期刊
JOURNAL OF NATURAL PRODUCTS
卷 81, 期 7, 页码 1651-1657出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.8b00289
关键词
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资金
- Scientific and Technological Innovation Project, Qingdao National Laboratory for Marine Science and Technology [2015ASKJ02, 2016ASKJ08-02]
- NSFC-Shandong Joint Fund for Marine Science Research Centers [U1606403]
- National Natural Science Foundation of China [21372208]
- Global Change and Air-Sea Interaction Project [GASI-IPOVAI-01-03]
Four new tetramic acids, cladosins H-K (1-4), and a related known compound, cladodionen (5), were isolated from the culture of the Mariana Trench (depth 6562 m) sediment-derived fungus Cladosporium sphaerospermum L3P3 treated with the histone deacetylase inhibitor SAHA (suberanilohydroxamic acid). Interestingly, compounds 1-5 existed as equilibrium E/Z mixtures and 1-4 were the first cases of tetramic acids containing aniline moieties. Their structures including absolute configurations were elucidated through a combination of NMR, MS, and Mosher's method, together with the consideration of biogenetic origins. Incubation experiments of exogenous aniline and N-phenyloctanamide revealed that the aniline moiety in cladosins H-K (1-4) is probably derived from the degradation of SAHA, indicating that the well-known histone deacetylase inhibitor SAHA could be metabolized by L3P3 and provide aniline as a precursor for biotransformation of chemically reactive polyketides. The cytotoxicity of 1-5 was evaluated against the PC-3, MGC-803, SH-SYSY, HCT-116, K562, and HL-60 cell lines, and compound 2 showed promising cytotoxicity against the HL-60 cell line with an IC50 value of 2.8 mu M.
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