期刊
JOURNAL OF NATURAL PRODUCTS
卷 83, 期 11, 页码 3397-3403出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.0c00873
关键词
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资金
- National Natural Science Foundation of China [21702067, 81573316, 81803387]
- Program for Changjiang Scholars of Ministry of Education of the People's Republic of China [T2016088]
- National Natural Science Foundation for Distinguished Young Scholars [81725021]
- Innovative Research Groups of the National Natural Science Foundation of China [81721005]
- Hubei Provincial Natural Science Foundation of China [2018CFB152]
Bioassay-directed isolation of secondary metabolites from an extract of Penicillium chrysogenum TJ403-CA4 isolated from the medicinally valuable arthropod Cryptotympana atrata afforded five new and 10 known compounds (1-15). All the compounds (except 14) belong to a minor class of highly rigid 6-5-5-5-fused tetracyclic cyclopiane-type diterpenes known to be exclusively produced by members of the Penicillium genus. The structures and absolute configurations of the new compounds (1-5) were elucidated by extensive spectroscopic analyses, including HRESIMS and 1D and 2D NMR, single-crystal X-ray diffraction, and comparison of the experimental electronic circular dichroism data. Compounds 1 and 2 represent the first examples of cyclopianes bearing a C-20 carboxyl group; compound 3 represents the first example of a cyclopiane with a gem-hydroxymethyl group; compound 4 represents the second example of a cyclopiane bearing a hydroxy group at C-7; compound 5 represents the first example of a cyclopiane bearing a hydroxy group at C-8. Compounds 2 and 3 exhibited activity against MRSA, with MIC values of 4.0 and 2.0 mu g/mL, respectively. In addition, the structure-antibacterial activity relationship (SAR) of compounds 1-15 is discussed.
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