young Scholars [81725021]
- National Science and Technology Project of China [2018ZX09201001-001-003]
- Innovative Research Groups of the National Natural Science Foundation of China [81721005]
- National Natural Science Foundation of China [81803387]
- Academic Frontier Youth Team of HUST
- Integrated Innovative Team for Major Human Diseases Program of Tongji Medical College (HUST)
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Six new 3,5-demethylorsellinic acid-based meroterpenoids, emeridones A-F (1-6), and eight known analogues (7-14) were isolated from Emericella sp. TJ29. Their structures and absolute configurations were elucidated by comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism calculations. Emeridone A (1) represents the first meroterpenoid featuring a unique rigid 6/6/5/6 tetracyclic carbon ring system with two additional lactone rings. Emeridones B and C (2 and 3) possess a 2,6-dioxabicyclo[2.2.1]heptane and a spiro[bicyclo[3.2.2]nonane-2,1'-cyclohexane] moiety, respectively, and both functionalities were found for the second time in meroterpenoids. These new compounds were evaluated for their cytotoxic activities against five human cancer cells, and compounds 2, 4, and 6 exhibited moderate cytotoxic activities, with IC50 values ranging from 8.19 to 18.80 mu M.
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