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. 2020 Jan 29;25(3):576.
doi: 10.3390/molecules25030576.

Naphthoquinone Derivatives with Anti-Inflammatory Activity from Mangrove-Derived Endophytic Fungus Talaromyces sp. SK-S009

Hongju Liu  1 , Chong Yan  1 , Changqun Li  1 , Tingting You  1 , Zhigang She  2
Affiliations

Naphthoquinone Derivatives with Anti-Inflammatory Activity from Mangrove-Derived Endophytic Fungus Talaromyces sp. SK-S009

Hongju Liu et al. Molecules. .

Abstract

Twelve 1, 4-naphthoquinone derivatives, including two new (1 and 2) and 10 known (3-12), were obtained from endophytic fungus Talaromyces sp. SK-S009 isolated from the fruit of Kandelia obovata. All structures were identified through extensive analysis of the nuclear magnetic resonance (NMR), mass spectrometry (MS) and circular dichroism (CD), as well as by comparison with literature data. These compounds significantly inhibited the lipopolysaccharide (LPS)-induced nitric oxide (NO) production in the murine macrophage cell line (RAW 264.7 cells). The half maximal inhibitory concentration (IC50) values, except for compound 2, were lower than that of indomethacin (26.3 μM). Compound 9 inhibited the LPS-induced inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) mRNA expressions in RAW 264.7 macrophages. Additionally, compound 9 reduced the mRNA levels of pro-inflammatory factors interleukin (IL)1β, IL-6, and tumor necrosis factor (TNF)-α. The results of this study demonstrated that these 1, 4-naphthoquinone derivatives can inhibit LPS-induced inflammation.

Keywords: 1,4-naphthoquinones; Talaromyces sp.; anti-inflammatory; marine fungus.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of compounds 1–12.
Figure 2
Figure 2
Key HMBC (red arrows) and COSY (blue bold lines) correlations of compounds 1 and 2.
Figure 3
Figure 3
Calculated and experimental electronic circular dichroism (ECD) spectra of 1.
Figure 4
Figure 4
RAW 264.7 murine macrophage cells were pre-incubated for 12h, and then cells were pretreated with compound 9 at the indicated concentration for 1 h and incubated with LPS (1 μg/mL) for 12h (real-time PCR). The effect of compound 9 on the mRNA expressions of inducible nitric oxide synthase (iNOS) (A), cyclooxygenase-2 (COX-2)(B), tumor necrosis factor (TNF)-α (C), interleukin (IL)-6 (D), and IL-1β (E) were detected by real-time PCR. The data represent the mean values ± SD of three experiments, * p < 0.05, ** p < 0.01 compared to LPS-treated group.
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